Homes for Sale Near Lakeview Middle in Winter Garden - 70 homes

Remarks: Don't miss this opportunity to own a well-maintained townhome in the sought-after gated community of Tucker Oaks. Featuring 3 bedrooms, 2.5 bathrooms, a 2-car garage, this home offers the perfect blend of comfort, convenience, and value. The open floor plan provides spacious living and dining areas, ideal for both everyday living and entertaining. A major recent improvement includes a roof installed in 2025, offering added peace of mind for years to come. Residents enjoy an array of community amenities, including a clubhouse, community pool, park, and playground. Ideally located just minutes from Historic Downtown Winter Garden, the West Orange Trail, shopping, dining, and major commuter routes including SR 429 and the Florida Turnpike, this home offers low-maintenance living with convenient access to everything Winter Garden has to offer.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Amy Moline (407-506-7447)

Remarks: 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, 2, 85-inch Samsung Frame TVs that convey, & 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.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: Golf cart district * motivated seller * Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden. It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!

Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)

Listing Agent: Mingke Li (352-973-2303)

Remarks: Under contract-accepting backup offers. Beautifully updated and move in ready, this Winter Garden home combines modern updates with generous living space and a convenient location. The sellers have completely remodeled the interior, creating a fresh and inviting atmosphere throughout. The updated kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and an open layout that flows seamlessly into the main living areas. One of the standout features of the home is the spacious game room and enclosed screened porch, providing flexible space for entertaining, hobbies, gatherings, or simply enjoying views of the backyard year round. Large windows bring in natural light and create a bright, welcoming environment throughout the home. Recent major improvements offer added peace of mind, including a brand new roof, new water heater, and updated landscaping completed in February 2026. The generously sized yard provides room to enjoy the outdoors while mature trees add character and shade. Located in the heart of Winter Garden, this property offers convenient access to historic downtown Winter Garden, the West Orange Trail, shopping, dining, parks, and major roadways for an easy commute throughout Central Florida. This is an excellent opportunity to own a thoughtfully updated home in one of the area's most desirable locations.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Liza Farzati (561-385-8271)

Remarks: Under contract-accepting backup offers. The Gateway to Winter Garden Elegance. Welcome to a life of unparalleled charm and exclusivity in the heart of historic Downtown Winter Garden. Tucked away within Lake Cove Pointe—the downtown Winter Garden's sole gated enclave featuring dual access—this exquisite residence sits gracefully on a sprawling, fully fenced corner lot. Here, the coveted, golf-cart-friendly lifestyle of Central Florida's most sought-after destination isn't just an amenity; it is your new everyday reality. Step through the front doors and let the narrative of luxury unfold. You are immediately greeted by expansive vaulted ceilings that establish a grand, airy tone, while flawless, modern engineered wood floors guide you seamlessly through the home's sunlit living spaces. At the heart of the main level lies an open and spacious kitchen, intuitively designed for both quiet mornings and lavish entertaining. It is beautifully appointed with sweeping granite countertops, classic 42-inch white shaker cabinetry, and premium stainless steel appliances—all elegantly anchored by a vent hood and a modern flat cooktop. The dual pantries will serve you well. A guest retreat and full bath finishes out the main living area. Making your way to the stairs to discover a second level thoughtfully designed for both personal retreat and family connection. A versatile loft space offers the perfect canvas for a multi-media hub, creative lounge, or playroom. The crowning jewel of the home is the luxurious owner's retreat—a true sanctuary of elegance and comfort. It features an unparalleled, custom-scale walk-in closet that is simply second to none. Three additional, generously proportioned guest bedrooms and a conveniently located upstairs laundry room complete this refined upper level. The story of this home extends effortlessly outdoors to a spacious screened patio, offering a tranquil haven for evening relaxation or intimate weekend gatherings. Practical luxury is evident throughout the property, highlighted by the peace of mind of a pristine new roof installed in 2024, and an expansive three-car garage that effortlessly accommodates vehicles, your community golf cart, and all organizational needs. Beyond the gates, the quintessential Winter Garden experience awaits. Enjoy immediate access to the scenic West Orange Trail, take a leisurely stroll or bike ride to the vibrant boutiques and dining of Plant Street, and immerse yourself in the local culture at the famed Saturday Farmers Market. This is more than a magnificent home; it is your invitation to an enchanted lifestyle.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Matthew Mckee (407-948-0658)

Remarks: PARADE of HOMES-OAKLAND PARK! Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. The chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, community connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)

Remarks: Under contract-accepting backup offers. This 4-bedroom, 2-bathroom single-story home offers a versatile and comfortable layout featuring a blend of carpet, wood, and ceramic flooring throughout. The interior is designed for spacious living, highlighted by oversized secondary bedrooms equipped with full-length mirrors that add both depth and functionality. The living spaces flow seamlessly to the outdoors, where a screen-enclosed back patio provides a private, pest-free retreat for year-round relaxation. Complete with an attached two-car garage, this home perfectly balances practical amenities with a diverse mix of quality interior finishes.

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless craftsmanship, thoughtful design, and elevated luxury living. Spanning 4,210 square feet of livable space (5,914 total sq ft) across a thoughtfully designed floor plan, The Wildflower offers 5 bedrooms, 5 full baths, and 2 half baths, providing ample room for families who prioritize space and style. From the moment you arrive, every detail speaks to the quality and care poured into this home. Inside, a versatile loft and flex room provides endless possibilities — a home office, media room, playroom, or private retreat. The open, flowing layout is designed for both everyday living and effortless entertaining. Step outside to your own private resort. A custom pool and spa take center stage in the backyard oasis, a covered rear lanai with roll down screens, a fireplace complemented by a summer kitchen and cabana — perfect for hosting under the Florida sun. Enjoy evenings at home with a built in fire pit and beautiful landscape lighting. A 3-car garage rounds out the thoughtful features that make this home as functional as it is beautiful. Located just minutes from downtown Winter Garden's vibrant dining and shopping scene, top-rated schools, and easy access to the Florida Turnpike, The Grove offers the rare combination of peaceful small-town living with big-city convenience. Estimated completion Spring 2027. Secure your lot today and experience the Justice & Wood difference — where every home is built with excellence, without cutting corners.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Palmetto floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open-concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, quartz countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Cypress floor plan, offering 4 bedrooms, 3 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates, an exclusive new community by award-winning Davila Homes, featuring just 40 luxury residences crafted with exceptional attention to detail. Each home is thoughtfully designed to blend comfort, durability, and timeless architectural elegance. Introducing The Maple floor plan, offering 4 bedrooms, 3.5 bathrooms, and a beautifully designed open- concept layout ideal for both everyday living and elevated entertaining. Premium upgrades are showcased throughout, including engineered hardwood flooring, striking Calacatta countertops, and a chef-inspired kitchen that pairs refined style with effortless functionality. Perfectly positioned in the heart of Winter Garden’s coveted Golf Cart District, residents enjoy a short walk to vibrant Plant Street — home to the Farmers Market, Crooked Can Brewery, boutique shopping, and some of the area’s most celebrated dining. Surrounded by charming parks, community events, and cultural destinations, Lakeview Village Estates offers a lifestyle where convenience, connection, and quality of life come together beautifully. All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice.

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award-winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Gardenia floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, Calacatta countertops, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. Land, Site, and Tax Infor

Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)

Listing Agent: Tatiana Souza (407-467-9914)

Remarks: Virtually Staged. 1028 Spring Landing Dr offers the perfect combination of comfort, style, and location in one of Central Florida's most desirable communities. This beautifully upgraded and meticulously maintained 4-bedroom, 3.5-bathroom home features a spacious fenced backyard, ideal for entertaining, pets, or enjoying Florida living year-round. Inside, you'll find gorgeous wood-look tile flooring throughout, adding both elegance and durability to the home's modern feel. Major updates provide peace of mind for the next owner, including a new roof installed in 2019, fresh exterior paint, and a brand-new A/C system replaced in 2025. Pride of ownership shines throughout every detail of this move-in-ready property. Conveniently located just minutes from vibrant Downtown Winter Garden, residents can enjoy easy access to the award-winning farmers market, local dining, boutique shopping, the West Orange Trail, parks, breweries, and community events. With quick access to major highways, Disney attractions, and all that Central Florida has to offer, this home truly delivers both lifestyle and convenience.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: 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.

Listing is courtesy of: REALNET FLORIDA REAL ESTATE (813-288-8000)

Listing Agent: Sami Warah (352-636-6738)

Remarks: An unparalleled lakefront opportunity in Downtown Winter Garden **Seize the rare chance to own a premier waterfront estate where the true value lies in the spectacular lot, private dock, and an enviable golf-cart lifestyle ** Launch your boat from your private lift for a scenic 30-minute cruise to Mt. Dora or take your golf cart just minutes away to the historic downtown Farmers’ Market and restaurants **Positioned within a private, gated enclave directly across from the West Orange Trail, this property offers the ultimate Florida resort lifestyle outside, featuring a heated saltwater pool, raised spa, and a fully fenced, expansive lakeside yard ** Inside, the home boasts a massive primary suite +/16x26’ with tray ceiling, fireplace and a balcony with lovely lake views and massive +/-23x25 bonus room including a wet bar and fireplace** The kitchen has a large cooking island w/sink plus a separate breakfast bar, stone counters, under cabinet lighting, a Jenn-Air double convection oven and lovely dining area overlooking the lake ** There's even an open wine closet/alcove with wine refrigerator off the kitchen ** First floor bedroom with an oversized walk in closet as a 5th bedroom or den (currently being used as a dining room) ** Other home upgrades include a newer roof +/-2022, 3 newer A/C units, a whole-home Katolight 40KW generator that runs +/- 90% of the home, crown molding throughout the home, ADT security system with cameras, boat house with new roof 2025, resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system and a 10’ seawall ** Relax on the covered screened patio with the Bose speaker system and prime outdoor living space including additional yard space beyond the pool and patio ** 2 car garage plus a 1 car garage with easy access to the back yard perfect for bringing your boat or lawn equipment through ** LOW HOA fees $200 quarterly ** All room measurements in MLS and on 3d floorplan are approximate. Buyer to verify. Tax record is incorrect - property has 5 bedrooms. Dock measurement is estimated. Buyer to verify. Solar panel lease to be transferred to buyer at closing.

Listing is courtesy of: INDEPENDENCE REALTY GROUP LLC (407-408-6662)

Listing Agent: Andrew Philippone (407-408-6662)

Remarks: Under contract-accepting backup offers. Beautifully maintained and truly turn-key, this 3-bedroom, 2.5-bath townhome is the kind of home where you can simply move in and start enjoying everything Winter Garden has to offer from day one, all while being located in the highly sought-after Golf Cart District just moments from the heart of charming Downtown Winter Garden! From the moment you walk in, you’re welcomed by bright, open living spaces, thoughtful design, and timeless finishes that make the home feel warm, elevated, and instantly inviting. Plantation shutters throughout add that polished custom touch, while the open-concept layout creates the perfect flow for both everyday living and entertaining. Upstairs, the spacious primary suite feels like its own private retreat, thoughtfully positioned away from the guest rooms so you can truly enjoy your own space. Wake up to beautiful open skies and unwind each evening with stunning sunset views right from your bedroom. This is townhome living exactly how it should be. Where else in Winter Garden can you enjoy a home like this, have pool access just a short walk away, and spend your weekends enjoying life instead of worrying about exterior upkeep? Lock it, leave it, travel when you want, and come home to a space that always feels effortlessly cared for. And the location? It’s hard to beat! Bending Oak Trail offers that true neighborhood feel with peaceful evening walks, friendly neighbors, and a sense of community that makes you feel right at home, all while being just moments from the heart of Downtown Winter Garden—one of Central Florida’s most beloved downtowns, known for its brick-lined streets, incredible local restaurants, charming boutiques, cozy coffee shops, weekend Farmer’s Market, and year-round community events that make this area so special. Hop on your golf cart and head down Plant Street for your morning coffee, dinner with friends, shopping, or an evening stroll. Even better, you’re right next to the West Orange Trail, making morning bike rides, walks, and outdoor living part of your everyday lifestyle. With quick access to 429, the Turnpike, SR-50, Disney, Downtown Orlando, and Orlando International Airport, convenience is seamlessly built into daily life. Winter Garden continues to be one of Central Florida’s most sought-after communities, and opportunities to own something this move-in ready, this well-located, and at this price point are incredibly hard to find.

Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)

Listing Agent: Lauren Bouchard (352-978-6837)

Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!

Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)

Listing Agent: Mauro Costa (321-231-6800)

Remarks: One or more photo(s) has been virtually staged. Welcome to Covington Chase, one of the most sought-after communities in Winter Garden, just minutes from the charm and energy of historic downtown. Situated on an oversized 0.38-acre lot, this 4-bedroom, 4 full bathroom home offers a rare combination of space, functionality, and flexibility. The fully fenced backyard provides plenty of room to relax, entertain, or create your own outdoor retreat, while the long driveway and 3-car garage give you ample parking and storage, including space for a golf cart so you can fully enjoy this golf cart district lifestyle. The floor plan is thoughtfully designed for both everyday living and long-term versatility. The primary suite is located downstairs, creating a private retreat with two walk-in closets and a large bathroom that offers both space and comfort. Also on the first floor is a dedicated office, perfect for working from home or creating a quiet, separate space for productivity. In addition, the first floor features a Jack and Jill bedroom and bathroom setup, ideal for guests, kids, or multigenerational living. This layout allows for privacy while still maintaining a connected and functional flow throughout the home. Upstairs, you will find a spacious loft that can be used as a second living area, media room, or play space, along with a full bedroom and full bathroom. This upstairs setup is perfect for guests, older children, or anyone who would benefit from having their own private area within the home. The overall layout gives you multiple living zones and flexibility, making it easy to adapt the home to your lifestyle, whether that means working from home, hosting guests, or simply enjoying extra space. The roof was replaced just a few years ago, offering added peace of mind and reducing one of the major future expenses for a new owner. Beyond the home itself, the lifestyle here is what truly stands out. You are just minutes from the Downtown Winter Garden Historic District, known for its brick-lined streets, locally owned restaurants, coffee shops, boutiques, and the popular weekly farmers market. Living in the golf cart district means you can easily head downtown for dinner, events, or a casual night out without needing to get in your car. You are also close to the West Orange Trail, a 22-mile scenic trail perfect for biking, walking, and enjoying the outdoors. Homes with this kind of lot size, a flexible floor plan with a downstairs primary suite, office, additional bedroom, plus an upstairs loft and private guest space, and a 3-car garage are hard to find this close to downtown. This is a unique opportunity to own a home that offers both the space you need and the lifestyle you want.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Erica Diaz (407-897-5400)