Homes for Sale Near Lakeview Middle in Winter Garden - 61 homes

Remarks: **Welcome to Golf Cart Life in Historic Downtown Winter Garden** Nestled within Stanton Estates — an exclusive enclave of just 45 luxury homes — this contemporary masterpiece places you in the heart of **Winter Garden’s vibrant Golf Cart District**, where every day feels like a getaway. Built in 2018, this one-story multigenerational estate offers 3,170 sq ft of refined living on a nearly 1/3-acre lot, just a quick golf cart ride from **Plant Street’s award-winning restaurants, live music, boutique shops, the famous Saturday Farmer’s Market, the Crooked Can Brewery, and the scenic West Orange Trail**. Take a look at Virtual Tour Link 2 to see all the exciting and fun things available to you in the downtown and historic area of Winter Garden. Inside, soaring 12-ft ceilings and natural light flow through an open, flexible layout with four bedrooms, four full baths, and a private office. The gourmet kitchen anchors the home with solid wood cabinetry, quartz countertops, an oversized island, walk-in pantry, and a full suite of KitchenAid Professional appliances with natural gas. The primary suite features a recessed ceiling, expansive custom walk-in closet, and a spa-inspired bath. Fully retractable sliders open to a covered lanai surrounded by mature, professionally designed landscaping and privacy fencing — your own private Florida retreat after a day of exploring downtown. Premium upgrades include smart-home technology, motorized shades, whole-home water filtration, 8-ft solid core doors, custom cabinetry, a three-car tandem garage with brick paver driveway, and a brand-new tankless gas water heater (2025). Just minutes from Disney, Universal, and SeaWorld, with seamless access to SR-429, the Turnpike, and 408, this address blends luxury living with the unbeatable charm and excitement of Downtown Winter Garden. Opportunities like this in Stanton Estates are rare. **Welcome to the lifestyle everyone wants**

Listing is courtesy of: FATHOM REALTY FL LLC (888-455-6040)

Listing Agent: Joe Thomas, Jr (813-724-1922)

Remarks: Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roff, new pluming, close to major roads, schools, minutes to Winter Garden dawn town.

Listing is courtesy of: STIRLING INTERNATIONAL REAL ES (407-250-1000)

Listing Agent: Rosa Rodriguez (407-832-1185)

Remarks: Welcome to 1335 Daniels Cove Drive, a move-in ready gem in the heart of Winter Garden. Ideally located just minutes from Winter Garden Village, you’ll enjoy easy access to shopping, dining, entertainment, and major roadways, putting convenience right at your doorstep. Inside, fresh interior paint and tile flooring throughout create a clean, bright, and low-maintenance living space with a modern feel. The beautifully updated primary bathroom adds a stylish touch, while double-pane windows enhance energy efficiency and everyday comfort. Major improvements include a 2017 roof, offering peace of mind and added value for the next owner. Step outside to a fully fenced backyard with plenty of room for pets, play, entertaining, or simply unwinding in your own private outdoor retreat. With bright living spaces, a functional layout, thoughtful updates, and an unbeatable location, this home delivers the perfect blend of comfort, convenience, and lifestyle.

Listing is courtesy of: KGV REALTY GROUP (407-474-0844)

Listing Agent: Jaclyn Crawford (386-837-4530)

Remarks: Experience elevated living in this exceptional custom home by J&J Building, perfectly positioned in one of Winter Garden’s most desirable locations directly across from the iconic West Orange Trail. Offering over 5,000 square feet of thoughtfully designed luxury, 811 Civitas Way blends sophisticated style, flexible living spaces, and impressive functionality rarely found in today’s market. Designed for both everyday comfort and unforgettable entertaining, the home features a truly jaw-dropping media room that delivers the ultimate cinematic experience. Multiple office and flex space options provide incredible versatility for remote work, creative pursuits, fitness, or multigenerational living. With bedrooms thoughtfully positioned on both the first and second floors, the layout offers ideal privacy and convenience for guests and family alike. Luxury details and custom upgrades are showcased throughout, including a whole-home generator, a one-year-old Sub-Zero refrigerator, two stunning crystal chandeliers installed last year, and elegant solid brass door hardware throughout the home. You'll fall in love with the large island in the garage that even includes a built-in gift wrapping station! Every space reflects exceptional craftsmanship and thoughtful design, with countless additional custom touches that elevate the home’s overall sophistication and character. One of the property’s standout features is its exceptionally rare amount of parking for 7 cars plus a golf cart— a coveted luxury that sets this home apart. Combined with its prime location near Downtown Winter Garden, scenic trail access, dining, shopping, and commuter routes, this residence offers a lifestyle that is as refined as it is practical. **There is room to add a pool and ADU on this lot, as well!

Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)

Listing Agent: Tracey Mcfadden (321-217-7808)

Remarks: LAKEFRONT ** 30 min boat ride from your backyard to Mt Dora or take your golf cart a few minutes to downtown historic Winter Garden Farmers' Market, restaurants & events ** Private gated downtown Winter Garden community ** Live the true Florida lifestyle here with breathtaking sunset views over Lake Apopka ** Spectacular designed heated saltwater pool with raised spa ** Dock w covered boat lift has new roof 2025** 10' sea wall ** Completely fenced yard and additional yard space beyond the patio ** Resurfaced pool +/-5 yrs ago & Aqualink pool/spa automation system ** Newer roof 2/2022 and 3 newer AC units inside and out ** Home generator Katolight 40KW runs +/- 90% of the home ** Scenic lake views from the bay window in the kitchen dining area and from the great room ** The great room features a corner firepl, Bose speakers & french doors w more lake views **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 ** +/-16x26 primary bedroom w a tray ceiling and cozy corner fireplace and serene lake views from the balcony ** HUGE +/-23x25 bonus room with wet bar and fireplace ** Use the first floor bedroom with a oversized walk in closet as a 5th bedroom or as a den-currently being used as a dining room ** Crown molding throughout the home ** 2 car garage plus a 1 car garage with easy access to the backyard perfect for bringing your boat or lawn equipment through ** Covered screened patio with ceramic tile, Bose speaker system and outdoor living space ** LOW HOA fees $200 quarterly ** ADT security system with cameras ** PRIME LOCATION with the West Orange Trail directly across from the front community gate and a charming Butterfly Garden a short walk away ** Only a few minutes to charming downtown historic Winter Garden with great restaurants, shopping, business services, incredible Farmers Market every Saturday and fun events to enjoy all year long ** 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: You found it with this Location! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Big backyard fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room in garage- perfect for the handyman. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools! Solar panels will be paid off at closing!

Listing is courtesy of: WATSON REALTY CORP (407-298-8800)

Listing Agent: Rick Evans, Ii (407-538-9295)

Remarks: 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: Welcome to this beautifully maintained 3-bedroom, 2-bath home in the highly desirable Spring Ridge area of Winter Garden. Offering 1,699 square feet of thoughtfully designed living space, this move-in ready property combines comfort, charm, and major updates—including a NEW ROOF and A/C installed in 2020 for added peace of mind. Situated on an oversized quarter-acre lot, the home features standout curb appeal, mature landscaping, and a spacious fenced backyard with endless possibilities—whether you envision a pool, garden, play area, or the ultimate entertaining space. Inside, you’ll find a bright and inviting floor plan filled with natural light and comfortable living areas designed for both everyday living and hosting guests. The main living space is centered around a beautiful masonry fireplace, creating the perfect setting for cozy nights and memorable gatherings. The private primary suite offers a walk-in closet and ensuite bath with soaking tub, providing a relaxing retreat at the end of the day. Secondary bedrooms are generously sized and flexible for guests, family, or a home office setup. Located just minutes from top-rated schools, shopping, dining, parks, and major roadways, this is an incredible opportunity to own a well-cared-for home in one of Winter Garden’s most sought-after communities. Homes with this lot size, condition, and location don’t come around often—schedule your private showing today.

Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)

Listing Agent: Milton James (407-572-4458)

Remarks: LUXURY LAKEFRONT ESTATE – Minutes from Historic Downtown Winter Garden! Experience elevated waterfront living in this beautiful 4-bedroom, 4.5-bath lakefront pool residence on just under 1 acre, ideally located just minutes from the heart of Winter Garden and the charm of Plant Street. Built in 2020 and situated within the coveted GOLF CART DISTRICT near Historic Downtown, this property offers the rare combination of private lakefront serenity and walkable convenience. RECENT CUSTOM UPGRADES with designer millworker throughout, new wide plank oak wood floors, entire property custom fenced and designer hardscape and landscape with lakefront hot tub and lakefront sauna house! Inside, gorgeous hardwood floors flow throughout the thoughtfully designed single-story layout. The open-concept living spaces are warm yet modern, highlighted by a cozy electric fireplace and seamless indoor-outdoor connection. A distinctive wine and bourbon room adds a refined touch—perfect for entertaining or curating your private collection. The primary suite is positioned to capture sweeping lake views and features a spa-inspired bath and generous walk-in closet. Each additional bedroom includes ensuite bath access, while a private guest cottage provides flexible space for visitors, extended family, or a studio retreat. Step outdoors to your personal resort-style setting. Enjoy the screened salt water heated pool and spa, summer kitchen, and private dock for boating and sunset cruises. A detached private sauna house offers a true at-home wellness experience, while the outdoor fire pit overlooking the lake creates an unforgettable gathering space framed by panoramic water views. OWNED and FULLY PAID SOLAR PANELS with extremely low utilities cost. With upscale finishes, distinctive amenities, and an unbeatable lakefront location just moments from dining, shopping, and the vibrant downtown district, this exceptional property delivers the ultimate Florida lifestyle—where luxury meets laid-back lakeside living. Schedule your private showing and discover one of Winter Garden’s most compelling lakefront opportunities.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Nicole Rader (407-484-4743)

Remarks: 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 of an 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. At the heart of the home, 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: One or more photo(s) has been virtually staged. Welcome home to 921 Bending Oak Trail in highly sought-after, downtown, golf cart district of Winter Garden! This spacious 4-bedroom, 2.5-bath home is perfectly situated on a private oversized corner lot with serene pond views, offering both privacy and a peaceful backdrop. The thoughtfully designed layout features a first-floor primary suite and convenient downstairs laundry room. The main living areas showcase updated modern, stone-like tile flooring, while the kitchen offers a large walk-in pantry that extends under the staircase for exceptional storage. The spacious Living Room and covered patio are wired for a surround sound system and have beautiful water views from the windows and paver patio. Upstairs, you’ll find generously sized secondary bedrooms, including one with an oversized walk-in closet, along with a large loft ideal for a home office, playroom, or flex space, all featuring engineered hardwood flooring. Enjoy outdoor living with a spacious entertaining area and the added benefit of a rear-entry garage accessed through a private, owners-only alleyway where you can also enter the home without climbing any stairs. Major updates include a roof replacement in 2025, making this home as practical as it is beautiful. Lastly, the location is incredible, the neighborhood is extremely well maintained, offering a tranquil walking community around Brandy Lake and duck filled ponds, a sparkling community pool, entertaining pavilion, community greenspace, and perfect playground for the little ones.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Claire Sims Llc (203-767-8109)

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. One of the largest homes in the highly desirable Courtlea Oaks community, this spacious 5-bedroom, 4.5-bath pool home offers over 4,000 square feet of living space and an exceptional opportunity in the heart of Winter Garden’s golf cart district. The flexible floor plan includes a rare apartment above the garage connected to the main home, providing ideal space for guests, extended family, a private office, or additional living quarters. Important updates have already been completed by these original to the home owners, including a new roof and A/C systems installed just two years ago, offering peace of mind for the next owner. Step outside to enjoy a beautiful pool and a private setting backing to the West Orange Trail, perfect for biking, walking, and outdoor recreation right from your backyard. Located just minutes from historic downtown Winter Garden, residents enjoy boutique shopping, dining, breweries, and the award-winning Saturday Farmers Market, along with numerous festivals and community events throughout the year. With its generous square footage, versatile layout, and unbeatable location, homes like this rarely come available in Courtlea Oaks.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Jennifer Coon (321-948-8056)

Remarks: One or more photo(s) has been virtually staged. Welcome to the Downtown Winter Garden Golf Cart District where lifestyle and location just make sense. This 4 bedroom, 2 bath pool home blends thoughtful upgrades with a layout that actually works for real life. From the moment you walk in, the natural light and open flow stand out. The main living spaces connect seamlessly, creating an easy, inviting feel whether you are hosting or just enjoying a night in. Throughout the home you will notice custom woodworking details that add warmth and character. From built ins to trim work, these touches elevate the space and give it a more intentional, finished look you do not see in every home. The kitchen offers a clean, updated feel with modern finishes, refreshed cabinetry, and functional space that opens directly into the dining and living areas. It is designed to be both practical and a place people naturally gather. One of the biggest advantages of this home is the fully paid off whole home solar system paired with multiple battery backups. This means lower monthly costs and added reliability during storms or outages, something that continues to matter more and more. Step outside and you get your own private backyard setup. The pool and spa create a true stay at home retreat. Whether it is weekends with friends or a quiet evening, the space is set up to be enjoyed year round. The three car garage is a rare find in this area and gives you all the room you need for a golf cart, bikes, storage or hobbies. Living here is where this home really stands out. Hop on your golf cart and head straight into downtown Winter Garden, one of the most loved small town districts in Central Florida. If exercise is your thing you're just a short distance to pickleball and tennis courts, baseball fields and the outstanding West Orange Bike Trail!! You are minutes away from a nationally recognized farmers market, the Crooked Can Brewery, the splash pad, Plant Street Market and a full calendar of events throughout the year. From live music and seasonal festivals to outdoor dining and boutique shopping, there is always something happening. The entire area has that walkable, charming feel that makes it feel like a Hallmark town brought to life. You are also close to Horizon West, major highways, top rated schools, downtown Orlando and the theme parks, giving you the perfect mix of convenience and small town charm. Homes like this in this location do not come up often. If you are looking for a home with character, smart upgrades, and a lifestyle that people move here for, this is it.

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

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

Remarks: Welcome to this fully renovated 3-bedroom, 2-bath home on an oversized 0.20-acre lot in one of Winter Garden’s growing corridors. This move-in ready property offers immediate livability with long-term upside. Recent upgrades include a new AC system and water heater (2026) and a roof replaced in 2019, minimizing near-term capital expenses. The home features updated interiors and a functional layout suited for both owner-occupants and investors. The large lot provides flexibility for outdoor use and potential future enhancements. Zoned R-4, the property may provide additional possibilities for expansion or income-producing use. Buyer to verify all zoning and development options with the city. Located just minutes from major highways, shopping, and ongoing development, this property is well-positioned for both convenience and future growth.

Listing is courtesy of: LIVE MVRK LLC (407-756-4563)

Listing Agent: Gabriel Flete (407-341-9663)

Remarks: Charming home located just blocks from Winter Garden's historical downtown in the highly sought-after GOLF CART DISTRICT! This 3 bedroom, 3 Bath house blends timeless character with modern living, featuring hardwood floors, vintage tiled bathroom, built-ins, and a traditional layout with separate dining room. The kitchen opens to a comfortable family room, ideal for everyday living. The primary suite offers a spacious, spa-like bath with freestanding tub, walk-in shower, and custom vanity. A recent addition includes an oversized two-car garage , HVAC , large pantry, and bathroom to the third bedroom, creating a private en-suite with separate exterior entrance, ideal for guests or flexible living. Situated on a fenced, .41-acre corner lot, enjoy the screened-in back porch, expansive yard with mature landscaping, and the pavered pool area-perfectly designed for entertaining. Live the Historical Downtown Winter Garden Life-Style with convenient access to dining, shopping, farmer's market, Lake Apopka sunsets, and more.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Alison Scorsone (321-689-3554)

Remarks: UPDATED THREE-STORY TOWNHOME IN THE HEART OF DOWNTOWN WINTER GARDEN! Welcome to 461 Geranium Place, where modern finishes, natural gas features, and one of Winter Garden’s most loved locations come together beautifully. This is the kind of home that changes your day-to-day rhythm — coffee, dinner, craft beer, the trail, live music, community events, and the SATURDAY FARMERS MARKET are all right outside your door. Located next door to Crooked Can and Plant Street Market, this stylish townhome offers a truly connected Downtown Winter Garden lifestyle. Inside, the home feels bright, polished, and easy to live in, with wood-look tile flooring, crisp white trim, crown molding, recessed lighting, modern door hardware, and decorative wall trim that adds a custom, finished feel. The three-story layout provides flexibility and function, while the ELEVATOR-READY design offers a valuable option for future convenience. The main living level is made for gathering. The kitchen, dining, and living areas flow together in one open, connected space, creating an easy setting for casual dinners, game nights, or hosting friends before walking next door to Plant Street Market. The kitchen features light cabinetry, quartz-style countertops, subway tile backsplash, stainless steel appliances, a NATURAL GAS RANGE, vent hood, pendant lighting, and an oversized island with seating. The dining and living areas offer generous space, abundant natural light, balcony access, and a comfortable layout that feels open without losing warmth. Decorative wall trim, tall windows, neutral finishes, and a modern stair railing add to the clean, contemporary presentation throughout the home. The primary bath features new flooring and a BRAND NEW STEAM SHOWER, recently replaced with floor-to-ceiling tile, a built-in bench, recessed niche, decorative tile accent, and a clean, spa-inspired feel. The separate vanity area offers excellent counter space and storage, while the overall bath layout provides comfort and function. Additional highlights include NATURAL GAS SERVICE, including a gas water heater, updated fixtures, excellent storage, and a cohesive neutral design palette throughout. With its updated interior, open main living level, flexible three-story design, and unmatched Downtown Winter Garden location, 461 Geranium Place offers a rare blend of comfort, convenience, and everyday enjoyment. This is the home where your weekends get easier, your evenings get more fun, and Downtown Winter Garden becomes part of your everyday life. Spend Saturday mornings at the farmers market, meet friends for dinner on Plant Street, enjoy craft beer next door at Crooked Can, hop on the West Orange Trail, and come home to a beautifully updated space that feels easy, stylish, and welcoming. Come see how well this home lives in person — schedule your private showing today.

Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)

Listing Agent: Cindy Rosenbloom (407-876-9175)

Remarks: There is a distinct rhythm to life in Oakland Park that cannot be replicated anywhere else in Central Florida. It is a refined balance of Old Florida charm and modern luxury, where tree-lined streets, curated green spaces, and intentional design create a true sense of place. As you enter the community, everything feels elevated and thoughtfully composed, with the 22-mile West Orange Trail serving as the heartbeat that connects residents to both nature and one another. At 931 Kylee Alley, this lifestyle is fully realized. Positioned on a prominent corner lot, this David Weekley Stoneybrook residence showcases timeless architecture with a clean, sophisticated presence. One of the greatest luxuries here is the ease of ownership. The homeowners' association provides full landscaping maintenance, allowing the property to remain in pristine condition without demanding your time. Your weekends are yours to enjoy, not manage. Inside, the home immediately impresses with intentional sightlines and natural light. Built in 2022, the design feels both current and enduring. Soaring ceilings and expansive windows, complemented by custom plantation shutters, create a bright yet grounded atmosphere. The gourmet kitchen anchors the home, featuring an oversized island with sleek, solid surface countertops that serve as the perfect setting for gathering, entertaining, or everyday living. The floor plan is designed for both connection and privacy. The main level offers a flexible and refined space that can function as a guest suite or executive-style home office. Upstairs, the private quarters provide a peaceful retreat. The primary suite is expansive and serene, complete with a spa-inspired bath designed for relaxation at the end of the day. Living here means immediate access to the West Orange Trail and the best of Winter Garden. Bike to Plant Street, enjoy the Saturday Farmers Market, or simply take in the charm of one of Central Florida’s most sought-after destinations. Within Oakland Park, residents enjoy resort-style amenities, including multiple pools, a clubhouse, and a dog park, all contributing to a true lock-and-leave lifestyle. From an investment perspective, this property stands out. It offers an exceptional price per square foot for Oakland Park, with pricing thoughtfully adjusted to reflect the opportunity for upstairs flooring customization. In a community where demand continues to outpace supply, especially for newer construction on premium corner lots, this home represents both immediate value and long-term upside. 931 Kylee Alley is more than a home. It is a strategic acquisition within one of Winter Garden’s most desirable communities.

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

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

Remarks: Welcome to one of Winter Garden's most coveted addresses — nestled in the heart of the Golf Cart District, this beautifully appointed Oakland Park home delivers the Florida lifestyle you've been waiting for. With 4 bedrooms, 3.5 bathrooms, and 3,012 square feet of thoughtfully designed living space, this 2013-built corner lot residence blends everyday comfort with elevated finishes at every turn. Step inside to soaring vaulted ceilings in the family room that create an immediate sense of volume and light. Rich wood flooring flows through the downstairs living areas, complemented by clean ceramic tile and plush carpet in the bedrooms — a seamless combination of warmth and function. The open layout is designed for real living, whether it's a quiet evening in or hosting the people you love most. Outside, brick pavers set the tone for an outdoor living experience that's genuinely special. A large covered back patio creates the perfect setting for morning coffee or evening entertaining, while a classic breezeway connects the home to the garage with both style and practicality. But it's the location that truly sets this home apart. Oakland Park is one of Central Florida's most sought-after communities — complete with two resort-style pools, a beautifully appointed clubhouse, and a dedicated dog park. Step outside your door and hop on your golf cart to access the iconic West Orange Trail, or cruise just minutes into the heart of Downtown Winter Garden, where Plant Street Market, award-winning restaurants, rooftop bars, and a thriving local food scene await. This is the rare home where community, convenience, and character all converge.

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

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

Remarks: Under contract-accepting backup offers. Welcome to this beautiful 3-bedroom, 2-bathroom home with a two-car garage in the heart of the Regal Pointe subdivision of Winter Garden. Upon entry, you are welcomed by the large kitchen overlooking the living room, embracing open-concept living. The kitchen features laminate countertops, a tile backsplash, a breakfast eating area, and stainless steel Whirlpool appliances. The primary bedroom offers a private retreat, situated on the opposite side of the house from the secondary bedrooms. The large, open living room provides sliding door access to a screened-in patio with a peaceful pond view, making it the perfect place to enjoy a morning coffee or evening drink. You’re conveniently located within 25 minutes of Orlando’s theme parks, the airport, and downtown Orlando. Schedule your showings today!

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

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

Remarks: Some properties check a box. This one opens a door. This 3-bed, 2-bath home in the heart of Winter Garden is more than a place to live. It's a wealth-building opportunity sitting in plain sight. The floor plan sets up beautifully for a duplex conversion: a 1/1 in the front and a 2/1 in the back. Live in one side and let your tenant cover the mortgage, or rent both and start building cash flow from day one. At approximately 1,184 sq ft, the footprint is manageable, the concept is proven, and the location makes it work. You're minutes from historic downtown Winter Garden, major shopping corridors, top dining, and highway access. The kind of address that attracts reliable tenants and holds long-term value in one of Orange County's strongest markets. House hacking, buy-and-hold, or straight investment play. However you run the numbers, this one makes sense. ROOF is 2020, WATER HEATER 2021 and HVAC 2016

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Phat Nguyen (407-452-8751)