How many homes from $300,000 to $500,000 are for sale in 32792?

There are roughly 40 to 50 active at any given time. The list on this page comes straight from the MLS and updates on its own.

What do homes from $300,000 to $500,000 cost in 32792?

The median list price is around $409,950, with the range running $315,000 to $495,000.

Can you show me homes from $300,000 to $500,000 in 32792?

Yes. Call or text 407-616-9019 and we will set up showings.

32792 Zip Code Homes $300,000 to $500,000

$349,900

3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 4 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Comfort, style, and convenience come together in this beautifully maintained 3-bedroom, 2-bath home in the desirable Villas of Casselberry community. Soaring vaulted ceilings, an open floor plan, and abundant natural light create a spacious, inviting feel. The kitchen features stone countertops, ample cabinet space, and a cozy breakfast area, while the split-bedroom layout provides added privacy. The primary suite offers a walk-in closet and en-suite bath. Enjoy relaxing or entertaining on the screened patio overlooking the backyard. Community amenities include a pool, playground, and park, all just minutes from shopping, dining, and major highways for easy commuting.

3328 Hamlet Loop, Winter Park

$495,000

3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code

Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained interior. Inside, the home features an open and functional layout accented by luxury wood-look flooring throughout, neutral designer colors, crown molding, recessed lighting, and abundant natural light. The spacious living areas flow seamlessly together, creating an ideal setting for both everyday living and entertaining. The generously sized bedrooms provide flexibility for families, guests, or a home office, while the updated bathrooms offer clean, contemporary finishes. The primary suite serves as a comfortable retreat with its own private en-suite bath. Step outside to your own private oasis featuring a sparkling in-ground pool surrounded by an expansive travertine paver deck, a screened lanai perfect for year-round relaxation, and a fully fenced backyard shaded by mature trees. Whether you're hosting weekend barbecues, enjoying a quiet evening by the pool, or letting pets and family play, this outdoor space offers endless possibilities. Additional upgrades include owned solar panels for enhanced energy efficiency and long-term savings, an attached two-car garage, and a spacious lot that provides both privacy and room to enjoy the outdoors. Ideally located, this home is just minutes from Downtown Winter Park and the renowned Park Avenue shopping and dining district, Rollins College, Full Sail University, AdventHealth Winter Park, UCF, Valencia College, and numerous parks, golf courses, and recreational amenities. Convenient access to SR-417, SR-436, University Boulevard, and Aloma Avenue makes commuting throughout Central Florida simple and efficient. Combining an exceptional location with modern updates and resort-style outdoor living, 5316 Halyard Court is a rare opportunity you won't want to miss.

5316 Halyard Court, Winter Park

$399,900

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Welcome home to this beautifully maintained, nearly new Pulte Townhome in the heart of Winter Park! Built in 2023, in the gated community of Grayson Square, this stylish two story residence offers 3 bedrooms, 2.5 bathrooms, and an attached one car garage, combining modern design with everyday convenience. The open-concept main living area is perfect for entertaining, featuring elegant quartz counter-tops, Whirlpool stainless steel appliances, ample cabinet space, and a large island overlooking the living and dining areas. Enjoy the upgraded smart home technology, high speed internet and cable already included into the low HOA, making working from home and streaming effortless. Upstairs, you will find a spacious primary suite complete with a generous walk-in closet and a private en-suite bathroom designed for comfort and relaxation. Two additional bedrooms provide plenty of room for family, guests. or a dedicated home office. Also to note is that there are no direct rear neighbors, allowing you to enjoy peaceful outdoor views on the back covered patio. The community is beautifully maintained and offers a resort-style pool and cabana and sidewalks for evening strolls. One of the homes most desirable features is the one thing you need the most but comes unseen is the 10 year transferable Pulte home warranty. Located just minutes from Winter Parks renowned shopping, dining, entertainment, parks and top commuter routes like 417, you'll enjoy easy access to everthing Central Florida has to offer while coming home to a quiet, friendly neighborhood. If your looking for a modern, energy efficient home with premium finishes and virtually maintenance free simple living, this is the one youve been waiting for!

2017 Canny Cove, Winter Park

$350,000

3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code

***ASSUMABLE VA LOAN 3.75%*** Welcome home to this charming 3-bedroom, 2-bathroom residence offering comfort, functionality, and the freedom of NO HOA! This inviting home features a desirable split-bedroom floor plan, a spacious living area, and a 2-car garage. Enjoy Florida living year-round from the screened and covered patio overlooking a fully fenced backyard—perfect for entertaining, pets, or simply relaxing in your own private outdoor retreat. Whether you're a first-time homebuyer, downsizing, or looking for a smart investment, this home offers the ideal combination of convenience and value. Located in the heart of Winter Park with easy access to shopping, dining, parks, major highways, and top-rated schools, this is an opportunity you won't want to miss!

7261 Abbey Lane, Winter Park

$435,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in all the bedrooms.The screened in pool is also heated and has a Heated Spa. It is conveniently located in Seminole County with a Winter Park address. It also features a ROOF that is only two years old ! You can cool off in the screened in pool on hot days. During the cooler time of year you can use the Heater for both the pool and Spa.The screen enclosure helps to make the pool more inviting. You also have a covered porch area for entertaining. There is yard space that is fully fenced. The back yard also has a shed for storing your yard tools. SOLD AS IS. Contact the Listing Agent for a personal tour !

3740 Hawthorne Lane, Winter Park

$425,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 SubDv. ⋅ 32792 Zip Code

Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and boasting a contemporary design, is the heart of this home—a perfect gathering place for family and friends. Indulge in the luxury of a private backyard oasis, where tranquility meets outdoor enjoyment. A delightful retreat awaits with a nice backyard, ideal for entertaining or simply unwinding under the stars. Plus, your vehicles and recreational gear are well taken care of with a 2-car garage and an additional boat space. The charm continues outdoors with a great covered lanai, providing the perfect setting for al fresco dining or cozy evenings by the fireplace. Every detail of this home has been thoughtfully curated to enhance your lifestyle. Don't miss the opportunity to make this Winter Park residence your own—where spacious living, thoughtful design, and comfort converge. Schedule your tour today and envision the possibilities that await in this truly remarkable home!

1886 Clematis Lane, Winter Park

$430,000

3 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code

Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyday living. The home features a well-appointed kitchen, open living areas, and generously sized bedrooms. Outside, enjoy a private backyard with a swimming pool, creating the perfect space for relaxing, entertaining, and enjoying the Florida lifestyle.

5409 Albert Drive, Winter Park

$339,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Subd Unit No 05 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, creating a seamless, modern look that's both attractive and easy to maintain. The home has two beautifully renovated bathrooms with contemporary finishes, along with a newer A/C and a new roof in 2026. The air-conditioned laundry room has plenty of storage space. Step outside to your spacious, fully fenced backyard, where you'll find plenty of room to entertain, play, or unwind around the cozy fire pit. The generous outdoor space offers endless possibilities for gatherings, gardening, or simply enjoying Florida's beautiful weather. A rare highlight is the oversized swing gate providing convenient side-yard access with ample room to park an RV, boat, trailer, or other recreational vehicles. Zoned for Seminole County Schools (A Rated school zone 2025/2026)! Best of all, there's no HOA, giving you the freedom to make the most of your property without additional HOA restrictions. Perfectly situated just minutes from Costco, grocery stores, shopping, dining, and the popular Cady Way Trail, this home offers the ideal combination of comfort, convenience, and outdoor recreation. With easy access to major roadways and everything Winter Park has to offer, this home truly has it all. Welcome home!

3562 Bougainvillea Drive, Winter Park

$469,000

3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code

Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house has some things going for it that are genuinely hard to find. Start with the location. In under 10 minutes in any direction, you could be having lunch on Park Ave, shopping at Altamonte Mall, or launching your boat up in Maitland. That kind of range is rare in Central Florida, and this spot has it. And there's no HOA here, which if you know, you know. Then there's the pool. A real pool, tucked behind a block wall for total privacy, so you can actually enjoy it without the whole street watching. That kind of setup doesn't come around often. This is a 3 bedroom, 2 bath home with real bones and real space. The layout gives you room to breathe, and the systems that actually matter have already been taken care of. Water heater, brand new in 2026. HVAC, also brand new in 2026. Roof was done in 2025. Plumbing was updated in 2017. So the expensive, unglamorous stuff, the stuff that actually protects your investment, is already handled. The home has been professionally cleaned and pressure washed, so it's not just clean, it's move in ready clean. You could genuinely move in as is and update it slowly, on your own timeline, as your taste and budget allow. No rush. No pressure. Just a solid home with good bones, a pool, an unbeatable location, and all the boring but important stuff already done for you. Sometimes the right house isn't the one that's already finished. It's the one that's ready for you to finish it.

2703 Tierra Circle, Winter Park

$499,000

Aloma SubDv. ⋅ 32792 Zip Code

Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or can serve as the site for future medical or office development. Professional Office Future Land Use, outstanding visibility, and the opportunity to assemble the adjacent parcel create an exceptional investment in one of Central Florida's premier healthcare corridors.

2231 Nairn Drive, Winter Park

$499,000

Aloma SubDv. ⋅ 32792 Zip Code

Medical Office Conversion Opportunity directly across from Advent Health Winter Park Hospital. Existing building offers potential for professional office conversion or can serve as the site for future medical or office development. Professional Office Future Land Use, outstanding visibility, and the opportunity to assemble the adjacent parcel create an exceptional investment in one of Central Florida's premier healthcare corridors.

230 Strathy Lane, Winter Park

$399,000

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Step into this beautifully designed townhome featuring an open-concept kitchen, dining, and living area—perfect for everyday living and entertaining. The modern kitchen boasts stainless steel appliances, gray cabinetry, and quartz countertops. Upstairs, the spacious primary suite offers a walk-in closet and a private in-suite bath with dual quartz vanities, while two additional bedrooms, a full bath, and a convenient laundry closet complete the second floor. Relax on the covered lanai and enjoy the privacy of this home's cul-de-sac location. The HOA includes landscaping, exterior maintenance and repairs, high-speed internet, and access to the gated community, providing low-maintenance living. With no CDD, this home is an excellent option for both homeowners and investors. Ideally located in highly desirable Winter Park, Grayson Square is just minutes from SR-436, SR-434, and SR-417, with Publix, Starbucks, shopping, dining, and top-rated Seminole County schools nearby. Park Avenue is only a short drive away, making this home the perfect combination of convenience, comfort, and value.

2033 Canny Cove, Winter Park

$425,000

Eastgate Sub SubDv. ⋅ 32792 Zip Code

A great opportunity to own land in one of Winter Park's most sought-after pockets. This property's true value lies in its prime homesite. You can build your dream home or renovate to suit, all while capturing the location that can't be replicated. Tucked in an established, tree-lined neighborhood minutes from Park Avenue's boutiques and dining, Winter Park's chain of lakes, and easy access to I-4, this address puts you at the center of it all. Zoned for top-rated Winter Park schools, this is the kind of location families compete for. Whether you're an investor, builder, or buyer looking to create something custom, this is a foundation worth building on. Land + location + schools — the trifecta that makes Winter Park real estate hold its value.

1909 Taylor Avenue, Winter Park

$335,000

3 Beds ⋅ 3 Baths ⋅ Via Lago/Hanging Moss Condo SubDv. ⋅ 32792 Zip Code

Great investment opportunity, tenant occupied/income producing Winter Park property in gated community.

2526 Passamonte Drive Unit 10F, Winter Park

$429,900

4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large Florida room. Shed. Existing irrigation well (but pump not working--no warranty on well). Double gate to back yard for parking RV/toys (back left). Roof 2018; water heater 2018; HVAC 2017; CPVC plumbing.

1401 Aster Court, Winter Park

$385,000

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door. Major improvements include a new roof (2024), new A/C (2023), complete home repipe (2022), updated electrical panel, and pavers in both the front and back of the home. The swimming pool was resurfaced with new tile in 2023 and is approximately 12 feet deep, creating the perfect backyard retreat.

885 Carnation Drive, Winter Park

$379,900

4 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code

**This property qualifies for $5,000 Buyer Credit** Updated 4/2 with New Roof, New AC (x2), and New Dual-pane Windows | No HOA | Top-Rated Winter Park School Zone ... Welcome to low-maintenance Winter Park living at 4965 Orange Ave in 32792 with no HOA constraints or fees. Nestled on a quiet lot zoned for top-rated Orange County Public Schools Lakemont Elementary, Maitland Middle, and Winter Park High School, this move-in ready four-bedroom single-family home offers major high-ticket capital improvements already completed. Upgrades include a NEW Roof, two NEW A/C systems for dual-zone energy efficiency, NEW dual-pane insulated windows, fresh interior and exterior paint, and modern fixtures throughout. The carpet-free interior boasts easy-to-clean polished terrazzo and modern ceramic tile flooring, an updated galley kitchen with stainless steel appliances and solid wood cabinets, and two thoughtfully remodeled bathrooms. Designed with incredible layout versatility, the split four-bedroom floor plan includes direct exterior access through sliding glass doors, making it exceptionally well-suited for a multi-generational setup, in-law suite, private guest retreat, or dedicated home office. Outside, the expansive fully fenced backyard provides ample room for pets, outdoor entertaining, or a future pool, while the attached carport offers covered parking and a dedicated laundry utility storage room. Enjoy an unbeatable Central Florida location just minutes from Park Avenue dining, boutique shopping, local parks, and major Orlando commute routes. $5,000 Buyer Credit for qualified buyers. Call for details.

4965 Orange Avenue, Winter Park

$315,000

2 Beds ⋅ 2 Baths ⋅ Aloma Park SubDv. ⋅ 32792 Zip Code

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.

5781 Shale Court, Winter Park

$399,800

4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the property could use some TLC, it features solid major updates and endless potential to add value. Situated on an oversized lot with NO HOA, this home features a spacious enclosed lanai, perfect for enjoying Florida living year-round. The thoughtfully designed split floor plan offers added privacy, with the primary suite separated from the secondary bedrooms. The recently updated kitchen serves as the heart of the home, while major improvements including a 2023 HVAC system, 2019 water heater, and newer roof, to provide peace of mind for years to come. Whether you're an investor or a buyer looking to personalize a home in one of Central Florida's most desirable locations, this property offers exceptional potential and a rare opportunity in Winter Park.

1610 Gladiolas Drive, Winter Park

$350,000

3 Beds ⋅ 3 Baths ⋅ Vistas At Lake Howell SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.

2521 Galliano Circle, Winter Park

$465,000

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed for both everyday living and entertaining. The well-appointed kitchen features stainless steel appliances, granite countertops, and ample cabinetry, creating a functional and stylish space for preparing meals and gathering with family and friends. The home's well-maintained interior reflects pride of ownership throughout, offering a warm and welcoming atmosphere from the moment you arrive. The spacious living areas and comfortable bedrooms provide plenty of room to relax and unwind, while the thoughtful layout maximizes both comfort and convenience. Whether you're hosting guests, working from home, or simply enjoying a quiet evening in, this home is designed to fit a variety of lifestyles. Located in the heart of Winter Park, you'll enjoy easy access to the area's renowned dining, shopping, parks, and cultural attractions. Spend weekends exploring the boutiques and cafés along Park Avenue, enjoying a scenic boat tour through Winter Park's picturesque lakes, or visiting nearby gardens, museums, and recreational trails. With convenient access to Downtown Orlando, major employers, top-rated schools, and world-famous attractions, this location offers the perfect balance of suburban charm and urban convenience. Don't miss this opportunity to own a well-cared-for home in one of Central Florida's premier neighborhoods. Schedule your private showing today and discover everything this wonderful Winter Park property has to offer!

3641 Hawthorne Lane, Winter Park

$389,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code

SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!

1605 Puritan Avenue, Winter Park

$490,000

4 Beds ⋅ 2 Baths ⋅ Cedar Ridge SubDv. ⋅ 32792 Zip Code

Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park with no HOA. Offering approximately 2,250 square feet of living space, this home also features a versatile flex room ideal as a nursery, home office, guest suite, media room, or private retreat. The 2025 remodeled kitchen offers abundant cabinetry and pantry storage, while the renovated bathrooms feature stylish, modern finishes. Ceramic tile flows throughout most of the home, with warm wood-look flooring in three bedrooms for added comfort. Enjoy peace of mind with major improvements already completed, including a 2024 roof, 2023 whole-home replumbing, and 2023 electrical panel replacement with generator hookup. These significant updates allow you to focus on enjoying your new home instead of tackling major projects. Step outside to an oversized, fully fenced backyard shaded by two magnificent mature oak trees, creating a private setting for relaxing, entertaining, or family gatherings. A side-entry two-car garage adds both curb appeal and everyday convenience. Conveniently located just minutes from Baldwin Park, UCF, shopping, dining, parks, and Seminole County schools, this Cedar Ridge home offers exceptional space, recent major updates, and the convenience of an established Winter Park neighborhood with no HOA.

2008 Houndslake Drive, Winter Park

$435,000

4 Beds ⋅ 3 Baths ⋅ Trinity Bay SubDv. ⋅ 32792 Zip Code

Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted by soaring vaulted ceilings, a formal dining area, and a stunning cathedral-style front window that fills the space with natural light. The separate enclosed kitchen offers functionality and charm, with French doors leading to a covered, tiled lanai. Step outside and enjoy a large patio surrounded by mature trees and lush landscaping—an ideal setting for morning coffee, outdoor entertaining, and family barbecues. The inviting family room showcases vaulted ceilings, a grand brick fireplace, and a versatile bonus den/office with a window, perfect for working from home or additional living space. Conveniently located off the family room is an indoor laundry area and half bath. The first-floor primary suite offers privacy and comfort, featuring a dual-vanity bathroom and private French door access to the covered lanai. Upstairs, you'll find three generously sized bedrooms, each equipped with ceiling fans and ample closet space, along with a second dual-vanity full bathroom. Whether you're a first-time homebuyer or looking for room to accommodate a growing family, this home offers exceptional value and functionality. Residents of Trinity Bay enjoy access to a community pool, community playground, and a private neighborhood boat ramp with access to the Lake Burkett and Lake Martha Chain of Lakes, where boating, water skiing, fishing, and other recreational activities are welcomed. Don't miss this opportunity to own a beautiful home in one of the area's most desirable neighborhoods!

8433 Commander Cove, Winter Park

$435,000

3 Beds ⋅ 2 Baths ⋅ Country Lane SubDv. ⋅ 32792 Zip Code

Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

1535 Lawndale Circle, Winter Park

$494,900

3 Beds ⋅ 2 Baths ⋅ Winter Park Pines Rep SubDv. ⋅ 32792 Zip Code

GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and irrigation well and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All room dimensions must be independently verified by the buyer.

2715 Prince John Road, Winter Park

$449,900

3 Beds ⋅ 2 Baths ⋅ Trinity Bay Ph 2 SubDv. ⋅ 32792 Zip Code

Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation just moments from home. This meticulously maintained residence stands out with fresh exterior paint, updated landscaping, and inviting curb appeal. Inside, soaring vaulted ceilings and abundant natural light create an open, airy atmosphere, enhanced by fresh interior paint throughout. The thoughtfully designed split-bedroom floor plan makes excellent use of every square foot, offering comfortable living with no wasted space. An indoor laundry room, spacious 2-car garage, and desirable semi cul-de-sac location add to the home's appeal. Beyond the lake, residents enjoy a community pool, playground, boat launch, and dock along with being located directly across the street from the Cross-Seminole Bike Trail, creating a true lifestyle community. Conveniently located with easy access to SR 417, shopping, dining, and everyday essentials, this home offers the perfect blend of recreation, convenience, and value. Experience the rare opportunity to enjoy private lake-access living in one of the area's most desirable neighborhoods.

5340 N Lake Burkett Lane, Winter Park

$399,990

3 Beds ⋅ 2 Baths ⋅ Howell Branch Woods SubDv. ⋅ 32792 Zip Code

No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof (transferable documentation included). Features include updated flooring throughout (no carpet), fully fenced backyard, and 2-car garage. Zoned for desirable Seminole County schools (Eastbrook Elementary/Lake Howell High) with quick access to SR-436, shopping, and downtown Winter Park. Ideal for remote professionals, small families, or savvy buyers seeking low-maintenance ownership with room to work and grow. Quick closing available. Schedule today!

5503 Albert Drive, Winter Park

$414,900

3 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code

Virtually Staged. Step into this well maintained 3 bedroom 2 bath home located in a highly sought after Winter Park, Garden Lake Estates. Nestled in Seminole County, A rated school zone! The home also sits on a large lot with plenty of room for outdoor living, No rear neighbors for added privacy, gardening or future expansion. This property offers endless potential. Featuring a newer roof, this home offers added value and peace of mind for its next owner. Conveniently located near shopping, schools, dining, parks and major roadways, you'll enjoy both comfort and convenience.One or more photo(s) have been virtually staged.

1840 Aster Drive, Winter Park

$474,000

4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 3 SubDv. ⋅ 32792 Zip Code

Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has ceramic tile throughout and bamboo flooring in the master bedroom. More updates include Trane A/C system, newer water heater, roof in 2021, and electrical panel in 2017. Also included are a garage door opener that has battery backup for power outages, ring door sensors on all main windows and doors, motion activated lights at night on all 4 sides of home, a water softener, and an I-Flo system on the A/C. All that, and a desirable neighborhood with highly rated schools! You don't want to miss this one! Make your appointment today!!!

1320 Gladiolas Dr, Winter Park

$450,000

4 Beds ⋅ 2 Baths ⋅ Winter Park Pines Merrie Oaks SubDv. ⋅ 32792 Zip Code

Opportunity knocks in one of Central Florida’s most sought-after locations! This 4-bedroom, 2-bath home at 316 Beckett Court has been completely demoed and is ready for your vision to come to life. Whether you’re an investor, builder, or buyer looking to create your dream home, this property offers the ultimate clean slate for a full renovation or custom redesign. Situated in highly desirable Winter Park, this property places you in the heart of one of Orlando’s premier communities, known for its tree-lined streets, charm, upscale shopping, dining, and cultural attractions. Enjoy easy access to Downtown Winter Park Historic District and iconic Park Avenue, home to boutique shopping, cafés, restaurants, and vibrant community events, along with the beauty of Central Park and the cultural appeal of The Charles Hosmer Morse Museum of American Art. Winter Park is also home to the prestigious Rollins College, adding to the area’s timeless character and desirability. Bring your contractor, your imagination, and your vision—properties with this kind of potential in Winter Park are rare. Endless possibilities await!

316 Beckett Court, Winter Park

$375,000

3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code

Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along with a full appliance package. Sliding glass doors provide abundant natural light and a peaceful backyard view. Upstairs, you’ll find all bedrooms, including a spacious primary suite with plush carpeting, a large walk-in closet, and an en-suite bathroom featuring dual vanities and a glass-enclosed shower. The second floor also includes a full guest bathroom, a convenient laundry closet with washer and dryer, multiple linen closets. Additional highlights include a one-car garage, extended driveway parking, and access to community amenities. Conveniently located near Park Avenue, University of Central Florida, Full Sail University, and Rollins College, with easy access to shopping, dining, and entertainment.

7522 Aloma Pines Court, Winter Park

$315,000

3 Beds ⋅ 3 Baths ⋅ Vistas At Lake Howell SubDv. ⋅ 32792 Zip Code

Come and see your new home in the sought after Vistas at Howell Branch community. This two story townhouse has 3 bedrooms, 2.5 baths, and open first floor, floor plan. Relax in the evening on your screened in porch. The master bedroom has a walk in closet and large master bath. Your washer and dryer are on the second floor centrally located to all the bedrooms. You will find yourself within walking distance of restaurants, grocery stores, and other retail outlets. It's central location puts within minutes of 436 and 417. Schedule your showing today!

1540 Florentino Lane, Winter Park

$390,000

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 8 SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting front porch, the perfect place to relax, enjoy conversations with friends, and greet neighbors passing by. Inside, the home features recently painted interiors and new laminate flooring in the bedrooms, creating a fresh and move-in-ready feel. Pride of ownership shines throughout, as this home has been lovingly cared for over the years. Step outside and enjoy the spacious, landscaped backyard complete with a private irrigation well, screened-in porch ideal for morning coffee or evening unwinding, and a charming brick fire pit perfect for cooler Florida nights. There's even an outdoor shower, a unique and convenient touch after gardening or enjoying time outside on warm summer days.

2512 Eastbrook Boulevard, Winter Park

$425,000

3 Beds ⋅ 3 Baths ⋅ Grayson Square SubDv. ⋅ 32792 Zip Code

Welcome to Grayson Square at Winter Park by Pulte Homes. This interior Springdale II two-story townhome has no direct rear neighbors, features 3 bedrooms, 2 full bathrooms, a powder room, single-car garage, a covered rear lanai, washer, dryer, refrigerator, and window blinds. The spacious first floor with over 9' ceilings is ideal for entertaining, featuring an open concept gathering room, cafe and kitchen equipped with a pantry, bright white cabinetry, white subway ceramic tile backsplash, Lyra quartz countertops, and durable ceramic tile flooring, and a powder room. After a long day, retreat upstairs to your private oasis. The Owner's Suite features a spacious walk-in closet and ensuite bathroom with double sink, quartz-topped vanity, linen closet, a private water closet and walk-in glass framed shower. Offering privacy and space for everyone, two additional bedrooms, the secondary bathroom and laundry are also on the second floor. Professionally curated design selections for this popular Springdale II townhome include designer cabinets with crown molding, quartz countertops, oversized ceramic tile flooring covering the first floor living areas and bathrooms, a washer, dryer, refrigerator, and blinds, soft, stain-resistant Shaw carpet in the bedrooms and second floor living areas and so much more! Grayson Square is an intimate gated luxury townhome community located minutes away from downtown Winter Park, right off of Howell Branch Road! Grayson Square is a low-maintenance neighborhood with gated access, a pond, no rear neighbors, a resort-style community pool with cabana,1GM high-speed fiber optic internet, along with 75 streaming cable and music channels, ground maintenance - all with no CDD. Boasting an unbeatable location in coveted Winter Park, just one mile from 436, 434, and less than 3 miles from 417, your like-new home at Grayson Square offers all of your daily conveniences, such as Starbucks and Publix, just minutes away! Plus, you'll have access to quality Seminole County schools. When it's time for a change of pace, you'll love your proximity to the famous shopping and dining of Park Avenue. Make Grayson Square at Winter Park your new address today!

1995 Canny Cove, Winter Park

$399,000

3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub SubDv. ⋅ 32792 Zip Code

Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled, there are new windows, new electric outlets throughout, new light fixtures, roof replaced in 2022,kitchen beautifully redone 2020 with new cabinets and Granite counter tops. Additional upgrades throughout the home include new luxury vinyl flooring, new vanity in master bath, new enhanced pool liner, new robot pool vacuum, new garage door house has been painted inside and out. The location is close to shopping, Costco and other stores also located near by. Full Sale, Rollins College and downtown Winter Park to the west and UCF to the East within close proximity. This is a must see. Owner is realtor.Buyer to verify room measurements.

1092 Eastbrook Boulevard, Winter Park

$360,000

3 Beds ⋅ 3 Baths ⋅ Villas Of Casselberry Ph 3 SubDv. ⋅ 32792 Zip Code

Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining room flow into the kitchen, where you’ll find lots cabinet storage, eat in space, and a view out to the backyard. The primary suite is conveniently located on the main floor, featuring generous windows that bring in natural light, a walk-in closet, and an updated en suite bath. A half bath downstairs adds convenience for guests. Upstairs, two spacious bedrooms share a full bath, offering comfortable separation from the main living areas. The Villas of Casselberry community has a pool for you to enjoy. The location places you just minutes from Park Ave’s shops, dining, events and great parks. With easy access to major roads and a central location close to Rollins, UCF, Full Sail and downtown Orlando, this home offers both comfort and connectivity. If you’ve been looking for space, privacy, and a well located Winter Park address, this one is worth seeing in person. Schedule your showing today!

3374 Hamlet Loop, Winter Park

$405,000

3 Beds ⋅ 3 Baths ⋅ Villas Of Casselberry Ph 4 SubDv. ⋅ 32792 Zip Code

Exceptional Single-Family Home in Winter Park, FL This beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC system (2023), new water heater (2026), providing peace of mind for years to come. Enjoy Florida living at its finest on the private screened patio - perfect for relaxing or entertaining. Ideally situated 25 minutes from Downtown Orlando, 30 min from OIA, and 40 min from world-class attractions, this home is also just 6 minutes from Full Sail University, 12 minutes from the prominent Rollins College, and 19 minutes from UCF - making it an ideal choice for families and investors alike. A true must-see - schedule your showing today.

3440 Allston Lane, Winter Park

$425,000

4 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home. Inside, the home offers a light and open layout with a seamless flow between the living, dining, and kitchen spaces—perfect for both everyday living and entertaining. The updated kitchen features modern cabinetry, granite countertops, stainless steel appliances, and a functional layout with bar seating, making it both stylish and practical. The bedrooms are comfortably sized with great natural light, offering flexibility for family, guests, or a home office. The bathrooms have been thoughtfully updated, including a beautifully renovated shower with modern tilework that adds a fresh, clean feel. The Florida room in the back creates a relaxing space for drinking coffee or curling up for a family movie night. Step outside to a generously sized backyard with endless potential—whether you envision creating an outdoor entertaining space, adding a pool, or simply enjoying the open green space. With plenty of room to spread out, this yard offers the kind of flexibility that’s hard to find. Conveniently located near local shopping, dining, and major roadways, this home offers both comfort and accessibility. Zoned for great Winter Park schools. Whether you’re a first-time buyer, investor, or looking to downsize, this property presents an incredible opportunity to own a home with room to make it your own.

814 Densmore Dr, Winter Park

$325,000

3 Beds ⋅ 2 Baths ⋅ Oakcrest-516 SubDv. ⋅ 32792 Zip Code

Short Sale. Short Sale – Subject to Lender Approval. Exceptional investment opportunity in the desirable Winter Park area. This property offers strong potential for value-add through renovation or repositioning. Located in an established community with no HOA, the home sits on a generously sized lot, providing flexibility for improvements and long-term upside. The current layout presents a solid starting point for updates, making it suitable for rental income, resale, or portfolio expansion. Conveniently positioned near shopping, dining, parks, and major roadways, with access to highly regarded schools and surrounding amenities. Winter Park continues to experience steady demand, supporting long-term investment potential. Property is being sold as-is. Buyer to verify all measurements, condition, and intended use. Don’t miss this opportunity to secure a property with upside in a sought-after Central Florida location. Highest and Best due April 17th

7393 Grand Avenue, Winter Park

$449,900

4 Beds ⋅ 2 Baths ⋅ Georgetown Estates SubDv. ⋅ 32792 Zip Code

Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer Roof: Installed in 2023 - Radiant Barrier & Blown-In Attic Insulation: Keeps the Florida heat out and significantly lowers cooling costs. - High-Efficiency HVAC: Energy Star rated AC unit ensuring consistent temperatures and peak savings. Step outside to an expansive backyard featuring a private pool, perfect for relaxing or entertaining. This large outdoor space offers endless possibilities for customization, such as a garden or an outdoor kitchen. Located in a quiet, established neighborhood within an A+ rated school zone, this home provides convenient access to top shopping, dining, parks, and major highways. Don't miss this incredible opportunity to own a fully updated turnkey property in one of the most desirable areas of Winter Park.

501 Heritage Boulevard, Winter Park

$430,000

4 Beds ⋅ 2 Baths ⋅ Winter Park Estates SubDv. ⋅ 32792 Zip Code

Updated 4-bedroom, 2-bath home in a premium Winter Park location with NO HOA and a spacious backyard. This home is currently in the final phase of renovation and has already undergone major upgrades, including remodeled bathrooms, updated kitchen, new flooring, upgraded electrical, new AC System and a newer roof. The interior has been thoughtfully modernized, offering a bright open layout ideal for comfortable living and entertaining. The property is being sold in its current condition; exterior improvements will not be completed, giving the future owner the opportunity to finish and customize the exterior to their preference. Conveniently located near shopping, dining, schools, and major roadways.

Winter Park

$460,000

3 Beds ⋅ 2 Baths ⋅ Howell Estates 1st Add SubDv. ⋅ 32792 Zip Code

PRICE REDUCED!! Welcome to your dream home! This beautifully renovated single-story residence features 3 spacious bedrooms and 2 baths, all set on an expansive .42-acre lot in the desirable Howell Estates community. Brand New Roof (2024) Replumbed (2024) New HVAC System, Gourmet Kitchen: Brand new upgraded white cabinets, stunning quartz countertops, and new stainless steel appliances. Luxurious Bathrooms: Both completely renovated, featuring modern finishes Oversized Bedrooms: Including a primary suite with his-and-hers closets and an ensuite bath with a gorgeous walk-in shower. In the Family Room: Spacious layout with a cozy wood-burning fireplace, Oversized Garage: Perfect for larger vehicles, including SUVs. The backyard has a: New Fence, New Pergola and New Extended Porch. This home is move-in ready and waiting for your family to create lasting memories. Don’t miss out on this exceptional opportunity in Winter Park!

1052 Manchester Circle, Winter Park

$399,900

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code

This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor entertaining, play space, or even adding your own backyard oasis. All of this with no HOA and close to top rated Winter Park schools, popular dining, shopping, and parks. This move-in ready home offers lifestyle, comfort, and value you have to see in person, so schedule your showing today before it’s gone!

1849 Viburnum Lane, Winter Park

$460,000

3 Beds ⋅ 2 Baths ⋅ Wrenwood Heights Unit 2 SubDv. ⋅ 32792 Zip Code

Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to parks, shopping, dining and main highways. Seminole County schools! Call today to schedule your private showing!

5331 Oak Court, Winter Park

Active listings	roughly 40 to 50
Median list price	$409,950
Price range	$315,000 to $495,000
Median size	1,616 sq ft
Median bedrooms	3
Median year built	1979
Median days on market	34

No association at all	2	No HOA, no dues, no architectural approval. You answer to the county and to any deed restrictions recorded on the plat, nothing else.
Association exists, membership optional	3	There is a community association but dues and membership are voluntary. No mandatory assessment, no enforcement arm, and usually no approval process for what you do with your own house. Many owners join for the amenities and nothing happens if you do not.

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