Homesinorlando.forsale Search Results

$199,000

Hot Oakland opportunity. Motivated seller, bring all offers. This two-bed, one-bath on a no HOA lot puts you minutes to John’s Lake boat access and the West Orange Trail, plus a short hop to downtown Winter Garden dining and shops. Fix and flip, hold as a rental, or tear down and build new. The upside is real and the seller is ready. Quiet small-town setting with outdoor perks and growth around you. Don’t wait. Opportunities at this price and location move fast.

2 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Hot Oakland opportunity. Motivated seller, bring all offers. This two-bed, one-bath on a no HOA lot puts you minutes to John’s Lake boat access and the West Orange Trail, plus a short hop to downtown Winter Garden dining and shops. Fix and flip, hold as a rental, or tear down and build new. The upside is real and the seller is ready. Quiet small-town setting with outdoor perks and growth around you. Don’t wait. Opportunities at this price and location move fast.

320 W Sadler Avenue, Oakland

$3,399,000

Set within the picturesque Briley Farm community in Oakland, Florida, this exceptional 5-bedroom, 7-bath estate offers an extraordinary blend of timeless design, spacious living, and resort-style amenities. Situated on an expansive 0.52-acre homesite, the residence encompasses approximately 5,092 square feet of beautifully designed living space, creating an ideal setting for both everyday living and unforgettable entertaining. Inside, soaring vaulted ceilings and thoughtfully designed living spaces create an impressive sense of scale and openness. A dedicated office provides the perfect environment for working from home, while the private sauna offers a peaceful retreat at the end of the day. A welcoming fireplace adds warmth and character to the home's elegant interiors. Step outside and discover your own private resort. The sparkling pool provides a refreshing escape, while the outdoor kitchen creates an exceptional setting for al fresco dining and entertaining family and friends. The spacious grounds provide plenty of room to relax and enjoy the peaceful surroundings of Briley Farm. The property also features a private sauna, three-car garage and a private casita/guesthouse, providing exceptional flexibility for guests, extended family, or a private retreat. Briley Farm offers a rare combination of tranquil countryside living and convenient access to the best of Central Florida. Located on 111 acres in Oakland, the community features resort-style amenities including pickleball courts, tennis, a basketball half-court, a resort-style pool, splash pad, and convenient golf-cart access to Downtown Winter Garden. A remarkable opportunity to own a truly exceptional luxury residence in one of Central Florida's most sought-after communities.

5 Beds ⋅ 7 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code

Set within the picturesque Briley Farm community in Oakland, Florida, this exceptional 5-bedroom, 7-bath estate offers an extraordinary blend of timeless design, spacious living, and resort-style amenities. Situated on an expansive 0.52-acre homesite, the residence encompasses approximately 5,092 square feet of beautifully designed living space, creating an ideal setting for both everyday living and unforgettable entertaining. Inside, soaring vaulted ceilings and thoughtfully designed living spaces create an impressive sense of scale and openness. A dedicated office provides the perfect environment for working from home, while the private sauna offers a peaceful retreat at the end of the day. A welcoming fireplace adds warmth and character to the home's elegant interiors. Step outside and discover your own private resort. The sparkling pool provides a refreshing escape, while the outdoor kitchen creates an exceptional setting for al fresco dining and entertaining family and friends. The spacious grounds provide plenty of room to relax and enjoy the peaceful surroundings of Briley Farm. The property also features a private sauna, three-car garage and a private casita/guesthouse, providing exceptional flexibility for guests, extended family, or a private retreat. Briley Farm offers a rare combination of tranquil countryside living and convenient access to the best of Central Florida. Located on 111 acres in Oakland, the community features resort-style amenities including pickleball courts, tennis, a basketball half-court, a resort-style pool, splash pad, and convenient golf-cart access to Downtown Winter Garden. A remarkable opportunity to own a truly exceptional luxury residence in one of Central Florida's most sought-after communities.

515 N Nixon Street, Oakland

$435,000

Virtually Staged. Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers 1,170 square feet of modern living space on a 0.09-acre homesite. The open-concept floor plan features luxury vinyl plank flooring throughout the main living areas and bedrooms, with porcelain tile flooring in both bathrooms for added durability and style. The kitchen is equipped with quartz countertops, modern cabinetry, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas, making it ideal for everyday living and entertaining. Contemporary lighting, designer fixtures, and quality finishes can be found throughout the home. The spacious primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms offer flexibility for family, guests, or a home office. Additional features include an indoor laundry area, energy-efficient windows, modern exterior finishes, and a paver driveway. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, parks, major highways, and local attractions, this move-in-ready home offers the opportunity to enjoy low-maintenance living in the desirable Town of Oakland. Don't miss your chance to own this newly built home in one of Central Florida's most sought-after communities.

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Virtually Staged. Welcome to this brand-new construction home in the heart of Oakland! This thoughtfully designed 3-bedroom, 2-bathroom residence offers 1,170 square feet of modern living space on a 0.09-acre homesite. The open-concept floor plan features luxury vinyl plank flooring throughout the main living areas and bedrooms, with porcelain tile flooring in both bathrooms for added durability and style. The kitchen is equipped with quartz countertops, modern cabinetry, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas, making it ideal for everyday living and entertaining. Contemporary lighting, designer fixtures, and quality finishes can be found throughout the home. The spacious primary suite includes a walk-in closet and an ensuite bathroom with a quartz vanity and a porcelain tile shower. Two additional bedrooms offer flexibility for family, guests, or a home office. Additional features include an indoor laundry area, energy-efficient windows, modern exterior finishes, and a paver driveway. Conveniently located near downtown Winter Garden, the West Orange Trail, shopping, dining, parks, major highways, and local attractions, this move-in-ready home offers the opportunity to enjoy low-maintenance living in the desirable Town of Oakland. Don't miss your chance to own this newly built home in one of Central Florida's most sought-after communities.

521 W Herriott Avenue, Oakland

$350,000

Sold Off Market

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Sold Off Market

521 W Herriott Avenue, Oakland

$3,295,000

Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.

6 Beds ⋅ 7 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code

Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.

312 Briley Avenue, Oakland

$3,375,000

Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive Euro-style 9'+ bifold slider, and a stunning gas fireplace anchoring the main living space. The chef’s kitchen boasts Wolf and Sub-Zero appliances, exquisite Quartzite counters in both the main and back kitchens, and a fully equipped back kitchen designed for effortless entertaining. A custom primary closet with lighted rods adds a boutique touch to everyday living. Outdoor living is equally exceptional. Enjoy a lap pool and hot tub, gas fire pit, and luxurious marble coping and pool decking, all beautifully framed by a $70,000 professionally designed landscaping package and a fully fenced yard for privacy. Additional upgrades include Sonos speakers, security system with cameras, clay tumbled pavers on the porches, and a Generac generator for added comfort and peace of mind. With a 4-car garage, impeccable craftsmanship, and a leaseback opportunity, this home offers the best of luxury and convenience. Furniture is negotiable, allowing you to tailor the space to your vision. Discover refined living in one of Oakland’s most desirable communities—this model home truly sets the standard.

5 Beds ⋅ 7 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code

Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive Euro-style 9'+ bifold slider, and a stunning gas fireplace anchoring the main living space. The chef’s kitchen boasts Wolf and Sub-Zero appliances, exquisite Quartzite counters in both the main and back kitchens, and a fully equipped back kitchen designed for effortless entertaining. A custom primary closet with lighted rods adds a boutique touch to everyday living. Outdoor living is equally exceptional. Enjoy a lap pool and hot tub, gas fire pit, and luxurious marble coping and pool decking, all beautifully framed by a $70,000 professionally designed landscaping package and a fully fenced yard for privacy. Additional upgrades include Sonos speakers, security system with cameras, clay tumbled pavers on the porches, and a Generac generator for added comfort and peace of mind. With a 4-car garage, impeccable craftsmanship, and a leaseback opportunity, this home offers the best of luxury and convenience. Furniture is negotiable, allowing you to tailor the space to your vision. Discover refined living in one of Oakland’s most desirable communities—this model home truly sets the standard.

510 Briley Avenue, Oakland

$3,495,000

Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive open-concept living areas, designer finishes, and seamless indoor-outdoor flow. The chef’s kitchen is the centerpiece of the home with premium appliances, custom cabinetry, oversized island, generous prep and storage space, and a fully equipped back kitchen designed for seamless entertaining and everyday functionality. The luxurious primary suite offers a spa-inspired bath and oversized walk-in closet, while additional guest suites, flex spaces, and entertaining areas provide comfort and functionality throughout. Outdoor living is equally impressive with a resort-style pool, covered lanai, and beautifully designed entertaining spaces perfect for enjoying Florida living year-round. Professionally furnished by Arhaus, the home showcases elevated designer selections and a warm modern aesthetic throughout. Located just minutes from downtown Winter Garden, top-rated schools, restaurants, shopping, the West Orange Trail, and major highways, Briley Farm offers a rare combination of privacy, luxury, and convenience. This professionally designed model home is available with a lease-back opportunity from the builder, offering a unique investment opportunity with immediate income potential. A rare opportunity to own one of Central Florida’s premier luxury model homes in one of the area’s most desirable custom home communities.

5 Beds ⋅ 6 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code

Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive open-concept living areas, designer finishes, and seamless indoor-outdoor flow. The chef’s kitchen is the centerpiece of the home with premium appliances, custom cabinetry, oversized island, generous prep and storage space, and a fully equipped back kitchen designed for seamless entertaining and everyday functionality. The luxurious primary suite offers a spa-inspired bath and oversized walk-in closet, while additional guest suites, flex spaces, and entertaining areas provide comfort and functionality throughout. Outdoor living is equally impressive with a resort-style pool, covered lanai, and beautifully designed entertaining spaces perfect for enjoying Florida living year-round. Professionally furnished by Arhaus, the home showcases elevated designer selections and a warm modern aesthetic throughout. Located just minutes from downtown Winter Garden, top-rated schools, restaurants, shopping, the West Orange Trail, and major highways, Briley Farm offers a rare combination of privacy, luxury, and convenience. This professionally designed model home is available with a lease-back opportunity from the builder, offering a unique investment opportunity with immediate income potential. A rare opportunity to own one of Central Florida’s premier luxury model homes in one of the area’s most desirable custom home communities.

402 N Pollard Street, Oakland

$2,353,078

Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

1204 Water Maple Drive, Oakland

$799,999

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

16 Oakland Pointe Circle, Oakland

$2,186,921

Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres in the beautiful Town of Oakland. The property is a seamless blend of charming Old Florida and modern-day Luxury Living at its finest. The community is thoughtfully designed to provide the ultimate retreat for our residents. Lot 15 will be custom pool home meticulously designed to complement its natural surroundings, with a spacious floor plan. Briley Farm offers a seamless combination of residential luxury and convenience, with custom homes designed for enjoying the best of indoor and outdoor living. At Briley Farm you'll discover comfortable countryside living amongst the welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

3 Beds ⋅ 6 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres in the beautiful Town of Oakland. The property is a seamless blend of charming Old Florida and modern-day Luxury Living at its finest. The community is thoughtfully designed to provide the ultimate retreat for our residents. Lot 15 will be custom pool home meticulously designed to complement its natural surroundings, with a spacious floor plan. Briley Farm offers a seamless combination of residential luxury and convenience, with custom homes designed for enjoying the best of indoor and outdoor living. At Briley Farm you'll discover comfortable countryside living amongst the welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

100 W Railway Avenue, Oakland

$3,800,000

Pre-Construction. To be built. Pre-Construction. To be built. Experience elevated living in this brand-new custom home by Element Home Builders, located within the highly sought-after Briley Farm community in Oakland. Set across 111 acres of beautifully preserved landscape, Briley Farm blends timeless Old Florida charm with modern luxury to create a peaceful and refined lifestyle. Surrounded by serene natural scenery and mature tree-lined views, this exceptional community offers the perfect balance of countryside tranquility and everyday convenience , with easy access to shopping, dining, and major highways. Designed as a private retreat for family and friends, Briley Farm embodies comfortable luxury living in one of Central Florida’s most desirable new communities.

5 Beds ⋅ 5 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Pre-Construction. To be built. Experience elevated living in this brand-new custom home by Element Home Builders, located within the highly sought-after Briley Farm community in Oakland. Set across 111 acres of beautifully preserved landscape, Briley Farm blends timeless Old Florida charm with modern luxury to create a peaceful and refined lifestyle. Surrounded by serene natural scenery and mature tree-lined views, this exceptional community offers the perfect balance of countryside tranquility and everyday convenience , with easy access to shopping, dining, and major highways. Designed as a private retreat for family and friends, Briley Farm embodies comfortable luxury living in one of Central Florida’s most desirable new communities.

533 N Pollard Street, Oakland

$2,395,000

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1137 Prado Lane, Oakland

$2,045,357

Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

1225 Water Maple Drive, Oakland

$1,049,000

Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, Oakland

$1,654,248

Pre-Construction. To be built. Discover the opportunity to build your dream home in the sought-after Briley Farm community with J&J Building. This thoughtfully designed custom residence will feature 4 spacious bedrooms and 4.5 luxurious bathrooms, blending timeless craftsmanship with modern comfort. From the moment you arrive, an oversized front porch welcomes you with classic Southern charm—perfect for relaxing evenings and morning coffee. Inside, the open and functional layout is ideal for both everyday living and entertaining, with high-end finishes and attention to detail throughout. Enjoy seamless indoor-outdoor living with both side and rear porches, offering additional space for gathering, grilling, or simply taking in the peaceful surroundings. The home also includes a three-car attached garage, providing ample room for vehicles, storage, or hobbies. Each bedroom is designed with comfort and privacy in mind, while the primary suite will serve as a true retreat with a spa-inspired bath. With 4.5 bathrooms, convenience is built into every corner of the home. This is your chance to personalize a beautifully crafted home in Briley Farm—where quality construction meets a serene, upscale setting.

4 Beds ⋅ 5 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Discover the opportunity to build your dream home in the sought-after Briley Farm community with J&J Building. This thoughtfully designed custom residence will feature 4 spacious bedrooms and 4.5 luxurious bathrooms, blending timeless craftsmanship with modern comfort. From the moment you arrive, an oversized front porch welcomes you with classic Southern charm—perfect for relaxing evenings and morning coffee. Inside, the open and functional layout is ideal for both everyday living and entertaining, with high-end finishes and attention to detail throughout. Enjoy seamless indoor-outdoor living with both side and rear porches, offering additional space for gathering, grilling, or simply taking in the peaceful surroundings. The home also includes a three-car attached garage, providing ample room for vehicles, storage, or hobbies. Each bedroom is designed with comfort and privacy in mind, while the primary suite will serve as a true retreat with a spa-inspired bath. With 4.5 bathrooms, convenience is built into every corner of the home. This is your chance to personalize a beautifully crafted home in Briley Farm—where quality construction meets a serene, upscale setting.

360 N Jefferson Street, Oakland

$619,999

NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

NEW PRICE IMPROVEMENT! Seller incentive available! Welcome home to this beautiful 2026 newly built residence in the desirable town of Oakland! This 4-bedroom, 2.5-bath home features modern finishes, an open-concept layout, and a spacious design perfect for today’s lifestyle. Enjoy the benefits of owning a newer construction home with peace of mind, energy-efficient features, and low-maintenance living. Don’t miss the opportunity to own a move-in-ready home in Oakland, conveniently located near parks, trails, and local amenities. Schedule your private showing today!

38 S Pollard Street, Oakland

$1,949,000

Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, offers a private retreat with a spa-inspired bathroom and generous walk-in closet. Upstairs, you’ll find additional bedrooms along with a versatile loft space ideal for a media room, office, or play area. Designed for the Florida lifestyle, the outdoor living space is truly exceptional. Enjoy a resort-style pool and spa, expansive lanai, and dedicated firepit area—perfect for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage with a separate golf cart bay, high ceilings, and thoughtful architectural details throughout. This is a rare opportunity to own a beautifully crafted home in one of the area’s most desirable communities.

5 Beds ⋅ 5 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code

Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, offers a private retreat with a spa-inspired bathroom and generous walk-in closet. Upstairs, you’ll find additional bedrooms along with a versatile loft space ideal for a media room, office, or play area. Designed for the Florida lifestyle, the outdoor living space is truly exceptional. Enjoy a resort-style pool and spa, expansive lanai, and dedicated firepit area—perfect for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage with a separate golf cart bay, high ceilings, and thoughtful architectural details throughout. This is a rare opportunity to own a beautifully crafted home in one of the area’s most desirable communities.

511 Briley Avenue, Oakland

$683,000

Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

310 E Gulley Avenue, Oakland

$2,300,000

Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept floor plan features expansive living and dining areas highlighted by vaulted ceilings in the living room, a fireplace, and seamless indoor-outdoor flow. The gourmet kitchen showcases premium finishes and connects effortlessly to the main living spaces, making it ideal for both everyday living and entertaining. A private office provides a dedicated space for work or study. The primary suite offers a serene retreat with a spa-inspired bath, while each secondary bedroom includes an ensuite bathroom for added privacy. A standout feature of the home is the interior sauna, offering a true wellness experience within the comfort of your own residence. Outdoor living is elevated with a custom pool and spa, summer kitchen, and covered entertaining areas designed for year-round enjoyment. Additional highlights include a 3-car garage and high-end finishes throughout. Located just a 10-minute golf cart ride from downtown Winter Garden and a 2-minute walk to the West Orange Trail, this home combines luxury living with unmatched access to recreation, dining, and shopping.

4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept floor plan features expansive living and dining areas highlighted by vaulted ceilings in the living room, a fireplace, and seamless indoor-outdoor flow. The gourmet kitchen showcases premium finishes and connects effortlessly to the main living spaces, making it ideal for both everyday living and entertaining. A private office provides a dedicated space for work or study. The primary suite offers a serene retreat with a spa-inspired bath, while each secondary bedroom includes an ensuite bathroom for added privacy. A standout feature of the home is the interior sauna, offering a true wellness experience within the comfort of your own residence. Outdoor living is elevated with a custom pool and spa, summer kitchen, and covered entertaining areas designed for year-round enjoyment. Additional highlights include a 3-car garage and high-end finishes throughout. Located just a 10-minute golf cart ride from downtown Winter Garden and a 2-minute walk to the West Orange Trail, this home combines luxury living with unmatched access to recreation, dining, and shopping.

1118 Sarah Mathews Drive, Oakland

$4,383,239

Under Construction. Under Construction Custom Home by Element Home Builders. Welcome to your dream home in Briley Farm. Briley Farm is one of Central Florida's most desirable custom home communities. The property is a seamless blend of charming Old Florida and modern-day luxury. Briley Farm consists of 111 acres of lush landscape in Oakland, Florida. The personal residence is a custom blend of luxury finishes and stunning design. All measurements etc are estimates.

5 Beds ⋅ 8 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code

Under Construction. Under Construction Custom Home by Element Home Builders. Welcome to your dream home in Briley Farm. Briley Farm is one of Central Florida's most desirable custom home communities. The property is a seamless blend of charming Old Florida and modern-day luxury. Briley Farm consists of 111 acres of lush landscape in Oakland, Florida. The personal residence is a custom blend of luxury finishes and stunning design. All measurements etc are estimates.

548 Walker Street, Oakland

$1,250,000

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

6 Beds ⋅ 8 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland

$2,675,000

Pre-Construction. To be built. Custom Home by Element Home Builders

4 Beds ⋅ 5 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Custom Home by Element Home Builders

1179 Prado Lane, Oakland

$360,000

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!

507 W Oakland Avenue, Oakland

$390,000

Welcome to 121 W. Oakland Ave. This Charming Bungalow is in the heart of Oakland, you can walk to the Farmers Market on Thursdays, and the downtown area to include West Orange Biking trail and adorned Speer park. Situated on a corner lot, this property offers added privacy & w/ fenced in yard and wooden deck for entertaining. As you enter from the cozy front porch, you are captivated by the spacious living room with vaulted ceilings and Hardwood flooring with a stunning Brick wood burning fireplace. The primary bedroom and the other 2 bedrooms all have hardwood flooring as well. The kitchen is appointed with lots of counter space and natural sunlight overlooking the backyard. For added convenience, the dining area is just off the kitchen. NO HOA>>>>Oaklands quaint town is a stones throw away from Bustling Winter Garden, Clermont, and Disney can be found within 25-30 mins drive. Convenient to all major Arteries & shopping too. Schedule your private showing today and experience the beauty of this "one of a kind" home.

3 Beds ⋅ 1 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Welcome to 121 W. Oakland Ave. This Charming Bungalow is in the heart of Oakland, you can walk to the Farmers Market on Thursdays, and the downtown area to include West Orange Biking trail and adorned Speer park. Situated on a corner lot, this property offers added privacy & w/ fenced in yard and wooden deck for entertaining. As you enter from the cozy front porch, you are captivated by the spacious living room with vaulted ceilings and Hardwood flooring with a stunning Brick wood burning fireplace. The primary bedroom and the other 2 bedrooms all have hardwood flooring as well. The kitchen is appointed with lots of counter space and natural sunlight overlooking the backyard. For added convenience, the dining area is just off the kitchen. NO HOA>>>>Oaklands quaint town is a stones throw away from Bustling Winter Garden, Clermont, and Disney can be found within 25-30 mins drive. Convenient to all major Arteries & shopping too. Schedule your private showing today and experience the beauty of this "one of a kind" home.

121 W Oakland Avenue, Oakland

$480,000

Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

4 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

312 W Hull Avenue, Oakland

$450,000

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

3 Beds ⋅ 2 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

310 E Gulley Avenue, Oakland

$367,500

One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You’ll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appliances—perfect for anyone who loves to cook or entertain. Enjoy the flexibility of a main-level bedroom and full bathroom, ideal for guests, multigenerational living, or a private home office. Upstairs, you’ll find two additional bedrooms and another full bathroom, offering comfort and privacy for the whole family. Set on a peaceful, nature-filled corner lot with attached an garage plus plenty of parking Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you’ll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces—modeled after Winter Garden’s beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland at an affordable value!

3 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You’ll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appliances—perfect for anyone who loves to cook or entertain. Enjoy the flexibility of a main-level bedroom and full bathroom, ideal for guests, multigenerational living, or a private home office. Upstairs, you’ll find two additional bedrooms and another full bathroom, offering comfort and privacy for the whole family. Set on a peaceful, nature-filled corner lot with attached an garage plus plenty of parking Residents of the 34760 zip code enjoy the unique charm of mail pickup at the historic Oakland Post Office, where you’ll also find the latest issue of the Orange Observer and a quaint Little Free Library out front. Oakland also hosts a variety of beloved community events, including Heritage Day, Santa meet-and-greets, Easter egg drops, and weekly farmers markets in-front of the Heritage Center, an ever changing art gala. The town is a scenic rest stop along the West Orange Bike Trail and is home to numerous parks and landmarks. Speer Park features two playgrounds, tennis, pickleball, and basketball courts. The Jake Voss public fishing pier provides a peaceful spot for watching sunsets on Lake Apopka. Prairie House Coffee serves local coffee, baked goods, floral arrangements, and gifts inside a charming 1860s residence. Disney enthusiasts will love Recycling the Magic, which offers an eclectic shopping experience filled with Walt Disney World props, resort decor, and memorabilia. Just 3.5 blocks from the upcoming boutique district at 300 S. Tubb Street, this location offers walkability to a future hub of shopping, dining, and community spaces—modeled after Winter Garden’s beloved Plant Street. Nearby, luxury estate communities like Briley Farm and The Grove are bringing multi-million-dollar homes to Oakland, setting the stage for strong equity growth. This is your chance to own a move-in ready gem in Oakland at an affordable value!

500 W Oakland Avenue, Oakland

$604,000

Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character meets small town charm in the heart of Oakland, FL. This beautifully maintained 4-bedroom, 2-bath, plus the Multi-generational suite home offers almost 2,500 square feet of living space, blending vintage appeal with the comfort and flexibility today's buyers are seeking. Nestled on a quiet street just minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the living room along with the built-in shelving, to the exposed beams in the dining room, this home is inviting and full of character. The home’s thoughtful layout includes the spacious in-law suite that includes a private entrance and an ADA accessible bathroom, prime for multigenerational living, hosting guests, or creating a private work-from-home retreat. Step inside and discover generously sized bedrooms and a living space that flows effortlessly through the dining space overlooking your outdoor oasis. Step out onto the vaulted ceiling, screened-in lanai that overlooks a spacious backyard—perfect for relaxing evenings, lively gatherings, or enjoying Oakland’s peaceful atmosphere. Whether you’re looking for a forever home with vintage charm or an opportunity to personalize a home with great bones, this is your canvas. Don't miss your chance to own a piece of Oakland's history! Schedule your private showing today and experience firsthand the character, comfort and community this home has to offer.

5 Beds ⋅ 3 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code

Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character meets small town charm in the heart of Oakland, FL. This beautifully maintained 4-bedroom, 2-bath, plus the Multi-generational suite home offers almost 2,500 square feet of living space, blending vintage appeal with the comfort and flexibility today's buyers are seeking. Nestled on a quiet street just minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the living room along with the built-in shelving, to the exposed beams in the dining room, this home is inviting and full of character. The home’s thoughtful layout includes the spacious in-law suite that includes a private entrance and an ADA accessible bathroom, prime for multigenerational living, hosting guests, or creating a private work-from-home retreat. Step inside and discover generously sized bedrooms and a living space that flows effortlessly through the dining space overlooking your outdoor oasis. Step out onto the vaulted ceiling, screened-in lanai that overlooks a spacious backyard—perfect for relaxing evenings, lively gatherings, or enjoying Oakland’s peaceful atmosphere. Whether you’re looking for a forever home with vintage charm or an opportunity to personalize a home with great bones, this is your canvas. Don't miss your chance to own a piece of Oakland's history! Schedule your private showing today and experience firsthand the character, comfort and community this home has to offer.

410 E Gulley Avenue, Oakland

$950,000

Custom Entertainer’s Dream Courtyard Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living. From the moment you arrive, you’ll be captivated by the circular driveway with dual entrances, mature shade trees, and the impressive side-entry garage. Step inside to discover an open, light-filled floor plan with abundant windows and large sliding doors that seamlessly connect indoor and outdoor living spaces. Modern upgrades continue throughout the home, including three HVAC units—including new systems in 2024 and 2025, a 2022 water heater, energy-efficient construction with ICF (Insulated Concrete Forms), double-pane windows and sliders, and spray foam insulation in the attic. Other updates include a new roof (2024), fresh interior paint and pool deck paint (2025), and remodeled kitchens and bathrooms. The foyer leads to spacious formal living and dining areas, each with views of the expansive screened patio—ideal for entertaining. The chef’s kitchen boasts stone countertops, modern cabinetry with illuminated uppers, built-in ovens, a cooktop, undermount lighting, an outdoor vent system, a corner pantry, and a picturesque window over the sink. It overlooks the sunny dinette, soaring two-story family room with a cozy fireplace, and a striking wood staircase with wrought iron railings. Designed with a split-bedroom layout, each of the four bedrooms offers ensuite bath access. The 1st floor primary suite is a private retreat, featuring high ceilings, wood floors, patio/pool access, and a two-sided gas fireplace that enhances the bedroom and private bath. The ensuite includes a soaking tub, separate glass-enclosed shower, dual vanities, linen closet, water closet, and a spacious walk-in closet. The 2-story family room is delightful, featuring a fireplace, high ceilings, and multiple windows that provide ample natural light. Adjacent to the family room is the spacious dinette. Two double-pane sliding doors lead to the covered patio, where you can enjoy the fenced backyard, which includes a fire pit. Down the hall is another bedroom suite with a remodeled bath, a full-size laundry room, and garage access. Upstairs, you’ll find two additional bedrooms—one with a private balcony overlooking the corner park—and a bonus room with its own balcony view of the pool. Each room shares another jack-and-jill full bath with separate vanities. The backyard is a true Florida oasis—fully fenced with pavers for a clean look, a large screened-in pool area, and ample space for pets and play. With direct access to the popular West Orange Trail, outdoor adventures are just steps away. This exceptional home combines location, design, and functionality—perfect for visiting relatives and entertaining. Don’t miss your chance to own this one-of-a-kind property in one of Central Florida’s most desirable communities.

4 Beds ⋅ 3 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code

Custom Entertainer’s Dream Courtyard Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living. From the moment you arrive, you’ll be captivated by the circular driveway with dual entrances, mature shade trees, and the impressive side-entry garage. Step inside to discover an open, light-filled floor plan with abundant windows and large sliding doors that seamlessly connect indoor and outdoor living spaces. Modern upgrades continue throughout the home, including three HVAC units—including new systems in 2024 and 2025, a 2022 water heater, energy-efficient construction with ICF (Insulated Concrete Forms), double-pane windows and sliders, and spray foam insulation in the attic. Other updates include a new roof (2024), fresh interior paint and pool deck paint (2025), and remodeled kitchens and bathrooms. The foyer leads to spacious formal living and dining areas, each with views of the expansive screened patio—ideal for entertaining. The chef’s kitchen boasts stone countertops, modern cabinetry with illuminated uppers, built-in ovens, a cooktop, undermount lighting, an outdoor vent system, a corner pantry, and a picturesque window over the sink. It overlooks the sunny dinette, soaring two-story family room with a cozy fireplace, and a striking wood staircase with wrought iron railings. Designed with a split-bedroom layout, each of the four bedrooms offers ensuite bath access. The 1st floor primary suite is a private retreat, featuring high ceilings, wood floors, patio/pool access, and a two-sided gas fireplace that enhances the bedroom and private bath. The ensuite includes a soaking tub, separate glass-enclosed shower, dual vanities, linen closet, water closet, and a spacious walk-in closet. The 2-story family room is delightful, featuring a fireplace, high ceilings, and multiple windows that provide ample natural light. Adjacent to the family room is the spacious dinette. Two double-pane sliding doors lead to the covered patio, where you can enjoy the fenced backyard, which includes a fire pit. Down the hall is another bedroom suite with a remodeled bath, a full-size laundry room, and garage access. Upstairs, you’ll find two additional bedrooms—one with a private balcony overlooking the corner park—and a bonus room with its own balcony view of the pool. Each room shares another jack-and-jill full bath with separate vanities. The backyard is a true Florida oasis—fully fenced with pavers for a clean look, a large screened-in pool area, and ample space for pets and play. With direct access to the popular West Orange Trail, outdoor adventures are just steps away. This exceptional home combines location, design, and functionality—perfect for visiting relatives and entertaining. Don’t miss your chance to own this one-of-a-kind property in one of Central Florida’s most desirable communities.

100 Demens Street, Oakland

$3,175,000

Pre-Construction. To be built. Custom Home to be built by Element Home Builders. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends! Conveniently located in Oakland, just minutes from shopping, dining, and entertainment options, this home offers the perfect combination of tranquility and convenience. Don't miss your chance to own this exceptional property and experience luxury living at its finest. Schedule your private tour today and make your dream home a reality!

6 Beds ⋅ 6 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Custom Home to be built by Element Home Builders. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends! Conveniently located in Oakland, just minutes from shopping, dining, and entertainment options, this home offers the perfect combination of tranquility and convenience. Don't miss your chance to own this exceptional property and experience luxury living at its finest. Schedule your private tour today and make your dream home a reality!

410 Briley Avenue, Oakland