Winter Garden Homes for Sale

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Single Family

764 LAKE BRIM DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,773Sqft
The dream house you’ve been waiting for in Oakland Park is now at your fingertips! This showstopper POOL and PARK-front home with partial lake views of Lake Brim is tastefully designed and packed full of customizations. Prepare to be impressed the moment you step inside. The model features 4 bedrooms (master downstairs), 3.
$745,000

Residential

14501 GROVE RESORT AVENUE, WINTER GARDEN, Florida 34787

2Bedroom(s)
2Bathroom(s)
25Picture(s)
1,265Sqft
Zoned for Short Term Rental. This 6th floor condo offers a fully-equipped kitchen, separate living and dining areas and an utility room. Set in the heart of The Grove Resort it is a perfect home away from home. The condo has all the amenities of a modern complex, in a lush tranquil setting. The condo is fully furnished with a screened in covered patio overlooking the central court yard.
$290,000

Single Family

2720 BALFORN TOWER WAY, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,588Sqft
This fantastic 3 bedroom and 2 bath home with a split floor plan is in the highly desirable ONLY 24 hour guard-gated subdivision in Winter Garden. As you enter, be prepared for the cozy and bright family room which is open to the kitchen with a breakfast bar and covered patio.
$317,000

Single Family

15336 SUGAR CITRUS DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
3Parking(s)
9Picture(s)
2,471Sqft
This beautiful Winter Garden home is located inside Hamlin Reserve subdivision in a fenced in lot and pond view from the front porch. Open concept floor plan with plank wood floor in the main living area, high ceilings, gourmet kitchen, stainless still kitchen appliances including a stainless still refrigerator, large center island with lots of storage space and a breakfast bar.
$475,000

Townhouse

6067 BLUE LILY WAY, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,582Sqft
Pre-Construction. To be built. Ryan Homes at Hamilton Gardens is the perfect blend of location and lifestyle, surrounded by nature while close to everything. Experience this one-of-a-kind community where restaurants, retail, entertainment, and wellness are within strolling distance at Hamlin Town Center.
$296,990

Single Family

13379 SUNSET LAKES CIRCLE, WINTER GARDEN, Florida 34787

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,036Sqft
One or more photo(s) has been virtually staged. WELCOME HOME! Move-in ready pool home located on over half an acre in the exclusive community of Sunset Lakes! Don’t miss this spacious 5 bedroom, 3 bath, with a bonus room.
$579,000

Lots And Land

720 GARDEN WEST TERRACE, WINTER GARDEN, Florida 34787

4Picture(s)
0.23Acre
Enjoy TRAILSIDE living at it's finest! Garden West, a brand new community located just a half mile from downtown Winter Garden on the corner of Plant St, Brayton Rd and the West Orange Fitness Trail. Experience the convenience of urban living only a short ride in your golf cart or walk to downtown shops, markets and restaurants.
$245,000

Lots And Land

724 GARDEN WEST TERRACE, WINTER GARDEN, Florida 34787

1Picture(s)
0.17Acre
Enjoy TRAILSIDE living at it's finest! Garden West, a brand new community located just a half mile from downtown Winter Garden on the corner of Plant St, Brayton Rd and the West Orange Fitness Trail. Experience the convenience of urban living only a short ride in your golf cart or walk to downtown shops, markets and restaurants.
$235,000

Single Family

13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, Florida 34787

4Bedroom(s)
5Bathroom(s)
5Parking(s)
25Picture(s)
4,961Sqft
One or more photo(s) has been virtually staged. BACK ON MARKET: Buyer's inability to obtain financing is now your opportunity to own what is now most sought after in 2020...a waterfront compound to enjoy social distancing at its finest – no close neighbors or HOA – but easy access to shopping, the Orlando international airport, hospitals, and Downtown Orlando.
$1,699,999

Lots And Land

15205 FARM STAND COURT, WINTER GARDEN, Florida 34787

6Picture(s)
0.34Acre
Build your own custom Modern Farmhouse in Winter Garden’s premier luxury new home community, Oakland Hills. Unlike anything else in Central Florida, this enclave of only 17 over-sized home sites is nestled among grand oak trees reminiscent of old Florida rural estates.
$310,000

Lots And Land

13377 LAKE BUTLER BOULEVARD, WINTER GARDEN, Florida 34787

10Picture(s)
12.42Acre
BACK ON MARKET: Buyer's inability to obtain financing is now your opportunity to own what is now most sought after in 2020...a waterfront compound to enjoy social distancing at its finest – no close neighbors or HOA – but easy access to shopping, the Orlando international airport, hospitals, and Downtown Orlando. This private 12+ acre compound (approximately 6.
$1,699,999

Lots And Land

691 LARGE OAK LANE, WINTER GARDEN, Florida 34787

6Picture(s)
0.36Acre
Build your own custom Modern Farmhouse in Winter Garden’s premier luxury new home community, Oakland Hills. Unlike anything else in Central Florida, this enclave of only 17 over-sized home sites is nestled among grand oak trees reminiscent of old Florida rural estates.
$315,000

Lots And Land

732 GARDEN WEST TERRACE, WINTER GARDEN, Florida 34787

4Picture(s)
0.15Acre
Enjoy TRAILSIDE living at it's finest! Garden West, a brand new community located just a half mile from downtown Winter Garden on the corner of Plant St, Brayton Rd and the West Orange Fitness Trail. Experience the convenience of urban living only a short ride in your golf cart or walk to downtown shops, markets and restaurants.
$230,000

Lots And Land

15198 E OAKLAND AVENUE, WINTER GARDEN, Florida 34787

6Picture(s)
0.37Acre
Build your own custom Modern Farmhouse in Winter Garden’s premier luxury new home community, Oakland Hills. Unlike anything else in Central Florida, this enclave of only 17 over-sized home sites is nestled among grand oak trees reminiscent of old Florida rural estates.
$300,000

Lots And Land

736 GARDEN WEST TERRACE, WINTER GARDEN, Florida 34787

6Picture(s)
0.15Acre
Enjoy TRAILSIDE living at it's finest! Garden West, a brand new community located just a half mile from downtown Winter Garden on the corner of Plant St, Brayton Rd and the West Orange Fitness Trail. Experience the convenience of urban living only a short ride in your golf cart or walk to downtown shops, markets and restaurants.
$230,000

Lots And Land

740 GARDEN WEST TERRACE, WINTER GARDEN, Florida 34787

5Picture(s)
0.19Acre
Enjoy TRAILSIDE living at it's finest! Garden West, a brand new community located just a half mile from downtown Winter Garden on the corner of Plant St, Brayton Rd and the West Orange Fitness Trail. Experience the convenience of urban living only a short ride in your golf cart or walk to downtown shops, markets and restaurants.
$225,000

Single Family

1230 PAINTED BUNTING AVENUE, Oakland, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,059Sqft
GREAT OPPORTUNITY to own a nearly new home in the historic town of OAKLAND! **** This Spacious family home is located just minutes (actually 3.
$455,000

Single Family

685 LARGE OAK LANE, WINTER GARDEN, Florida 34787

5Bedroom(s)
5Bathroom(s)
3Parking(s)
9Picture(s)
4,170Sqft
Under Construction. Fall in love with this modern farmhouse masterpiece that is in the early stages of construction within Winter Garden’s premier luxury new home community, Oakland Hills. Unlike anything else in Central Florida, this enclave of only 17 over-sized home sites is nestled among grand oak trees reminiscent of old Florida rural estates.
$1,240,000

Single Family

16029 TOLLINGTON ALLEY, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
3Picture(s)
2,341Sqft
This beautiful MODEL HOME WITH LEASEBACK delivers 3 beds, 2.5 bath, and a 2-car alley-loaded garage. Close now, and the builder rents it back from you! Inside, the kitchen delivers shaker-style cabinets with glass door accents, slide-out trash, crown molding, and hardware, maintenance-free quartz countertops, and GE® stainless steel appliance package including a natural gas range.
$517,730

Single Family

2807 WILLIAMS ROAD, WINTER GARDEN, Florida 34787

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,878Sqft
Lakefront living on Lake Avalon in desirable Winter Garden! Breathtaking views of the sunrise! Potential is endless! NO HOA! Plenty of room for your boat, RV and cars! The home sits back on the lot with a long driveway leading up to the house. 3 bedrooms and 2 baths with a spacious floor plan. There is a screened 25x12 patio overlooking the lake.
$395,000

Single Family

15210 E OAKLAND AVENUE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
3Parking(s)
9Picture(s)
3,640Sqft
Under Construction. Fall head-over-heels for this modern farmhouse custom masterpiece situated within Winter Garden’s premier luxury new home community, Oakland Hills. Unlike anything else in Central Florida, this enclave of only 17 over-sized home sites is nestled among grand oak trees reminiscent of old Florida rural estates.
$1,120,000

Single Family

11036 AVALON RIDGE WAY, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
25Picture(s)
2,046Sqft
4.66 Acres in Winter Garden so bring your horses, RV, boat, cars. Plenty of room here at this well built solid brick home featuring metal roof and a 47x40 4Car garage with room to park 6-8 cars PLUS a 191sqft workshop and a 24x12 carport with new wood plank 12ft ceilings for additional parking/storage.
$649,900

Single Family

14047 ALDFORD DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,226Sqft
Latham Park community gem is located-in the increasingly popular Hamlin area of Winter Garden and it has it all! Near top-rated schools, shopping, and entertainment, enjoy Disney's nightly fireworks on an oversized lot.
$415,000

Condominium

225 SOUTHERN PECAN CIRCLE, WINTER GARDEN, Florida 34787

2Bedroom(s)
2Bathroom(s)
1Parking(s)
12Picture(s)
1,264Sqft
Great Investment property 2 Bedroom 2 Bathroom Condominium in the community of Southern pines . Tennant occupied at 1,300.
$179,900

Single Family

2414 BALFORN TOWER WAY, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,428Sqft
Home: 2428 square foot Lot: 9052 square feet Added enclosed patio: 750 square feet Premium lot with large backyard Lovely home located in a low traffic cul-de-sac, move-in ready and has everything you've been looking for. 4 bedrooms, 2.5 baths.
$449,000

Single Family

8181 TOPSAIL PLACE, WINTER GARDEN, Florida 34787

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
3,811Sqft
LUXURY HOME on PREMIUM LOT! Why Build when this STUNNING Toll Brothers 5 Bedroom Madeira Craftsman Model with $170,000 of UPGRADES is available NOW! ENGINEERED HARDWOOD FLOORS on 1st Floor, Deluxe GOURMET KITCHEN, Surrounded by PARK and GREEN SPACE so NO REAR NEIGHBORS, Bonus Room, EXTENDED Covered Patio, TILE ROOF and 3 CAR GARAGE! Kitchen features WHITE SHAKER CABINETS, Large Walk-In Pant
$750,000

Lots And Land

17805 MARSH ROAD, WINTER GARDEN, Florida 34787

10Picture(s)
9.81Acre
Incredible opportunity to own nearly 10 acres, high and dry, overlooking John’s Lake. This prime property sits right in the path of development to the West of the Waterside on Johns Lake complex and offers maximum potential.
$1,250,000

Single Family

2020 STANDING ROCK CIRCLE, Oakland, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,564Sqft
Fantastic opportunity to purchase a beautiful like NEW energy efficient 4 bedroom, 2 and 1/2 bathroom home in the very desirable Oakland Trails. Just completed in 2019 and has all the energy saving features you seek built in! Clean, MOVE-IN ready! Located in the Town of Oakland and sitting along the West Orange Trail, this home has so much to offer.
$509,900

Single Family

1787 WHITE FEATHER LOOP, Oakland, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,183Sqft
It really is all about Location and this Meritage community hit the nail on the head! Tucked away enough to feel private yet convenient enough to the Turnpike, SR50 and adjacent to Killarney Station on the West Orange Trail for your evening walks or bike rides with the family.
$359,900

Lots And Land

1647 TRUMBO STREET, WINTER GARDEN, Florida 34787

1Picture(s)
0.13Sqft
Come check out this super affordable vacant lot in Orlando, Florida. Just a short drive to all of Central Florida attractions. Lots of stores and restaurants are located nearby. Connect easily to the major highways 429 and the turnpike. Vacant land in Orlando is almost gone however I have a few vacant lots available.
$30,000

Single Family

16774 SANCTUARY DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,031Sqft
Under Construction.
$785,060

Single Family

1152 HULL ISLAND DRIVE, Oakland, Florida 34787

5Bedroom(s)
5Bathroom(s)
3Parking(s)
3Picture(s)
4,009Sqft
Under Construction. With 5 beds, 4 ½ baths, a loft, a sunroom, and a 3-car garage, this plan puts the space where you need it without skimping on the style and design. Enjoy beautiful views of Lake Apopka through the plethora of glass on the back of the home. The family room showcases a stunning tray ceiling and beautiful unobstructed views of the lake.
$861,835

Single Family

16822 SANCTUARY DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
3Parking(s)
6Picture(s)
2,507Sqft
Under Construction. The award-winning Corina II SL is one of our most Flexible 4 bedroom Plans and may be the perfect plan for you! This 4-way split bedroom plan offers homeowners and guests privacy, as well as incredible amounts of living space right where you need it.
$732,410

Single Family

1088 HULL ISLAND DRIVE, Oakland, Florida 34787

4Bedroom(s)
3Bathroom(s)
3Parking(s)
2Picture(s)
2,815Sqft
Under Construction. Check out this must-see 1-story 4 bedroom, 3 bath home with large open spaces. Upon entry, a spacious foyer with a tray ceiling leads to the formal dining room, also with a tray ceiling. Two guest rooms, both with walk-in closets, a full guest bathroom with a double sink vanity can be found down the hall.
$708,260

Single Family

10284 SPRING SHORES DR, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,170Sqft
Come see this MOVE IN READY HOME in Winter Garden’s newest phase of Waterleigh. This DR Horton “Bellake” floor plan features 3 bedrooms, 2.5 bathrooms, a flex space that can be used as an office / den / formal living or dining & has been lovingly maintained by its original owners.
$350,000

Single Family

227 CHARLOTTE STREET, WINTER GARDEN, Florida 34787

4Bedroom(s)
2Bathroom(s)
1Parking(s)
24Picture(s)
1,325Sqft
Updated home on quite street, walking distance to Historical Downtown Winter Garden. Close to shopping, grocery, and City Park. Ranch style home with Bedroom #1 with full bath. Chain link fenced back yard, just needs fencing from the sides of the house to be totally fenced. Garage was reduced to just laundry room to increase the size of the living room.
$264,500

Single Family

16112 HAMPTON CROSSING DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,542Sqft
Move in ready, meticulously maintained, 4 bedroom 3 bath home with a huge open back area owned by the community which provides space between your back neighbors. This open floor plan's kitchen is appointed with an oversized granite island and counter tops with plenty of room for preparing meals and flows nicely in the family room.
$450,000

Single Family

912 JOHNS POINT DRIVE, Oakland, Florida 34787

5Bedroom(s)
6Bathroom(s)
4Parking(s)
25Picture(s)
6,065Sqft
This LUXURY LAKEFRONT ESTATE is nestled in the private, gated community of John’s Cove on a large, beautifully landscaped .63 acre homesite. Upon entry into your home, you will be awed by the stunning LAKE VIEWS through magnificent windows and over 30’ ceilings of the grand living area.
$1,749,000

Single Family

8729 EDEN COVE DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,000Sqft
One or more photo(s) has been virtually staged. TURN-KEY *Energy Efficient* 4BD/3.
$600,000

Single Family

1215 CASTLEPORT ROAD, WINTER GARDEN, Florida 34787

4Bedroom(s)
3Bathroom(s)
3Parking(s)
25Picture(s)
3,864Sqft
This huge house is located in stonybrook west, with a custom built pool and a beautiful view of both the pool and the golf course from both the ground floor and the upstairs balcony. There are multiple benefits in the community, such as the gated entry and the community standards.
$550,000

Single Family

830 GAYLE MILL DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
4Bathroom(s)
2Parking(s)
1Picture(s)
2,738Sqft
Beautiful David Weekly Sea-Side Model Home in OAKLAND PARK. 4 spacious bedrooms 3 1/2 full bathrooms and a flex-loft media room space or second den upstairs! Eco friendly installations and techniques. Double-Pane vinyl windows with Low-E glass, 14 SEER Rating HVAC System, paper-free Fiberglass insulation, and HVAC jump ducts in which improve indoor air quality.
$649,000

Condominium

1333 BROKEN OAK DRIVE, WINTER GARDEN, Florida 34787

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,544Sqft
One or more photo(s) has been virtually staged. Enjoy **MAINTENANCE FREE** Central Florida living at its finest in this lovely Waterfront 3BD/2.
$215,000

Single Family

749 CANOPY ESTATES DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
3,624Sqft
DON'T LOOK ANY FURTHER, YOU'VE REACHED YOUR DESTINATION...CANOPY OAKS in beautiful WINTER GARDEN, FLORIDA. This Mediterranean inspired SANIBEL, is a Parade of Homes GRAND AWARD WINNER! It's secluded in a 24-hour gated community along with 48 other luxury homes.
$899,000

Lots And Land

16825, 16829, 16812 W PHIL C PETERS ROAD, WINTER GARDEN, Florida 34787

10Picture(s)
22.04Acre
22 ACRES with LAKEFRONT on Flat Lake in three adjoining parcels (12.06, 5.14, & 4.83 acres) and NO HOA! Multiple homesites featuring mature oaks to build your dream home(s), farm/ horse ranch, family compound, nursery, etc.
$899,000

Single Family

719 CANOPY ESTATES DRIVE, WINTER GARDEN, Florida 34787

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
3,940Sqft
NEW PRICE!! Ideally located in the AWARD WINNING Canopy Oaks Development, a gated community of only 49 luxury homes, minutes from Winter Garden Village for shopping and dining, close to hospitals and schools, major transportation routes and to lovely downtown Winter Garden. The home features a French Country styled exterior of stone and stucco.
$1,319,000

Single Family

618 CANOPY ESTATES DRIVE, WINTER GARDEN, Florida 34787

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,250Sqft
**View this home 24-hrs a day with our 3D virtual tours** Located in a multi Award-Winning Winter Garden community, is a fantastic 2 story home with mid-construction modifications to the 2nd floor unlike other models in the area. Why compromise for an existing pool if you can design your own pool in this 4200 sq ft executive home.
$925,000

Single Family

4054 REX DRIVE, WINTER GARDEN, Florida 34787

5Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,140Sqft
DESIRABLE WINTER GARDEN LOCATION!! This is a beautiful, over 3,000 sq ft home, has a freshly painted exterior and interior and was remodeled and updated in 2017 and with almost 5 acres that are cross fenced, irrigated, with 2 barns and an aviary!! Bring your horses!! This property has been used as a mini farm by the owner with goats, horses, chickens, turkeys, and even a small cow.
$975,000

Residential

15651 GROVE RESORT AVENUE, WINTER GARDEN, Florida 34787

2Bedroom(s)
2Bathroom(s)
25Picture(s)
1,375Sqft
Stunning luxury second /investment home in building 1. In the Grove Resort and Spa Orlando Florida. High finish, state of the art, two bedroom, fully furnished condotel. Stainless steel appliances, quartz counter tops. All utilities included in the association fee. The Grove Resort is located 5 minutes from Disney Springs. Free shuttle to Disney World theme parks every day from the Grove Resort.
$289,000
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