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$503,000
3 Beds ⋅ 2 Baths ⋅ Lake Hancock Preserve SubDv. ⋅ 34787 Zip Code
Move-in ready and ideal for first-time homebuyers, downsizers, or empty nesters seeking low-maintenance living, this beautiful single-family home offers the perfect blend of comfort, convenience, and style. From the moment you arrive, you'll appreciate the welcoming covered front porch overlooking a peaceful pond—an ideal spot to enjoy morning coffee or relax at the end of the day. Inside, soaring ceilings, durable laminate and porcelain tile flooring, and an open-concept layout create a bright and inviting atmosphere. The spacious living room features a decorative fireplace and flows seamlessly into the heart of the home: a well-appointed kitchen with a large island, pendant lighting, walk-in pantry, and plenty of space for casual dining, entertaining guests, or everyday living. Designed for easy living, the open floor plan provides comfortable gathering spaces without the upkeep of a larger home. Best of all, yard maintenance is included through the HOA, allowing you to spend more time enjoying life and less time working outdoors. Whether you're purchasing your first home, looking to simplify your lifestyle, or searching for a move-in-ready retreat, this home offers the convenience and carefree living you've been looking for. Conveniently located near shopping, dining, healthcare, and major roadways, this charming property is ready for its next owner. Don't miss your opportunity to enjoy comfortable, low-maintenance living in a beautiful setting.

14451 Windsor Hall Way, Winter Garden
$650,000
3 Beds ⋅ 2 Baths ⋅ 0000 SubDv. ⋅ 34787 Zip Code
Rare opportunity in Winter Garden! This property sits on approximately one acre with no HOA, offering exceptional space, flexibility, and privacy in a highly desirable location. Conveniently located just minutes from Downtown Winter Garden), with easy access to major roadways, shopping, dining, and top-rated schools—and even the option to ride your golf cart into downtown to enjoy everything the area has. The expansive lot provides ample room for RVs, boats, recreational vehicles, and more, making it ideal for those seeking additional space and versatility. The home features generous living areas and a functional layout with great potential for customization or renovation. Outdoor amenities include a private pool, hot tub, and an extended driveway with plenty of parking space. Located approximately 2 miles from Lake Apopka and about 3 miles from Downtown Winter Garden. Properties with this amount of land and no HOA in this area are rare—schedule your showing today!

1261 E Fullers Cross Road, Winter Garden
$210,000
1 Beds ⋅ 1 Baths ⋅ Southern Pines Condominium SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines in the heart of Winter Garden! This clean and well-maintained 1-bedroom, 1-bath upstairs condo offers bright, open living with a rare combination of features you won’t often find in the community. Positioned on the upper level, the home enjoys enhanced privacy and abundant natural light with windows on both sides of the building, creating an airy and inviting atmosphere throughout the open-concept living and dining area. The kitchen flows seamlessly into the main living space and features granite countertops, ample storage, and all appliances convey with the sale — making this home truly move-in ready. Enjoy peaceful views overlooking the community tennis courts and resort-style pool. Downstairs, the attached 1-car garage and generous under-stair storage closet provide exceptional storage space — a true rarity within the neighborhood. Enjoy maintenance-free living, with HOA fees covering lawn care, cable, internet and water. Spend your weekends exploring Winter Garden Village, just 1.5 miles away, or immerse yourself in the charm of historic Downtown Winter Garden, filled with cozy cafés, boutique shops, farmers markets, and more. Outdoor enthusiasts will appreciate easy access to the West Orange Trail, perfect for biking, jogging, or leisurely strolls. Commuting is effortless with quick connections to the Florida Turnpike, SR 408, and SR 429. The gated Southern Pines community offers impressive amenities, with the pool, hot tub, and clubhouse located across the street. Additional features include a covered playground, movie theater, game room, office space, outdoor kitchen with grills, tennis court, indoor basketball and racquetball courts, sand volleyball, and even a car wash station. Don’t miss your opportunity to own in one of Winter Garden’s most convenient and amenity-rich communities. Schedule your showing today.

317 Southern Pecan Circle Unit 102, Winter Garden
$1,695,000
5 Beds ⋅ 5 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offering a fifth bedroom, full bath, wet bar, office, and walk-in closet—an ideal setup for extended family, a private workspace, or guest quarters. The first-floor owner’s suite is a true retreat, with hardwood floors, two generous walk-in closets, and a spa-inspired bath. Engineered hardwood flows through the main living areas, while the kitchen is designed for both gathering and everyday living—featuring a large island with seating, quartz countertops, ceiling-height wood cabinetry, and Bosch appliances, including a built-in refrigerator and gas cooktop. Ten-foot ceilings, custom wood beams, crown moulding, and an open stairwell give the home a bright, inviting feel. Upstairs, a loft connects three additional bedrooms and two full baths, providing plenty of space for family and guests. Outdoors, the private saltwater pool with waterfall is perfect for relaxing weekends. The covered patio with summer kitchen makes entertaining effortless. HOA dues include access to two community pools, clubhouse, parks, playgrounds, and a community activities director.Located along the West Orange Fitness Trail and just a golf cart ride to downtown Winter Garden, this home also provides quick access to the Turnpike.

854 Tilden Oaks Trail, Winter Garden
$1,170,000
4 Beds ⋅ 4 Baths ⋅ Oakland Park Un #4a SubDv. ⋅ 34787 Zip Code
Welcome to Oakland Park, Winter Garden's premier community known for its majestic canopy oak trees and inviting green spaces! This stunning, custom-built home by J & J Building embodies the charm of traditional Florida vernacular architecture with an impressive, expansive front porch, perfect for enjoying those beautiful Florida evenings. Inside, discover a thoughtfully designed layout, perfect for both family living and entertaining. The heart of the home is the spacious great room, flowing seamlessly into the dining area and a modern kitchen. There is a guest room and full bathroom downstairs, allowing privacy and separation for your visitors. Upstairs, you'll find a luxurious master suite along with 2 generously sized bedrooms. A versatile loft area provides additional living or work space. You'll be amazed by the huge attic storage space too! Extend your living outdoors onto the large lanai, ideal for al fresco dining and relaxing. The large corner lot has plenty of additional space to add a pool, outdoor kitchen, casita, or whatever you can imagine. There are so many exciting custom features in this home: EV plug in, oversized garage, soundproofing on primary bedroom, Lutron Caseta WiFi outlets, smart thermostats, WiFi smart deadbolts on all doors, Swing set, GE Cafe appliances, Mudroom custom woodwork, Wainscoting custom in dining room and powder bath, Trex decking on front porch, Level 7 tile in the Primary bathroom and Custom built ins in the living room! Located in the desirable Oakland Park community, you'll enjoy access to beautiful parks, walking trails, and a vibrant neighborhood atmosphere that is right in the golf cart district and near downtown Winter Garden. Don't miss out on this incredible opportunity to own a piece of paradise! This home is priced to sell and won't last long!

1071 Kershaw Drive, Winter Garden
$257,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to your move-in ready condo in the heart of Winter Garden! Located in a gated resort-style community, this beautifully updated 2-bedroom, 2-bathroom first-floor unit offers low-maintenance living and fantastic amenities. Step inside to find brand new luxury vinyl flooring, fresh carpet in the bedrooms, and a split-bedroom layout for added privacy. The kitchen shines with new appliances, including a sleek over-the-range microwave. You'll also love the dedicated bonus space—perfect for a home office, reading nook, or playroom. The community offers ample open parking, and a long list of amenities: a resort-style pool, tennis and basketball courts, sand volleyball, a fitness center with on-site daycare, and even a private theater. Your HOA covers all amenities plus internet, making this condo both convenient and budget-friendly. Whether you're downsizing, investing, or buying your first home, this Winter Garden gem has it all—comfort, convenience, and community.

430 Southern Pecan Circle Unit 101, Winter Garden
$870,000
3 Beds ⋅ 3 Baths ⋅ Oakland Park SubDv. ⋅ 34787 Zip Code
BEST DEAL IN OAKLAND PARK!! Welcome to 1024 Prosperity Dr, Winter Garden, FL! This stunning 3 bedroom 2.5 bathroom home in the desirable Oakland Park neighborhood has an open floorplan and large windows that fill it with natural light. The heart of the home is the chef's kitchen, featuring stainless steel appliances, a large island with plenty of counter space, and sleek cabinetry – perfect for cooking and entertaining. The study/den is perfect for working from home or a hobby area, because it has a stylish barn door that keeps it nice and private. And there's a downstairs powder room for your guest's convenience. Upstairs you will find the spacious primary suite and two additional bedrooms, the laundry room and also a bonus loft area that could be your second TV room, play room, exercise room or whatever you can imagine. Entertain a crowd or enjoy a peaceful beverage on both the large front porch and the screened back porch. The expansive backyard is fully fenced and perfect for creating your dream outdoor retreat, with plenty of room to add a pool. (additional pool renderings available) This home is equipped with a full-home water filtration system, and an electric car charger in the garage. Not to mention that it's in the golf cart district and just a short ride to charming Downtown Winter Garden and the West Orange hike and bike trail! Don’t miss the opportunity to make this your forever home- Schedule a showing today!

1024 Prosperity Drive, Winter Garden
$950,000
5 Beds ⋅ 3 Baths ⋅ Cambridge Crossing Ph 01 SubDv. ⋅ 34787 Zip Code
Spacious lakefront executive home with 3,500+ sq ft in gated Windermere Crossing community. Oversized screened lanai and pool allow for fantastic Florida entertaining. Huge and inviting yard that can easily fit more than 50 people. Enjoy beautiful Sunset from your oversized pool and yard. Home features a 3-way split plan with 5 bedrooms and 3 baths. 12 ft soaring ceilings, fireplace in family room and large kitchen with island, breakfast bar, desk and closet pantry. Breakfast area has a beautiful bowed window, 8 ft sliding doors in family room and master bedroom offering wonderful pool and lakefront views. Home has a 3 car garage and sits on an oversized lot adjacent to community park. Roof was replaced in 2018. Renovated master bathroom. Excellent Lake Whitney Elementary zoning.

12146 Windermere Crossing Circle, Winter Garden