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$515,000
4 Beds 3 Baths Chapin Station SubDv. 34787 Zip Code
Under contract-accepting backup offers. Virtually staged. Welcome to Chapin Station! On an almost quarter-acre lot, this four-bedroom, three-bath home offers a light and spacious split-bedroom open floor plan designed for comfort and functionality. Go inside to find soaring ceilings and an open layout featuring a formal dining room, a large family room and a bright breakfast nook overlooking the kitchen. Double-pane windows provide added energy efficiency throughout the home. The living areas seamlessly connect to the expansive covered rear patio and private backyard, creating the ideal setting for everyday living and entertaining. The thoughtfully designed split floor plan provides privacy for all. The primary suite features vaulted ceilings, dual walk-in closets and an en-suite bath with double vanities, a garden tub and a separate shower. On the opposite side of the home, two secondary bedrooms share a full bath, while a separate guest suite and additional bath offer ideal accommodations for visitors or multigenerational living. The oversized backyard provides ample space to create your dream outdoor oasis, whether you envision a pool, play area, garden or outdoor entertainment space. The large covered patio is ideal for grilling, relaxing, and gathering with family and friends. In the sought-after Chapin Station community, this well-maintained home offers easy access to the West Orange Trail, historic downtown Winter Garden, major highways, hospitals, shopping, dining and Central Florida's world-famous theme parks.

1142 Dunbrooke Street, Winter Garden

$684,000
4 Beds 3 Baths Hull Island/Oakland Ph 2 SubDv. 34787 Zip Code
This turnkey, better-than-new single-story home offers an elegant and modern retreat within Oakland’s highly desirable waterfront community of Hull Island. Nestled in a friendly neighborhood surrounded by nature, the property immediately welcomes you with tasteful customizations, upgraded lighting, and stylish accent walls that bring warmth and character to the entire layout. The thoughtfully crafted split floor plan features four bedrooms and three bathrooms, maximizing both privacy and efficiency for daily living and entertaining. Right off the foyer, a comfortable guest bedroom boasts its own ensuite bath, creating an ideal setup for visitors or multi-generational families. The main living area flows seamlessly into a beautifully upgraded kitchen equipped with quartz countertops, under-cabinet lighting, a tile backsplash, and premium stainless steel appliances including a cooktop with a hood and a built-in oven and microwave. Tucked quietly away at the back of the home, the primary suite serves as a private oasis with an expansive spa-like bathroom featuring separate vanities, sleek quartz counters, a large shower, and dual walk-in closets with custom storage systems. The remaining bedrooms are equally impressive, offering ample space, custom closets, and electronic shades. The sophisticated interior transitions smoothly to a private backyard retreat where a covered lanai, extensive pavers, and a full screen enclosure set the perfect stage for relaxed Florida outdoor living. Practical needs are also effortlessly met in the two-car garage, which showcases durable epoxy flooring and a modern electric vehicle charger. Beyond the property lines, the Hull Island community provides an exceptional lifestyle centered around outdoor recreation and convenience. Residents enjoy access to a resort-style pool, a playground, a dog park, and a scenic boardwalk that winds its way to a community dock and fishing pier on Lake Apopka. Nature lovers will appreciate the neighborhood's private entrance to the 120-acre Oakland Nature Preserve, as well as close proximity to the famous 22-mile West Orange Trail, local golf courses, and pickleball courts. Complete with fast access to the Turnpike, 408, and 429, this location connects you quickly to excellent shopping, dining, and the charming downtown districts of Winter Garden, Clermont, and Oakland, while keeping Orlando’s theme parks and international airport within easy reach.

2022 Boss Hewett Street, Winter Garden

$2,190,000
5 Beds 5 Baths Boyd-Lutz Sub SubDv. 34787 Zip Code
Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Custom built pool renderings and pricing available. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. Craftsmanship, luxury, and location—now at an even more compelling price.

20 W Crest Avenue, Winter Garden

$649,900
4 Beds 3 Baths Waterleigh Ph 1c SubDv. 34787 Zip Code
Welcome to your private oasis in the highly desirable community of Waterleigh! This rare gem stands out as one of the few homes in the neighborhood to feature its very own private, heated saltwater pool, complete with a spacious covered patio, an impressive newly screened lanai, and the ultimate privacy of no rear neighbors. Boasting one of the most sought-after single-story designs, this open and light-filled home welcomes you with sophisticated new wainscoting architectural details and brand-new, upgraded flooring throughout all four bedrooms. The heart of the home is an incredible gourmet kitchen featuring a massive quartz island illuminated by high-end glass pendant lighting, premium appliances, custom cabinetry, and a stunning backsplash that flows seamlessly into the spacious living and dining areas. Unwind in a luxurious primary suite showcasing elegant tray ceilings and a grand walk-in closet outfitted with a brand-new custom organization system. The upgraded primary bath offers a spa-like experience with granite counters, double sinks, a large shower, and an oversized soaking tub. Every detail has been meticulously enhanced, including a fully renovated laundry room, a pristine epoxy-finished garage floor, sealed and cleaned outdoor pavers, and a freshly repainted exterior. The home is also equipped with permanent outdoor Govee smart lights, allowing you to easily customize your exterior illumination for holidays or everyday ambiance. Located just 15 minutes from Walt Disney World, you can even enjoy the magic of the nightly Disney fireworks right from your own home. Waterleigh offers an unmatched, low-maintenance resort lifestyle where the HOA includes all lawn care, giving you more time to enjoy the two community clubhouses, resort pools, fitness centers, garden, mini-golf, volleyball, and scenic lake viewing docks. Schedule your tour today to experience this highly upgraded, move-in-ready masterpiece!

16131 Hampton Crossing Drive, Winter Garden

$1,700,000
4 Beds 4 Baths G T Smith Sub 2 SubDv. 34787 Zip Code
**MULTIPLE OFFERS RECEIVED** Welcome to 121 West Maple Street…a Downtown Winter Garden one-of-a-kind statement home spanning nearly 5,500 square feet of indoor & outdoor living space. Originally constructed in 1999 and thoughtfully expanded in 2019…yet this special residence has the heart & soul of a time long ago when character, craftsmanship and attention to details mattered. Private Pool & Spa. Poolhouse. Drawing Room & Study. Courtyard with Fountain. Renovated Kitchen & Bathrooms. 10’ Ceilings. Wood Floors. Handmade (USA) Solid Wood Doors. Custom Wood Trim Throughout. Three-Car Garage with Carriage House. Three Fireplaces. Natural Gas. Custom Built Wood Fence with Copper Caps. Located on one of the few remaining brick roads just TWO BLOCKS from Plant Street, this home with spectacular curb appeal is situated on a rare corner double lot with extensive landscaping & beautiful mature trees…including the incredible Southern Live Oak in front that is part of the Winter Garden Heritage Trees project & walking tour. Enjoy historical charm appropriate for the location...yet live without the pains & aches of owning an old historic home. The incredible drawing room & study (2019) was designed by the historical architect for the City of Charleston…twenty-nine windows, extensive trim work & built-ins, historically accurate sconces & lighting and automatic privacy shades. Live the Florida lifestyle outdoors in this incredible outdoor oasis with heated pebble tec saltwater pool & spa. Following a 2023 transformation with a cost of $225,000, the outdoor living space now features a custom poolhouse cabana with a gas fireplace, multiple seating areas, outdoor kitchen with island, built-in grill, burner and refrigerator, retractable screen to astroturf lawn, Trex decking, custom lighting, water features, extended covered lanai and SunBrite outdoor television. (Hayward Natural Gas Pool/Spa Heater - 2025; Hayward Tristar Pool Pump - 2023; Filter Unit - 2020; Salt Cell - 2020). Fantastic & FLEXIBLE floor plan...four bedrooms, three full bathrooms and one half bathroom. Primary suite on main floor. The carriage house above the garage features a separate staircase entrance with private bedroom, bathroom and walk-in closet with built-ins. Stunning kitchen renovation (2021) including custom cabinetry, backsplash, quartz countertops, farm sink, designer lighting, new appliances and an open-concept design that flows effortlessly into the family room. Roof -- July 2019. HVAC -- 2025 (upstairs); 2018 (downstairs - damper system). Tankless Gas Water Heater -- Dec 2015. Garage Epoxy Floor. Whole Home Natural Gas Generator. FULL UPGRADE & SPECIAL FEATURES LIST AVAILABLE. Furnishings and decor (inside & outside), golf cart & custom holiday decorations NEGOTIABLE. Zoned R-2. NO HOA...live without rules & restrictions. You COULD NOT be closer to enjoying the lifestyle of Central Florida's most desirable and growing historic downtown...GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer's market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation...come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. This is THE ONE you have been waiting for in Downtown Winter Garden.

121 W Maple Street, Winter Garden

$297,900
3 Beds 2 Baths Southern Pines Condo SubDv. 34787 Zip Code
Under contract-accepting backup offers. Seller Offering Up to $7,000 Toward Buyer Closing Costs and a one YEAR AHS Home Warranty. Use our Preferred Lender and they will contribute $1000 towards closing costs with loan approval at closing! $8000 total value to BUYER at closing!! Move-in ready and priced under $298,000, this beautifully updated condominium in the gated Southern Pines community offers exceptional value just minutes everything needed for a balanced lifestyle. Located only 7 minutes from Historic Downtown Winter Garden, this second-floor residence combines modern upgrades, generous storage, and resort-style amenities in one of the area's most convenient locations. The open-concept floor plan features spacious living and dining areas accented by engineered hardwood flooring that extends throughout the main living spaces and into a dedicated office alcove with custom built-in shelving. Fresh interior paint, updated lighting fixtures, ceiling fans and plenty of windows create a bright, contemporary feel throughout. The primary suite offers brand-new carpet, a generous walk-in closet, and a private bath featuring a large walk-in shower, granite-topped vanity, and updated lighting. Two additional bedrooms also feature new carpeting, updated fans and lighting fixtures, and oversized walk-in closets. A well-appointed secondary bath includes an extended granite vanity with abundant storage and a versatile tub/shower combination. At the center of the home, the upgraded kitchen showcases white cabinetry, granite countertops, a new stainless-steel sink with drying rack and pull-down faucet, plus a complete suite of brand-new appliances including refrigerator, range, microwave, and dishwasher. A dedicated laundry area with storage shelving and a separate adjacent linen closet provide added convenience, while multiple walk-in closets in the bedrooms have an uncommon amount of storage for condominium living. Major systems have already been addressed for peace of mind. The HVAC system has recently had seasonal servicing. The hot water heater is awaiting permitting and will be replaced in June 2026, and the home is protected by a transferable home warranty plan. (Covers Appliances, Ceiling Fans, HVAC, HWH, disposal, plumbing and more) Southern Pines residents enjoy an impressive amenity package including gated entry, on-site management, resort-style pool and spa, fitness center, tennis courts, indoor basketball court, volleyball court, playground, pet park, clubhouse with theater room, billiards room, computer center, BBQ area, and even a resident car wash station. Conveniently located just minutes from Publix, Winter Garden Village, the West Orange Trail, Downtown Winter Garden, major shopping, dining, and entertainment, with quick access to the Turnpike, SR 429, I-4, Orlando attractions, and area employers. HOA dues include internet, basic cable, recreational amenities, trash service, and exterior lawn and maintenance. No worries here about Roof Replacement or Exterior Maintenance cost, true worry free living. This is the complete condominium lifestyle package—updated with NEW NEW NEW is really move-in ready in an amenity-rich, and ideally located community. Come see it today, we would love to show it to you.

142 Southern Pecan Circle Unit 205, Winter Garden

$419,000
4 Beds 3 Baths Hamlin Reserve SubDv. 34787 Zip Code
Look no further!!!! This beautifully upgraded 4-bedroom, 3-bathroom townhome offers the perfect blend of luxury, style, and convenience in the highly sought-after Hamlin Reserve community. Thoughtfully enhanced with designer finishes throughout, this spacious residence is truly one of a kind and ready for its next owner. From the moment you enter, you'll appreciate the custom ceramic tile flooring, expanded luxury recessed lighting, and open-concept design that creates a bright and inviting atmosphere. The first floor features a generously sized bedroom and full bath, providing the perfect space for guests, a home office, fitness room, or multigenerational living. At the heart of the home is the spectacular, completely remodeled and expanded chef’s kitchen, renovated in 2024. Designed to impress, it features a massive custom 5' x 8' quartz island, abundant cabinetry, farmhouse sink, wine refrigerator, custom wood range hood, ceiling-height designer backsplash, a large walk-in pantry, and a new range installed in 2024. The kitchen seamlessly flows into the dining and family rooms, creating the ideal setting for entertaining family and friends. Step outside to your private, fully paved courtyard, complete with a dedicated dog run and plenty of space for outdoor dining and relaxation. The courtyard leads directly to the spacious two-car garage, offering both convenience and functionality. A beautifully remodeled open staircase leads to the second floor, where you'll find a desirable split-bedroom layout designed for privacy and comfort. The spacious primary retreat features a private balcony, creating the perfect place to enjoy your morning coffee or unwind at the end of the day. The luxurious en-suite bathroom offers dual vanities, a glass-enclosed shower, and a large walk-in closet. Two additional bedrooms, a full bathroom, and a conveniently located laundry room complete the upper level. Residents enjoy a maintenance-free lifestyle with HOA-covered exterior maintenance, landscaping, and roof care, along with access to outstanding community amenities including a resort-style pool, clubhouse, playground, dog park, and beautifully maintained green spaces. Location is everything, and this home delivers. Situated just a short walk or quick five-minute drive from Hamlin Town Center, you'll enjoy easy access to exceptional shopping, dining, entertainment, and everyday conveniences, including Cinépolis Luxury Cinemas. Nearby attractions include Orlando Health Horizon West Hospital, Orange County National Golf Center, Horizon West Regional Park, and major highways for effortless commuting. Best of all, all Walt Disney World parks are just 15 minutes away. This exceptional townhome offers luxury upgrades, an unbeatable location, and a lifestyle you'll love. Schedule your private showing today—you will not be disappointed!

15524 Honeybell Drive, Winter Garden

$1,125,000
4 Beds 4 Baths Oakland Park SubDv. 34787 Zip Code
Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

925 Easley Avenue, Winter Garden

$764,990
5 Beds 4 Baths Serenade At Ovation SubDv. 34787 Zip Code
Virtually Staged. Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. Anna Maria Bonus offers 5 Bedrooms, 3 baths and a 2 Car Garage. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.“It includes high-speed fiber optic internet.”

13392 Peaceful Melody Drive, Winter Garden

$699,990
4 Beds 3 Baths Serenade At Ovation SubDv. 34787 Zip Code
Virtually Staged. Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. Anna Maria offers 4 Bedrooms, 3 baths and a 2 Car Garage. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando, where Dream Finders Homes proudly presents Serenade at Ovation. Nestled amidst picturesque lakes and pristine conservation areas, our collection of award-winning single-family homes and contemporary townhomes beckons you. Embracing the essence of classic Florida architectural styles, each residence seamlessly blends indoor and outdoor living. Enrich your life with Winter Garden's local history and charm, while relishing easy access to top-tier schools, Orlando's business hubs, delectable dining, iconic attractions, and endless entertainment. Whether indulging in nearby theme parks or local shopping, your options are limitless. Within the community, relish leisurely walks to the pavilion, let the little ones thrive at the tot lot, and embrace tranquil evenings under the starlit sky. At Serenade at Ovation, a meticulously crafted home designed by experts eagerly awaits, ready to cocoon your cherished memories within the embrace of Florida living.“It includes high-speed fiber optic internet”

13380 Peaceful Melody Drive, Winter Garden

$538,990
3 Beds 3 Baths Serenade At Ovation SubDv. 34787 Zip Code
Virtually Staged. Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the primary suite offers a perfect end-of-day retreat with a large walk-in closet and a generously sized bedroom. Introducing Serenade at Ovation, within the fast-growing Horizon West community, offers a prime location near top Winter Garden schools, Walt Disney World, Hwy 192, SR 429, Flamingo Crossings, and Hamlin. The diverse housing options include townhomes, new bungalows, and award-winning single-family homes, providing affordable living in this burgeoning area. Abundant green spaces, pocket parks, and the central Area Community Park with its engineered wood fiber playground, shaded pavilion, and dog parks, make this community an ideal, family-friendly choice at the heart of Horizon West.

13019 Serene Glade Road, Winter Garden

$569,990
3 Beds 3 Baths Serenade At Ovation SubDv. 34787 Zip Code
Virtually Staged. Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the primary suite offers a perfect end-of-day retreat with a large walk-in closet and a generously sized bedroom. Introducing Serenade at Ovation, within the fast-growing Horizon West community, offers a prime location near top Winter Garden schools, Walt Disney World, Hwy 192, SR 429, Flamingo Crossings, and Hamlin. The diverse housing options include townhomes, new bungalows, and award-winning single-family homes, providing affordable living in this burgeoning area. Abundant green spaces, pocket parks, and the central Area Community Park with its engineered wood fiber playground, shaded pavilion, and dog parks, make this community an ideal, family-friendly choice at the heart of Horizon West.

13031 Serene Glade Road, Winter Garden

$659,900
5 Beds 4 Baths Johns Landing SubDv. 34787 Zip Code
Welcome to this exceptional pool home located in the sought-after gated lakefront community of Johns Landing. Situated on an oversized 13,000+ square-foot corner lot with a mostly fenced backyard, this spacious home offers over 3,000 square feet of thoughtfully designed living space. Featuring 4 bedrooms, 4 full bathrooms, a dedicated office, media room, and spacious loft, this home provides the perfect balance of comfort and functionality for today’s lifestyle. The open-concept floor plan is highlighted by soaring ceilings, abundant natural light, and a gourmet kitchen that seamlessly connects to the main living and dining areas, making it ideal for both everyday living and entertaining. The first-floor primary suite serves as a private retreat, complete with dual vanities, separate his-and-her walk-in closets, and a spacious en-suite bath. Upstairs layout is Bedroom/Full bath, loft and Large media room that could be 5th bedroom. Downstairs features 3 bedrooms and 3 full bathrooms. Step outside to your screened lanai and sparkling private pool, where you can enjoy Florida’s beautiful weather year-round. The expansive backyard offers plenty of space for outdoor entertaining, while the three-car garage provides ample room for vehicles and storage. Residents of Johns Landing enjoy exclusive amenities including a private boat ramp and community dock, playground, tennis and pickleball courts, basketball court, and access to beautiful Johns Lake. Ideally located just minutes from historic downtown Winter Garden, the West Orange Trail, Costco, shopping, dining, and major highways, this home offers the perfect combination of luxury, convenience, and an active Florida lifestyle. Recent updates include a new roof (2019) and two HVAC systems (2019 and 2017), providing added peace of mind for years to come. *Sold As-is . Bring your design ideas! *Seller offers a $10,000-$20,000 credit for updates or buyer's closing costs.*

710 Regina Circle, Oakland

$824,900
6 Beds 4 Baths Signature Lakes Ph 3b-4 SubDv. 34787 Zip Code
Welcome to 15121 Evergreen Oak Loop, a stunning 6-bedroom, 4-bathroom home offering over 4,200 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities. Situated on an oversized homesite with no rear neighbors, this exceptional property combines space, comfort, and privacy with beautiful conservation views and breathtaking Florida sunsets. The heart of the home is the expansive gourmet kitchen featuring stainless steel appliances, a large center island, abundant cabinetry, and an open-concept design that flows seamlessly into the main living areas—perfect for entertaining family and friends. Flexible living spaces include a first-floor bedroom and full bath, ideal for guests, a home office, or multigenerational living. Upstairs, you'll find a spacious theater room complete with reclining theater seating, projector, screen, and surround sound system—all included with the home—creating the ultimate space for movie nights, sporting events, and gaming. The luxurious primary suite serves as a private retreat with a spa-inspired bath, dual vanities, soaking tub, separate shower, and oversized walk-in closet. Step outside to enjoy peaceful conservation views from multiple outdoor living spaces, offering a level of privacy rarely found in Horizon West. Whether you're enjoying your morning coffee or winding down in the evening, this home provides the perfect backdrop for Florida living. Location is everything, and this home delivers. Just minutes away is the newly opened Horizon West Regional Park, a 215-acre recreational destination featuring an inclusive playground, walking and biking trails, picnic pavilions, athletic fields, open green space, and recreational facilities. Future phases are planned to bring additional trails, expanded recreational amenities, and nature-focused areas, adding even more value to this already exceptional location. Residents enjoy convenient access to top-rated schools, shopping, dining, major highways, Disney attractions, and everything that makes Horizon West one of Central Florida's most sought-after places to live. Offering an ideal combination of size, functionality, entertainment, and location, this is a rare opportunity to own a truly special home in the heart of Winter Garden.

15121 Evergreen Oak Loop, Winter Garden

$499,999
2 Beds 3 Baths Overlook 2/Hamlin Ph 2 & 5 SubDv. 34787 Zip Code
Under contract-accepting backup offers. Beautiful home in The Cove at Hamlin Now Available. This is part of the highly desirable Overlook at Hamlin community in Winter Garden. This home has been Well Maintained, and Tastefully Upgraded by the Original Owner. Amenities and Upgrades include: Gourmet Kitchen (with 42" Cabinetry, Gas Range, Farmer's Sink, Large Center Island), Hardwood Flooring, Plantation Shutters throughout, Shiplap Accent Walls, Custom Wine Room, and more. Improvements continued to the Outdoors as well with a Large Screened Paver Patio Outdoor Living Area, Summer Kitchen complete with TV mount, and Fenced Yard (wrought iron). Relax on the front porch overlooking the community park, or take advantage of the resort-style amenities including a clubhouse, fitness center, pool, splash pad, pavilion, event space, sports lawn, amphitheater, fire pit, canoes, private boat ramp and playground. Landscaping is maintained by the community. Located just minutes from SR 429, Florida’s Turnpike, shopping, dining, medical facilities, and the major theme parks, this home combines modern comfort with unbeatable convenience in one of Winter Garden’s most sought-after neighborhoods. Don't miss your opportunity to own this amazing home. Schedule your private showing today!

15073 Valverse Alley, Winter Garden

$580,000
3 Beds 3 Baths Winter Oaks SubDv. 34787 Zip Code
Experience the quintessential Winter Garden lifestyle in this exceptional 3 bedroom/2.5 bathroom home, perfectly positioned within the highly sought-after Golf Cart District. This residence offers a rare park-side setting, providing picturesque views of majestic oaks with green space. For those who enjoy active community life, you are just steps away from the neighborhood pool and playground. Just a few minutes away from Downtown Winter Garden!  Exceptional Curb Appeal & Interior Elegance: from the moment you arrive, the covered front porch welcomes you with outdoor column lights, coach lights, landscaping and a framed transom over the front door. The first-floor features stylish Bahama shutters, formal living room with a double paddle ceiling fan, spacious dining area, a family room that features a gas fireplace, with tile flooring, engineered wood floors and LVP throughout the first floor. Chef-Inspired Kitchen : The heart of the home is the kitchen, which has been upgraded from an electric to a gas stove and features a redesigned pantry to maximize storage. You will also find under-cabinet lighting and modern lighting. Primary suite: The 1st floor Primary Bedroom suite serves as a private sanctuary with new flooring throughout the bedroom, closet, and bathroom, as well as a completely remodeled primary bathroom.   The second story split floor plan: The transition to the second floor is highlighted by a staircase and balcony where traditional wood newels have been replaced with elegant rod iron. The second story features 2 spacious bedrooms , a full sized guest bathroom and at center stage of the upstairs landing is a bonus area for additional lounging area/home office or play area. Outdoor Oasis: Step outside to your private retreat: a rear enclosed screened-in room that perfectly encompasses the lanai and soaker pool area. The outdoor space is further enhanced by: An extended patio deck around the pool, a new fan on the lanai for year-round comfort, a rebuilt pool pump with pool equipment housing, a new fence with a leveled concrete retaining wall base, accented by fence and landscape lighting.  Systems & StorageSolutions: This home offers incredible peace of mind with a new roof (installed 11/2020) and a brand-new AC condenser and coils ) with a transferable warranty. Storage is a priority here, with a garage featuring built-in file cabinets, recessed ceiling lights, shelves, appliance storage, and overhead shelving, plus additional attic storage. Functional extras include a built-in wall safe, a generator pad, and a security camera at the rear of the home.  Schedule your private showing today!

638 Autumn Oaks Loop, Winter Garden

$525,000
3 Beds 2 Baths Stoneybrook West SubDv. 34787 Zip Code
Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully landscaped 3-bedroom, 2-bathroom home in the 24-hour guard-gated Stoneybrook West community. Featuring a split-bedroom floor plan, the layout includes a versatile flex room ideal for a home office or den. The kitchen is equipped with white appliances and granite countertops and flows easily into the main living spaces, with ceiling fans installed throughout the home for comfort. A standout feature of this property is the seamless outdoor integration: the living room, family room, and primary suite all open directly onto a spacious, screened-in porch. The primary suite serves as a quiet retreat, complete with an attached bath featuring a garden tub and a separate walk-in shower. Residents of Stoneybrook West enjoy robust community amenities, including a clubhouse, swimming pool, golf course, tennis courts, and a private community boat dock with direct access to Black Lake.

1343 Castleport Road, Winter Garden

$424,990
3 Beds 3 Baths Serenade At Ovation SubDv. 34787 Zip Code
Virtually Staged. Under Construction. SAMPLE IMAGES The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two and a half bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a versatile loft, providing additional living space or an ideal work-from-home area. With a two-car garage and laundry room conveniently located on the second floor, the Porter combines functionality with comfort, making it a standout home choice.

13303 Peaceful Melody Drive, Winter Garden

$575,000
4 Beds 3 Baths Belle Meade Ph 2 SubDv. 34787 Zip Code
Welcome to 15336 Firelight Drive, located in the highly desirable gated community of Belle Meade in Winter Garden. Situated directly across from the lake, this beautifully maintained 4-bedroom, 3-bathroom home with a 3-car garage offers a spacious split-bedroom floor plan designed for both comfort and privacy. Inside, you'll find wood flooring, elegant architectural details, and a well-appointed kitchen featuring granite countertops, solid wood cabinetry, stainless steel appliances, a pantry, and a breakfast nook. The spacious primary suite includes dual walk-in closets, French doors leading to the screened lanai, and a spa-inspired bathroom with a garden tub, separate shower, and dual vanities. Major updates include a NEW ROOF installed in 2023 and a BRAND NEW HVAC system installed in June 2026, providing valuable peace of mind for the next owner. Conveniently located just minutes from Winter Garden Village, Highway 429, shopping, dining, and top-rated schools, this home offers the perfect combination of location, functionality, and lifestyle. Schedule your private showing today.

15336 Firelight Drive, Winter Garden

$535,000
3 Beds 2 Baths Lakeview Reserve 46/149 SubDv. 34787 Zip Code
Under contract-accepting backup offers. Some homes check the boxes. Others feel like home the moment you walk in. Located in the gated community of Lakeview Reserve, this beautifully updated 3-bedroom, 2-bath home blends comfort, style, and everyday functionality. The open-concept layout features engineered hardwood floors, a spacious living area, and a thoughtfully designed kitchen with updated appliances, abundant storage, and a custom baker’s pantry. Step outside to a screened lanai and enjoy a private, nearly quarter-acre homesite with a spacious fenced backyard—perfect for entertaining, relaxing, gardening, or giving pets room to roam. Major updates provide peace of mind, including a newer roof (2018), storm-rated insulated windows (2021), a whole-home generator with propane tank installed in 2021, HVAC (2023), updated kitchen appliances (2023), and engineered hardwood flooring (2024–2025). Enjoy the best of Central Florida living with access to Lakeview Reserve's community fishing pier on Lake Apopka, direct access to the West Orange Trail, and the charm of Historic Downtown Winter Garden just minutes away. As part of Winter Garden's golf cart district, you can hop on your golf cart and head downtown to enjoy the award-winning Farmers Market, locally owned restaurants, boutique shopping, and year-round community events. Orlando, Disney, Universal, SR-429, and the Florida Turnpike are all within easy reach. Move-in ready, beautifully updated, and ideally located, this home offers the perfect blend of comfort, convenience, and the sought-after Winter Garden lifestyle.

57 Lakeview Reserve Boulevard, Winter Garden

$500,000
4 Beds 2 Baths Winter Garden Trls 01-3 SubDv. 34787 Zip Code
UPDATE 6/10/2026: Multiple offers situation. Asking for highest and best by 5pm today. Welcome home to a property where absolute pride of ownership shines through every single detail. Meticulously maintained and exceptionally clean, this residence offers the ultimate Winter Garden experience on a rare, sprawling lot of nearly a quarter acre. Enjoy the perfect lifestyle blend situated just minutes from the dining and charm of historic downtown while offering effortless access to major highways for an stress-free commute. As an added bonus, the seller is offering allowances towards closing costs and flooring to help make your move even smoother! Step inside to find a light and airy interior boasting a completely fresh coat of modern, neutral paint that elevates the entire living space. The heartbeat of the home is the pristine kitchen, which comes fully equipped with a suite of brand-new appliances only two weeks old . Every room feels bright and inviting, a direct result of rigorous upkeep and flawless maintenance and immaculate cleanliness over the years. This home provides total peace of mind, allowing you to unpack your bags and start living from day one without the hassle or expense of immediate renovations. All measurements are approximate and to be verified by the buyers.

1520 Mistflower Lane, Winter Garden

$885,000
4 Beds 5 Baths Bay Isle 48 17 SubDv. 34787 Zip Code
Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

14411 Hampshire Bay Circle, Winter Garden

$755,000
4 Beds 4 Baths Black Lake Preserve SubDv. 34787 Zip Code
Luxury At its Finest. This Beautiful Immaculate Open Concept 4 bedrooms, 4 baths residence featuring a spacious loft with a full bath. Loft on 2 nd Floor can potentially be used as a 5th bedroom. Ideal for guests retreat, home office, media lounge, media room or additional entertainment for the entire family. The Amazing Gourmet Chefs kitchen with under cabinet lighting Gas stove, double oven showcases an extra large extended island perfect for entertaining. Complemented by elegant finishes. Open concept living spaces and exceptional comfort throughout the home in its entirety. French Doors gives access to the resort style pool with 4 therapy jets, bubblers on the sun shelf, custom hand rail with multi led lights with a Wet Edge Pool Interior. Elegant Pavers. The Pool is 3 ft on the shallow end and 6 ft on the deep end and measures 15 x 31. This home is taken care with lots of Pride and Tender Loving care. This home sits on a corner Lot with lots of privacy for all entertainment and relaxation. Garage has overhead racks for extra storage. This is a very small community that is peaceful and tranquil for great evening walks. By Appointment Only. Thank You.

14378 Black Lake Preserve Street, Winter Garden

$1,749,000
4 Beds 4 Baths Johns Cove 43/104 SubDv. 34787 Zip Code
Seller financing available! Discover an extraordinary waterfront retreat where luxury, privacy, and breathtaking lake views come together in perfect harmony. This exceptional 4-bedroom, 4-bath custom residence offers over 4,000 square feet of thoughtfully designed living space on the shores of highly sought-after Johns Lake, delivering an unparalleled Florida lifestyle. Designed with both elegance and functionality in mind, the custom-built home features a desirable split-floor plan that provides ultimate privacy. The expansive primary suite occupies its own private wing, creating a true owner's retreat complete with serene lake views, generous sized closets, and a spa-inspired ensuite bath featuring a luxurious steam shower for the ultimate relaxation experience. The additional bedrooms are thoughtfully positioned on the opposite side of the home, offering comfort and privacy for family and guests. From the moment you enter, you'll be captivated by the abundance of natural light, soaring ceilings, and panoramic water views. Recent updates enhance both style and value, including fresh interior paint throughout and brand-new waterproof luxury laminate flooring with a lifetime warranty installed throughout the entire home. These elegant upgrades provide a seamless, modern aesthetic while offering exceptional durability for years to come. Designed for today's lifestyle, the home also features a spacious executive office, ideal for remote work or a private study, along with a highly desirable game room that offers endless possibilities for recreation, media, or entertaining. The heart of the home is a spacious chef's kitchen that opens effortlessly to the main living spaces, allowing you to enjoy lake views while cooking, dining, or entertaining. Expansive windows and glass doors flood the home with natural light while framing the stunning waterfront scenery and creating a seamless connection between indoor and outdoor living. Step outside to your private resort-style oasis featuring a sparkling pool, spa, covered lanai, and private boat dock. Enjoy direct access to Johns Lake, one of Central Florida's premier recreational lakes, offering endless opportunities for boating, fishing, jet skiing, paddleboarding, wakeboarding, and unforgettable sunset cruises right from your backyard. Whether relaxing poolside, entertaining guests, or enjoying a quiet evening overlooking the water, every day feels like a vacation. What's more you have easy access to Florida's turnpike and 429 for seamless access to downtown Orlando, area theme parks, and Orlando International Airport!! Schedule for showing today.

902 Johns Point Drive, Winter Garden

$514,990
3 Beds 3 Baths Serenade At Ovation SubDv. 34787 Zip Code
Major Price Improvement!! Take advantage of the 4.99% interest rate (call for details) and a 2% concession!! Welcome to Serenade at Ovation, one of Winter Garden's most desirable new home communities, where modern design meets an unbeatable Central Florida lifestyle. This completed brand-new Cooper floor plan offers 2,078 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 baths, a versatile loft, and a 2-car garage, all perfectly positioned with the front of the home overlooking peaceful conservation views. The open-concept layout is ideal for both everyday living and entertaining. At the heart of the home, the gourmet kitchen showcases beautiful quartz countertops, elegant linen cabinetry, and abundant workspace while seamlessly connecting to the spacious dining and living areas. Stunning level-three natural wood-look plank tile flooring flows throughout the first floor, creating warmth, durability, and timeless appeal. Upstairs, the spacious primary suite serves as a private retreat featuring a large walk-in closet, dual-sink vanity, and oversized walk-in shower. Two additional bedrooms, a full bath, and a flexible loft provide plenty of space for a home office, media room, playroom, or additional gathering area. Modern finishes, energy-efficient construction, and thoughtful design details throughout make this home truly move-in ready. Residents of Serenade at Ovation enjoy an exceptional location in the heart of Winter Garden, one of Central Florida's fastest-growing and most sought-after communities. Just minutes away, Historic Downtown Winter Garden offers charming brick-lined streets, boutique shopping, farmers markets, live entertainment, and an impressive selection of local restaurants, cafés, breweries, and outdoor dining options. Nearby Winter Garden Village provides convenient access to popular retailers, grocery stores, fitness centers, and everyday conveniences. Outdoor enthusiasts will appreciate close proximity to the award-winning West Orange Trail, numerous parks, lakes, golf courses, and recreational opportunities throughout the area. Families and professionals alike will enjoy the community's convenient access to major roadways including State Road 429, Florida's Turnpike, State Road 535, and Interstate 4, providing quick connections to Downtown Orlando, Disney, Orlando International Airport, and the region's major employment centers, entertainment destinations, and attractions. Experience the perfect combination of contemporary living, natural surroundings, and unmatched convenience in this exceptional new home at Serenade at Ovation.

13011 Tranquil Water Alley, Winter Garden