Homes for Sale in Windermere

Windermere offers home buyers the exclusivity associated with some of Florida’s finest established communities, with a quaint historic downtown and easy access to Dr. Phillip’s world class dining and entertainment. The Erica Diaz Team offers tremendous insight into Windermere’s real estate market, offering unmatched knowledge and access to off-market homes.

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$795,000

11689 SPRAWLING OAK DRIVE
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
44Picture(s)
2,795Sqft
Welcome to your dream home in Ashlin Park, Windermere, FL! This stunning property offers unparalleled views of the serene Lake Story, providing a picturesque backdrop for your everyday life. Situated in one of Windermere's most sought-after neighborhoods, this four-bedroom, three-and-a-half-bathroom home boasts modern elegance and comfort.

$375,000

8264 MARITIME FLAG STREET
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
28Picture(s)
1,455Sqft
Welcome to your upscale oasis in the heart of Windermere! This stunning 3 bedroom, 2 bathroom condo offers the epitome of luxury living in a serene setting. As you step inside, you'll be greeted by the elegance of granite kitchen counters complemented by the warmth of wood flooring that extends gracefully throughout the entire space.

$1,995,000

5409 TILDENS GROVE BOULEVARD
WINDERMERE, Florida

6Bedroom(s)
4Bathroom(s)
44Picture(s)
5,457Sqft
Located in the sought after, 24-hour guarded community of Tildens Grove in beautiful Windermere, this meticulously landscaped 6-bedroom, 4 full and 2 half bath home boasts over 5,457 SF of gorgeous living space on well over a half acre of land. As you enter this contemporary masterpiece, you are greeted by sweeping pond views just outside the formal living room.

$415,000

11561 CENTER LAKE DRIVE
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
50Picture(s)
1,300Sqft
Discover a rare gem in the Lake Burden South community - a meticulously renovated townhouse showcasing breathtaking pond views just steps away. Step onto the welcoming front porch, setting the tone for a delightful living experience for you and your loved ones. The open floor plan seamlessly connects the bright and airy living room to the kitchen, creating an ideal space for gatherings.

$840,000

12851 WESTSIDE VILLAGE LOOP
WINDERMERE, Florida

5Bedroom(s)
3Bathroom(s)
60Picture(s)
3,694Sqft
Discover the epitome of luxury living at 12851 Westside Village Loop, Windermere, FL, where elegance meets functionality. This exquisite home boasts a striking stone finish on the front, immediately setting a tone of sophistication and grandeur.

$1,195,000

1439 BELFIORE WAY
WINDERMERE, Florida

5Bedroom(s)
4Bathroom(s)
57Picture(s)
3,789Sqft
Luxury Home located in the beautiful Tuscany Ridge gated community of Windermere. Conveniently located to shopping, eateries, and easy access to 408, 429 and turnpike. This nearly 3,800 sqft home full of amazing features, as you approach the property you are greeted with beautiful mature trees, beautiful landscaping and paver driveway, fully fenced yard with an amazing pool with water fountains.

$515,000

14252 CONFETTI DRIVE
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
3Picture(s)
2,380Sqft
Welcome to your new home at 14252 Confetti Drive in the charming Windermere, FL 34786! Prepare to be captivated by this stunning townhome that offers not just a residence, but a lifestyle of luxury and convenience. Step inside the main home and be greeted by 2000 sq ft of inviting living space, meticulously designed for comfort and functionality.

$4,950,000

4233 DOWN POINT LANE
WINDERMERE, Florida

6Bedroom(s)
6Bathroom(s)
100Picture(s)
6,478Sqft
Stunning LAKEFRONT estate on LAKE DOWN connected to the BUTLER CHAIN OF LAKES! Welcome to the cozy, quaint subdivision of Sunset Bay, all unique custom-built homes, located directly across the street from Isleworth Golf & Country Club affording you the conveniences of private golf membership opportunities nearby while residing in a community with NO HOA. This nearly 6,500 SF, 6 BR, 6.

$1,990,000

1128 ESTANCIA WOODS LOOP
WINDERMERE, Florida

5Bedroom(s)
6Bathroom(s)
70Picture(s)
5,382Sqft
This charming and meticulously maintained home is a hidden gem nestled in the serene and desirable community of Estancia Woods. With its superb location, well-appointed features, and inviting ambiance, this property built by Taylor Morrison offers the perfect blend of comfort, style, and convenience.

$2,300,000

9204 TIBET POINTE CIRCLE
WINDERMERE, Florida

5Bedroom(s)
4Bathroom(s)
54Picture(s)
5,291Sqft
Stunning Keene's Pointe home! Everything you are looking for in a custom home. Built by Stonebridge, this home has plenty of space for everyone and everything. The first floor boasts beautiful travertine and hardwood flooring throughout the formal living room with gas fireplace, dining room with adjoining dry bar and office with book niche.

$1,200,000

635 BUTLER STREET
WINDERMERE, Florida

3Bedroom(s)
3Bathroom(s)
61Picture(s)
2,353Sqft
Welcome to your dream home nestled in the heart of Downtown Windermere, just steps away from Main Street and directly across from the Fernwood Boat Ramp. This stunning three-bedroom, three-bath house blends traditional small town charm with modern conveniences. Enjoy picturesque views of the Butler Chain of Lakes from your front porch and the primary bedroom suite.

$2,285,000

11227 MACAW COURT
WINDERMERE, Florida

5Bedroom(s)
5Bathroom(s)
43Picture(s)
5,030Sqft
Offering amazing water views and overlooking the 4th fairway of the popular Jack Nicklaus designed golf course at the Golden Bear Club!  A CUSTOM BUILT stunning home that offers an incredible floor plan coupled with a long list of recent improvements! Updated with modern transitional design in mind, this OPEN and airy concept features 5 bedrooms, 5 full bathrooms, 2 separate PRIVATE OFFICE SP

$2,650,000

3992 ISABELLA CIRCLE
WINDERMERE, Florida

5Bedroom(s)
4Bathroom(s)
67Picture(s)
4,339Sqft
Welcome to your dream home! Situated in the esteemed community of Casabella, this stunning property offers a grand, light-filled first floor, featuring an expansive open living space, primary bedroom, guest bedroom, and office. Adorned with beautiful ceramic tile flooring, high ceilings, and impeccable finishes, every aspect exudes opulence.

$325,000

8256 MARITIME FLAG STREET
WINDERMERE, Florida

2Bedroom(s)
2Bathroom(s)
30Picture(s)
1,161Sqft
Welcome to your new haven at 8256 Maritime, nestled in the sought after Windermere zip code and located in Lakeside of Windermere community. This is an incredible opportunity to secure an affordable piece of paradise in one of Orlando’'s most desirable locations, Windermere.

$385,000

8271 MARITIME FLAG STREET
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
9Picture(s)
1,349Sqft
Come enjoy the Windermere lifestyle (it’s all about location!) in this cozy 3 bedroom, 2.5 bath condo. The kitchen features granite countertops, tall cabinets and a corner walk in pantry. All bedrooms are upstairs; has a laundry closet as well. All kitchen appliances are included, washer and dryer are also included! There is tile throughout the first floor.

$395,000

6314 SOUTHBRIDGE STREET
WINDERMERE, Florida

4Bedroom(s)
2Bathroom(s)
26Picture(s)
1,640Sqft
A beautiful townhome located in the highly sought after Windermere area, where you'll find this beautifully maintained 4 bedroom, 2 1/2 bathroom and 2 car garage. As you approach this attractive home, you're greeted with a large, covered porch, perfect for enjoying the Florida weather. Step inside and you'll find a large open floor plan with lots of storage and plenty of natural light.

$530,000

13347 OVERSTREET ROAD
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
30Picture(s)
2,058Sqft
MOVE IN READY HOME in Windermere’s desirable Windermere Terrace! This City Homes built “Hampton” floor plan features 3 beds/2 baths, a flex space that can be used as an office/playroom/man cave or formal living space, an open floor plan, spacious kitchen open to the dining room and family room and a screened in patio! You will love the neutral colors, the ceramic tile floors in t

$1,299,000

8457 TIBET BUTLER DRIVE
WINDERMERE, Florida

5Bedroom(s)
4Bathroom(s)
57Picture(s)
3,234Sqft
Welcome to a truly exceptional home nestled in the sought after country club golf community of Keene's Pointe. This exquisite residence boasts 5 bedrooms, 4 bathrooms and 3234 square feet of meticulously designed living space, offering an extraordinary lifestyle in a premier location.

$1,850,000

5608 MARLEON DRIVE
WINDERMERE, Florida

5Bedroom(s)
5Bathroom(s)
71Picture(s)
5,228Sqft
Enjoy the luxurious Florida lifestyle you’ve envisioned in Windermere's prestigious Lake Cypress Cove. On nearly an acre of land, this opulent 5-bedroom, 5 1/2-bath executive residence exudes elegance, with recent upgrades to flooring, counters, cabinetry, paint, and lighting fixtures.

$2,135,000

1449 MARAVILLOSO LOOP
WINDERMERE, Florida

5Bedroom(s)
5Bathroom(s)
47Picture(s)
5,290Sqft
Welcome to the Woods of Windermere, an exclusive enclave comprising just 12 distinguished residences. Presenting the remarkable Siena model, this home exemplifies refined craftsmanship and sophistication. Upon arrival, you are greeted by a courtyard with fountain, setting a tone of elegance and charm.

$895,000

9207 REFLECTION POINTE DRIVE
WINDERMERE, Florida

4Bedroom(s)
3Bathroom(s)
25Picture(s)
3,010Sqft
Step into this magnificent residence featuring 4 bedrooms and 3 bathrooms. The open-concept layout effortlessly blends the living room and kitchen, creating a warm and inviting atmosphere for both daily living and entertaining. The kitchen is a chef's dream, equipped with high-end stainless steel appliances, dual sinks, solid wood cabinets and stunning granite counters.

$1,199,900

5933 CAYMUS LOOP
WINDERMERE, Florida

4Bedroom(s)
4Bathroom(s)
45Picture(s)
2,766Sqft
This newly renovated masterpiece boasts 4 bedrooms, 4.5 bathrooms, and is perfectly positioned overlooking the breathtaking Hole 14 of the renowned Golden Bear golf course. Step into a world of elegance as you enter the meticulously designed interiors featuring high-end finishes, stunning floors, and an abundance of natural light.

$574,990

6620 BRIDGEWATER VILLAGE ROAD
WINDERMERE, Florida

3Bedroom(s)
2Bathroom(s)
34Picture(s)
2,115Sqft
Welcome to your charming 3-bed, 2-bath home nestled on a premium corner lot in Windermere. This home also features an extra room that can be used as an office, den, or playroom area. Step into modern elegance with an updated kitchen boasting sleek finishes with quartz counter tops, walk-in pantry, and a large kitchen island with room for seating and ample storage.

$550,000

6412 EARTHGOLD DRIVE
WINDERMERE, Florida

4Bedroom(s)
2Bathroom(s)
36Picture(s)
2,005Sqft
Move-In ready, Cozy, Corner Lot Home in the highly desirable Gated Community of Eden Isle! This split plan home boasts 4 Bedrooms + 2 Bathrooms with 2,000+ square feet of living space, located only a few miles north of Disney’s Magic Kingdom and within walking distance to Publix at Summerport.
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