Homes for Sale in Winter Garden
Whether you’re looking to move-up or downsize, Winter Garden has the perfect living space for you. Winter Garden’s active downtown, with an award-winning farmer’s market, bike trail, and brewery, has been a favorite of locals for years. Buyer’s can choose homes located next to the 22-mile West Orange trail, countless restaurants in the historic downtown or in new communities of the surrounding suburbs.
As Winter Garden’s top Buyer’s Agent, the Erica Diaz Team has the experience to find what you’re looking for; find your Winter Garden Home using the filter below, or explore what else Winter Garden has to offer.
$999,000
17930 ADRIFT ROAD
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
37Picture(s)
3,327Sqft
If you enjoy Amazing Sunsets over the water then..Here is your new home! This Sea Cliff model is a beautiful 4 bedroom 3.5 bath home with a spacious entry featuring tray ceilings, Formal dining room or possible flex space for entertaining. Gourmet kitchen features stainless steel appliances, smooth stone counter tops, and glass tile back splash, as well a convenient butlers pantry.
$1,225,000
16702 OTTERCHASE LANE
WINTER GARDEN, Florida
4Bedroom(s)
4Bathroom(s)
100Picture(s)
3,597Sqft
*INCLUDED Tesla solar is PAID in FULL! Properly named “Waterside”, this luxurious gated community was created to savor the shoreline along Johns Lake. Stunning resort style amenities are perched high above the waters edge to fully experience the natural beauty. A perfect escape to enjoy a swim & daily workout in the fitness center.
$740,000
14639 WHITTRIDGE DRIVE
WINTER GARDEN, Florida
5Bedroom(s)
4Bathroom(s)
72Picture(s)
3,411Sqft
Independence ** Lush conservation lot location & dynamite home with many upgrades & beautifully maintained** Fantastic wrap around covered screened patio with new epoxy lanai floor in 2022 plus a new patio +/- 2020 overlooking this beautiful wooded lot ** Plantation Shutters throughout ** 1st flr den with newer wood floors 2020 ** FIRST FLOOR MASTER BEDROOM w en-suite master bath and large
$619,990
15231 HONEYBELL DRIVE
WINTER GARDEN, Florida
3Bedroom(s)
2Bathroom(s)
18Picture(s)
2,083Sqft
BEAUTIFUL single-family home located in new Winter Garden area, with 3 bedrooms and 2 bath. The kitchen is spectacularly designed with stainless steel appliances ,2 car Garage, near to Publix, Walmart, expressways, very close to Winter Garden Village, Disney, cinemas, restaurants, etc. Community includes pool and club house.
$637,000
5506 NEW INDEPENDENCE PARKWAY
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
39Picture(s)
2,369Sqft
Welcome to 5506 New Independence Pkwy, an exceptional 4-bedroom, 3-bathroom home nestled in the highly desirable Independence neighborhood of Winter Garden. Built in 2013, this spacious residence offers 2,369 square feet of thoughtfully designed living space, ideal for families seeking both style and convenience.
$1,198,000
17572 DAVENPORT ROAD
WINTER GARDEN, Florida
4Bedroom(s)
4Bathroom(s)
85Picture(s)
2,756Sqft
No HOA! Discover your dream home in the heart of central Florida's Winter Garden! Welcome to your charming rural retreat! at 17572 Davenport Road, a stunning 4-bedroom, 4-bath, with a independent access studio/apartment or granny's suite home nestled on more an acre of land, this private haven boasts a fully fenced yard for privacy along with exquisite landscaping for a tranquil atmosphere.
$349,900
7038 BROOMSHEDGE TRAIL
WINTER GARDEN, Florida
2Bedroom(s)
2Bathroom(s)
53Picture(s)
1,178Sqft
BACK TO MARKET!! PRICED TO SELL. FINAL REDUCTION TO SEEL!! Don't miss this great opportunity.
Welcome to this stunning 2-bedroom, 2.5-bathroom home located in the heart of Winter Garden, Florida. Step inside to find an inviting open floor plan, a gourmet kitchen equipped with stainless steel appliances, and a spacious master suite.
$818,999
2602 SHIREHALL LANE
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
32Picture(s)
2,900Sqft
Step into luxury with this fully renovated 4-bedroom, 3-bathroom home, nestled in the Sought-afte gated and golf community of Winter Garden; Stoneybrook West. The grand foyer welcomes you with soaring ceilings, leading to the formal living and dining rooms, featuring porcelain flooring and elegant upgrades like modern light fixtures, upgraded baseboards, and neutral paint tones.
$919,900
15859 SHOREBIRD LANE
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
39Picture(s)
2,812Sqft
Experience a refined luxury with the Bavaro model by Toll Brothers, a magnificent residence spanning 2,812 square feet with 4 bedrooms and 3.5 bathrooms. Designed with an expansive open floor plan, this home sets the stage for sophisticated entertaining.
Upon entering the grand 2-story foyer, you'll be captivated by the seamless flow of the dining room, living room, and kitchen.
$625,000
181 ZACHARY WADE ST
WINTER GARDEN, Florida
5Bedroom(s)
3Bathroom(s)
64Picture(s)
2,940Sqft
One or more photo(s) has been virtually staged. Welcome to your dream home in the exclusive gated community of Lakeview Reserve, nestled in the heart of charming downtown Winter Garden! This stunning 5-bedroom, 3-bathroom residence offers the perfect blend of modern luxury and serene lakefront living.
$279,000
330 STORY ROAD
WINTER GARDEN, Florida
2Bedroom(s)
1Bathroom(s)
11Picture(s)
760Sqft
Welcome to a great opportunity for your first home!. Just a stone's throw away from the vibrant heart of plant street in downtown Winter Garden! where you'll enjoy easy access to a delightful array of local shops, restaurants, and entertainment options. This cozy home features two comfortable bedrooms, perfect for small families or couples looking to settle into a welcoming community.
$499,900
1140 HARBOR HILL STREET
WINTER GARDEN, Florida
4Bedroom(s)
2Bathroom(s)
73Picture(s)
2,180Sqft
This is your opportunity to own a spacious 4 bedroom, 2 bath home on a beautiful tree lined street in the popular Stoneybrook West community in Winter Garden!! From the moment you step inside, you'll be impressed with the high ceilings throughout making the large floorplan feel grander! From the foyer you have a spacious formal living room and formal dining room that can easily be used for a home
$575,000
17682 NORTHLAKE GROVE DRIVE
WINTER GARDEN, Florida
3Bedroom(s)
2Bathroom(s)
31Picture(s)
1,906Sqft
Welcome to 17682 Northlake Grove Dr, a sophisticated residence situated in Ovation at North Lake
Upon entering this, 3-bedroom, 2.5-bathroom home, you'll be greeted by an open concept main floor, featuring an eat in kitchen, solid stone countertops, tasteful vinyl floors, an abundance of natural light, comfortable living space and space for a dining table.
$134,900
1710 BAY STREET
WINTER GARDEN, Florida
2Bedroom(s)
1Bathroom(s)
6Picture(s)
972Sqft
Great Investment Opportunity on this 2/1 with a bonus room that could become bedroom 3. Newer Roof. As-Is Cash Only. Make this one your next rehab or add it to your investment portfolio. Quiet street close to all the shops, resturants and amenities of Downtown Winter Garden. Minutes to the 429, 408 and the Turnpike. This one will not last. Call today for more details.
$390,000
WINTER GARDEN, Florida
3Bedroom(s)
2Bathroom(s)
44Picture(s)
1,758Sqft
Location Location. Beautiful CORNER townhome, ready to move with 3 bedrooms and 2.5 baths, located just minutes from historic and highly sought after downtown Winter Garden, shops, restaurants, and interstate travel. The ORCHARD community offers community pool, playground to enjoy and beautiful lanscape. This unit offers fresh interior paint, 2 car garage, outdoor fenced patio.
$735,000
17404 LAKE STAR ROAD
WINTER GARDEN, Florida
3Bedroom(s)
2Bathroom(s)
30Picture(s)
2,122Sqft
Don't miss this rare chance to own a brand-new home, completed in November of 2023 with a transferable builder warranty, on over a .25-acre lot with stunning conservation views in Northlake at Ovation.
$225,000
913 BUTTERFLY BOULEVARD
WINTER GARDEN, Florida
2Bedroom(s)
2Bathroom(s)
23Picture(s)
938Sqft
One or more photo(s) has been virtually staged. Discover this incredible opportunity to own a 2/2 condo in Winter Garden, Florida. This charming and cozy property is ideal for first-time homebuyers looking for a perfect place to call home.
Investors will also find this property highly attractive, as it would be a valuable addition to any portfolio.
$725,000
13639 GLYNSHEL DRIVE
WINTER GARDEN, Florida
5Bedroom(s)
4Bathroom(s)
8Picture(s)
3,470Sqft
Welcome to your luxurious Winter Garden retreat in this stunning property located in a gated community. Boasting 5 bedrooms with 4 full baths with a home office and beautiful formal dining and living. The downstairs features a spacious quartz kitchen with built in oven, a wine refrigerator and updated cabinets throughout, just waiting for the gourmet meals.
$700,000
10265 SPRING SHORES DRIVE
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
55Picture(s)
2,909Sqft
Welcome to your future home in Waterleigh, where modern living meets peaceful surroundings just minutes from the magic of Disney. This beautifully crafted 4-bedroom, 3-bathroom home is more than just a place to live—it’s where comfort, style, and endless possibilities come together. From the moment you arrive, you’re greeted by a warm and inviting atmosphere.
$459,990
10642 WORDS DRIVE
WINTER GARDEN, Florida
4Bedroom(s)
2Bathroom(s)
21Picture(s)
1,992Sqft
Discover contemporary living in this almost brand-new townhome (2023), perfectly situated in the vibrant and desirable Winter Garden community of Storey Grove. This spacious residence boasts 4 bedrooms, 2.5 bathrooms, and an array of modern finishes that blend style with functionality. Key features of this property include modern, sleek interior finishes featuring high-quality materials.
$775,000
18303 OLIVER TWIST WAY
WINTER GARDEN, Florida
4Bedroom(s)
3Bathroom(s)
46Picture(s)
3,316Sqft
Home located in the much sought after Waterleigh Community, The home is the Sea Cliff offered by DR Horton and is a beautiful 4 bedroom 3.5 bath home with a spacious entry featuring tray ceilings. Formal dining room or possible flex space for entertaining.
$1,357,995
13234 TOLLCROSS WAY
WINTER GARDEN, Florida
5Bedroom(s)
4Bathroom(s)
12Picture(s)
3,778Sqft
Under Construction. Fractional Ownership. Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. The 5 bedroom 4.5 bath home Delray home is a very private and oversized lot that has both a conservation and water view.
$1,099,995
13259 TOLLCROSS WAY
WINTER GARDEN, Florida
5Bedroom(s)
4Bathroom(s)
11Picture(s)
3,318Sqft
Under Construction. Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. This 5 bedroom 4 bath home an has oversized first floor primary suite overlooking the water. The two story foyer creates an impressive entry into this home. This is a very open floor plan that has a casual dining area and great room adjacent to each other.
$499,900
16229 PEBBLE BLUFF LOOP
WINTER GARDEN, Florida
3Bedroom(s)
2Bathroom(s)
51Picture(s)
1,685Sqft
Welcome to this cozy house in Waterleigh Winter Garden! When you walk in the door, a beautiful porch welcomes you, as you enter the foyer, you’ll find two guest bedrooms that share a full bathroom. As you continue into the home you will find the well-appointed kitchen overlooks the family room, dining room, and outdoor lanai.
Who’s Your Winter Garden Buyer’s Agent?
Every home shopper should have a Buyer’s Agent – it’s free to the buyer. Agents at the Erica Diaz Team know Winter Garden best! They know how to help you negotiate a better deal, and close faster than the average Winter Garden Realtor. Ask us about the local neighborhoods, we’ll know where to find the best homes for your goals in each price range.
