Location: Winter Garden
Keyword(s): Lakeview Middle
Keyword(s) Middle School: Lakeview Middle
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1979 STANDING ROCK CIR, WINTER GARDEN, FL 34787
$520,00028 Days on yellowkey MLS ID: S5150723
0 Days Off yellowkey (back on 6/18/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2082 Built: 2019Monthly Fee: $105 Tax: $8,301 (2025)Community: Oakland Trails Ph 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,301
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: BUY THIS HOME WITH 100% FINANCING! LOCATION, LOCATION, LOCATION! Welcome to Your Trailside Oasis in Historic Oakland/Winter Garden! Nestled directly along the scenic West Orange Trail, this meticulously maintained, lightly lived-in bungalow offers the ultimate Florida lifestyle. Cycle straight into vibrant, historic downtown Winter Garden, or retreat to your own peaceful haven under the towering Live Oaks of Oakland Trails. Sophisticated Design Meets Modern Comfort...From the moment you arrive, the extended paver driveway and charming, shaded front porch welcome you home. Step inside to an airy, open-concept living area adorned with gleaming ceramic tile floors, quartz countertops, and upgraded builder finishes. Thoughtful, highly functional details elevate the main floor, including a stylish drop zone by the two-car garage, an under-stair coat closet, and a convenient powder room. High-end custom shades, luxury ceiling fans, and designer light fixtures make this residence completely turn-key and move-in ready. The second level opens into a versatile loft perfect for a media room, home office, or play space. The primary suite serves as a true sanctuary, boasting a grand double-door entrance, two spacious walk-in closets, and an ensuite bath with elegant quarts countertops. Two additional bright bedrooms and a dedicated upstairs laundry room complete this flawlessly designed upper level. Equipped with modern exterior lighting and a security camera system, this home offers total peace of mind. Outside your door, the vibrant Oakland Trails community features a resort-style pool, playground, dog park, and endless walking trails. Abundant dedicated street parking makes hosting family and friends effortless. Positioned perfectly between Clermont and Orlando, you will enjoy rapid access to the Florida Turnpike, 429, 408, and Highway 50. With Killarney Station right outside the neighborhood and the breathtaking Oakland Nature Preserve on the shores of Lake Apopka less than five minutes away, this is a dream destination for outdoor enthusiasts. Don't miss the chance to own this pristine, upgraded gem in one of Central Florida's most desirable trailside communities! Offering a lender credit towards costs or interest rate buy-down, when the client uses the preferred lender ACE Lending Group, ASK HOW.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Ariel Vargas (407-558-5161)
420 E CYPRESS ST, WINTER GARDEN, FL 34787
$420,00023 Days on yellowkey MLS ID: O6412414
REDUCED by $5,000 (1.2%) on 06/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1616 Built: 1950 Tax: $5,517 (2025)Community: Overstreet CrateSingle Family
Taxes:$5,517
Elementary School: Maxey Elem
Remarks: Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Trevor Zwick (863-303-6114)
214 S WOODLAND ST, WINTER GARDEN, FL 34787
$800,00021 Days on yellowkey MLS ID: O6413395
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 2868 Built: 1925 Tax: $2,450 (2025)Community: Fries Winter GardenSingle Family
Taxes:$2,450
Elementary School: Dillard Street Elem
Remarks: Coming Soon! Awesome Opportunity to own in Historic Winter Garden. LOT parcels in the front are being sold seperate.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nicole Prince (407-712-5688)
811 CIVITAS WAY, WINTER GARDEN, FL 34787
$2,199,00040 Days on yellowkey MLS ID: O6403760
REDUCED by $51,000 (2.3%) on 06/18/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5138 Built: 2017Monthly Fee: $208 Tax: $24,126 (2025)Community: Oakland Park Un # 2ASingle Family
Taxes:$24,126
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! Artist renderings with the pool included in the photos.
Listing is courtesy of: OAK AVENUE REAL ESTATE LLC (407-720-5000)
Listing Agent: Tracey Mcfadden (321-217-7808)
15316 OAK APPLE CT #B, WINTER GARDEN, FL 34787
$339,50076 Days on yellowkey MLS ID: O6397688
REDUCED by $499 (0.1%) on 06/17/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008 Tax: $4,738 (2025)Community: Tucker OaksCondo
Taxes:$4,738
Elementary School: SunRidge Elementary
Remarks: Welcome to your new dream home! Located in the gated community of Tucker Oaks, this 2-story townhome offers 3 bedrooms, 2.5 bathrooms, and 1,544 square feet of comfortable, thoughtfully designed living space. As a corner unit backing to a peaceful conservation area, you’ll enjoy added privacy and tranquil views with no rear neighbors! Step inside to an open-concept first floor where high ceilings, recessed lighting, and natural light create a warm and inviting atmosphere. The layout is ideal for both everyday living and entertaining, with a seamless flow between the living, dining, and kitchen spaces. A conveniently located half bath downstairs adds ease and privacy when hosting guests. The kitchen is designed for functionality and style, featuring stainless steel appliances, crown-molded cabinetry, ample counter space, and a breakfast bar that’s perfect for quick meals or morning coffee. Upstairs, all bedrooms and full bathrooms are tucked away for optimal privacy. The primary suite offers a spacious retreat with a large closet and a private en suite bath complete with a generous vanity and a roomy shower, making it perfect for starting your day or winding down in the evening. Additional bedrooms provide comfortable space for family, guests, or a home office setup. Beyond the home, Tucker Oaks offers amenities including a community pool, playground, dog park, and sidewalks for enjoying the outdoors. The location places you just minutes from major highways, making commuting simple, while also being close to downtown Winter Garden where you can explore local farmers markets, community events, and boutique shopping. The nearby West Orange Trail offers even more ways to stay active and enjoy the Florida sunshine. With theme parks like Walt Disney World and Universal Studios just 25 minutes away, this home combines convenience, comfort, and lifestyle all in one. Don't wait on this amazing opportunity, schedule your private showing TODAY!!!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Daniel Deluca (407-916-9780)
1105 LINCOLN TER, WINTER GARDEN, FL 34787
$255,0008 Days on yellowkey MLS ID: O6416937
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 814 Built: 1961 Tax: $1,586 (2025)Community: Bay St ParkSingle Family
Taxes:$1,586
Remarks: This beautifully updated 3 bedroom, 1 bathroom home offers modern comfort at an unbeatable value. With 814 sq ft of living space, it features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with a new fridge, and brand new remodeled bathrooms—giving you peace of mind and a move-in ready lifestyle. Located in the heart of Winter Garden, this home is close to shops, dining, and entertainment, all while being tucked into a welcoming neighborhood. Whether you’re a first-time buyer, downsizing, or looking for an investment property, this gem checks all the boxes. Don’t miss this rare opportunity to own a beautifully renovated home in one of Central Florida’s most sought-after communities—for less than $300K! **All measurements must be verified by the buyer.**
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Christopher Sukhram (407-558-8460)
1437 SCARLET OAK LOOP, WINTER GARDEN, FL 34787
$350,00019 Days on yellowkey MLS ID: O6411620
1 Days Off yellowkey (back on 6/16/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1684 Built: 2014Monthly Fee: $300 Tax: $3,213 (2025)Community: Tucker OaksTownhouse
Taxes:$3,213
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 Agent: Amy Moline (407-506-7447)
648 ORANGE BELT LOOP, WINTER GARDEN, FL 34787
$499,990118 Days on yellowkey MLS ID: S5144591
3 Days Off yellowkey (back on 6/16/2026)
REDUCED by $25,010 (4.8%) on 04/06/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1688 Built: 2018Monthly Fee: $338 Tax: $4,171 (2024)Community: Heritage/Plant StreetTownhouse
Taxes:$4,171
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Welcome to your opportunity to own in one of the most desirable locations near downtown Winter Garden—just off iconic Heritage at Plant Street in the GOLF CART DISTRICT. This beautiful 3-bedroom, 2.5-bath home offers nearly 1,700 square feet of thoughtfully designed living space in an unbeatable setting. Step inside to an expansive great room featuring stylish wood-look tile and an open-concept layout that seamlessly connects the living, dining, and kitchen areas—perfect for entertaining. The kitchen is designed for both function and style, offering abundant stylish cabinetry, gorgeous backsplash, elegant gold hardware, granite countertops, NEW Refrigerator, NEW microwave, NEW dishwasher, GAS stove and generous prep space. A screened courtyard with pavers creates a more private/secure outdoor retreat between the home and the detached 2-car garage. Whether you envision an outdoor lounge, garden oasis, or entertainment space, the possibilities are endless. Upstairs you will find upgraded- low maintenance flooring through out and your own private owner’s retreat. The spacious primary suite features a walk-in closet and an impressive ensuite bath designed to impress. Two additional bedrooms share a full bathroom, offering flexibility for guests, family, or a home office setup. A convenient half bath is located downstairs for visitors. Enjoy your summer months cooling off in the COMMUNITY POOL which is located just a couple of minutes from your front door. This community is ideally positioned between the West Orange Trail Park and the Winter Garden Branch Library, and just minutes from the 429 for easy commuting. If you like to run or bike this home is the perfect place for you since it is located along the West Orange Trail. Walk—or hop on your golf cart—to downtown Winter Garden where you’ll enjoy the vibrant atmosphere of Plant Street Market, known for its local food vendors, craft brews, artisan goods, and year-round community events. Located close to the community pool and surrounded by everything that makes Winter Garden special, this home truly offers the lifestyle buyers are searching for. Lower utility bills since it's an inside unit, double pane windows and a Instant Hot Gas Water Heater. Schedule your private showing today and experience why this location is so highly sought after.
Listing is courtesy of: CORCORAN CONNECT LLC (407-953-9118)
Listing Agent: Milinda Knollinger (321-624-7384)
925 EASLEY AVE, WINTER GARDEN, FL 34787
$1,175,0009 Days on yellowkey MLS ID: O6412977
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2667 Built: 2016Monthly Fee: $208 Tax: $12,692 (2025)Community: Oakland ParkSpa: YesSingle Family
Taxes:$12,692
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)
1672 MALCOLM POINTE DR, WINTER GARDEN, FL 34787
$499,900299 Days on yellowkey MLS ID: S5133690
REDUCED by $10,000 (2.0%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2035 Built: 2001Monthly Fee: $33 Tax: $6,403 (2024)Community: Tuscany Ph 02Single Family
Taxes:$6,403
High School: Ocoee High
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)
1049 SPRING LANDING DR, WINTER GARDEN, FL 34787
$547,90013 Days on yellowkey MLS ID: O6412927
1 Days Off yellowkey (back on 6/15/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2167 Built: 1990Monthly Fee: $25 Tax: $5,582 (2025)Community: Crown Point SpgsSingle Family
Taxes:$5,582
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)
405 LONE HERON WAY, WINTER GARDEN, FL 34787
$875,00012 Days on yellowkey MLS ID: O6416551
0 Days Off yellowkey (back on 6/14/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3848 Built: 2013Monthly Fee: $94 Tax: $5,763 (2025)Community: Lake Cove PointeSingle Family
Taxes:$5,763
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.
720 LAKE BRIM DR, WINTER GARDEN, FL 34787
$1,699,000110 Days on yellowkey MLS ID: O6387519
REDUCED by $26,000 (1.5%) on 06/14/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3781 Built: 2020Monthly Fee: $208 Tax: $14,831 (2025)Community: Oakland ParkSpa: NoSingle Family
Taxes:$14,831
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)
1544 MISTFLOWER LN, WINTER GARDEN, FL 34787
$469,90023 Days on yellowkey MLS ID: O6407815
0 Days Off yellowkey (back on 6/8/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2348 Built: 2005Monthly Fee: $55 Tax: $7,220 (2025)Community: Winter Garden Trls 01-3Spa: NoSingle Family
Taxes:$7,220
Elementary School: William Frangus Elem
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)
705 GARDEN WEST TER, WINTER GARDEN, FL 34787
$1,275,00051 Days on yellowkey MLS ID: O6403363
REDUCED by $25,000 (1.9%) on 06/08/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2698 Built: 2020Monthly Fee: $232 Tax: $10,345 (2025)Community: Garden WestSingle Family
Taxes:$10,345
Remarks: Nestled within the intimate Garden West enclave — just 11 exclusive homesites — this 4-bedroom, 3-bathroom J&J Building masterpiece spans 2,698 square feet of meticulously curated living space and sits directly on the West Orange Trail. Lace up your sneakers and you're seconds from one of Florida's premier multi-use trails, stretching 22 scenic miles through the heart of West Orange County. Located in the heart of Winter Garden's beloved Golf Cart District, Downtown Winter Garden's vibrant Plant Street is just a half mile away — putting award-winning restaurants, the beloved Saturday farmers market, boutique shops, and year-round community events right at your doorstep. From the moment you arrive, the Florida-inspired architecture, lush professionally re-landscaped grounds with low-voltage landscape lighting, and inviting covered front porch signal that every detail has been considered. Inside, the owners have transformed this already exceptional home into something truly turnkey. Two stunning shiplap feature walls anchor the main living spaces, while all-new designer lighting fixtures — inside and out — have been upgraded throughout and are fully programmable via the Leviton app, so you can set the perfect ambiance from anywhere. The chef's kitchen remains the heart of the home, featuring a Dacor 36" gas range, Samsung Pro dark stainless appliances, quartz countertops, subway tile backsplash, and ceiling-height cabinets beneath a one-of-a-kind shiplap vented hood. A reverse osmosis water filtration system at the kitchen sink adds a thoughtful, health-forward touch. Natural oak hardwood floors, crown molding, and custom woven wood window treatments on the first floor carry sophistication from room to room, while cordless blinds keep the second floor clean and effortless. The main floor offers an open living area with a guest bedroom and full bath — ideal for visitors or multigenerational living. The living room features a mounted, tilt-and-extend TV (included) paired with a Sonos sound system, controlled seamlessly by app for both the living room and lanai. Upstairs, the primary suite, two additional bedrooms, and a versatile loft provide space to spread out. Step outside and the screened lanai — enclosed with premium no-see-um screen material — becomes a true outdoor living room. Backyard café string lights, a mounted TV (included), Sonos audio, a natural gas BBQ stub-out, a retractable privacy blind, and no rear neighbors make this the ultimate Florida entertaining space. Additional outdoor power outlets and thoughtfully designed landscape lighting round out the backyard experience. Built for efficiency and peace of mind, the home features spray foam insulated block walls, energy-efficient double-pane windows, a radiant roof barrier, and a tankless gas water heater. Programable keyless entry locks secure all exterior doors, including the garage. The detached two-car garage — complete with a dedicated golf cart bay and overhead SafeRack storage — connects to the main house via a covered breezeway, a nod to the community's lifestyle-first design. This is more than a home. It's a lifestyle — trail, town, golf cart community, and turnkey luxury all in one.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Alexis Anderson (561-670-5901)
243 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$1,374,50097 Days on yellowkey MLS ID: O6391909
REDUCED by $24,000 (1.7%) on 05/22/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3097 Built: 2004Monthly Fee: $58 Tax: $6,565 (2025)Community: Lakeview Reserve 46/149Single Family
Taxes:$6,565
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.
1155 PRADO LN, WINTER GARDEN, FL 34787
$2,575,00012 Days on yellowkey MLS ID: O6415007
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4210 Built: 2027Monthly Fee: $150 Tax: $399 (2025)Community: Grove/OaklandSpa: YesSingle Family
Taxes:$399
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.
642 MEDORA WAY, WINTER GARDEN, FL 34787
$1,137,15015 Days on yellowkey MLS ID: O6413483
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2995 Built: 2026Monthly Fee: $155 Tax: $993 (2025)Community: Lakeview Village EstatesSingle Family
Taxes:$993
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)
650 MEDORA WAY, WINTER GARDEN, FL 34787
$1,157,19015 Days on yellowkey MLS ID: O6413464
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2902 Built: 2026Monthly Fee: $155 Tax: $993 (2025)Community: Lakeview Village EstatesSingle Family
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.
611 SIGLER DR, WINTER GARDEN, FL 34787
$899,76015 Days on yellowkey MLS ID: O6415005
Bed: 4 Bath: 3.5 Gar: 22 Liv Area Sq Ft: 2432 Built: 2026Monthly Fee: $155 Tax: $993 (2025)Community: Lakeview Village EstatesSingle Family
High School: None
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.
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