Location: Winter Garden
Do Not Show Listings
5561 CYPRESS HILL RD, WINTER GARDEN, FL 34787
$595,00057 Days on yellowkey MLS ID: O6383015
0 Days Off yellowkey (back on 4/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2470 Built: 2016Monthly Fee: $188 Tax: $5,339 (2025)Community: Orchard Hills Phase 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,339
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Welcome home to this truly exceptional, move-in ready two-story gem in the highly desirable Orchard Hills community of Winter Garden—showing like a brand-new model home! Meticulously maintained by the owners, this nine-year-old home feels fresh, modern, and beautifully cared for from the moment you arrive. Step inside to an inviting open-concept design featuring stylish wood-look tile throughout the first floor, a bright and spacious living area, and a stunning, modern kitchen complete with a large center island, stainless steel appliances, quartz countertops, and abundant cabinetry—perfect for entertaining or everyday living. A versatile bonus room near the rear of the home offers the ideal space for a home office or guest retreat, along with a convenient half bath and extra storage. Enjoy Florida living with the charming, enclosed patio that connects to the rear-entry two-car garage with additional storage. Upstairs, a generous loft leads to three bedrooms, including a serene primary suite with a private balcony overlooking tranquil pond views. The spa-like ensuite bath features a walk-in shower, soaking tub, and private water closet. Additional upgrades include a full home fire sprinkler system, helping reduce homeowners’ insurance costs, and rain gutters. Residents of Orchard Hills enjoy an amenity-rich lifestyle, including a pool, clubhouse, fitness center, playgrounds, dog park, grilling area, and frequent events. The HOA covers exterior maintenance, lawn care, landscaping, and outdoor pest prevention—making life truly low-maintenance. Just minutes from Disney World, major highways, shopping and dining, this home is a rare opportunity you won't want to miss!
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Kathy Mcdonald (407-973-4026)
5526 TINY RD, WINTER GARDEN, FL 34787
$1,675,000250 Days on yellowkey MLS ID: O6334009
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2474 Built: 2007 Tax: $10,165 (2024)Community: NoneSingle Family
Taxes:$10,165
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Under contract-accepting backup offers. A Rare Slice of Serenity in the Heart of Horizons West – 5526 Tiny Road Tucked away on nearly five peaceful, rolling acres, this one-of-a-kind property offers the perfect blend of natural beauty, privacy, and access to everything the Horizons West area has to offer — all without the restrictions of an HOA. Located within the boundaries of the desirable Independence/Summerport area, this estate gives you the best of both worlds: rural charm and freedom, with the benefits of nearby neighborhoods, sidewalks, and community trails. Set just off Tiny Road, where major improvements are planned — including landscaped medians and 10-foot sidewalks — the entrance to the property will soon benefit from enhanced curb appeal and accessibility. Just a short walk away, the brand-new Orange County Library is currently under construction, promising a state-of-the-art community resource just minutes from your doorstep. Directly behind the property, the 225-acre Horizons West Sports Complex is taking shape, featuring planned amphitheaters, walking and biking paths, equestrian trails, and expansive green spaces — a future hub for recreation, events, and gathering. This property is also zoned for horses, a rare offering in such a prime location. You can enjoy sunrises and sunsets from the elevated ridge, surrounded by wide-open skies, a private pond, and visits from wild turkeys, native birds, and even a few roosters in the distance. The custom-built home (2007) offers 2,400 sq ft under air, with 3 bedrooms, a spacious loft, and 2.5 bathrooms — plus a half bath in the oversized 3+ car garage. A flex space provides room for an office, home gym, or guest suite. Inside, the layout is filled with natural light and includes a gourmet kitchen and flowing open spaces. Relax on the expansive front porch under the attached gazebo, or enjoy peaceful views from the screened-in rear lanai overlooking the nature preserve. All of this just a bike ride away from the restaurants, shops, and movie theater at Hamlin Town Center, with convenient access to top-rated schools and major roads. 5526 Tiny Road is a rare chance to live in peaceful privacy, with room to grow, create, and connect — a lifestyle property with heart, freedom, and long-term value.
Listing is courtesy of: BUYER REBATES REALTY (407-629-2300)
Listing Agent: Sean Popat (407-399-1669)
1073 VINSETTA CIR, WINTER GARDEN, FL 34787
$725,000268 Days on yellowkey MLS ID: O6328215
INCREASED by $10,000 (1.4%) on 04/02/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3568 Built: 2014Monthly Fee: $95 Tax: $5,710 (2024)Community: Avalon Reserve Village 1Single Family
Taxes:$5,710
Elementary School: Whispering Oak Elem
High School: West Orange High
Middle School: Hamlin Middle
Remarks: PRIME Winter Garden location off Hardwood Marsh and Avalon! It’s not often a home hugs you when you walk through the door, the hint of warmth through the window and the enveloping feeling of home. A true place of stillness that is so hard to find nowadays. The Hawthorne model is really the perfect floor plan! With space for everyone still managing to embody an inviting coziness with over 3,500 sq ft of living space for you, your family…an unexpected guest! A quaint entry with 2 areas for an office, formal living opens up to a 2-story ceiling in the family room with adjacent kitchen! A large island has seating and room for a full size dining table in the breakfast nook! An abundance of windows and sliding glass doors reveal a lovely view of the tropical foliage. Enjoy cooking while watching movies keeping everyone together! The thoughtful design gives ample prep space and tons of cabinet storage! This perfect entertaining area spills into the oversized screened lanai that can be enjoyed year round with an array of fruit trees and a natural privacy from the mature landscape. The primary suite is on the first floor ensuring you can enjoy this home even into your golden years! A relaxing escape with back yard views, ensuite bath with large soaking tub, shower, dual vanities and 2 walk-in closets! Again, storage is not an issue in this home! On the second floor, stairs lead to a huge loft/bonus room that peers over the family room with a half wall that aids in noise reduction. Want a more open feel? Check out Etsy’s decorative railings to personalize your loft! Built-in character ensures many creative ways to utilize the space! This upstairs is “cart wheel” worthy and the options are endless! The bedrooms are spread apart giving every occupant their own area! A centrally located study/art nook even has an opening to the downstairs so you never miss the words "dinner's ready"! This fantastic layout allows you to fulfill your every wish for not only a beautiful, but organized space! No more trying to make things work, because it all fits! They say #1 rule in buying real estate is LOCATION & this community of well manicured lawns ensures your biggest investment is a good one! You can still find that hometown feel you see in movies, with the weekly Farmer's Market in Historic Downtown, soccer and baseball fields bustling on Saturday mornings! Monthly and seasonal events are also abundant and so fun! Pop over to Epic or Disney for the afternoon or enjoy delicacies from around the world at Epcot! All just a short drive from home! The house across the street recently sold for 870k!
Listing is courtesy of: LAKEFIELD REALTY GROUP LLC (407-383-6497)
Listing Agent: Autumn Makin (352-455-0044)
10007 LITTLE ALCOVE LOOP, WINTER GARDEN, FL 34787
$999,990246 Days on yellowkey MLS ID: S5132434
1 Days Off yellowkey (back on 4/3/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2921 Built: 2018Monthly Fee: $250 Tax: $6,381 (2024)Community: Waterleigh Ph 2BSingle Family
Taxes:$6,381
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Under contract-accepting backup offers. Stunning Emerald serie house, Selden model built in 2018 well maintained, featuring 4 bedrooms, 3.5 bathrooms, and approximately 2,920 sq ft of living space. Situated on a premium corner lot of about 10,585 sq ft, this home offers a 3-car tandem garage, spacious backyard, private wooded views, and a screen-enclosed private pool—perfect for year-round Florida living. The open-concept design includes a formal dining room, elegant foyer with wrought-iron staircase, and a gourmet kitchen with a large island, 42” cabinets with crown molding, granite countertops, stainless steel appliances, and a convenient drop zone from the garage. The owner’s suite boasts a tray ceiling, a spa-like en-suite bathroom with dual sinks, a garden tub, and a spacious walk-in closet. Additional features include a durable concrete tile roof, dual A/C units, and numerous upgrades: exterior lighting, sealed paver driveway and porch, landscape lighting, decorative stonework, epoxy-finished garage floor, and professional landscaping. Lawn care is included with HOA fee. Located in the highly sought-after Waterleigh community in Winter Garden, residents enjoy resort-style amenities: two community clubhouses, 4 resort-style pools, 2 fitness center, beach volleyball, 2 tennis courts, mini-golf, community garden, dog park, fishing pier, and scenic walking/biking trails. The neighborhood is beautifully landscaped with lakes, green spaces, and planned community events. Conveniently located just minutes from Historic Downtown Winter Garden, Winter Garden Village, and easy access to SR-429 for a quick commute to Orlando and Walt Disney World. Zoned for top-rated schools: Atwater bay Elementary, Water Spring Middle, and Horizon High School.
Listing is courtesy of: MBT REALTY LLC (407-283-3351)
Listing Agent: Victor Barroeta (407-818-5286)
617 CANOPY ESTATES DR, WINTER GARDEN, FL 34787
$1,200,00033 Days on yellowkey MLS ID: O6389100
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3624 Built: 2019Monthly Fee: $255 Tax: $16,181 (2025)Community: Canopy Oaks Ph 1Single Family
Taxes:$16,181
Elementary School: Lake Whitney Elem
Middle School: SunRidge Middle
Remarks: One or more photo(s) has been virtually staged. One or more photos are virtually staged. Location. Luxury. Architectural character. Welcome to The Sanibel, affectionately known as “The Castle,” an award-winning home just minutes from the charm and energy of Historic Downtown Winter Garden. This stunning residence blends timeless Italian-inspired architecture with modern comforts, creating a home that feels both elegant and inviting. From the moment you arrive, the home makes a memorable first impression with its arched wood double doors, custom soffit lighting, and classic concrete tile roof. Step inside and you’re greeted by soaring ceilings, detailed beams, and crown molding that add warmth and sophistication to the open-concept living spaces—perfect for both everyday living and entertaining. The gourmet kitchen is designed to impress, featuring premium KitchenAid appliances, a natural gas cooktop, built-in refrigerator, 42” custom cabinetry, a hidden walk-in pantry, and a reverse osmosis water system. Whether hosting guests or enjoying a quiet night at home, this kitchen is the heart of it all. The first floor offers exceptional flexibility with a private office and a Junior Owner’s Suite—ideal for guests or multi-generational living. Upstairs, the primary suite becomes your personal retreat with a unique round spa-inspired bathroom, oversized walk-in closet, wet bar, and access to a private balcony. Two additional en-suite bedrooms, a loft, and an upstairs laundry room complete the second level. Step outside and enjoy multiple spaces designed for relaxing and entertaining, including Trex-decked balconies, a summer kitchen, and a peaceful fountain feature. Additional highlights include surround sound wiring, a whole-home generator, and thoughtful upgrades throughout the home. Beyond the property itself, the location truly sets this home apart. You’re just minutes from Downtown Winter Garden’s award-winning farmers market, vibrant restaurants, charming boutiques, scenic parks, and top-rated schools—with easy access to major highways for commuting throughout Central Florida. Recognized as Florida’s Best Model Home by the SEBC Excel Awards, The Sanibel offers a rare opportunity to own a home that combines architectural distinction, luxury features, and an unbeatable Winter Garden lifestyle. Note: One image includes a virtually added pool to illustrate potential backyard possibilities.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
7389 JOHN HANCOCK DR, WINTER GARDEN, FL 34787
$1,200,00068 Days on yellowkey MLS ID: O6379851
2 Days Off yellowkey (back on 2/16/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4006 Built: 2019Monthly Fee: $140 Tax: $14,349 (2024)Community: Overlook 2 At HamlinSingle Family
Taxes:$14,349
Elementary School: Independence Elementary
Remarks: This impressive 5-BEDROOM, 4-bath POOL HOME offers over 4,006 sq ft of living space, designed for comfort, functionality, and modern living. Built in 2019, this home sits on a well-positioned lot with sidewalks and paved streets in the highly sought-after HAMLIN COMMUNITY. A large paver driveway and covered entry framed by upgraded landscaping set the tone for this beautifully appointed home. Inside, a grand two-story foyer opens to formal living and dining spaces accented by soaring ceilings, architectural detailing, and an inviting mix of upgraded ceramic tile and carpet throughout. The open-concept floor plan is ideal for both everyday living and entertaining. The gourmet kitchen features upgraded cabinetry with crown molding, granite countertops, stainless steel appliances, a center island, butler’s pantry, and a breakfast nook, all flowing seamlessly into the expansive two-story family room. Additional FLEX SPACES include a study/media room and a spacious loft, offering options for a home office, playroom, or additional living area. A private FIRST-FLOOR PRIMARY SUITE provides a relaxing retreat with a spacious bath and walk-in closets, while the additional bedrooms offer versatility for guests or multi-generational living. Step outside to a backyard that feels like a tropical escape, with a CUSTOM POOL & SPA, OUTDOOR KITCHEN, and gorgeous WATER VIEW. This backyard is perfect for relaxing or hosting gatherings. Built in 2019 and situated on a well-positioned lot with sidewalks and paved streets, this home is located in a resort-style community featuring a clubhouse overlooking Lake Hancock, pool, fitness center, playground, amphitheater, walking and biking trails, canoes, and a full calendar of social activities. Conveniently located just off SR-429, this home offers easy access to downtown Orlando, shopping, dining, and entertainment.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jason Asa (407-337-7702)
1923 JEAN MARIE DR, WINTER GARDEN, FL 34787
$580,00087 Days on yellowkey MLS ID: G5106903
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2916 Built: 2007Monthly Fee: $90 Tax: $4,275 (2024)Community: Carriage Pointe A-I & LSingle Family
Taxes:$4,275
Remarks: GATED COMMUNITY !! ENTICING CURB APPEAL !! 3 CAR GARAGE !! Welcome home to Carriage Pointe !! One of the most highly desired communities in Winter Garden !! This home has beautifully manicured lush landscaping and complimented by a BRICK PAVER DRIVEWAY AND WALK leading to the COVERED FRONT PORCH with DOUBLE LEADED GLASS ENTRY DOORS !! ROOF 2022 !! This 4 bed/ 3 bath VERSATILE FLOOR PLAN boasts 2,916 climate controlled sq. ft. The grand foyer with SOARING CEILINGS opens to the formal Living Room and the elegant trey ceiling Dining Room both providing plentiful NATURAL LIGHT !! The chef friendly kitchen has ABUNDANT CABINETRY, granite counters, tasteful backsplash, SS appliances, BREAKFAST BAR ISLAND and spacious Dinette/Nook that flows seamlessly into the oversized Family Room that overlooks the lanai. The EXPANSIVE PRIMARY ENSUITE has a trey ceiling, bay window-sitting area, an enormous walk-in closet, dual vanities, garden tub and large shower stall. The opposite side of the home has two additional bedrooms with a shared bath, and a GUEST SUITE complete with full bath and separate entry. The SCREENED LANAI overlooks the backyard with a HOT TUB !! The community has a tennis court, playground, soccer field and walking path. Location benefits include close drive to Disney/Theme parks, shopping, Toll 429, and numerous activities in downtown HISTORIC WINTER GARDEN !! Make this home your new address !!
Listing is courtesy of: EXIT REALTY TRI-COUNTY (352-385-3948)
Listing Agent: Steven Boone (352-430-4144)
514 DUNBAR AVE, WINTER GARDEN, FL 34787
$295,00013 Days on yellowkey MLS ID: O6394414
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1162 Built: 2006 Tax: $2,616 (2025)Community: Joe Louis ParkSingle Family
Taxes:$2,616
Elementary School: Maxey Elem
Middle School: Lakeview Middle
Remarks: Under contract-accepting backup offers. Welcome to this charming and beautifully updated 3-bedroom, 2-bath bungalow located minutes from the heart of highly desirable Winter Garden! This move-in ready home offers the perfect blend of character, comfort, and modern upgrades—including a brand-new roof for peace of mind. Step inside to discover a warm and inviting layout with stylish updates throughout, creating a light and airy feel that’s perfect for both everyday living and entertaining. The cozy bungalow design offers functionality and charm, making it an ideal primary residence, second home, or investment opportunity. Living in Winter Garden means enjoying one of Central Florida’s most sought-after communities, known for its historic downtown, vibrant lifestyle, and strong sense of community. Just minutes away, you’ll find the award-winning Winter Garden Farmers Market, held every Saturday and featuring over 100 vendors, live music, and a lively, family-friendly atmosphere . Stroll along the charming brick-lined streets of downtown, filled with boutique shops, local dining, and cultural attractions. Don’t miss your opportunity to own this adorable, updated bungalow in one of Central Florida’s most beloved communities—schedule your private showing today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Tara Heard (407-637-4634)
6072 GLORY BOWER DR, WINTER GARDEN, FL 34787
$479,00032 Days on yellowkey MLS ID: O6389207
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2128 Built: 2020Monthly Fee: $97 Tax: $7,764 (2025)Community: Hamilton GardensSingle Family
Taxes:$7,764
Elementary School: Hamlin Elementary
Remarks: Welcome to this beautiful single-family home located in the desirable Winter Garden, within the charming Hamilton Gardens-Natural gas community. Built in 2020, this well-maintained home features 3 bedrooms plus a Flex area on the first floor, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan that is perfect for modern living. The spacious living and dining areas flow seamlessly into the kitchen, creating an ideal space for both everyday living and entertaining. All bedrooms are conveniently located upstairs, offering privacy and a quiet retreat from the main living areas. The second floor also includes a versatile loft, perfect for a home office, media room, or play area. One of the highlights of this location is its exceptional convenience. The home is minutes away from Hamlin Town Center, where you’ll find a wide variety of restaurants, shopping, entertainment, and everyday conveniences. Families will appreciate the highly rated A-school zone, making this neighborhood especially desirable for homeowners. Residents of Hamilton Gardens enjoy fantastic community amenities including a resort-style swimming pool, soccer field, and playground, providing plenty of outdoor recreation options for all ages. With its modern layout, prime location, and excellent community amenities, this home offers the perfect combination of comfort, convenience, and lifestyle in one of Central Florida’s most sought-after areas.
Listing is courtesy of: INTOP REALTY LLC (407-233-5453)
Listing Agent: Yujie Jiang (201-328-7856)
15070 SUMMER HARVEST ST, WINTER GARDEN, FL 34787
$729,90013 Days on yellowkey MLS ID: S5146881
REDUCED by $15,100 (2.0%) on 04/03/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 2931 Built: 2025Monthly Fee: $233 Tax: $9,545 (2024)Community: Harvest/OvationSingle Family
Taxes:$9,545
Remarks: PRICED TO SELL! 5BR Corner Lot + Private In-Law Suite + Soaring Ceilings Near Amenities Rare opportunity to own a spacious 5-bedroom home with a private in-law suite above the garage. Located on a premium corner lot just steps from the amenity center, this home offers flexibility, privacy, and modern upgrades. Priced aggressively for a quick sale—this one will not last. Welcome to this beautifully designed 5-bedroom, 4.5-bathroom home offering space, flexibility, and modern comfort in a highly desirable location. Situated on a corner lot near the community amenity center, this home stands out with its thoughtful layout, soaring ceilings, and multiple private living areas—perfect for today’s lifestyle. A rare and valuable feature, the separate suite above the garage includes a private bedroom, kitchenette, and full bathroom, ideal for extended family, guests, or a dedicated home office. The open-concept first floor features a bright, inviting living space paired with a cabinet-rich gourmet kitchen designed for both everyday living and entertaining. Kitchen highlights include an oversized island with ample counter space, gas range, upgraded refrigerator, exterior-vented microwave, garbage disposal, and a hidden trash cabinet. The kitchen overlooks a paved private courtyard, creating a low-maintenance outdoor space perfect for relaxing or entertaining. A first-floor bedroom with a full bathroom and a dedicated flex space—perfect for a home office—add even more versatility. Upstairs, you’ll find a spacious primary suite with high ceilings, two additional bedrooms, and a convenient laundry room with washer and dryer. Additional features include a corner lot offering added privacy, a fence planned or installed for outdoor enjoyment, gas tankless water heater, EV charging station in the attached garage, and landscaping included. The home is walking distance to community amenities including a pool, clubhouse, and parks (currently in progress). Schedule your private showing today!—homes with this layout, location, and value don’t come available often.
Listing is courtesy of: 365 REALTY, INC. (407-944-1365)
Listing Agent: Robert Benenati (407-944-1365)
2031 WINTERMERE POINTE DR, WINTER GARDEN, FL 34787
$489,00019 Days on yellowkey MLS ID: O6394075
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 2000Monthly Fee: $90 Tax: $4,516 (2025)Community: Wintermere PointeSingle Family
Taxes:$4,516
Remarks: Under contract-accepting backup offers. Opportunity Awaits – 4 Bedroom Pool Home in a Prime Location! Welcome to this spacious 4-bedroom, 2-bath home tucked away on a quiet dead-end street in a highly desirable neighborhood. As you enter the home, you will find a generous open floor plan and a beautiful kitchen. The primary bedroom features an en suite bathroom with a double vanity, separate shower and garden tub. Step out to a large enclosed patio and a fully fenced backyard featuring a private pool- perfect for relaxing or entertaining. There’s also an additional fenced-in area, ideal for pets, gardening, or creating your own outdoor retreat. Conveniently located just minutes from shopping, dining, and everyday essentials, you'll love the balance of peaceful living and easy access to everything you need. With your personal touch, this property can truly shine and become your dream home or a fantastic investment opportunity. Schedule your showing today!
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Desiree Pizio (321-663-9104)
10067 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787
$1,170,000145 Days on yellowkey MLS ID: O6361968
5 Days Off yellowkey (back on 4/2/2026)
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4305 Built: 2020Monthly Fee: $159 Tax: $13,997 (2024)Community: Watermark Ph 4Single Family
Taxes:$13,997
Elementary School: Panther Lake Elementary
Remarks: Under contract-accepting backup offers. Welcome Home! This beautifully renovated 4,305 sq. ft. single-family residence offers the perfect blend of modern upgrades and inviting comfort, located in one of Winter Garden’s well sought-after communities. Discover elegant porcelain tile flooring throughout the first floor, leading to a spacious, updated kitchen featuring quartz countertops, a smart cooktop, and decorative glass cabinetry, ideal for both everyday living and entertaining. The gorgeous master suite includes a custom built-in walk-in closet, providing both style and functionality. With 6BR/5BA, there’s plenty of space for family and guests alike. Enjoy Florida living at its finest in your outdoor oasis, complete with a gazebo and a built-in fire pit seating area, perfect for relaxing evenings or weekend gatherings. The three-car split garage adds convenience and ample storage.Recently renovated and freshly painted, this home is truly move-in ready. Located in a wonderful community offering two sparkling pools and a playground, you’ll love the nearby amenities that make Winter Garden such a special place to live. Tour Today!
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Shi Knoblock (407-719-8651)
869 BENDING OAK TRL, WINTER GARDEN, FL 34787
$535,000155 Days on yellowkey MLS ID: O6358341
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1975 Built: 2012Monthly Fee: $109 Tax: $5,262 (2024)Community: Oaks/Brandy Lake 01 Rep A & BSingle Family
Taxes:$5,262
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bath home located in The Oaks at Brandy Lake; Situated in the highly desirable golf cart district of Winter Garden. The home offers an open-concept layout featuring a spacious dining and living area with sliding glass doors that leads to a covered patio and FENCED back and side yard. The kitchen includes stainless steel appliances (New Refrigerator 2024), (New Garbage Disposal 2025) and generous counter space. The home features FULLY PAID SOLAR PANELS and rear 2-car garage (New Garage Door Opener 2025) and ample parking in the front of the home. Residents have access to community amenities including a pool and playground. Conveniently located a little over 1 mile away from Downtown Winter Garden, you can enjoy the weekly Farmer's Market and plethora of shops and restaurants. You also have access to major highways (about a 5 minute drive to 429 and Turnpike).
Listing Agent: Xiomara Pratts (407-993-2865)
11045 HOLLOW BAY DR, WINTER GARDEN, FL 34787
$749,90017 Days on yellowkey MLS ID: O6394192
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2113 Built: 2025Monthly Fee: $295 Tax: $3,196 (2025)Community: WaterleighSingle Family
Taxes:$3,196
Remarks: Why wait to build when you can move right into this gently used, practically brand-new home in the highly sought-after Waterleigh community? Nestled on a peaceful, quiet street with no rear neighbors, this 4-bedroom, 3-bathroom gem offers over 2,000 sq. ft. of functional living space, perfect for modern family living. Step inside and immediately appreciate the open, airy layout, featuring wood-look tile floors throughout for a sleek, low-maintenance finish. The heart of the home is an inviting living area, ideal for both everyday living and entertaining. The spacious kitchen offers ample storage, and the bright bedrooms provide a retreat at the end of the day. No detail has been overlooked in this home’s design. Situated on a beautiful conservation/water lot, you’ll enjoy serene views and privacy with no rear neighbors. It's the perfect backdrop for your outdoor living moments, whether you're relaxing on your patio or taking in the tranquil surroundings. Waterleigh offers an active and vibrant community lifestyle, with access to multiple resort-style amenity centers, including clubhouses, indoor fitness centers, walking trails, playgrounds, and sports fields—perfect for all ages. The community also provides lawn care and weed control as part of the HOA, so you can spend more time enjoying your beautiful home and less time maintaining it. The community is conveniently located near top-rated schools, including Water Spring Elementary and Middle School, and Horizon High School, making it ideal for families. You’re just a short drive away from everything Central Florida has to offer—amusement parks, shopping, dining, and entertainment. With easy access to I-4 and 429, commuting to all parts of the area is a breeze. Plus, the charming historic district of Downtown Winter Garden is just minutes away, featuring unique boutiques, restaurants, and entertainment options. This beautiful home is truly move-in ready and waiting for its next owner. Don’t miss out on the chance to make it yours—schedule your private showing today before it's SOLD!
Listing is courtesy of: VOSS REALTY INC (407-456-0777)
Listing Agent: Lindsay Kaye Voss (407-456-0777)
419 WINTER GROVE BOULEVARD, WINTER GARDEN, FL 34787
$874,99012 Days on yellowkey MLS ID: O6395693
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2650 Built: 2026Monthly Fee: $240 Tax: $1,955 (2025)Community: Winter GroveSingle Family
Taxes:$1,955
Elementary School: SunRidge Elementary
Remarks: Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. Step into the Imperial by Pulte Homes, where luxury and convenience seamlessly combine to create a truly elevated living experience. This remarkable 5-bedroom, 3.5-bathroom home with a 2-car garage offers unparalleled craftsmanship and thoughtful design throughout. The open-concept layout flows effortlessly, creating an expansive, airy feel that exudes both sophistication and comfort. On the first floor, discover a private en suite bedroom with a walk-in closet and elegant quartz countertops—a perfect retreat for guests. At the heart of the home, the chef-inspired kitchen is a true masterpiece, featuring 42” soft-close cabinetry, striking quartz countertops and decorative tile backsplash. Whirlpool stainless steel appliances, including a built-in natural gas cooktop and a refrigerator, make cooking a pleasure. The kitchen seamlessly connects to the café and gathering room, where a sliding glass door opens to the covered lanai, enhancing the flow of indoor-outdoor living. The first floor also offers a convenient powder room, perfect for guests. Upstairs, the luxurious owner’s suite is a private sanctuary, featuring a spacious walk-in closet and a spa-like en suite bathroom with quartz-topped dual vanity sinks and a frameless glass enclosed shower. The loft area provides the perfect space to unwind, while three additional bedrooms and a bathroom complete the upper level. For added convenience, a thoughtfully located upstairs laundry room with utility sink simplifies everyday tasks. Beautiful wood-look luxury vinyl plank flooring is found throughout the main living areas of the first-floor, at the stair case, and first floor bedroom, while plush, stain-resistant Shaw carpet can be found throughout the upstairs bedrooms and loft, and tile complements the bathrooms and laundry room. Designer-curated finishes elevate every corner of this home, including pendant light pre-wire and under cabinet lighting in the kitchen, brushed nickel plumbing fixtures and hardware, 2” faux wood blinds, and Whirlpool washer and dryer enhance the home's style and comfort. This home is equipped with a smart thermostat, smart doorbell, and LED downlights, ensuring your home is as connected as it is beautiful. This home offers the perfect combination of luxury, convenience, and modern design—an ideal place to live and relax. Schedule a tour today!
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
WINTER GARDEN, FL 34787
$688,78913 Days on yellowkey MLS ID: G5110452
0 Days Off yellowkey (back on 4/1/2026)
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3117 Built: 2026Monthly Fee: $150Community: Hamlin Meadows At HamlinSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Carter offers a thoughtfully designed layout featuring 4 bedrooms, 3.5 baths, and a 2-car garage. The open-concept floor plan showcases a spacious family room that flows seamlessly into a well-appointed gourmet kitchen with a large island, ample cabinetry, and a walk-in pantry, along with a dedicated dining area perfect for everyday living and entertaining. The primary suite provides a private retreat, complete with a luxurious en-suite bath and a generous walk-in closet. Additional bedrooms are well-sized and offer comfort and privacy for family or guests. A standout feature of this home is the above-garage apartment, complete with its own bedroom, full kitchen, living area, laundry, and closet—ideal for guests, multigenerational living, or potential rental income
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
17061 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$565,99013 Days on yellowkey MLS ID: G5110436
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2515 Built: 2026Monthly Fee: $122Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. SAMPLE IMAGE PRE DESIGN CENTER PRICING The Carter at Hamlin Meadows: Luxury Living with Unmatched Privacy. Discover the perfect blend of elegance and functionality in the Carter model by Dream Finders Homes. This impressive 2,515 sq. ft. residence features 4 bedrooms, 3.5 bathrooms, and a rear-load 2-car garage, thoughtfully designed for modern lifestyles. The heart of the home is an expansive open-concept main level, where a 15' x 17' great room flows seamlessly into the gourmet kitchen and dining area. The kitchen is a chef's dream, anchored by a massive center island and a walk-in pantry. A rare and highly desirable feature is the first-floor bedroom with a walk-in closet—perfect for visitors or a quiet home office. The primary Owner’s Suite offers a spa-like experience with a generous walk-in closet and luxurious bath. Hamlin Meadows is the newest jewel of Horizon West, offering a diverse mix of rear-load homes in a highly sought-after Winter Garden location. Enjoy being minutes away from the vibrant Hamlin Town Center and major expressways.
8197 LAKEVIEW CROSSING DR, WINTER GARDEN, FL 34787
$434,900113 Days on yellowkey MLS ID: TB8458488
0 Days Off yellowkey (back on 4/2/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1685 Built: 2016Monthly Fee: $265 Tax: $6,511 (2024)Community: Waterleigh Ph 1BSingle Family
Taxes:$6,511
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. SELLERS ARE MOTIVATED AND ARE OFFERING CLOSING COST CONCESSIONS PLUS A FREE HOME WARRANTY TO THE BUYER, MAKING THIS AN EXCEPTIONAL OPPORTUNITY. Welcome to 8197 Lakeview Crossing Drive in Winter Garden, Florida, a MOVE-IN-READY 3 BEDROOM, 2 BATHROOM home located in one of Central Florida’s most desirable and fast-growing areas, known for TOP-RATED SCHOOLS, convenient access to major highways, shopping and dining, and the charm of DOWNTOWN WINTER GARDEN with its farmers markets, trails, and community events. This home has had ONE ORIGINAL OWNER SINCE 2016, has been PROFESSIONALLY CLEANED, and features CARPETS JUST CLEANED THROUGHOUT THE PROPERTY WITH RECEIPT ATTACHED. The kitchen offers STAINLESS STEEL APPLIANCES, and the home includes a WASHER AND DRYER, plus an ADDITIONAL NEVER-USED WASHER AND DRYER IN THE GARAGE along with an EXTRA REFRIGERATOR, providing excellent functionality and storage. The AC WAS JUST SERVICED RECEIPT AND SERCIVE REPORT ATTACHED, and the TWO-CAR GARAGE adds everyday convenience. For full transparency and buyer peace of mind, a FULL HOME INSPECTION REPORT IS ATTACHED DONE DEC 2025, ALONG WITH A PASSING 4-POINT AND WIND MITIGATION REPORT COMPLETED IN DECEMBER 2025; the ROOF HAS APPROXIMATELY 16 YEARS OF REMAINING LIFE, which may allow the buyer to RECEIVE INSURANCE DISCOUNTS. ALL DOCUMENTATION IS ATTACHED IN THE MLS, making this a truly turnkey home in a prime Winter Garden location.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Betsy Tinervin (727-270-0912)
1836 WINGED ELM PL, WINTER GARDEN, FL 34787
$462,00030 Days on yellowkey MLS ID: O6390771
REDUCED by $13,000 (2.7%) on 04/02/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1712 Built: 2005Monthly Fee: $55 Tax: $6,075 (2025)Community: Winter Garden Trls 01-3Single Family
Taxes:$6,075
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) have been virtually staged to showcase the incredible potential of this beautiful home. A 100-Day Home Warranty is also available at closing, offering added peace of mind for the new owner. Welcome to your dream home in the highly desirable city of Winter Garden, where comfort, space, and location come together perfectly! This beautiful 4-bedroom, 2-bath residence offers a spacious and functional layout designed for both everyday living and effortless entertaining. Step inside to discover a private and relaxing primary suite featuring a walk-in closet, a luxurious soaking tub, and a separate walk-in shower—creating the perfect retreat at the end of the day. The modern kitchen is equipped with stainless steel appliances and a convenient breakfast bar, ideal for casual dining, morning coffee, or gathering with family and friends. Enjoy Florida living at its best with a screened-in patio, perfect for relaxing evenings or weekend get-togethers while enjoying the outdoor breeze. Additional highlights include a two- car garage, ample living space, and a layout designed with comfort in mind. Location is everything, and this home delivers! With quick and easy access to 429, commuting is a breeze. You'll also be just minutes from Downtown Winter Garden. With its prime location, desirable features, and move-in ready appeal, this home is an incredible opportunity you won’t want to miss. Schedule your private showing today before this Winter Garden gem is gone!
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Jeff Jones (205-902-3584)
4937 WILDWOOD POINTE RD, WINTER GARDEN, FL 34787
$869,00072 Days on yellowkey MLS ID: S5142834
1 Days Off yellowkey (back on 4/2/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3289 Built: 2015Monthly Fee: $187 Tax: $10,004 (2024)Community: Orchard Hills Ph 2Single Family
Taxes:$10,004
Remarks: Under contract-accepting backup offers. Welcome to this spacious and beautifully maintained 5-bedroom, 4-bathroom home in the desirable Winter Garden area. Situated on a premium lot with no rear neighbors, this home backs onto a peaceful preserve, offering privacy and natural views. The open-concept layout features a large kitchen with granite countertops, stainless steel appliances, and a center island—perfect for cooking and entertaining. The first floor includes a guest bedroom and full bath, ideal for visitors or multi-generational living. Upstairs, the generous master suite offers a walk-in closet and a luxurious en-suite bathroom. Three additional bedrooms and a versatile loft complete the second floor. Enjoy outdoor living on the open lanai, overlooking a spacious backyard and the quiet conservation area—an ideal setting for morning coffee or evening relaxation. Located in a well-maintained community that offers access to a clubhouse, resort-style pool, and fitness center, and conveniently close to top-rated schools, shopping, dining, and major highways—this home delivers both comfort and lifestyle.
Listing is courtesy of: OLIVO REALTY GROUP, LLC (917-687-3373)
Listing Agent: Yadira Olivo (917-687-3373)
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