Winter Garden, FL Homes

/58
$2,799,000
- 3 Beds
- 3.5 Baths
- 3,041 Sq Ft
9751 Quiet Ln, Winter Garden, FL 34787

Encompassing five pristine acres, this exceptional compound offers a rare blend of privacy, craftsmanship, and refined outdoor living. Framed by mature oaks and approached by a picturesque, tree-lined drive, the property unfolds as a secluded retreat designed for casual entertaining and boundless enjoyment of serious hobbies and collections. At the heart is a 3,041-square-foot farmhouse rich in

Judy Black

UPSIDE REAL ESTATE INC

(321) 364-3574

9751 Quiet Ln, Winter Garden, FL 34787
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/17
$2,800 per month
- 3 Beds
- 1 Bath
- 2,102 Sq Ft
- House for Rent
502 S Highland Ave, Winter Garden, FL 34787

AVAILABLE NOW! Location, location, location*HISTORIC WINTER GARDEN. 3br/1bath mid-century single family home. Short walk or golf-cart ride to Plant Street. Completely remodeled.

Arletis Delram NEW SOLUTIONS REALTY INC

502 S Highland Ave, Winter Garden, FL 34787
/46
$915,000 Sold May 14, 2025

15143 Ovation Dr, Winter Garden, FL 34787
- 7 Beds
- 4 Baths
- 4,692 Sq Ft
- Built 2010
Last Sold Summary
- 2% Below List Price
- $195/SF
- 22 Days On Market
Current Estimated Value $920,730

Last Listing Agent Evie Anderson PREFERRED REAL ESTATE BROKERS

15143 Ovation Dr, Winter Garden, FL 34787

/2
Est $436,414 Not Listed For Sale

15819 Gem View St, Winter Garden, FL 34787
- 2 Beds
- 2 Baths
- 1,579 Sq Ft
- Built 2024
15819 Gem View St, Winter Garden, FL 34787

Last Sold Summary
- 2% Above List Price
- $272/SF
- 81 Days On Market
- Last Sold Price $429,000
- Apr 30, 2025
Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

/60
$786,868
- 5 Beds
- 4.5 Baths
- 3,324 Sq Ft
14416 Travois Way, Winter Garden, FL 34787

PRICE IMPROVEMENT! Experience luxury living in one of Winter Garden’s most desirable communities near Hwy 50 & Florida’s Turnpike—just 25 minutes to Downtown Orlando and 20 minutes to Disney. This upgraded Summerlin floor plan offers 5 bedrooms, 4.5 baths, and designer finishes throughout. The fully remodeled kitchen is the true centerpiece—featuring a stunning waterfall-edge island, new

Carla Robles

WATSON REALTY CORP

(689) 306-1837

14416 Travois Way, Winter Garden, FL 34787
/39

$1,629 - $3,039 per month

Solay Horizon West

1 - 3 Beds

9005 Solay Rd, Winter Garden, FL 34787

Enjoy UP TO 2 MONTHS FREE on Select Homes! Live like youre on vacation every day at our brand new community, offering spacious apartments and the largest amenity offering in the area. With a dedicated onsite team, we are committed to providing exceptional customer service. Call or come by today!

9005 Solay Rd, Winter Garden, FL 34787
/43
$330,000 Sold Apr 17, 2026

823 Magnolia Ave, Winter Garden, FL 34787
- 3 Beds
- 2 Baths
- 1,210 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $273/SF
- 192 Days On Market
Current Estimated Value $278,707

Last Listing Agent Bosco Meira BELLA FLORIDA REALTY LLC

823 Magnolia Ave, Winter Garden, FL 34787

/2
Not Listed For Sale

16560 Point Rock Dr, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,216 Sq Ft
- Built 2023
16560 Point Rock Dr, Winter Garden, FL 34787

Last Sold Summary
- $255/SF
- 7 Days On Market
- Last Sold Price $565,000
- Apr 29, 2025
Last Listing Agent Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

/32
$295,000
- 3 Beds
- 2 Baths
- 1,453 Sq Ft
330 Southern Pecan Cir Unit 204, Winter Garden, FL 34787

Spacious 3-bedroom, 2-bath condo with an attractive traditional design and an open floor plan that makes daily living easy. The entry foyer with a closet is on the first floor, while all living spaces are located upstairs for added privacy. Features include built-in accents, a laundry room conveniently off the kitchen, and ceiling fans throughout. The community offers resort-style amenities

Kristi Matthew

CENTURY 21 CARIOTI

(321) 529-3491

330 Southern Pecan Cir Unit 204, Winter Garden, FL 34787
/13
$2,200 per month
- 2 Beds
- 2.5 Baths
- 1,228 Sq Ft
- Townhouse for Rent
14443 Prunningwood Place, Winter Garden, FL 34787

Beautiful 2-bedroom, 2.5-bath townhome in the heart of Winter Garden! This well-maintained home features a bright and functional layout, with en-suite bathrooms in both bedrooms for added comfort and privacy. Conveniently located near shopping, dining, and major highways, offering both convenience and a great lifestyle. Move-in ready and a must-see!

Fernanda Pupo WRA BUSINESS & REAL ESTATE

14443 Prunningwood Place, Winter Garden, FL 34787
/2
$645,000 Sold Sep 19, 2025

1208 Castleport Rd, Winter Garden, FL 34787
- 5 Beds
- 3.5 Baths
- 3,074 Sq Ft
- Built 2001
Last Sold Summary
- 8% Below List Price
- $210/SF
- 85 Days On Market
Current Estimated Value $643,804

Last Listing Agent Barbara Waltman KELLER WILLIAMS CLASSIC

1208 Castleport Rd, Winter Garden, FL 34787

/2
Not Listed For Sale

932 Kylee Aly, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 1,936 Sq Ft
- Built 2022
932 Kylee Aly, Winter Garden, FL 34787

Last Sold Summary
- $369/SF
- 6 Days On Market
- Last Sold Price $715,000
- Apr 28, 2025
Last Listing Agent Rema Perras CORCORAN PREMIER REALTY

/40
$765,000 Open Sat 1PM - 4PM
- 4 Beds
- 4.5 Baths
- 3,871 Sq Ft
2015 Sandy Garden Ln, Winter Garden, FL 34787

One or more photo(s) has been virtually staged. Welcome home to a lifestyle of space, comfort, and effortless entertaining in this beautifully designed two-story residence with charming exterior stone accents, set on an almost 1⁄4-acre lot in a gated community. From the moment you step inside, you’ll appreciate the open, airy layout, high ceilings, and bamboo flooring throughout — no carpet

Kristi Matthew

CENTURY 21 CARIOTI

(321) 599-3873

2015 Sandy Garden Ln, Winter Garden, FL 34787
/47

$1,752 - $3,691 total monthly price

Homestead at Hamlin

1 - 3 Beds

15100 Free Range Run, Winter Garden, FL 34787

There’s no place like Home(stead). Inspired by nature’s bounty, our thoughtfully designed one, two, and three-bedroom apartment residences blend perfect neutral tones and ample natural light to create spaces that help you discover the joy of simply being.

15100 Free Range Run, Winter Garden, FL 34787
/2
$510,000 Sold Nov 14, 2025

16394 Silver Brook Way, Winter Garden, FL 34787
- 4 Beds
- 2.5 Baths
- 2,114 Sq Ft
- Built 2025
Last Sold Summary
- $241/SF
Current Estimated Value $511,126

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

16394 Silver Brook Way, Winter Garden, FL 34787

/2
Not Listed For Sale

17066 Water Spring Blvd, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 2,489 Sq Ft
- Built 2022
17066 Water Spring Blvd, Winter Garden, FL 34787

Last Sold Summary
- $253/SF
- 61 Days On Market
- Last Sold Price $630,000
- Apr 28, 2025
Last Listing Agent Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

/55
$734,990
- 4 Beds
- 4.5 Baths
- 2,920 Sq Ft
3439 Buoy Cir, Winter Garden, FL 34787

Searching for a 4-bedroom home in Winter Garden with lake views, a private office, and a 3 car garage in a gated community? Welcome to 3439 Buoy Circle, a well maintained single family residence offering approximately 2,900 square feet, 4 bedrooms, a dedicated office, and 4.5 bathrooms, thoughtfully positioned to capture peaceful water views and stunning evening sunsets. Built by Taylor Morrison,

Patricia Solivan Lopez

EXP REALTY LLC

(689) 344-8859

3439 Buoy Cir, Winter Garden, FL 34787
/35
$3,000 per month
- 4 Beds
- 3 Baths
- 2,030 Sq Ft
- House for Rent
16435 Parable Way, Winter Garden, FL 34787

Discover the perfect rental home at 16435 Parable Way in Winter Garden, where comfort meets convenience in one of the area’s most desirable locations. Nestled in a highly sought-after school zone, this home is ideal for families looking to combine quality education with a vibrant community lifestyle. Enjoy easy access to nearby shopping, dining, parks, and major roadways, making daily commutes

Jing Yue INTEREALTY SERVICE

16435 Parable Way, Winter Garden, FL 34787
/2
$550,000 Sold May 19, 2025

16447 Hamlin View St, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,078 Sq Ft
- Built 2024
Last Sold Summary
- 3% Below List Price
- $265/SF
- 0 Days On Market
Current Estimated Value $554,896

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

16447 Hamlin View St, Winter Garden, FL 34787

/2
Est $354,526 Not Listed For Sale

203 Horstfield Dr, Winter Garden, FL 34787
- 3 Beds
- 2 Baths
- 1,097 Sq Ft
- Built 2001
203 Horstfield Dr, Winter Garden, FL 34787

Last Sold Summary
- 3% Below List Price
- $333/SF
- 33 Days On Market
- Last Sold Price $365,000
- May 01, 2025
Last Listing Agent Randal Longo KEYS REALTY REDEFINED LLC

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$725,000 Pending
- 5 Beds
- 3.5 Baths
- 3,568 Sq Ft
1073 Vinsetta Cir, Winter Garden, FL 34787

Under contract-accepting backup offers. 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

Autumn Makin

LAKEFIELD REALTY GROUP LLC

(321) 395-5514

1073 Vinsetta Cir, Winter Garden, FL 34787
/75

$1,852 - $2,973 total monthly price

Windermere Cay

1 - 3 Beds

8200 Jayme Dr, Winter Garden, FL 34787

So close yet a world away. Windermere Cay, the premier luxury and 100% Smoke-Free community is NOW OPEN! We are conveniently located on Reams Road, adjacent to Walt Disney World, just minutes from Orlando International airport, area theme parks, Winter Garden Village, Millenia Mall, and much more. Our four-story buildings offer elevators, high-end details, finishes, and an exclusive resident

8200 Jayme Dr, Winter Garden, FL 34787
/2
$695,000 Sold Oct 20, 2025

9863 Summerlake Groves St, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 2,072 Sq Ft
- Built 2020
Last Sold Summary
- 7% Below List Price
- $335/SF
- 103 Days On Market
Current Estimated Value $696,980

Last Listing Agent Viviane Rocha WRA BUSINESS & REAL ESTATE

9863 Summerlake Groves St, Winter Garden, FL 34787

/2
Est $471,184 Not Listed For Sale

636 Bainbridge Loop, Winter Garden, FL 34787
- 4 Beds
- 2 Baths
- 1,606 Sq Ft
- Built 2010
636 Bainbridge Loop, Winter Garden, FL 34787

Last Sold Summary
- 1% Below List Price
- $296/SF
- 5 Days On Market
- Last Sold Price $475,000
- Apr 30, 2025
Last Listing Agent Kristina Mollo ALL REAL ESTATE & INVESTMENTS

/42
$449,000
- 3 Beds
- 2.5 Baths
- 1,853 Sq Ft
8156 Wood Sage Dr, Winter Garden, FL 34787

Winter Garden – Rare, immaculate end-unit townhome in highly sought-after Summerlake, fully updated and truly MOVE-IN READY. Step onto the charming front porch—perfect for morning coffee as the neighborhood comes to life—and then into a bright, open interior with soaring ceilings, a freshly painted interior, and an inviting floor plan.The chef’s kitchen features abundant real wood cabinetry,

Kathy Aparo-Griffin

APARO-GRIFFIN PROPERTIES INC

(321) 384-8375

8156 Wood Sage Dr, Winter Garden, FL 34787
/43
$2,995 per month
- 3 Beds
- 2 Baths
- 1,867 Sq Ft
- House for Rent
2227 Oakington St, Winter Garden, FL 34787

Must see!! Welcome Home, beautiful property with a lots of upgrades, freshly painted. Four ample bedrooms, separated Living and Dining,kitchen with granite counter tops. All appliances are included. Master suite with a large walking closet, and separate upgraded master bathroom with skylights. Big patio fenced. Conveniently Gated Community with Security Guard 24 hrs, closed Shopping centers,

Milena Nunez REALTY ONE GROUP EVOLUTION

2227 Oakington St, Winter Garden, FL 34787
/43
$439,990 Sold Oct 28, 2025

15034 Grove Lake Dr, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 1,881 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $234/SF
- 23 Days On Market
Current Estimated Value $444,068

DRB Homes Parkview at Hamlin

15034 Grove Lake Dr, Winter Garden, FL 34787

/2
Est $359,625 Not Listed For Sale

15319 Oak Apple Ct Unit 9C, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 1,699 Sq Ft
- Built 2008
15319 Oak Apple Ct Unit 9C, Winter Garden, FL 34787

Last Sold Summary
- 3% Above List Price
- $205/SF
- 62 Days On Market
- Last Sold Price $348,000
- Apr 30, 2025
Last Listing Agent Jessica Stone CENTURY 21 CARIOTI

/48
$1,100,000
- 4 Beds
- 3.5 Baths
- 2,758 Sq Ft
10174 Merrymeeting Bay Dr, Winter Garden, FL 34787

Welcome to 10174 Merrymeeting Bay Dr — a gorgeous 4-bedroom, 3.5-bath home in the heart of Winter Garden that checks all the boxes and then some. Step inside and you'll notice the open floor plan right away. Tile floors run through the main living areas with cozy carpet in the bedrooms. The kitchen is a dream with quartz counters, stainless appliances, wood cabinets, and a walk-in pantry. The

Deanna Meredith

LUXE PROPERTIES LLC

(321) 382-5840

10174 Merrymeeting Bay Dr, Winter Garden, FL 34787
/52

$1,603 - $2,327 total monthly price

Apollo Apartments

Studio - 2 Beds

7000 Kiran Patel Dr, Winter Garden, FL 34787

Apollo boast four stunning buildings that usher in a variety of iving spaces, including spacious studios, stylish one-bedroom, and comfortable two-bedroom apartments. Discover elegant kitchen islands, oversized windows that fill your space with natural light, and modern fixtures that add a touch of sophistication to every room.

7000 Kiran Patel Dr, Winter Garden, FL 34787
/2
$600,000 Sold Dec 17, 2025

3390 Current Ave, Winter Garden, FL 34787
- 5 Beds
- 3 Baths
- 2,916 Sq Ft
- Built 2020
Last Sold Summary
- 6% Below List Price
- $206/SF
- 74 Days On Market
Current Estimated Value $618,003

Last Listing Agent Jessica Macias KELLER WILLIAMS ADVANTAGE III

3390 Current Ave, Winter Garden, FL 34787

/2
Est $1,389,611 Not Listed For Sale

234 N Lakeview Ave, Winter Garden, FL 34787
- 4 Beds
- 4 Baths
- 3,267 Sq Ft
- Built 1920
234 N Lakeview Ave, Winter Garden, FL 34787

Last Sold Summary
- 4% Below List Price
- $444/SF
- 10 Days On Market
- Last Sold Price $1,450,000
- Apr 30, 2025
Last Listing Agent Matt McKee COMPASS FLORIDA LLC

/59
$1,895,000 Open Sat 12PM - 2PM
- 4 Beds
- 4.5 Baths
- 3,185 Sq Ft
1021 Temple Grove Place, Winter Garden, FL 34787

LUXURY LAKEFRONT ESTATE – Minutes from Historic Downtown Winter Garden! Experience elevated waterfront living in this beautiful 4-bedroom, 4.5-bath lakefront pool residence on just under 1 acre, ideally located just minutes from the heart of Winter Garden and the charm of Plant Street. Built in 2020 and situated within the coveted GOLF CART DISTRICT near Historic Downtown, this property offers

Nicole Rader

MAINFRAME REAL ESTATE

(321) 486-8407

1021 Temple Grove Place, Winter Garden, FL 34787
/42
$3,350 per month
- 4 Beds
- 3.5 Baths
- 2,781 Sq Ft
- House for Rent
12112 Encore at Ovation Way, Winter Garden, FL 34787

Gorgeous newer home 5 years old. 4-bedroom 3.5 bath home across the street from the pool and fitness center, Off Western Way on the west side of Disney. This home has a covered and paved front porch with direct views across the street to the community clubhouse, fitness center, pool and open park. When you want a little more privacy, you can sneak off to the small side covered patio. this home

Bryce Rysewyk SPRING REALTY ONE LLC

12112 Encore at Ovation Way, Winter Garden, FL 34787
/2
$739,000 Sold Jan 05, 2026

214 S Main St, Winter Garden, FL 34787
- 4 Beds
- 4 Baths
- 2,268 Sq Ft
- Built 1993
Last Sold Summary
- 1% Below List Price
- $326/SF
- 0 Days On Market
Current Estimated Value $739,083

Last Listing Agent Joe Wynkoop CHARLES RUTENBERG REALTY ORLANDO

214 S Main St, Winter Garden, FL 34787

/2
Est $662,925 Not Listed For Sale

704 Tangelo Ct, Winter Garden, FL 34787
- 3 Beds
- 2 Baths
- 1,797 Sq Ft
- Built 1978
704 Tangelo Ct, Winter Garden, FL 34787

Last Sold Summary
- 19% Above List Price
- $309/SF
- 177 Days On Market
- Last Sold Price $555,000
- Apr 30, 2025
Last Listing Agent Christian Dyas THE REAL ESTATE COLLECTION LLC

/42
$834,000
- 3 Beds
- 3.5 Baths
- 1,906 Sq Ft
131 Oak Laurel Dr, Winter Garden, FL 34787

131 Oak Laurel Drive is a stunning, modern townhome built in 2019 in the highly desirable Park Place community in the heart of historic Winter Garden, Florida. This beautifully designed three-story home offers 3 bedrooms, 3.5 bathrooms, and 1,906 square feet of heated living space. Each bedroom features its own en-suite bathroom, providing privacy and comfort for all. This home includes an

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

(321) 405-1381

131 Oak Laurel Dr, Winter Garden, FL 34787
$1,425 - $7,745 per month

Halston Waterleigh

1 - 3 Beds

10091 Tuller Loop, Winter Garden, FL 34787

Step into a world of luxury at Halston Waterleigh, an upscale community in Winter Garden, Florida. Experience exquisite design, abundant natural light, advanced technology, and endless comfort in your new home. Enjoy a vacation-like atmosphere daily with our heated saltwater pool, expansive fitness center, and a variety of additional top-tier amenities. Schedule your personal tour today and

10091 Tuller Loop, Winter Garden, FL 34787
/2
$650,000 Sold Apr 03, 2026

14008 Jomatt Loop, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,952 Sq Ft
- Built 2019
Last Sold Summary
- $220/SF
- 35 Days On Market
Current Estimated Value $648,515

Last Listing Agent David Fontana CHARLES RUTENBERG REALTY ORLANDO

14008 Jomatt Loop, Winter Garden, FL 34787

/2
Est $701,491 Not Listed For Sale

342 Lake Amberleigh Dr, Winter Garden, FL 34787
- 5 Beds
- 2.5 Baths
- 3,239 Sq Ft
- Built 2001
342 Lake Amberleigh Dr, Winter Garden, FL 34787

Last Sold Summary
- 1% Above List Price
- $215/SF
- 4 Days On Market
- Last Sold Price $695,000
- Apr 30, 2025
Last Listing Agent Chad Williams OLYMPUS EXECUTIVE REALTY INC

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Winter Garden, FL Homes

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