Location: Winter Garden , 34787
Do Not Show Listings
14501 GROVE RESORT AVE #1439, WINTER GARDEN, FL 34787
$180,00023 Days on yellowkey MLS ID: O6407410
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 2009Monthly Fee: $904 Tax: $6,553 (2025)Community: Grove Resort And Spa Hotel CondominiumSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,553
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Fully Furnished & Turn-Key Ready! Welcome to your dream vacation retreat at the highly sought-after Grove Resort & Spa—a full-service luxury resort just 10 minutes from Disney World! Enjoy the ultimate resort lifestyle with incredible on-site amenities: a full water park with dual water slides, a FlowRider® double surf simulator, lazy river, splash zones, multiple pools, private cabanas, restaurants, spa, fitness centers, arcade game room, mini golf, walking trails, and more. The resort also features a convenient alfresco market and offers complimentary shuttle service to Disney for your added ease. The unit is fully furnished with a king-sized bed in the primary suite and a queen bed in the secondary bedroom—perfect for families or guests. Located just off I-192, you’re minutes from shopping, dining, and all of Orlando’s top attractions. Truly turn-key and resort living at its best—call today to schedule your private showing!
Listing is courtesy of: INTEREALTY SERVICE (626-328-8535)
Listing Agent: Emma Yue (626-328-8535)
12554 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$599,000258 Days on yellowkey MLS ID: O6346537
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2743 Built: 2025Monthly Fee: $96 Tax: $1,862 (2024)Community: Osprey Ranch-Ph 1Single Family
Taxes:$1,862
Tax Year: 2024
Remarks: This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with washer and dryer. Osprey Ranch, in the highly sought-after Horizon West area, offers a lifestyle of comfort and recreation. Community amenities include a resort-inspired pool and cabana currently under construction, plus a splash pad, playground, and dog park. Showings must be scheduled in advance with the listing agent.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Adriana Pl Franzoi (407-924-0872)
2230 ROMANUM DR, WINTER GARDEN, FL 34787
$565,00089 Days on yellowkey MLS ID: O6389947
1 Days Off yellowkey (back on 5/17/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2562 Built: 2014Monthly Fee: $207 Tax: $8,425 (2025)Community: Alexander RdgSingle Family
Taxes:$8,425
Elementary School: Hamlin Elementary
High School: West Orange High
Middle School: Hamlin Middle
Remarks: Motivated seller – bring your offers! Location, Location, Location! Don't miss the opportunity to own this beautiful and cozy 4-bedroom, 4-bath home featuring thoughtfully designed living spaces that combine comfort, functionality, and inviting charm. The main floor features all four bedrooms, offering convenience and privacy for everyday living. Upstairs, you’ll find a spacious bonus room with a full bathroom, perfect for a media room, game room, home office, or additional living space. This is the only area of the home with carpet, creating a comfortable and cozy environment for relaxation or entertainment. Throughout the main living areas, the home features luxury vinyl flooring, providing durability and a modern look while enhancing the overall warmth of the home. The kitchen opens beautifully to the main living area, creating a welcoming space for gathering with family and friends. The kitchen cabinets were recently refinished and painted, giving the kitchen a refreshed and updated appearance. Step outside and enjoy the screen-enclosed patio, offering a comfortable outdoor space where you can relax and enjoy Florida living with added protection from insects. The home also features attractive landscaping and brick pavers on the driveway and entrance, creating great curb appeal and a welcoming first impression. Additionally, the property includes solar panels, contributing to improved energy efficiency. This home offers a warm and inviting atmosphere with well-distributed spaces that make it perfect for both everyday living and entertaining. Schedule your private showing today and come experience the comfort and charm this home has to offer in a perfect location!
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcelle Da Silva Sampaio (407-369-3621)
9549 BOLERO RD, WINTER GARDEN, FL 34787
$997,000280 Days on yellowkey MLS ID: O6340193
2 Days Off yellowkey (back on 5/17/2026)
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3910 Built: 2021Monthly Fee: $271 Tax: $13,484 (2024)Community: Waterleigh Ph 3ASingle Family
Taxes:$13,484
Elementary School: Water Spring Elementary
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: Under contract-accepting backup offers. The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen faucet, recessed lighting, tile roof for added longevity, and more! Admire the curb appeal as you walk up to your covered front porch by way of the sealed brick paver sidewalk amidst luscious landscaping maintained entirely by the HOA. Relish in the wood plank tile that floor most of the downstairs for a highly desirable look as well as ease of maintenance. To the right of the entrance is a flex space (named the formal dining room by the builder) ready for you to make of it what you want. Continue into the main living space and soak in all of the lake views through the many windows on the back of the home. The gourmet kitchen is also in this open concept space for taking in the lake views, and it is truly a home chef's dream being lined with tons of cabinetry and countertop space. The dining space is right off the kitchen overlooking those beautiful lake views. The primary suite is tucked away privately in the back of the home downstairs and contains even more opportunities for lake viewing. A tray ceiling and custom designed closet make this space even more admirable. The en suite showcases a split dual vanity, massive walk-in shower, and a garden tub that all overlook the lake. Head upstairs via an upgrade staircase lined with wrought iron spindles and luxury vinyl flooring. The loft greets you with endless opportunities of how to customize this space for your enjoyment. A ceiling-mounted projector and theater screen are included with the sale. More windows allow in natural lighting as well as the views of the lake. A Jack-and-Jill bathroom connect bedrooms 2 and 3, and both rooms feature custom designed closets. Bedrooms 4 and 5 are also upstairs and adorned with custom designed closets, and their bathroom is outside of the bedrooms and houses a dual vanity with separate water closet. Head out back where your gargantuan backyard extends from the house to the edge of the waters of Lake Ihrig. Relish in the fact that the HOA maintains this entire extended backyard so you have even more time to enjoy this outdoor space that is extremely rare in Horizon West. The tandem 3-car garage efficiently utilizes every opportunity for space. Situated in the back of the community, you truly get the best of both worlds by enjoying the peace and quiet yet also being a short walk away from the vast amount of amenities, A-rated schools, and the shopping plaza. Waterleigh is building out its final phase, and the Emerald Series is no longer offered making this an even more unique and special opportunity. Inquire today on how to make this gem your own!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Jacquelyn Voigt (941-356-3956)
9318 MCLAREN ALLEY, WINTER GARDEN, FL 34787
$489,00024 Days on yellowkey MLS ID: S5150019
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1685 Built: 2020Monthly Fee: $257 Tax: $7,221 (2025)Community: Waterleigh Phase 3ASingle Family
Taxes:$7,221
Remarks: Beautiful corner-lot home in a highly desirable location and excellent condition featuring 3 spacious bedrooms, 2 full bathrooms, a 2-car garage, and a long driveway with space for 2 additional vehicles. This well-maintained, move-in ready property also includes solar panels and a water purification system, offering both comfort and energy efficiency. With great natural lighting and located in a quiet and convenient area, this home is perfect for families looking for comfort, savings, and an outstanding location.
Listing is courtesy of: MD3 HOMES LLC (407-557-8810)
Listing Agent: Jorge Sanchez Nunez (720-503-2753)
10103 AUSTRINA OAK LOOP, WINTER GARDEN, FL 34787
$970,00024 Days on yellowkey MLS ID: O6407394
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4305 Built: 2019Monthly Fee: $159 Tax: $13,406 (2025)Community: Watermark Ph 4Single Family
Taxes:$13,406
Remarks: Located in the highly desirable Watermark community in Horizon West, this beautifully maintained home offers the perfect combination of space, privacy, and convenience in one of Central Florida’s fastest-growing areas. One of the home’s standout features is the spacious first-floor primary suite, providing both comfort and privacy with an ideal layout for everyday living. The oversized backyard backs directly to a wooded conservation area with no rear neighbors, creating a peaceful setting rarely found in newer communities. Zoned for highly rated schools and just minutes from Hamlin Town Center, Disney, SR-429, and Winter Garden Village, the location offers exceptional access to shopping, dining, entertainment, and major roadways while still maintaining a quiet residential feel. Residents of Watermark enjoy resort-style amenities including a clubhouse, fitness center, tennis courts, playgrounds, walking trails, community pool, and even Disney fireworks views throughout the neighborhood. With generous living spaces, a highly functional layout, and a premium homesite offering both privacy and natural views, this home is a rare opportunity in one of Winter Garden’s most sought-after communities.
Listing is courtesy of: AMERICA REAL ESTATE COMPANY LL (407-234-5219)
Listing Agent: Wendy Wu (407-276-3691)
5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787
$618,00099 Days on yellowkey MLS ID: O6386791
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2458 Built: 2015Monthly Fee: $324 Tax: $8,569 (2025)Community: Overlook At HamlinSingle Family
Taxes:$8,569
Remarks: Under contract-accepting backup offers. Welcome to this beautiful 4-bedroom, 3.5-bath home in the highly sought-after Overlook at Hamlin community of Winter Garden. Ideally positioned with a serene front lake view, this well-maintained residence offers over 2,400 square feet of thoughtfully designed living space. The open-concept floor plan features a spacious kitchen overlooking the main living and dining areas, perfect for everyday living and entertaining. Upstairs, the generous primary suite and additional bedrooms provide comfort and privacy for the whole family. Enjoy outdoor living from the rear patio and the convenience of nearby Hamlin Town Center shopping, dining, parks, and top-rated schools, with easy access to FL-429. A wonderful opportunity to own in one of Winter Garden’s most desirable communities.
Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)
Listing Agent: Phoebe Yu (407-446-7588)
15518 FOUNTAIN COVE CT, WINTER GARDEN, FL 34787
$574,99026 Days on yellowkey MLS ID: O6407942
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2040 Built: 2018Monthly Fee: $342 Tax: $8,434 (2025)Community: Waterleigh Ph 1ASpa: NoSingle Family
Taxes:$8,434
Elementary School: Panther Lake Elementary
Remarks: Nestled within the exclusive Marina Bay enclave of Waterleigh, one of Horizon West’s most sought-after luxury communities, this beautifully upgraded 3-bedroom, 3-full-bathroom single-story home built in 2018 offers a rare combination of privacy, tranquility, and resort-style living. Marina Bay is a completed, quiet hideaway tucked away from the newer phases of the community with ongoing home construction and through traffic, while still offering access to Waterleigh’s extensive luxury amenities. Positioned on a peaceful cul-de-sac with a charming garden park at its center, this home enjoys a serene setting where neighbors gather to enjoy nightly Walt Disney World Resort fireworks views visible from the park, front porch, and multiple scenic areas throughout the community. Freshly repainted in Spring 2026, the home showcases thoughtful upgrades throughout. Inside, luxury vinyl plank flooring installed in 2025 flows through the main living areas, complementing the open-concept design with both style and durability. One standout feature is the oversized 3-car tandem garage with overhead storage racks, offering exceptional storage space rarely found in comparable homes. But you won’t need to store lawn care equipment. The HOA provides professional lawn maintenance including mowing, edging, weeding, landscape care, and irrigation maintenance for truly low-maintenance living. Outdoor living is equally impressive. The fully fenced backyard offers exceptional privacy thanks to the premium corner lot location tucked away from major roads and traffic. In 2025, the screened lanai was expanded with an extended paver patio, creating the perfect setting for entertaining, outdoor dining, or relaxing while enjoying breathtaking sunset views over the lake to the west. A dedicated paver pad for trash and recycling bins hidden behind landscaping was also added in 2025. Life in Waterleigh is designed to feel like an upscale resort vacation year-round, with scenic lakes, trails, parks, and gathering spaces woven naturally throughout the community. Residents enjoy multiple resort-style amenity centers, fitness centers, pools, playgrounds, sports fields, fishing, beach volleyball, hammock beach areas, scenic walking trails, dog parks, and even a private mini-golf course — a rare feature that helps set Waterleigh apart. Located minutes from State Road 429, the home offers quick access to Universal Orlando Resort, Walt Disney World Resort, Downtown Orlando, and Orlando International Airport. Nearby Hamlin features upscale dining, entertainment, luxury cinemas, and top-rated schools, while Downtown Winter Garden offers charming boutiques, dining, farmers markets, and historic charm. From the peaceful cul-de-sac setting and nightly Disney fireworks to the lake views, luxury upgrades, oversized garage, and unmatched amenity package, this home offers an exceptional opportunity to enjoy one of Horizon West’s premier resort-style communities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Erin Rison (407-844-8168)
6212 ARALIA IVY LN, WINTER GARDEN, FL 34787
$430,00074 Days on yellowkey MLS ID: O6394386
REDUCED by $4,900 (1.1%) on 05/14/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1560 Built: 2020Monthly Fee: $289 Tax: $6,732 (2025)Community: Hamilton Gardens Ph 2A & 2BTownhouse
Taxes:$6,732
Remarks: LOCATION! LOCATION! LOCATION! This spacious and beautiful two-story townhome offers the perfect blend of comfort, privacy, and convenience in the highly desirable Hamilton Gardens community. Enjoy an open-concept floor plan, freshly painted interior, and a private outdoor courtyard leading to a rear-entry two-car detached garage. The bright kitchen features granite countertops, a spacious pantry, and overlooks the dining area and great room, creating a seamless space ideal for entertaining. Large windows with blinds fill the home with natural light, enhancing the open feel throughout. Storage is abundant with a pantry, an under-stairs closet, and a generous walk-in closet in the owner’s suite. Upstairs, you’ll find 3 generous bedrooms, 2 bathrooms, and a convenient second-floor laundry. The owner’s suite boasts an enormous walk-in closet and peaceful views of beautiful mature trees. With no neighbors behind, this home offers a quiet, private setting that’s truly rare. Hamilton Gardens provides exceptional amenities, including a resort-style beach-entry pool, cabana, dog park, sports lawn, playgrounds, and scenic garden paths. Residents also enjoy nightly views of the Disney fireworks right from the community. Located just moments from Hamlin Town Center, you’ll have restaurants, cafés, entertainment, and a weekly farmers market less than a mile away. Convenient to SR 429, A-rated schools, top medical facilities, Winter Garden Village, Historic Downtown Winter Garden, and Windermere. A perfect combination of privacy, convenience, and resort-style living—come see it today!
Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)
Listing Agent: Olga Recean (253-285-2595)
16425 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787
$435,000104 Days on yellowkey MLS ID: O6383709
REDUCED by $25,000 (5.4%) on 05/16/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1662 Built: 2021Monthly Fee: $284 Tax: $6,683 (2024)Community: Hawksmoor-Ph 3Townhouse
Taxes:$6,683
Remarks: Welcome to 16425 Prairie School Dr, an exceptional 2021-built residence offering 3 bedrooms, 2.5 baths, and 1,662 square feet of thoughtfully designed living space in one of Winter Garden’s most sought-after growth corridors. Crafted for modern lifestyles, this impeccably maintained townhome showcases a bright, open-concept main level adorned with elegant ceramic tile flooring for both sophistication and durability. The seamless flow between the living, dining, and kitchen areas creates an inviting atmosphere perfect for entertaining or unwinding in refined comfort. Expansive windows bathe the space in natural light, enhancing its airy, upscale ambiance. Upstairs, a private retreat awaits. The spacious primary suite features a well-appointed en suite bath and generous closet space, offering a serene escape at the end of the day. Two additional bedrooms provide versatility for guests, a home office, or family living, complemented by a full bath. Plush carpeting throughout the upper level adds warmth and comfort, while a stylish half bath on the main floor ensures convenience for visitors. Set on a 2,538-square-foot lot, the property offers the ease of low-maintenance living without sacrificing outdoor enjoyment. The attached two-car garage provides secure parking and valuable storage — a premium feature in townhome communities. Located in Florida 34787, residents enjoy effortless access to upscale shopping, dining, scenic parks, and major thoroughfares connecting to Orlando and surrounding destinations. Offered at $460,000, this move-in-ready residence presents a rare opportunity to own a newer construction home that blends contemporary design with everyday luxury in the heart of Central Florida. Schedule your private showing today and experience elevated townhome living at its finest.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nairobi Rondon (786-935-0365)
15078 CANOPY COVER DR, WINTER GARDEN, FL 34787
$975,00038 Days on yellowkey MLS ID: O6404208
Bed: 3 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2270 Built: 2024Monthly Fee: $545 Tax: $10,412 (2025)Community: Del Webb OasisSingle Family
Taxes:$10,412
Remarks: This is it—the one buyers wait for and rarely catch in time. One of the final opportunities to own in Del Webb Oasis, a highly sought-after 55+ community by Pulte Homes, where lifestyle isn't an upgrade—it's built in. This extended Stardom Echelon isn't just a home—it's a fully dialed-in experience. Thoughtfully expanded and meticulously upgraded, it offers a private heated pool and extended lanai, creating a backyard designed for morning coffee, evening wine, and everything in between. The backyard view is pure nature—a lush tree line that provides a true sense of privacy with no rear neighbors in sight. The outdoor kitchen, electronic blinds, and fully fenced yard elevate both privacy and ease. And for those who appreciate a well-appointed bar setup, a custom coffee and bar station was added by the owner—a thoughtful touch not included in the original kitchen build. Inside, natural light pours into open living spaces anchored by a gourmet kitchen with an oversized island, built-in cabinetry, upgraded tile and flooring, and high-end appliances including a Samsung refrigerator. Every detail has been considered—from custom shelving throughout (primary suite, pantry, laundry, study, even garage entry) to a built-in vacuum system and in-wall pest control. The extended 3-car garage with epoxy floors and added storage offers the space you actually need—and even comes prepped for a whole-home water filtration system, ready for the next owner to complete. And then there's the community. Del Webb Oasis is where neighbors become friends and every day feels like a getaway—resort-style pool and spa, pickleball and tennis, a stunning clubhouse, fitness center, exercise equipment along the walking path trail and Parkette, fire pits, social clubs, and curated events. Lawn care is handled, so your time is truly your own. All just minutes from Walt Disney World Resort, Hamlin Town Center, and Downtown Winter Garden—with easy access to everything Central Florida offers. Homes like this don't come back around—especially not in communities like this. This is your chance to step into the next chapter, already fully upgraded and ready to enjoy from day one.
Listing is courtesy of: COLDWELL BANKER REALTY (407-696-8000)
Listing Agent: David Weiss (407-765-9020)
15401 PORTER RD, WINTER GARDEN, FL 34787
$549,900161 Days on yellowkey MLS ID: S5140743
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2455 Built: 2015Monthly Fee: $242 Tax: $8,271 (2024)Community: SummerlakeSpa: NoSingle Family
Taxes:$8,271
Elementary School: Summerlake Elementary
Remarks: (3D tour link attached!) Welcome to this well-appointed single-family home offering 2,455 sq. ft. of living space in the desirable Winter Garden area. Featuring 5 bedrooms and 3 full bathrooms, this residence provides generous space and flexibility for comfortable everyday living, guests, or work-from-home needs. All the bedrooms upstairs and the stairs are laminate flooring. Only the bedroom downstairs is carpet. The thoughtfully designed floor plan includes multiple living areas and a layout well suited for both relaxation and entertaining. With five bedrooms, the home offers versatility for growing households or those seeking additional space. Situated within a welcoming residential community, residents enjoy sidewalk-lined streets, green spaces, and a neighborhood-friendly atmosphere ideal for outdoor enjoyment and daily walks. When using our preferred lender, the buyer will receive a 1 percnt lender credit of the loan amount, which can be applied toward closing costs or an interest rate buydown. Conveniently located near major roadways, this home offers easy access to shopping, dining, parks, and schools, and is just a short drive from Walt Disney World, making it an excellent option for a primary residence, vacation home, or investment opportunity. This property presents a wonderful opportunity to enjoy space, location, and community living in one of Central Florida’s most sought-after areas.
Listing is courtesy of: MULTI CHOICE REALTY LLC (352-404-6542)
Listing Agent: James Song (407-405-3140)
17425 LAKE INGRAM RD, WINTER GARDEN, FL 34787
$1,199,99960 Days on yellowkey MLS ID: O6397109
Bed: 4 Bath: 1.5 Gar: 2 Liv Area Sq Ft: 2246 Built: 1977 Tax: $9,794 (2025)Community: Mt Park Orange GroveSingle Family
Taxes:$9,794
Remarks: Rare opportunity to own 6.8 acres in the heart of Horizon West! Zoned A1 with NO HOA. Zoned for top rated schools. Bring your horses, goats, chickens and build your dream home. The property is located at the end of a dead end street. Very private and isolated. One side of the property is flanked by retention ponds, the other side is the future home of a community park, and far in the backyard is Hamlin Elementary and Middle Schools. The home has been gutted and ready to customize your ideal floor plan. Plenty of room on the land to add a barn, ADU, or workshop. The lot contains wetland so a pond ebbs and flows on the property bringing all sorts of life to the land. Enjoy the tranquil ranch life with beautiful sunsets while remaining within minutes of shopping, restaurants, Disney, and access to the 429. Refer to Orange County Land Use Table for property use. Check with county to verify all current and future use.
Listing is courtesy of: THE PROPERTY PROS REAL ESTATE, INC (407-879-7591)
Listing Agent: Tamar Hill (818-445-8263)
317 SOUTHERN PECAN CIR #102, WINTER GARDEN, FL 34787
$225,000105 Days on yellowkey MLS ID: O6384866
REDUCED by $3,000 (1.3%) on 05/14/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 738 Built: 2005Monthly Fee: $309 Tax: $245 (2025)Community: Southern Pines CondominiumCondo
Taxes:$245
Elementary School: SunRidge Elementary
Middle School: SunRidge Middle
Remarks: Welcome to Southern Pines in the heart of Winter Garden! This clean and well-maintained 1-bedroom, 1-bath upstairs condo offers bright, open living with a rare combination of features you won’t often find in the community. Positioned on the upper level, the home enjoys enhanced privacy and abundant natural light with windows on both sides of the building, creating an airy and inviting atmosphere throughout the open-concept living and dining area. The kitchen flows seamlessly into the main living space and features granite countertops, ample storage, and all appliances convey with the sale — making this home truly move-in ready. Enjoy peaceful views overlooking the community tennis courts and resort-style pool. Downstairs, the attached 1-car garage and generous under-stair storage closet provide exceptional storage space — a true rarity within the neighborhood. Enjoy maintenance-free living, with HOA fees covering lawn care, cable, internet and water. Spend your weekends exploring Winter Garden Village, just 1.5 miles away, or immerse yourself in the charm of historic Downtown Winter Garden, filled with cozy cafés, boutique shops, farmers markets, and more. Outdoor enthusiasts will appreciate easy access to the West Orange Trail, perfect for biking, jogging, or leisurely strolls. Commuting is effortless with quick connections to the Florida Turnpike, SR 408, and SR 429. The gated Southern Pines community offers impressive amenities, with the pool, hot tub, and clubhouse located across the street. Additional features include a covered playground, movie theater, game room, office space, outdoor kitchen with grills, tennis court, indoor basketball and racquetball courts, sand volleyball, and even a car wash station. Don’t miss your opportunity to own in one of Winter Garden’s most convenient and amenity-rich communities. Schedule your showing today.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Anna Gay Hunter (407-446-9878)
13527 DANIELS LANDING CIR, WINTER GARDEN, FL 34787
$335,00025 Days on yellowkey MLS ID: O6408480
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1365 Built: 2004Monthly Fee: $320 Tax: $3,745 (2025)Community: Daniels Lndg A-JTownhouse
Taxes:$3,745
Remarks: Beautiful maintained 3 bedroom 2.5 bath townhome located in the highly desirable DANIELS LANDING community in WINTER GARDEN. This property features recent mayor updates including brand new carpet. Rooms on second floor. It has a screened porch to enjoy the afternoons with family and friends. Spacious layout, ideal location and low maintenance living make this property a standout. Top rated schools. Community amenities included gated access, pool, a clubhouse, fitness center and a playground. Conveniently located near Winter Garden Villages that offers shopping and gathering opportunities for everyone needs! Close to Mayor highways Turnpike, 429 and I-4. Minutes from Disney World and many other attractions! Great as a primary home or investment opportunity. A must see today!
Listing Agent: Julieta Kraponick (407-432-5102)
7280 WINDY WILLOW ST, WINTER GARDEN, FL 34787
$493,58325 Days on yellowkey MLS ID: G5112439
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1772 Built: 2026Monthly Fee: $225Community: Hamlin MeadowsTownhouse
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Sage floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Sage floor plan offers modern living tailored to meet everyday needs with style and functionality.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
17007 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$491,49025 Days on yellowkey MLS ID: G5112438
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1764 Built: 2026Monthly Fee: $225Community: Hamlin MeadowsTownhouse
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Porter floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Porter floor plan offers modern living tailored to meet everyday needs with style and functionality. Sample Images
17001 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$485,70525 Days on yellowkey MLS ID: G5112433
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1644 Built: 2026Monthly Fee: $225Community: Hamlin MeadowsTownhouse
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality.
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00099 Days on yellowkey MLS ID: O6386607
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: 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)
7007 TWILIGHT BAY DR, WINTER GARDEN, FL 34787
$465,00094 Days on yellowkey MLS ID: O6388545
REDUCED by $2,990 (0.6%) on 04/07/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1845 Built: 2024Monthly Fee: $180 Tax: $1,742 (2024)Community: MezzanoTownhouse
Taxes:$1,742
Remarks: Attention investors!! Welcome to this beautiful townhome like new and rented until April 2027!!! Is located in the desirable Mezzano community in Winter Garden. This well-maintained property features a modern open-concept layout with spacious living and dining areas, perfect for both relaxing and entertaining. The main level includes a versatile flex space that can be used as a home office, study, guest space, or playroom, providing extra functionality. The kitchen offers contemporary cabinetry, quality appliances, and ample counter space.Residents enjoy a low-maintenance lifestyle with convenient access to shopping, dining, major highways, and top-rated schools. The community is ideally located just minutes from Winter Garden Village, downtown Winter Garden, and other popular Central Florida attractions. Whether you're looking for a primary residence, second home, or investment opportunity, this property offers comfort, convenience, and a great location in one of Winter Garden’s growing communities. Schedule your private showing today and experience everything this home has. Priced to sell!!!
Listing Agent: Andrea Dale Gonzalez (407-984-1426)
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