Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
Do Not Show Listings
1152 PRADO LN, WINTER GARDEN, FL 34787
$2,615,32024 Days on yellowkey MLS ID: O6413825
Bed: 6 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4658 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove/OaklandSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$399
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own private ensuite bath, delivering the ultimate in comfort and privacy for family and guests alike. A dedicated home office provides the perfect retreat for focused work, while the airy upper-level loft adds flexible living space ideal for a media room, playroom, or secondary lounge. Step outside and experience true Florida luxury a custom pool serves as the centerpiece of the outdoor living area, perfectly positioned to capture serene pond views that make every morning and evening feel like a private escape. Seamless indoor-outdoor integration defines this home's design philosophy, with expansive windows flooding the interior with natural light and blurring the line between inside and out. Inside, Davila Homes' signature craftsmanship is evident at every turn: timeless architecture, high-end finishes, an open-concept layout designed for effortless entertaining, and a gourmet kitchen appointed with state-of-the-art appliances. Every detail was thoughtfully curated and personalized through Davila's exclusive Design Center experience. The Grove is one of Oakland's most intimate and sought-after communities, featuring just 44 homesites surrounded by lush common areas, water features, walking trails, and bike paths. Minutes from the vibrant shops and dining of Downtown Winter Garden, top-rated West Orange County schools, and the beloved West Orange Trail, yet tucked away in the quiet charm of one of Central Florida's most historic small towns.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Alexis Anderson (561-670-5901)
483 PENNSYLVANIA AVE, WINTER GARDEN, FL 34787
$339,900101 Days on yellowkey MLS ID: O6398208
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1008 Built: 1988 Tax: $2,702 (2025)Community: East Garden Manor Add 03Single Family
Taxes:$2,702
Elementary School: Maxey Elem
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 roof, new plumbing, 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)
16161 BARKLY RIDGE CT, WINTER GARDEN, FL 34787
$1,690,00085 Days on yellowkey MLS ID: O6402785
4 Days Off yellowkey (back on 6/30/2026)
REDUCED by $110,000 (6.1%) on 06/03/2026
Bed: 6 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5284 Built: 2024Monthly Fee: $225 Tax: $2,826 (2025)Community: Avalon RdgSpa: NoSingle Family
Taxes:$2,826
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: Under contract-accepting backup offers. Sunset Lake Views | Luxury Upgrades | Move in Ready | Positioned on a Cul-de-Sac homesite with unobstructed views of Lake Avalon, this six-bedroom residence offers a functional two-level layout. Built in 2024 and enhanced with extensive owner improvements completed after purchase. The main floor supports single-level living with a primary suite, guest bedroom with en-suite bathroom, study, and an extensively upgraded kitchen and butler’s pantry featuring an oversized 10’ x 7’ island, quartz countertops, stacked cabinetry, dual Bosch dishwashers, Thermador microwave, and Samsung appliances. New luxury vinyl flooring extends throughout the first level, complemented by 12-foot ceilings. The primary suite features tray ceilings, automatic blinds, a large walk-in closet, and a remodeled bath with floor to ceiling tile and seamless glass shower. Upstairs includes a 33x22 loft, media room, four additional bedrooms, climate-controlled storage, and a balcony with elevated lake views. Other recent updates include interior paint, lighting, and gutters. Community amenities include a recreation area and walking trails, with convenient access to the 429, downtown Orlando, Walt Disney World, and top-rated schools.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Renee Funk (407-559-8596)
205 SURPRISE DR, WINTER GARDEN, FL 34787
$1,200,000232 Days on yellowkey MLS ID: O6365188
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2171 Built: 1950 Tax: $3,406 (2024)Community: Winter Garden Shores RepSingle Family
Taxes:$3,406
Elementary School: Dillard Street Elem
Tax Year: 2024
Remarks: PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value- with vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA- all within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, ideal for hobbyist or future conversion opportunities. Outside, the property transforms into a private oasis featuring a sparkling heated saltwater pool, outdoor fireplace and lush mature landscaping complete with fruit trees - all fully fenced for privacy. This property offers potential to subdivide into two to three lots for an investment opportunity or the ability to expand the current Square Footage. A large shed, rated as a detached garage, on the property provides additional space for a workshop or equipment storage. There is ample room for all your recreational toys; golf-cart, boat, and more. The current owners also have plans for a kitchen renovation and poolside wraparound porch, which they are willing to share with the buyer - opening the door to greater customization. Whether you're seeking a serene retreat, developmental potential, or the charm of downtown Winter Garden living, this property is truly one of a kind. This private paradise location is a convenient commute to Downtown Orlando, Disney and other Orlando attractions. You're dream estate awaits.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Alison Scorsone (321-689-3554)
2640 GROVE VIEW DR, WINTER GARDEN, FL 34787
$784,90091 Days on yellowkey MLS ID: O6401215
0 Days Off yellowkey (back on 6/30/2026)
REDUCED by $5,000 (0.6%) on 05/31/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3738 Built: 2001Monthly Fee: $90 Tax: $10,261 (2025)Community: Wintermere Pointe Ph 02 46/141Single Family
Taxes:$10,261
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Virtually Staged. Nestled in the sought after gated community of Wintermere Pointe in Winter Garden, this beautifully renovated residence offers a serene and private retreat with a truly like new feel. Situated on an oversized lot backing to conservation, with no neighbors on one side and located near a cul de sac, this home delivers exceptional privacy and peaceful surroundings. The entire home has been thoughtfully remodeled from top to bottom, creating a fresh, modern ambiance throughout. Updates include a brand new roof, luxury vinyl plank flooring, fresh interior paint, and all new contemporary lighting and finishes. The newly designed oversized kitchen showcases 42" soft close cabinets, quartz countertops with built-in technology charging port, modern tile backsplash, under cabinet lighting, brand new stainless steel appliances, center island and breakfast bar. The open concept layout flows seamlessly into a breakfast nook and a spacious family room, where large sliding glass doors open to a covered rear patio extending the full length of the home, overlooking tranquil conservation views. A two story foyer welcomes you upon entry, flanked by an airy formal living room and dining room along with a double access stairway. The first level also features a spacious bedroom with French door access, offering split living for enhanced privacy, perfect for guests, multi generational living or a home office. Upstairs, an open loft anchors the second floor, creating a desirable split plan with bedrooms positioned on either side. Sliding doors lead to a covered second level providing serene conservation views. The vast primary suite features tray ceilings, private balcony access, dual walk in closets, and a completely redesigned ensuite bath offers a luxury feel with dual quartz vanities, LED lighted anti-fog mirrors, glass enclosed tile shower, and a statement soaking tub. Three additional bedrooms are situated on the opposite side of the loft, along with a hallway bath featuring a double vanity and modern tiled tub/shower combination. Completing the second level is an expansive bonus room, perfect for a theater, recreation space, or home gym - endless flexibility. This exceptional home combines serene surroundings, modern upgrades, and a like new feel, all within one of Winter Garden’s premier communities, close to multiple shopping and dining options, FL-429 and just 20 minutes from Disney attractions. Don't miss out! Schedule your viewing today!
Listing is courtesy of: GECKO REALTY, INC (407-929-0264)
Listing Agent: Jeffrey Petch (407-928-1134)
131 SOUTHERN PECAN CIR #201, WINTER GARDEN, FL 34787
$235,000120 Days on yellowkey MLS ID: O6393946
REDUCED by $15,000 (6.0%) on 04/14/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 738 Built: 2005Monthly Fee: $309 Tax: $2,176 (2025)Community: Southern Pines CondoCondo
Taxes:$2,176
Elementary School: SunRidge Elementary
Remarks: Welcome to Southern Pines in the heart of Winter Garden. This well-maintained 1-bedroom, 1-bath upper-level condo offers a bright and functional layout with abundant natural light. The kitchen features granite countertops, ample cabinetry, and a practical layout that connects to the living and dining areas, creating a comfortable flow for everyday living. The open layout and high ceilings help maximize the space and give the unit an airy feel. The bedroom is comfortable and well-sized, offering a quiet and private retreat. This unit also includes an attached 1-car garage and additional storage, a valuable feature within the community. Southern Pines is a gated community with resort-style amenities including a pool, fitness center, tennis courts, basketball, racquetball, sand volleyball, playground, and clubhouse. The HOA covers lawn care, water, cable, and internet for added convenience. Ideally located near Winter Garden Village, Historic Downtown Winter Garden, and the West Orange Trail, with easy access to SR-429, Florida Turnpike, SR-408, and SR-50. Daily conveniences are just minutes away, including Publix (approx. 3 minutes) and Costco (approx. 8 minutes). Make this property your home today.
Listing is courtesy of: EC REAL ESTATE INVEST.& RENTAL (954-217-8649)
Listing Agent: Eloisa Armas Camacho (954-217-8649)
16893 BROADWATER AVE, WINTER GARDEN, FL 34787
$2,795,90043 Days on yellowkey MLS ID: O6415972
2 Days Off yellowkey (back on 6/29/2026)
Bed: 7 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 6289 Built: 2019Monthly Fee: $383 Tax: $25,448 (2025)Community: Waterside 90'SSingle Family
Taxes:$25,448
Elementary School: Whispering Oak Elem
Remarks: Under contract-accepting backup offers. Experience elevated lakefront living in this former builder model home, perfectly positioned along the shores of Johns Lake in the sought-after Waterside community of Winter Garden. Designed to impress from the moment you enter, the residence showcases soaring ceilings, designer lighting, and expansive windows that fill the home with natural light while framing tranquil water views. The open-concept floorplan seamlessly connects the living, dining, and kitchen spaces, creating an ideal setting for both everyday living and entertaining. At the heart of the home, the chef's kitchen features an oversized island, abundant cabinetry, and generous prep space overlooking the main living areas. The first-floor primary suite serves as a private retreat with a spa-inspired bath featuring dual vanities, a freestanding soaking tub, walk-in shower, and two large walk-in closets. Offering six bedrooms, four-and-a-half baths, a dedicated office, formal dining room, bonus room, and an expansive upstairs game and media space, the home provides exceptional flexibility for multigenerational living, guests, remote work, and recreation. Designed to embrace its waterfront setting, the outdoor living spaces are a true extension of the home. A covered lanai with a summer kitchen overlooks a private backyard highlighted by a striking fountain, creating a resort-inspired atmosphere for entertaining or relaxing. Just beyond, a private dock provides direct access to Johns Lake for boating, fishing, paddleboarding, and unforgettable sunset views. Located just minutes from Historic Downtown Winter Garden, the West Orange Trail, Winter Garden Village, major highways, dining, shopping, and top-rated schools, this exceptional residence offers the rare combination of luxury, space, and waterfront living in one of Central Florida's most desirable locations.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Matt Tomaszewski (407-719-5956)
402 E MAPLE ST, WINTER GARDEN, FL 34787
$900,00043 Days on yellowkey MLS ID: O6412747
Bed: 6 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 2876 Built: 2021 Tax: $7,658 (2025)Community: East Garden Manor Add 03 RepSingle Family
Taxes:$7,658
Remarks: Rare opportunity to own a unique corner-lot property featuring two attached residences, each with its own street frontage, private entrance, covered front porch, two-car garage, no HOA, and identical floor plan. Unlike a traditional side-by-side duplex, each residence faces a different street, creating the appearance and feel of two individual homes while offering the convenience of a connected design. Designed for both comfort and flexibility, each home features a spacious living and dining area, a bright kitchen with French doors leading to the backyard, and a convenient first-floor guest powder bath. Upstairs, all bedrooms are thoughtfully positioned for added privacy. The primary suite includes a private ensuite bath, while the secondary bedrooms are generously sized and complemented by abundant storage throughout each residence. The Wilson Street residence has been thoughtfully upgraded with luxury vinyl flooring, an enhanced kitchen with stone counters and gas cooking, beautifully updated bathrooms, and an attractive staircase that adds character and style. The Maple Street residence has been a consistently popular rental and has been exceptionally maintained, offering a spotless interior that reflects pride of ownership. The location offers exceptional convenience with nearby access to Downtown Winter Garden, one of Central Florida’s most sought-after destinations. Enjoy a vibrant mix of locally owned restaurants, cafés, boutiques, specialty shops, the award-winning Winter Garden Farmers Market, seasonal festivals, live entertainment, and the renowned West Orange Trail. The property also provides convenient access to the Florida State Road 429, Florida State Road 408, and Florida’s Turnpike, making travel throughout Central Florida simple. Popular destinations, including Winter Garden Village, Walt Disney World Resort, major employment centers, shopping, dining, entertainment, parks, and everyday conveniences, are all nearby. Whether you’re seeking a property that offers exceptional flexibility for evolving lifestyle needs, the opportunity to generate rental income, or the convenience of two complete residences under one roof, this distinctive property delivers a rare combination of privacy, functionality, and long-term versatility. Opportunities like this are seldom available, especially with a layout that allows each residence to maintain its own identity while remaining connected.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)
Listing Agent: David Dorman (407-948-8295)
397 ERON WAY #42, WINTER GARDEN, FL 34787
$225,00029 Days on yellowkey MLS ID: O6420092
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1988 Tax: $276 (2025)Community: Townhomes Winter GardenCondo
Taxes:$276
Remarks: Virtually Staged. Welcome to one of the cutest townhomes in the heart of Downtown Winter Garden! This charming 3 Bedroom, 2 bath home offers the perfect blend of comfort, covenience and one of Central Florida's most sought-after lifestyles. Whether you're a first-time homebuyer, looking to downsize or searching for a fantastic investment opportunity, this home checks all the boxes. Inside, you'll find a functional floor plan with comfortable living spaces, spacious bedrooms and low-maintenance living so you can spend more time enjoying everything the area has to offer. Location is everything, and this one is hard to beat! Just minutes from the award-winning Historic Downtown Winter Garden, you'll love spending weekends exploring the nationally recognized Winter Garden Farmers Market, browsing unique boutiques, enjoying locally owned restaurants, coffee shops, breweries and year-round community events. Living here means embracing the famous Golf Cart District lifestyle. Hop in your golf cart and head downtown for dinner, live music, festivals or an evening stroll along Plant Street. Outdoor enthusiasts will appreciate easy access to the scenic West Orange Trail, offering miles of paved paths for walking, running and biking. Winter Garden continues to be one of Central Florida's most desirable communities thanks to its small-town charm, top-rated amenities, vibrant downtown, and convenient access to major highways, Orlando, world-famous attractions, shopping, dining and entertainment. Whether you're looking for a place to call home or an income-producing property in a highly desirable location, this adorable townhome offers incredible value and endless potential. Don't miss your opportunity to own a piece of the Downtown Winter Garden lifestyle! Schedule your private showing today and discover why so many people are proud to call Winter Garden home.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
17056 RED BIRD RD, WINTER GARDEN, FL 34787
$795,00032 Days on yellowkey MLS ID: G5113999
0 Days Off yellowkey (back on 6/27/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1709 Built: 1981 Tax: $1,474 (2025)Community: N/ASpa: NoSingle Family
Taxes:$1,474
Remarks: Under contract-accepting backup offers. Nestled on 2.5 beautiful acres just off Highway 429 in the highly desirable Avalon community of Winter Garden, this charming 3-bedroom, 2-bath home offers the perfect blend of privacy, tranquility, and convenience. Surrounded by mature trees and a peaceful, fenced setting, the property features a spacious Florida Room overlooking the serene backyard, creating the ideal space to relax and enjoy nature. Additional highlights include an oversized garage and a storage shed, providing plenty of room for vehicles, hobbies, and equipment. Located in ever-growing Winter Garden in West Orange County, residents enjoy easy access to the area's vibrant downtown filled with unique local shops, restaurants, walking and biking trails, parks, and year-round recreational activities. This exceptional property offers a rare opportunity to enjoy country-style living while remaining close to Orlando's world-famous attractions, major roadways, both Florida coasts, and everything that makes Central Florida such an outstanding place to live, work, and play.
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (352-729-6528)
Listing Agent: Betty Hensinger (352-267-5028)
14312 SUNBRIDGE CIR, WINTER GARDEN, FL 34787
$1,100,00035 Days on yellowkey MLS ID: O6414430
REDUCED by $100,000 (8.3%) on 06/26/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4225 Built: 2019Monthly Fee: $166 Tax: $13,616 (2024)Community: Bradford Creek IiSingle Family
Taxes:$13,616
Remarks: Welcome to luxury living in the highly desirable Bradford Creek community of Winter Garden. This stunning 5-bedroom, 4-bathroom residence offers 4,225 square feet of thoughtfully designed living space, combining elegance, comfort, and functionality. Built in 2019, this two-story home features an open-concept floor plan with spacious living and dining areas, a gourmet kitchen with premium finishes, and abundant natural light throughout. The expansive primary suite provides a private retreat with a spa-inspired bathroom and generous walk-in closets. Step outside to your own private backyard oasis featuring a beautiful screened-in pool, perfect for entertaining, relaxing, and enjoying Florida's year-round sunshine. Additional highlights include a 3-car garage, modern finishes, and ample space for family and guests. Conveniently located near top-rated schools, shopping, dining, major highways, and Orlando's world-class attractions, this exceptional property offers the perfect blend of luxury and location. Schedule your private showing today and discover everything this remarkable Winter Garden home has for you.
Listing is courtesy of: REALTY ONE GROUP MAGIC CITY (407-589-9080)
Listing Agent: Karen Vasquez Rodriguez (407-721-8642)
14187 JOMATT LOOP, WINTER GARDEN, FL 34787
$949,900121 Days on yellowkey MLS ID: O6393373
0 Days Off yellowkey (back on 6/24/2026)
Bed: 6 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4181 Built: 2019Monthly Fee: $70 Tax: $7,632 (2025)Community: Cypress Reserve Ph 2Single Family
Taxes:$7,632
Remarks: Rare opportunity to own a 6-bedroom, 4,181 sq ft home with water views in Winter Garden's Cypress Reserve community. Built in 2019, this spacious residence sits on a premium homesite with expanded distance from neighboring properties, providing privacy rarely found in newer construction neighborhoods. The home features a gourmet kitchen with two oversized islands, ideal for entertaining and everyday living. The open-concept layout flows seamlessly into large living and dining spaces filled with natural light and scenic water views. With six bedrooms and 3.5 bathrooms, this home offers exceptional flexibility for multigenerational living, guest accommodations, or dedicated work-from-home spaces. Located just minutes from Downtown Winter Garden, residents enjoy easy access to award-winning restaurants, boutique shopping, the popular Winter Garden Farmers Market, and miles of outdoor recreation along the West Orange Trail. The property is also near the highly anticipated Tucker Ranch Park development, which will bring new green spaces, trails, and community amenities to the area. Homes offering over 4,000 square feet with water views in Winter Garden are rarely available, making this an exceptional opportunity in one of Central Florida’s most desirable communities.
Listing is courtesy of: ELEVATE REAL ESTATE BROKERS (954-772-3870)
Listing Agent: Kelly Roth (352-514-5045)
14540 SUNBRIDGE CIR, WINTER GARDEN, FL 34787
$675,00036 Days on yellowkey MLS ID: O6416033
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2800 Built: 2019Monthly Fee: $180 Tax: $9,815 (2025)Community: Bradford CreekSingle Family
Taxes:$9,815
Remarks: Under contract-accepting backup offers. Virtually Staged. Welcome to luxury living in the exclusive gated community of Bradford Creek in Winter Garden. Built in 2019, this beautifully designed one story residence offers 4 bedrooms, 4 full bathrooms, 2 car garage, high ceilings, and an abundance of natural light. The open floor plan is perfect for everyday living and entertaining, showcasing elegant tile flooring throughout main living areas. The spacious family room flows seamlessly into the gourmet kitchen, which comes with a gas cooktop, premium cabinetry, and generous counter space. A separate formal dining room provides an elegant setting for gatherings and special occasions. Owner's suite features a luxurious spa inspired bathroom, an oversized walk in closet, and the convenience of direct access to the laundry room. All 3 additional bedrooms come with its own private bathrooms. Enjoy Florida outdoor living on the covered lanai overlooking the fenced backyard, with no rear neighbors for added privacy. Additional highlights include a Tesla NEMA 14-50 outlet for convenient EV charging, mature landscaping, and a quiet, beautifully maintained neighborhood atmosphere. Conveniently located just minutes from SR429, this home offers easy access to downtown Winter Garden, Winter Garden Village, Orlando Health facilities, shopping, dining, entertainment, and major commuter routes. Please call today for a private showing!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Priscilla Chan, Pa (407-588-8867)
1979 STANDING ROCK CIR, WINTER GARDEN, FL 34787
$520,00058 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
Taxes:$8,301
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 Agent: Ariel Vargas (407-558-5161)
13722 FOX GLOVE ST, WINTER GARDEN, FL 34787
$755,000199 Days on yellowkey MLS ID: O6371378
REDUCED by $4,990 (0.7%) on 06/01/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3082 Built: 2004Monthly Fee: $247 Tax: $10,614 (2024)Community: Stoneybrook West Ut 04 48 48Spa: YesSingle Family
Taxes:$10,614
Remarks: Under contract-accepting backup offers. BACK ON MARKET!!!! WOW!!! RECENT PRICE DROP BY $10,000 AND $3500 LENDER CREDIT OFFERED WITH JASON BAKER AT PRIMIS MORTGAGE!!! Welcome to this stunning 5 Bed, 3 Bath *POOL* home located on the 14TH HOLE in the esteemed community of Stoneybrook West in Winter Garden! Offering more than 3,000 square feet of living space, this residence combines elegance with functionality. You’ll be greeted by beautiful landscaping with stone accent columns as you walk up the pavered driveway to the front door. Step inside to the open floor plan with formal living room and dining room to each side of the foyer, and high ceilings and modern light fixtures throughout the home. Double doors open up to a bonus room, that can be used as a bedroom, game room, office, or other flexible space. The spacious kitchen boasts modern appliances, cabinetry with crown moulding, tile backsplash and a massive wrap-around breakfast bar overlooking the family room. A dinette is conveniently located just off the kitchen. The huge primary bedroom suite features extra sitting space with accented half walls and a bay window overlooking the backyard and French doors leading out to the lanai. The large en-suite primary bathroom includes his & hers sinks, a separate commode, beautifully tiled garden tub and standing shower with glass door, plus a walk-in closet with built-in organization. Four additional spacious bedrooms share two additional full baths, and there’s a full laundry room with a sink off of the two-car attached garage with additional storage space. Step outside the French doors from the living room to the beautiful screened-in lanai, featuring a built-in summer kitchen with bar perfect for entertaining friends and family! The sparkling blue HEATED POOL and HOT TUB are encompassed by the pavered pool deck and overlooks the beautiful backyard. The community offers a boat ramp, fishing areas, and lake access for water enthusiasts, a clubhouse, fitness center, and a large resort-style community pool. Residents can enjoy tennis courts, a golf course, basketball court, a playground, and feel at ease with a 24-hour guard-gated entrance ensuring a secure and peaceful living environment. This home offers a harmonious blend of comfort, style, and community amenities, making it an excellent choice for those seeking a vibrant and secure neighborhood in Winter Garden.
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Nastassja Toombs (910-703-6453)
214 S WOODLAND ST, WINTER GARDEN, FL 34787
$800,00051 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
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
$2,199,00070 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
$339,500106 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
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 Agent: Daniel Deluca (407-916-9780)
15327 HERON HIDEAWAY CIR, WINTER GARDEN, FL 34787
$885,000167 Days on yellowkey MLS ID: G5107891
REDUCED by $30,000 (3.3%) on 06/17/2026
Bed: 7 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4267 Built: 2012Monthly Fee: $128 Tax: $11,470 (2025)Community: Johns Lake Pointe A & SSingle Family
Taxes:$11,470
Remarks: Welcome to this stunning and spacious 7-bedroom home, located in one of Winter Garden’s most desirable areas, just minutes from Historic Downtown Winter Garden. Recently painted and thoughtfully updated, this property offers the perfect blend of comfort, style, and convenience. The expansive layout features generous living spaces, ideal for both everyday living and entertaining. Step outside to your private backyard oasis, complete with a beautiful pool—perfect for relaxing, hosting gatherings, or enjoying sunny days year-round. Recent updates enhance the home’s bright, fresh feel while preserving its timeless appeal. Ideally situated close to Winter Garden Village, as well as shopping, popular restaurants, top-rated schools, hospitals, and everyday essentials, this home delivers exceptional lifestyle convenience without sacrificing privacy or space. A rare opportunity to own a move-in-ready home in a prime location—this one truly has it all.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Marcus Correa, Pa (407-952-4470)
17314 BAL HARBOUR DR, WINTER GARDEN, FL 34787
$850,00057 Days on yellowkey MLS ID: G5112878
0 Days Off yellowkey (back on 6/15/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3261 Built: 2018Monthly Fee: $215 Tax: $11,383 (2025)Community: WatersideSingle Family
Taxes:$11,383
Remarks: Welcome to 17314 Bal Harbour Drive, a beautifully upgraded pool home in the sought-after Waterside community in Winter Garden, where luxury finishes, smart-home technology, and breathtaking water views come together in one exceptional property. From the moment you arrive, the home’s elegant curb appeal, fully fenced backyard, and impressive architectural details set the tone for what awaits inside. Step through the front entry into a bright and inviting foyer featuring ceramic tile plank flooring, tray ceilings throughout, and thoughtfully designed living spaces filled with upscale finishes. At the front of the home, Bedroom 2 offers a custom California walk-in closet, making it ideal for guests or multigenerational living. Nearby, Bathroom 2 features a stylish stand-alone shower, tile backsplash, and upgraded vanity. The flex room is perfect for a home office, media room, or playroom and showcases decorative shiplap accents, double-pane windows, custom-made glass double doors, and window treatments that complement the space. Continue into the heart of the home, where the gourmet kitchen is designed to impress with quartz countertops, stainless steel appliances, under-cabinet lighting, a convection oven, spacious pantry, pendant lighting with dimmers, and two coffee bars. The adjacent formal dining room is ideal for entertaining and includes designer lighting, shades, and curtains that convey with the home. The expansive great room is perfect for everyday living and gatherings, featuring built-in surround sound and beautiful views of the outdoor living area. Privately situated on the main floor, the primary suite offers tray ceilings, can lighting, a decorative light fixture, and elegant window treatments. The spa-inspired primary bathroom includes dual quartz vanities, a tiled walk-in shower with twin shower heads, a water closet, linen closet, and an oversized California walk-in closet. Upstairs, engineered hardwood stairs lead to a spacious loft area and Bedrooms 3, 4, and 5. Bedroom 3 features French closet doors, Bedroom 4 includes a walk-in closet and ceiling fan, and Bedroom 5 offers French doors, making it ideal as a bedroom, office, or hobby room. Bathroom 3 is appointed with dual sinks, granite countertops, and a tub/shower combination. Step outside to your private backyard retreat. The covered lanai overlooks a stunning saltwater pool with a 5-foot deep end, sundeck, and serene views of Avalon Lake. Entertain with ease using the outdoor kitchen featuring a gas grill, sink, and mini fridge while enjoying the Florida lifestyle. Additional upgrades include Ecobee smart thermostats, a Lutron lighting system with dimmers, Alexa voice-controlled lighting, motion-activated closet lights, reverse osmosis system, water softener, washer and dryer, and Simply Safe doorbell and security cameras. For added peace of mind, the home also features a brand-new AC system with a 10-year warranty. Residents of Waterside enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dock, and pavilion. Don’t miss this opportunity to own a move-in-ready luxury home with premium upgrades, exceptional outdoor living, and stunning water views in one of Winter Garden’s most desirable communities.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Regina Cruz (352-988-7488)
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