Location: Winter Garden , 34787
Do Not Show Listings
22 WINDTREE LN #203, WINTER GARDEN, FL 34787
$189,900151 Days on yellowkey MLS ID: S5139914
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1983Monthly Fee: $305 Tax: $875 (2025)Community: Windtree Gardens Condo Ph 01Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$875
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: THE BEST VALUE IN WINTER GARDEN | NEW ROOF | MOVE-IN READY. OWNER IS READY TO MAKE A DEAL! Stop your search at the LOWEST-PRICED, MOVE-IN-READY home in one of Central Florida’s most coveted zip codes. This solid BLOCK-STRUCTURE residence at 22 Windtree Ln #203 features a BRAND-NEW ROOF and unbeatable proximity to the magic of DOWNTOWN WINTER GARDEN. Just minutes from your front door, you can explore the boutiques of PLANT STREET, grab a craft brew at CROOKED CAN, or enjoy the famous weekly FARMERS MARKET. For the outdoor enthusiast, IMMEDIATE ACCESS to the WEST ORANGE TRAIL offers miles of scenic biking and jogging, while nearby LAKE APOPKA provides stunning sunsets. Whether you’re commuting via easy highway access or heading to WALT DISNEY WORLD just a short drive away, this home offers an INCREDIBLE LIFESTYLE at a price point that simply doesn't exist elsewhere in the area. Don’t miss the BEST DEAL IN TOWN—schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (407-706-5000)
Listing Agent: Daniel Betancourt (407-375-9142)
14501 GROVE RESORT AVE #3737, WINTER GARDEN, FL 34787
$350,00015 Days on yellowkey MLS ID: O6400544
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1396 Built: 2018Monthly Fee: $889 Tax: $6,686 (2025)Community: Grove Resort And Spa Hote Condominium 3Condo
Taxes:$6,686
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Turn-Key, Fully Furnished 3-Bedroom Condo at The Grove Resort & Water Park!Welcome to your personal slice of paradise at The Grove Resort & Water Park, one of Orlando’s most sought-after vacation destinations just 10 minutes from Walt Disney World! This beautifully appointed 3-bedroom, 2-bathroom model offers 1,396 sq ft of spacious living, located on a high floor with tranquil views from your private screened balcony—the perfect spot to unwind after a day of adventure.Inside, you’ll find a fully equipped kitchen with quartz countertops and stainless steel appliances, seamlessly connecting to an open-concept living and dining area designed for comfort and entertaining. The primary suite features a king-size bed, luxurious en-suite bathroom with double vanity, soaking tub, and separate glass shower. Two additional bedrooms with queen-size beds and a second full bathroom ensure privacy and comfort for family and guests alike.Indulge in resort-style living with world-class amenities, including Surfari Water Park with dual water slides, a FlowRider® double surf simulator, lazy river, multiple pools, spa, fitness center, arcade, mini golf, and Lake Austin access for fishing, paddle boating, and lakeside relaxation. The resort offers on-site dining, alfresco market, and complimentary shuttle service to Disney,making your vacation effortless and unforgettable.The Grove’s professional management team can handle everything, from maintenance to short-term rentals, ensuring your investment works for you even when you’re away. HOA fees cover all utilities, including electricity, water, cable, and high-speed internet.Whether you're seeking a luxurious vacation home or a high-demand investment property, this turn-key condo offers the ultimate Florida lifestyle.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Franklin Ortega (321-315-3017)
15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787
$1,100,00051 Days on yellowkey MLS ID: O6390971
1 Days Off yellowkey (back on 4/24/2026)
REDUCED by $50,000 (4.3%) on 03/31/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3556 Built: 2023Monthly Fee: $128 Tax: $10,299 (2025)Community: Johns Lake PointeSingle Family
Taxes:$10,299
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Under contract-accepting backup offers. Welcome to this Beautifully Designed David Weekley home, built in 2023 and meticulously maintained in the Overlook portion of Johns Lake Pointe offering over 3,500 square feet of thoughtfully designed living space on an oversized lot. From the moment you step inside, you’re greeted by luxury vinyl plank flooring, expansive 10-foot ceilings, and abundant natural light that create a warm yet refined first impression. Just off the entry, a private office provides the ideal work-from-home space, while a guest bedroom with a nearby full bath is perfectly tucked away for privacy and convenience. As you continue into the heart of the home, you’ll fall in love with the open-concept living area, where the family room, dining space, and gourmet kitchen come together seamlessly—perfect for both everyday living and entertaining. The kitchen serves as a true centerpiece, featuring an oversized island, designer finishes, and ample cabinetry, all overlooking the main living space. Upstairs, you will be greeted by a spacious bonus room that offers endless flexibility—ideal for a media room, game room, or secondary living area. The Master suite is a true retreat, complete with a private walk-out balcony, Tray ceiling and a luxurious en-suite bathroom featuring a standalone garden tub, oversized walk-in shower, and a massive walk-in closet. On the other side of the home, two bedrooms share a convenient Jack-and-Jill bathroom, while a third bedroom is nestled with a full bath just outside its door, providing privacy and ease. The upstairs laundry room adds everyday convenience. This home has been meticulously maintained throughout. The community features a resort-style pool, tennis courts, playground and clubhouse that includes a gym, yoga room, gathering area and kitchen. Neighborhood is minutes from Downtown Winter Garden and Winter Garden Village as well as within walking/biking distance from the elementary and middle school. Also conveniently located to most major highways making commuting to work easier than ever. Don't hesitate, make your appointment today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: T.J. O'Donnell (317-246-8190)
16716 WINGSPREAD LOOP, WINTER GARDEN, FL 34787
$495,00030 Days on yellowkey MLS ID: O6397108
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1676 Built: 2019Monthly Fee: $127 Tax: $5,006 (2025)Community: Hawksmoor-Ph 1Single Family
Taxes:$5,006
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Under contract-accepting backup offers. Welcome to 16716 Wingspread Loop, a beautifully maintained single-story home in the highly sought-after Hawksmoor community of Winter Garden. Built in 2019 and cared for by its original owner, this 3-bedroom, 2-bath residence is move-in ready with thoughtful upgrades throughout. The open layout creates an easy flow between the kitchen, dining, and living areas. The kitchen features warm honey-toned cabinetry, granite countertops, and generous storage. The spacious primary suite serves as a private retreat with a large bedroom, walk-in closet, and an en-suite bath with quartz countertops. Additional highlights include built-in cabinetry in the laundry room, with the washer and dryer conveying for added convenience. Enjoy Florida living outdoors on the private patio, perfect for relaxing or hosting friends. The two-car garage includes a durable epoxy-coated floor, and the paved driveway enhances the home’s curb appeal. All kitchen and laundry appliances are included. Located along Avalon Road, this home places you just minutes from Hamlin Town Center, Flamingo Crossings, Walt Disney World, FL-429, Orange County National Golf Center, Clermont, Windermere, and top-rated Orange County schools. Residents of Hawksmoor enjoy a variety of resort-style amenities, including a clubhouse with rentable event space, fitness center, pool and splash pad, outdoor summer kitchen and grill, yoga lawn, shaded playground, dog park, and scenic walking paths. Schedule your private showing today and experience everything this Winter Garden home has to offer. Transferable lifetime termite contract from Massey available.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
632 DHARMA CIR, WINTER GARDEN, FL 34787
$380,00036 Days on yellowkey MLS ID: O6396151
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1315 Built: 2000Monthly Fee: $78 Tax: $5,780 (2025)Community: Daniels Crossing Ph 03Single Family
Taxes:$5,780
Remarks: Located in Winter Garden, this 3-bedroom, 2-bath home features a private in-ground pool and a solar energy system. The home includes a new A/C unit, stainless steel appliances, and an extended driveway for guests. The pool (28’ x 15’) offers a screened enclosure, lighting, auto cleaner, child safety fence, and is both saltwater and solar-heated—perfect for year-round enjoyment. The home has a Screened in Patio. There is an underground drainage next to the pool for the overflow. Conveniently located near Highway 429 and the Florida Turnpike, with easy access to Winter Garden Village, Disney, the West Orange Trail, and Publix. Please schedule showings in advance.
Listing is courtesy of: LA ROSA RTY WINTER GARDEN LLC (407-614-5158)
Listing Agent: Edul Mohamed, Pa (407-760-0090)
9062 SONOMA COAST DR, WINTER GARDEN, FL 34787
$785,000206 Days on yellowkey MLS ID: O6352763
0 Days Off yellowkey (back on 4/24/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2909 Built: 2021Monthly Fee: $261 Tax: $10,736 (2024)Community: Waterleigh Ph 3B 3C & 3DSingle Family
Taxes:$10,736
Tax Year: 2024
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Special Financing Available — Ask for Details! Experience resort-style living in the highly desirable Waterleigh community of Winter Garden. This one-of-a-kind home sits on a rare, oversized lot with no rear neighbors, offering ultimate privacy and tranquility — perfect for families or anyone seeking a private retreat in one of Central Florida’s most sought-after neighborhoods. Step inside and fall in love with the bright open-concept layout, filled with natural light and elegant finishes throughout. The gourmet kitchen features stainless steel appliances, quartz countertops, and a large island that connects seamlessly to the dining and living areas — ideal for family gatherings and entertaining. The primary suite provides a private retreat with a spa-inspired bathroom and a generous walk-in closet. Enjoy peaceful mornings, weekend barbecues, or evening relaxation in your spacious backyard, with plenty of room for outdoor activities. Live your best life at Waterleigh — a community known for its resort-style amenities, including two clubhouses, sparkling pools, fitness centers, tennis courts, playgrounds, walking trails, dog parks, and even a community beach with lake access. HOA includes lawn care for true low-maintenance living. Located near Disney, Horizon West shopping and dining, top-rated schools, and major highways, this home offers both luxury and convenience in one of Winter Garden’s premier neighborhoods. Special Incentive: Through the seller’s preferred lender, qualified buyers can access temporary rate buydowns and forgivable down payment assistance, designed to lower monthly payments and increase affordability. (No obligation to use preferred lender. Programs subject to qualification and market conditions.) Please note: Photos #2–17 have been virtually staged for marketing purposes only.
Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)
Listing Agent: Asher Chen (407-717-5232)
5531 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$610,000100 Days on yellowkey MLS ID: O6378167
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2204 Built: 2016Monthly Fee: $188 Tax: $8,644 (2025)Community: Orchard Hills Ph 2 Signature LakesSingle Family
Taxes:$8,644
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills community of Winter Garden. Situated on a premium lot with no rear neighbors, this move-in-ready home offers a peaceful pond view and exceptional privacy. Soaring ceilings, elegant 20" tile flooring, and abundant natural light enhance the open-concept design. The designer kitchen features upgraded mocha cabinetry, granite countertops, an oversized eat-in island, drinking water filtration system, and a new Samsung refrigerator with transferable warranty through November 2030. High-end upgrades include dimmable lighting throughout, Level 2 EV charger, and a private home theater with Klipsch Reference Premiere speakers, Dolby Atmos surround sound, and a 150" motorized screen (theater components negotiable). Additional highlights include a two-car garage with custom built-in cabinetry and charging station. Residents enjoy resort-style amenities: zero-entry pool, clubhouse, fitness center, playgrounds, dog park, scenic bike trails, and included lawn care and landscaping. Prime location just minutes to Publix, Walmart, Aldi, TJ Maxx, Cinepolis, Urban Air, dining and cafés; 10 minutes to Winter Garden Village, 17 minutes to Costco. Zoned for A-rated, highly sought-after schools within a short bike ride.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Olga Kaza, Pa (407-756-6318)
5413 NEW INDEPENDENCE PKWY, WINTER GARDEN, FL 34787
$488,00038 Days on yellowkey MLS ID: S5146601
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2131 Built: 2012Monthly Fee: $264 Tax: $5,449 (2025)Community: Signature Lakes Ph 02 A B H I JTownhouse
Taxes:$5,449
Remarks: Beautiful 4-bedroom, 2.5-bathroom townhouse located in the desirable Winter Garden area. The primary bedroom is conveniently located downstairs, offering comfort and privacy, while upstairs you’ll find additional spacious bedrooms. This home features a modern layout perfect for everyday living and entertaining, along with a cozy patio, a 2-car garage, and ample natural light throughout. The community also offers great amenities including a pool and clubhouse, tennis court and more ...Located in a quiet community, close to everything you need. Perfect for living or investing.Ideally located near Publix, Walmart, major expressways, and just minutes from Winter Garden Village, Walt Disney World Resort, cinemas, restaurants, and more. All appliances and the pergola on the patio are included.
Listing is courtesy of: MD3 HOMES LLC (407-557-8810)
Listing Agent: Monica Duran (407-702-5796)
7526 SPRING VALLEY ST, WINTER GARDEN, FL 34787
$676,24516 Days on yellowkey MLS ID: G5111448
0 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2680 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Taxes:$0
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley model features 2,102 square feet of well-designed living space across two stories, with an above-garage Apt 576 sqft.This home includes 3 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for both daily living and entertaining. The primary suite is located on the first floor for added privacy, with a luxurious bath and walk-in closet. Upstairs, two additional bedrooms and a full bath provide flexible living options for guests or family members. The apartment is above the garage with a private entrance. This neighborhood features a variety of townhomes and single-family homes on multiple-sized homesites, with spacious floor plans designed to support a wide range of lifestyles, from growing families to move-up buyers seeking more room to live and entertain. Located just minutes from Hamlin Town Center, Winter Garden Village, and historic Downtown Winter Garden, Hamlin Meadows places shopping, dining, and entertainment close to home. Residents will also enjoy access to nearby parks, trails, and outdoor recreation, along with proximity to highly regarded Orange County schools, including Hamlin Elementary, Hamlin Middle, and Horizon High School.
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
776 RAINFALL DR, WINTER GARDEN, FL 34787
$550,00016 Days on yellowkey MLS ID: O6400904
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2238 Built: 2007Monthly Fee: $92 Tax: $7,884 (2025)Community: Black Lake Park Ph 02Single Family
Taxes:$7,884
Remarks: GREAT LOCATION & LAKE VIEWS! Welcome to this immaculately maintained corner-lot gem, featuring 3 bedrooms plus a versatile Office/Den and 2 full bathrooms. The open-concept floor plan is designed for both elegant entertaining and comfortable daily living, flowing seamlessly from the formal living/dining area into a spacious family room. The gourmet kitchen is a chef’s dream, boasting granite countertops, a cooktop, built-in oven, and beautiful 42” cabinetry. Retreat to the private Master Suite—a true oasis featuring a generous walk-in closet, dual sinks, a garden tub, and a separate shower. Step outside to your covered rear patio to unwind and enjoy breathtaking lake views and sunsets. Located just minutes from Winter Garden Village and Historic Downtown, this upscale community offers unparalleled amenities: a private boat ramp on a skiable lake, fishing dock, community pool, tennis, basketball, soccer fields, and a playground. With easy access to the 429, 408, and Turnpike, your commute is a breeze. Don’t miss this opportunity—start living your best life today!
Listing is courtesy of: ONLI REALTY GROUP LLC (352-278-8544)
Listing Agent: Vinny Machado Da Silva (352-278-8544)
14501 GROVE RESORT AVE #2534, WINTER GARDEN, FL 34787
$225,000137 Days on yellowkey MLS ID: O6369252
REDUCED by $10,000 (4.3%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1396 Built: 2018 Tax: $8,154 (2024)Community: Grove Residence & Spa Hotel Condo IiCondo
Taxes:$8,154
Remarks: VACATION Investment opportunity at The Grove Resort & Water Park, Orlando—welcome to Unit 2534. This fully furnished 3-bedroom, 2-bath CONDO-HOTEL is positioned in one of Central Florida’s highest-demand VACATION RENTAL communities. The spacious Jasmine floor plan sleeps 8 and includes a king suite, two queen beds in the guest room, and a pull-out sofa in the living room. Designed for durability and guest appeal, the unit features quartz countertops, stainless steel appliances, in-unit laundry, and an oversized screened balcony overlooking tranquil resort and conservation views. AS A SHORT-TERM RENTAL PROPERTY, owners are allowed personal use up to 179 days a year, with full on-site property management available to handle bookings, housekeeping, maintenance, and guest services year-round. This hassle-free model makes it ideal for out-of-state, international investors, or active vacation home investors seeking passive income. The Grove Resort is a full-service destination featuring Surfari Water Park with lazy river and FlowRider surf simulator, three additional pools, Lake Austin access for water sports and fishing, fitness center, arcade, indoor glow mini golf, restaurants, bars, spa, and 24-hour concierge. Daily Disney shuttles and proximity to major attractions that drive strong guest occupancy. HOA fee covers all utilities, including electric, water, cable, WiFi, pest control, and insurance—offering predictable, streamlined costs for owners. With high rental demand, professional management, and a below-market price point, this unit offers strong ROI potential in a market with continued tourism growth. Act now to capitalize on this prime income-producing asset in the heart of Orlando’s booming short-term rental zone. Agents, please Realtor's remarks for details.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jackie Cavada-Barrero (407-443-7776)
14766 ELLINGSWORTH LN, WINTER GARDEN, FL 34787
$1,099,00054 Days on yellowkey MLS ID: O6390518
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4661 Built: 2018Monthly Fee: $210 Tax: $14,115 (2025)Community: Oxford ChaseSpa: YesSingle Family
Taxes:$14,115
Remarks: Welcome to this beautifully upgraded 5 bedroom, 4 and a half bath pool and spa home located in the highly desirable, fully gated community of Oxford Chase! Zoned for top-rated schools, this home offers the perfect combination of luxury, privacy, and energy efficiency. This spacious residence features a 3-car garage, paver driveway, and impressive curb appeal. Inside, you’ll find thoughtfully designed living spaces including a formal dining room with a custom built-in bar, perfect for entertaining guests or hosting special occasions, multiple office spaces, upgraded flooring throughout, a large laundry room, private gated doggie retreat, and so much more. The primary suite is located on the first level, secluded for optimal privacy with oversized his and hers closets. Upstairs you'll find guest bedrooms, a large open air loft space, and plush movie theatre room. Step outside to your own gorgeous backyard oasis featuring a fully enclosed heated pool and spa, ideal for year-round Florida living. The backyard overlooks a peaceful green space with no rear neighbors, providing extra privacy and relaxing views. Enjoy outdoor entertaining with the fully equipped summer kitchen featuring a custom vented hood, perfect for grilling and gatherings. The home is also equipped with PAID IN FULL SOLAR PANELS offering incredible energy efficiency and the benefit of little to no electric bill. Located in a secure gated neighborhood close to top schools, shopping, dining, and major highways, this home truly has it all — privacy, premium upgrades, and resort-style outdoor living. Schedule your showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Jenna Palmero (407-697-8727)
15306 GILLIGAN CT, WINTER GARDEN, FL 34787
$925,00022 Days on yellowkey MLS ID: O6399653
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3127 Built: 2020Monthly Fee: $102 Tax: $8,308 (2025)Community: Winding Bay Ph 1BSpa: NoSingle Family
Taxes:$8,308
Remarks: Set within one of Winter Garden’s most sought-after communities, this thoughtfully designed two-story home offers a lifestyle defined by ease, connection, and everyday enjoyment. This 4-bedroom, 3.5-bath home with over 3,000 square feet features an open floor plan with a gourmet kitchen and a large island, perfect for both everyday living and entertaining. The main level includes a dedicated den/office, while the second floor offers a spacious loft, along with a fourth bedroom and full bath—ideal for guests or multi-generational living. Tree-lined sidewalks, friendly neighbors, nearby parks, and resort-style amenities create a setting that feels both relaxed and vibrant, while top-rated schools, convenient access to shopping and dining, and close proximity to Walt Disney World Resort. Positioned on arguably one of the BEST lots in the community, this home sits at the end of a quiet cul-de-sac with breathtaking, unobstructed pond and tree-lined views that create a peaceful and private backdrop. Inside, the home showcases extensive upgrades and thoughtful design throughout, including a kitchen with 42-inch cabinetry and additional custom upper cabinets, GE Profile appliances, and a seamless flow into the main living space highlighted by two expansive tri-sliders opening to the outdoor oasis. Custom floor-to-ceiling drapery adds elegance, while upgrades such as 8-foot doors throughout, level 4 wood-look tile flooring, upgraded carpet with 8-pound padding, 5 1/4-inch baseboards, and 7 1/4-inch shiplap accents in the hallway, kitchen, tech nook, and primary bedroom elevate the interior. Additional features include custom plantation shutters on the first floor, upgraded glass doors in the front den/office, Cat 6 wiring throughout with pre-wiring for PoE security cameras, and a new alarm system with wireless sensors on all doors and windows. The home has been meticulously maintained with quarterly HVAC servicing, gutters installed since purchase, and a freshly painted exterior completed in 2025 using upgraded Sherwin Williams 25-year paint. Step outside to a private outdoor retreat featuring fresh landscaping, a fully fenced side yard, a privacy-enhancing podocarpus hedge, and custom paver walkways with additional space for storage. The backyard feels like a private Central Florida escape, where an 18,000-gallon resort-style saltwater pool serves as the true centerpiece, complete with a lounging platform overlooking the serene pond and tree-lined backdrop. The pool is thoughtfully designed with sealed pavers, a striking midnight blue interior finish, a fountain with dual deck jets, two multicolor LED lights, and a Pentair smart system for remote control, all professionally serviced weekly. The screened enclosure allows for year-round enjoyment, while the community dog park directly across the street adds everyday convenience for pet lovers. From the upstairs loft and bedrooms, enjoy views of Disney fireworks, adding a magical touch to everyday living. This move-in ready home is prepared for its next chapter, with community amenities that include a resort-style pool, oversized cabana, sports fields, playground, sidewalks, and a dog park. More than just beautifully upgraded, this home offers a rare opportunity to own a meticulously maintained, design-forward property in a premier location, delivering both luxury and lifestyle in one exceptional package—a place to settle in, build memories, and truly feel at home in Winter Garden.
Listing is courtesy of: REAL ESTATE HOUSE FL INC (407-484-0005)
Listing Agent: Gretchen Carlson (407-484-0005)
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00068 Days on yellowkey MLS ID: O6386607
1 Days Off yellowkey (back on 4/23/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2125 Built: 2015Monthly Fee: $41 Tax: $2,734 (2024)Community: Island Pointe SubSingle Family
Taxes:$2,734
Remarks: Under contract-accepting backup offers. Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, with a versatile flex room to the right—perfect for a home office, formal dining room, playroom, or whatever suits your lifestyle.The open-concept design seamlessly connects the kitchen, dining, and family areas, creating an ideal space for entertaining. The large kitchen island is perfect for cooking, casual meals, or hosting friends and family. Sliding glass doors open to create an effortless indoor-outdoor living experience—perfect for those quintessential Florida days. The split floor plan offers privacy, with the primary suite serving as a true retreat, complete with high ceilings, a double vanity, and a spa-like shower. On the opposite side of the home, you’ll find three additional spacious bedrooms, each with plantation shutters and high end laminate flooring. After a long day, unwind on your fully screened back porch with space for multiple seating areas, or head to the side yard to tend your garden. The thoughtfully designed outdoor living space offers plenty of room for grilling, dining, and relaxing—an entertainer’s dream. Just minutes from your front door, Winter Garden’s vibrant Plant Street awaits, offering an award-winning farmer’s market, local dining, boutique shopping, art galleries, Crooked Can Brewery, the West Orange Trail, and year-round festivals.This is a rare opportunity to own a beautifully crafted home in one of Winter Garden’s most desirable neighborhoods—where modern living meets small-town charm. Call for your private showing today.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
15659 JUNGLE ALY, WINTER GARDEN, FL 34787
$435,00049 Days on yellowkey MLS ID: S5143684
INCREASED by $75,000 (20.8%) on 04/23/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1732 Built: 2021Monthly Fee: $203 Tax: $6,265 (2024)Community: Winding Bay Ph 2Townhouse
Taxes:$6,265
Remarks: Seller motivated. Beautifully maintained town home 3 bed and 3 bath in the desirable Horizon West area of Winter Garden! This charming alley-facing property features an open-concept floor plan with spacious living and dining areas, a modern kitchen with solid surface countertops, stainless steel appliances, and a large island perfect for entertaining. Upstairs offers generously sized bedrooms, including a private primary suite with walk-in closet and an-suite bath. Enjoy low-maintenance outdoor living with a private patio and rear-entry garage. Conveniently located near top-rated schools, shopping, dining, and major roadways. A fantastic opportunity to own in one of Central Florida’s most sought-after communities! Offers may be entered ONLINE through Tuesday, April 14, 2026 at 3:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing Agent: Dinorah Navarro (407-625-7522)
15543 PEBBLE RIDGE ST, WINTER GARDEN, FL 34787
$645,900568 Days on yellowkey MLS ID: O6250356
2 Days Off yellowkey (back on 4/23/2026)
REDUCED by $3,900 (0.6%) on 04/17/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3359 Built: 2001Monthly Fee: $233 Tax: $8,538 (2023)Community: Stoneybrook WestSpa: NoSingle Family
Taxes:$8,538
Elementary School: Whispering Oak Elem
Tax Year: 2023
Remarks: Under contract-accepting backup offers. Popular Stoneybrook West Subdivision - A gated golf community with 2255 homes. 2 Story, 4 Bedrooms, 3 Full Baths. Master is upstairs, huge bedroom, with walk in closet and master bath. A large 27x24 Bonus room over 3 Car Garage. One bedroom with guest bath downstairs also LR, DR, FR, Kitchen and Laundry. Off the master bedroom is a 12x22 Deck overlooking the screened pool and golf course. Nice quiet street also. The seller will give an allowance for new flooring & kitchen appliances, so buyer can pick their favorite colors.
Listing is courtesy of: RE/MAX SELECT GROUP (407-352-5800)
Listing Agent: Paul Mcgarigal (407-352-5800)
328 BAYSIDE AVE, WINTER GARDEN, FL 34787
$445,00022 Days on yellowkey MLS ID: O6396654
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $7 Tax: $5,354 (2025)Community: Kings BaySingle Family
Taxes:$5,354
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to easy Florida living in this charming 3-bedroom, 2-bath ranch-style home, perfectly positioned on a spacious corner lot in one of Winter Garden’s most desirable areas. With its single-story layout and inviting curb appeal, this home offers both comfort and convenience in a relaxed, open setting. Step inside to discover a bright and functional floor plan designed for everyday living and effortless entertaining. The generous living spaces flow seamlessly, while ample natural light enhances the home’s warm and welcoming feel. The split-bedroom design provides privacy, with a well-appointed primary suite and comfortable secondary bedrooms. Outside, the oversized corner lot offers endless possibilities—plenty of room for outdoor gatherings, gardening, or simply enjoying the Florida sunshine. Located well within the golf cart district, you’re just a short ride from the charm and energy of historic downtown Winter Garden. Enjoy easy access to local shops, dining, community events, and the popular weekly farmers market, all just minutes from your doorstep. This is a rare opportunity to own a beautifully situated home that combines classic ranch-style living with an unbeatable location. Call Today!
Listing is courtesy of: SOUTHERN HERITAGE REALTY, INC (407-877-6928)
Listing Agent: Jim Kernohan (407-450-3861)
14501 GROVE RESORT AVE #2438, WINTER GARDEN, FL 34787
$224,000359 Days on yellowkey MLS ID: O6306977
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1396 Built: 2018 Tax: $8,035 (2024)Community: Grove Residence Y Spa Hotel Condo IiCondo
Taxes:$8,035
Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Perfect as a family getaway or a high-performing investment property, this beautifully designed fully furnished 3-bedroom, 2-bath condo is located in the luxurious Grove Resort & Water Park in Winter Garden, FL. Thoughtfully outfitted with every comfort, this turn-key home welcomes you with style and convenience. Enjoy resort-style living with world-class amenities including a thrilling water park with slides, a lazy river, surf simulator, multiple pools, a full-service spa, fitness center, on-site dining, and 24-hour concierge service. The Grove also offers a hassle-free rental program, making ownership seamless and profitable. Situated just minutes from Walt Disney World and Orlando’s premier attractions, this is a rare opportunity to own a slice of paradise in a prime location. Don’t miss out—schedule your private tour today! Offers may be entered ONLINE through Friday, May 8, 2026 at 4:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Rick Brown (407-393-5901)
15327 GILLIGAN CT, WINTER GARDEN, FL 34787
$664,80023 Days on yellowkey MLS ID: O6398756
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2506 Built: 2021Monthly Fee: $103 Tax: $7,266 (2025)Community: Winding Bay Ph 1BSingle Family
Taxes:$7,266
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained multi-generational home nestled on a quiet cul-de-sac in the highly desirable Winding Bay community of Horizon West in Winter Garden. This thoughtfully designed 4-bedroom, 3-bath residence features a private 1-bedroom suite, perfect for in-laws, aging parents, or guests. The suite offers its own laundry closet, kitchenette, and a well-appointed bathroom with a walk-in shower and granite vanity, providing both comfort and independence. Inside the main home, you’ll find a bright and spacious open-concept split floor plan that blends functionality with modern style. Elegant plantation shutters are featured throughout the home, adding both charm and privacy, while tile flooring spans the main living areas for durability and easy maintenance. A versatile flex space is ideal for a home office, art studio, or den. The chef-inspired gourmet kitchen is the heart of the home, showcasing a large island, abundant cabinetry, granite countertop and built-in stainless-steel appliances, including a new cooktop. It flows seamlessly into the expansive family room, complete with built-in surround sound, perfect for entertaining or relaxing movie nights. The primary owner’s suite is a private retreat featuring a tray ceiling, walk-in closet, and a spa-like ensuite bathroom with dual sink vanity with granite countertop and an impressive walk-in shower with multiple shower heads, including a rain feature. Step outside to enjoy the wide, screened-in covered lanai overlooking a fully fenced backyard, ideal for entertaining or unwinding in a peaceful setting. The 2-car garage offers additional storage space to meet your needs. Residents of Winding Bay enjoy access to resort-style amenities, including a community pool and playground, all just minutes from Walt Disney World, Hamlin Town Center, top-rated dining, shopping, placing you close to the best of Winter Garden and the greater Central Florida area. Convenient access to Highway 429 makes commuting a breeze. Don’t miss the opportunity to own this exceptional home. Schedule your private showing today!
Listing Agent: Giovanni Sanginesi (407-276-0025)
13386 PEACEFUL MELODY DR, WINTER GARDEN, FL 34787
$799,99071 Days on yellowkey MLS ID: S5144786
5 Days Off yellowkey (back on 4/23/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2856 Built: 2026Monthly Fee: $125 Tax: $500 (2025)Community: Serenade At OvationSingle Family
Taxes:$500
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Step into modern elegance with this stunning new construction home that perfectly blends style, comfort, and MULTI-GENERATIONAL LIVING. Nestled on a premium lot that backs directly to serene conservation land, this home offers the ultimate in privacy and picturesque views. As you enter the home, one is greeted by 8 foot doors, Mohawk nimbus oak luxury vinyl flooring and 5 inch baseboards throughout. The open-concept living space is an entertainer’s dream, with a chef-inspired kitchen boasting Barnett Linen color cabinets with light rail and 6" bow pull hardware, Carrara Breve eased edge quartz countertops, polished chrome Sterling Traverse pulldown faucet, stainless steel single basin undermount sink and Passion Blanco gloss 3x8 backsplash tile to the ceiling. The sleek finishes, ample cabinetry, and large island overlooking the sunlit dining and living areas provide the perfect entertaining space. The thoughtfully designed layout features a first-floor master suite, providing a private retreat with spa-like amenities such as 12x24" Emser Porto Ivory Matte colored floor tile, Barnett Linen colored gentlemen's height vanity with Carrara Breve Quartz countertops, oval undermount sinks, Sterling Valton 4" Centerset Lavatory Faucet and glass shower enclosure with chrome handle finish and 12x24" inch tile walls to the ceiling. Back through the living area, a first-floor guest wing adds convenience and flexibility, making hosting visitors or multi-gen living a breeze. Upstairs, a spacious loft/game room offers endless possibilities - home theater, playroom, or even a stylish home office. The second floor also consists of 3 beds and 2 baths, one with full ensuite, the other Jack and Jill style. Outside, enjoy the best of Florida living with an oversized porch for al fresco dining and a backyard that feels like your own private oasis, bordered by lush, untouched conservation land. Whether you’re sipping your morning coffee on the patio or gathering for an evening barbecue, the setting is sure to impress. Only 20 minutes to Magic Kingdom (NO highway driving needed for access!), less than 3 miles to Flamingo Crossing Shopping area, less than 10 miles to Hamlin Town Center, and 30 minutes to Millenia and the Outlet Malls, this home provides all that Orlando Living has to offer.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Marissa Crawford (407-361-7400)
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