Winter Garden Homes for Sale

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Single Family

14314 ELLERBEE STREET, WINTER GARDEN, Florida 34787

2Bedroom(s)
1Bathroom(s)
2Parking(s)
13Picture(s)
1,304Sqft
Private showcase lot on nearly 1 acre on Black Lake to build your estate and proudly show your family’s legacy. Enjoy the gorgeous view and lake access to the spectacular Black Lake. Well established neighborhood in a very quiet, upscale community. This well-loved property was meticulously maintained and serviced in every detail.
$968,000

Single Family

15720 SHOREBIRD LANE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,327Sqft
If you are a buyer seeking a LIFESTYLE and not just a neighborhood, Lakeshore Preserve is it! Only 1 exit from Disney off the Western Beltway, this location is great for a primary or second home. The lowest-priced 4-bedroom home in Lakeshore and no need to wait for new construction.
$549,000

Lots And Land

14913 ARRENA ROAD, WINTER GARDEN, Florida 34787

10Picture(s)
6Acre
Orange County future use Zoning is 10 UNITS /1 acre or PROFESSIONAL OFFICES. ****PRIME LOCATION***** This property is located in WINTER GARDEN, Fl, just over 6 acres right off of HWY 192 (Irlo Bronson Blvd) in between Hwy 27 and the 429. One of only a few vacant land opportunities in this fast growing area.
$935,000

Single Family

875 HEISTON LANE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
22Picture(s)
2,503Sqft
Back on the market. Buyer's financing fell through. Seller's have recently reduced the price by $20,000 as they are more motivated to sell today! This 2 Year New Home, is Absolutely Breathtaking. You will want to move right in and unpack-as there's literally nothing else to do. Master Bedroom, Master Bathroom, All Living/Dining/Family etc. Downstairs.
$519,800

Single Family

312 BAYSIDE AVENUE, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,237Sqft
Live in the desirable Historic Downtown Winter Garden GOLF CART DISTRICT! This beautiful 3 bedroom, 2 bathroom home has been completely renovated and is move in ready for you and your family. When you step inside you are greeted with brand new vinyl flooring that flows seamlessly throughout the home.
$339,900

Townhouse

13791 ORCHARD LEAF WAY, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,744Sqft
Be wowed by this beautiful townhome from the moment you pull up to it. The HOA maintains the lovely landscaping, lawn maintenance, exterior paint, and roof replacement (which is taking place at the end of this year!). The spacious front porch is the perfect place to have your morning coffee as it is covered for weather protection, and the matured landscaping truly gives you that oasis feeling.
$260,000

Rental

2227 REDMARK LANE, WINTER GARDEN, Florida 34787

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,290Sqft
Gorgeous 5 bed, 3.5 bath 3 car garage home in Carriage Pointe gated community. This home has an upgraded saltwater pool with spa that steals the show. 3 beautiful waterfall features, built in planting areas, pool heater and built in gas fire pit.
$3,995

Lots And Land

188 MARY ST, WINTER GARDEN, Florida 34787

3Picture(s)
0.09Acre
Are you looking for vacant land? What about a property that is free and clear and has no leins? Build on your lot today! This is lot is great for tiny house movement. or can also be used for small single family residential build.
$20,000

Rental

15369 HONEYBELL DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,902Sqft
This home has 4 bedrooms and 3 bathrooms. The downstairs bedroom could double as an office, master bedroom or games room. The large kitchen has granite counters, stainless steel appliances and a breakfast bar. With its private balcony and brick patio, you will not miss the beautiful night sky. The fenced in yard and 2 car garage will give you a great feeling of privacy and personal space.
$2,100

Lots And Land

14730 SIPLIN ROAD, WINTER GARDEN, Florida 34787

0.13Sqft
Vacant Residential lot in Siplin Hights Subdivision of Winter Garden. This lot backs up to the very new SunRidge Middle School. Large shade tree on lot. Zoned for modular home or standard construction. Priced reduced to sell.
$27,500

Single Family

971 PAWLEY WAY, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
2,106Sqft
The home of your dreams awaits! Welcome home to this stunning 3-bedroom, 2-bath David Weekley home with 2,106 sq. ft., 2-car garage, and direct community park GREEN SPACE FRONTAGE in the highly sought-after Oakland Park community. As soon as you step up to the large front porch, you will be impressed by this home’s wonderful curb appeal.
$508,000

Single Family

860 RHETT STREET, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
1,974Sqft
This home is the ONE you’ve been looking for in Oakland Park! Shows like a model, designed like a model. Some furnishings are available for sale. This ONE story gem will wow you the moment you walk in the door.
$495,000

Single Family

648 BAINBRIDGE LOOP, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
1,904Sqft
**Click on the Walk-through Tour** MOVE-IN READY; NEW A/C; NO Carpet; UPDATED Flooring; UPDATED Appliances; NEWER Paint; GOLF-CARTS Allowed; FREE Home Warranty. This beautiful Move-In Ready, 4-Bedroom, 3-Bathroom home is located in the highly desired “Golf Cart District” of Winter Garden.
$350,000

Single Family

14332 Vista del Lago, #4243, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
10Picture(s)
1,152Sqft
This turnkey home is move-in ready. The home is conveniently located across the street from the Phase IV pool. It features side-by-side parking and laminate wood flooring in the living room and kitchen. The home has been freshly painted and has been well-maintained. The roof was replaced in 2017 and the A/C unit in 2019.
$70,000

Residential

16531 Avenida del Lago, #1071, WINTER GARDEN, Florida 34747

2Bedroom(s)
2Bathroom(s)
10Picture(s)
1,056Sqft
This two bedroom two bath home is being sold fully-furnished. The home features spacious bedrooms and built-in cabinets for extra storage space. The guest bathroom floor and vanity have been replaced and the home has all new plumbing. The roof was replaced in 2004 and the A/C unit in 2008.
$55,000

Residential Lease

9975 TAWNY MEADOW ALLEY, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
4Picture(s)
1,689Sqft
Brand new house - you'll be the first tenants! Nestled within Winter Garden's beautiful Horizon West area. The unique architectural details and mix of modern, craftsman and prairie-inspired designs add to the unique streetscapes of this community.
$2,150

Single Family

261 VIRGINIA DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,160Sqft
Perfect downtown Winter Garden starter home located in the Golf Cart District. 3/2 Block home situated on huge lot zoned R2 with NO HOA! This is a very friendly neighborhood and just a short walk to Plant Street and all the fun things to do downtown. Price has been recently reduced, seller is motivated.
$294,900

Single Family

1831 BURDOCK DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
3Parking(s)
1Picture(s)
2,780Sqft
This Winter Garden one-story three car garage home is in the Carriage Pointe gated community near Horizon West that offers a tennis court, an open play field, playground, and walking trail. This home was built in 2012 by Taylor Morrison, and the kitchen features maple cabinets, granite countertops and an oversized island.
$440,000

Single Family

15602 SUNQUAT DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,690Sqft
Welcome to Hamlin Reserve, Gorgeous like new home by Ashton Woods located in the highly desirable, Winter Garden. This house is located on a premium corner lot, with a open green field on the front door. Just a few steps from the club house. All the upgrades was hand picked by seller, you are going to find so many options in this two-story home.
$469,900

Rental

1651 HIGHBANKS CIRCLE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,278Sqft
Roper Reserve a cozy Gated community this like new home offers an open floor plan with upgraded kitchen, GE appliances granite counters 42” soft close cabinets oversized island and eat in space in the kitchen. There is a separate dining room and the large great room has a wall of sliding doors to patio area. Living areas all tiled. High ceilings and 9 ft doors make space feel enormous.
$2,450

Single Family

1942 PANTHEON DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
18Picture(s)
2,562Sqft
HUGE PRICE DECREASE!!! MOTIVATED SELLER!!! This meticulously maintained, move in ready home features 4 Bedrooms and 3 full Bathrooms on the first floor, with a HUGE bonus loft and 4th full bathroom on the second floor. Located in the highly desired neighborhood of Alexander Ridge.
$385,000

Single Family

15011 GAULBERRY RUN, WINTER GARDEN, Florida 34787

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,937Sqft
Strikingly beautiful, simply spectacular. Welcome to lakefront living in an immaculately elegant and chic 6-bedroom home with massive upstairs loft and separate theater room – boasting sunset views, water vistas, and one of the largest lots on Lake Hancock. This sophisticated residence sits on a giant 2.
$1,350,000

Single Family

15100 NIGHT HERON DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,994Sqft
Why wait for new construction? Look no further… THIS is the one: MOVE - IN READY single-family home is two story and includes three bedrooms, two and a half bathrooms, and a two-car garage. This home’s layout is where entertainment and family is always the main focus. The kitchen island allows open sight lines to the oversized family room, dining room and study.
$384,900

Single Family

1070 HUNTSPOINT STREET, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,260Sqft
Situated in the heart of picturesque Oakland Park and only two miles from Winter Garden's vibrant downtown area, this three years young home shows like new, but better! Improvements in 2020 include new carpeting, fresh interior paint, front porch screen, rear lanai screen, and a gorgeous paver patio.
$525,000

Single Family

1651 HIGHBANKS CIRCLE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,278Sqft
So convenient to West Colonial and the downtown historic district, and an abundance of shopping dining and entertainment options at Winter Garden Village. This gated community offers a beautiful playground, outdoor fitness pavilion and BBQ area with picnic tables.
$414,000

Townhouse

8148 WOOD SAGE DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,853Sqft
Gorgeous Beazer built upgraded smart townhome in the populare Summerlak Community in Horizon West in Winter Garden! It has the convenience of a townhome with with tons of resort style amenities! All lawn maintenance in front and rear is included in the modest HOA fee.
$319,900

Residential

5101 REX DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
2Bathroom(s)
3Picture(s)
1,737Sqft
Rare Find! 10 beautiful acres in equestrian friendly community of Lake Avalon. 4 bedroom home ready for move in or can build new on this parcel. Impact fees paid, existing well on property.
$789,000

Single Family

14765 ELLINGSWORTH LANE, WINTER GARDEN, Florida 34787

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,680Sqft
PRICE IMPROVEMENT! Home MUST go, Go, GO! MOVE IN READY! Minutes to charming Historic Downtown Winter Garden and the West Orange Bike Trail! Gorgeous 2019 Craftsman “Yorkshire” floorplan by Mattamy Homes boasting 5 spacious bedrooms and 4.5 baths in GATED community Oxford Chase! Ceramic tile and carpet flooring throughout.
$608,900

Single Family

1039 BRITTON ALLEY, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,085Sqft
The BEST of both worlds with an oversized (~1/4 of an acre) CORNER lot with POND views and trail-side fun! This beauty features 4 bedrooms, 3.
$625,000

Single Family

284 VIRGINIA DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,782Sqft
Beautiful 3 bedroom 2 bath POOL HOME for sale within MINUTES TO DOWNTOWN WINTER GARDEN! The gorgeous fenced-in backyard with in-ground pool, paver patio perfect for summer days! Fire pit for those cool evenings. Offers formal living, over-sized family room, inside utility room with hook-ups. Hardwood floors through out.
$389,800

Single Family

16131 WIND VIEW LANE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,170Sqft
MOTIVATED SELLER! SELLER WILL CONTRIBUTE $10,000 TOWARDS CLOSING COST. Beautiful a 2 story, 3 bedroom 2.5 bath Home with an office/den in Waterleigh! The kitchen features stainless steel appliances, granite counter tops and upgraded wood cabinets. The large island looks over the large family room and opens up to the dining room and covered lanai.
$375,000

Rental

16143 AZURE KEY STREET, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
16Picture(s)
1,758Sqft
Great Home in Waterleigh a New Resort style community. HOA maintains yard. 3/2 Split Plan HOA does lawn care.
$1,999

Single Family

875 HEISTON LANE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,479Sqft
Beautiful 4BR Oakland Park home with WOW factor at every turn! You'll be impressed from the moment you arrive. Meticulously landscaped corner lot with classic picket border fence and quaint covered front porch. Homefront faces a pretty common green, one of many that are dotted throughout the community. Alley access for all the garages on this block enhances the homes' facades.
$525,000

Townhouse

8812 BISMARCK PALM DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,972Sqft
Embrace luxurious Florida living in this immaculate Toll Brothers townhouse, nestled in Winder Garden’s exclusive Lakeshore community. ***SELLER MOTIVATED*** Filled with Italian cypress, palm trees, and native wildflowers, the neighborhood’s resort-style atmosphere makes coming home the best part of your day.
$375,000

Single Family

14018 ALDFORD DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,066Sqft
Prepare to be impressed with this single story, Ashbury II model by Ashton Woods! This well-appointed, 3 bedroom, 2 bathroom, craftsman style home backs up to protected conservation for ultimate privacy. Loaded with upgrades and impeccable design features, this home offers the much desired open concept layout with the privacy of true split bedrooms.
$415,000

Single Family

1200 UNION CLUB DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,911Sqft
The video is worth a watch... www.1200unionclub.site/mls and the 3 d tour of this masterpiece... http://1200unionclub.site/360-Floorplan-MLS For sale for the first time by the original owners, one lucky buyer will be the second owner of this J & J construction masterpiece in Winter Gardens signature community Oakland Park.
$968,800

Single Family

1134 HARBOR HILL STREET, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,754Sqft
check out the video... www.1134harborhillstreet.site/video-mls Amazing buying opportunity in establish Stoneybrook West, the only 24 hr man guarded community in Winter Garden. Large 2 story with HUGE fenced yard on quiet side street with ONE YEAR NEW ROOF and 4 year new A/C, taking all the worries out of buying.
$348,800

Single Family

7725 MINUTEMEN LOOP, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,914Sqft
The famous Jamestown model in the Overlook at Hamlin now available! The most sought after single story floor plan in all of Horizon's West now available to the public for the very first time.  These extraordinarily lucky sellers purchased this exquisite Jamestown model directly from Taylor Morrison, but are now ready to pass the torch on to the next lucky buyer.
$524,900

Rental

510.5 VARSITY STREET, WINTER GARDEN, Florida 34787

2Bedroom(s)
1Bathroom(s)
6Picture(s)
780Sqft
Primo location. Hip patio villas situated on a quiet oak lined street featuring stunning polished concrete flooring throughout, new kitchen, granite counter tops. Huge rear yard with open brick patio & two parking pads. All located within close proximity of the picturesque historic downtown Winter Garden.
$1,300

Single Family

427 ENGLISH LAKE DRIVE, WINTER GARDEN, Florida 34787

5Bedroom(s)
3Bathroom(s)
3Parking(s)
25Picture(s)
3,065Sqft
Wow, almost a double fenced lot. Great Home with many nice upgrades. All your living on one floor except bonus room is up. Oversized screened patio with covered porch. Great Schools. Minutes from everywhere you need to be and want to be, Winter Garden Village, Downtown Winter Garden, The West Orange Trail, 429, Turnpike, 408, Disney, Universal...Make it yours today.
$469,900

Single Family

839 CIVITAS WAY, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,731Sqft
Wow, this is a show stopper. Put this home at the top of your list. Ever popular David Weekly Seaside floor-plan. Many fine custom touches throughout this home. Hardwood flooring in the living areas. Amazing kitchen and island fit for a chef. Master bedroom downstairs, bonus room and 3 bedrooms 2 full baths up-stairs. Screened patio overlooking the back yard.
$565,000

Single Family

15120 SPINNAKER COVE LANE, WINTER GARDEN, Florida 34787

4Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
2,526Sqft
Beautiful one story golf course home in the highly desired Stoneybrook West neighborhood of Winter Garden! This great home features 4 bedrooms, 2 bathrooms, very open floor-plan, inviting formal living and dining rooms with 10ft ceilings and plenty of natural light, roomy kitchen with 42” Cabinets, dinette, breakfast bar, and ceramic tile floors, cozy family room with backyard access, ga
$355,000

Single Family

1113 BRANDY CREEK DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
9Picture(s)
2,080Sqft
Fall in love with this beautiful 4 bedroom POOL home that's nestled on a fenced in oversized homesite close to Historic Downtown Winter Garden.
$365,000

Single Family

211 VALENCIA SHORES DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,782Sqft
Welcome to the Downtown Winter Garden lifestyle! Incredible value for such a PRIME LOCATION - just steps from the popular West Orange Recreational Trail + less than a mile from all of the great shops, restaurants, and the Saturday Farmers' Market on Plant St. Well-maintained 3 bed / 2 Bath with formal dining + living rooms situated on .33 ACRES.
$329,000

Single Family

213 HORSTFIELD DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
1Parking(s)
19Picture(s)
1,048Sqft
Fantastic Location! Located just off Highway 50, 3 minutes to the 429. 5 minutes to the vibrant city of Downtown Winter Garden with shopping, dining and an amazing local brewery. This is a great starter house. Fresh paint outside. Well maintained inside. Great local schools. Featuring 3 bedrooms, 2 bathrooms- laminate flooring. Community features a dog park, large community pool and playground.
$215,000

Single Family

14784 TULLAMORE LOOP, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
10Picture(s)
3,101Sqft
Fractional Ownership. Lowest priced pool/spa home in the area. Beautiful home in wonderful gated community.Home has multiple upgrades including crown molding,intercom inside and out,huge yard w/ extra green space behind, security system,extended kitchen cabinets with island, lots of storage,great condition,no rear neighbors,move in ready in 30 days or less.
$470,000

Single Family

7448 POMELO GROVE DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,683Sqft
PRICE REDUCTION: This is a BEAUTIFUL HOME with 4 BEDROOMS & 3 FULL BATHROOMS looks like a model home. Tile floors throughout greet you as you enter the foyer. The layout offers a three-way split floorplan. With two bedrooms upfront that has there own bathroom with tub and shower.
$491,500

Condominium

1250 S DENNING DRIVE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
10Picture(s)
913Sqft
Here is a fantastic opportunity to purchase this beautifully renovated condo in the heart of Winter Park! The kitchen has been tastefully appointed with brand new soft close wood cabinetry, quartz countertops, backsplash and stainless steel appliances. Additional upgrades include; brand new carpets throughout, fresh paint, newly installed baseboards and crown molding.
$204,900
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