0.43 mi
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
81 OAKDALE STREET
Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year
Living Area:
4284 Sqft.
|
5
Beds,
5
Baths
|
$2,500,000 |
299 W 4TH AVENUE
This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, r
Living Area:
2410 Sqft.
|
4
Beds,
3
Baths
|
$895,000 |
2958 MARQUESAS COURT
This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies
Living Area:
4716 Sqft.
|
5
Beds,
5
Baths
|
$1,998,000 |
9508 Windy Ridge Road
Discover this Perfectly positioned Georgian Estate situated on 12 acres (additional 6 acres available) of lakefront property with meticulously manicured grounds. This walled and gated compound includes approx 614 feet of pristine lake frontage and panoramic views on Lake Down of the Butler Chain of
Living Area:
20865 Sqft.
|
6
Beds,
14
Baths
|
$22,995,000 |
3328 WAX BERRY COURT
One or more photo(s) has been virtually staged. A rare find in the heart of Downtown Windermere! This 4 bedroom, 4 full bath home with an inground pool sits not only on 1 acre but also in a semi-private cul-de-sac with only 8 other homes. You are welcomed by the circular driveway plus rear side entr
Living Area:
2636 Sqft.
|
4
Beds,
4
Baths
|
$975,000 |
2828 INGEBORG COURT
Welcome to this Mediterranean dream home tucked away at the end of a quiet cul-de-sac in Windermere, just steps from beautiful Lake Down. Sitting on over an acre of fenced land, this property is one of the most unique opportunities in the area. From the moment you arrive, the curb appeal stands out
Living Area:
3190 Sqft.
|
5
Beds,
5
Baths
|
$1,225,000 |
1803 GLENBAY COURT
Welcome to The Reserve at Belmere. Experience refined living in this exclusive guard-gated enclave, where sophistication meets comfort. Perfectly positioned on a premium corner lot, this elegant 4-bedroom, 3-bath home showcases a seamless blend of timeless design and modern luxury. The newly remodel
Living Area:
3040 Sqft.
|
4
Beds,
3
Baths
|
$875,000 |
1003 DOWN RESERVE COURT
Welcome to a rare modern estate inside an intimate gated enclave, offering 6,816 square feet of fully furnished luxury with six bedrooms, six full baths and two half baths. Every detail of this custom-built masterpiece was designed for those who value privacy, prestige and perfection. Go inside to d
Living Area:
6816 Sqft.
|
6
Beds,
8
Baths
|
$5,499,999 |
436 E 7TH AVENUE
Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-s
Living Area:
3136 Sqft.
|
4
Beds,
5
Baths
|
$2,425,000 |
2844 MARQUESAS COURT
Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmering waters of Lake Crescent. Nestled within the exclusive gated community of Lake Crescent Reserve, this lakefront masterpiece offers just under 6,000 square feet of newly remodeled, reimagined luxury living.
Living Area:
5365 Sqft.
|
4
Beds,
3
Baths
|
$3,700,000 |
2 CHASE ROAD
Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Co
Living Area:
3889 Sqft.
|
4
Beds,
5
Baths
|
$3,200,000 |
101 LEE STREET
A new long elegantly paved driveway leads up to this beautifully updated 5-bedroom, 4,200 sq. ft. home in the charming Town of Windermere. With lush views of established landscaping & surrounding trees, this home combines comfort, style, and plenty of space for family and friends. The bright, open k
Living Area:
4186 Sqft.
|
5
Beds,
4
Baths
|
$1,550,000 |
2012 BELLAMERE COURT
Exquisitely appointed and elegantly packaged former model home, showcasing the pinnacle of perfection, from luxury home builder Element Homes. This masterpiece stands supreme for its high-quality fit and finish and a highly desirable floorplan – featuring a great room combination of family room, d
Living Area:
4701 Sqft.
|
5
Beds,
6
Baths
|
$3,375,000 |
311 E 8TH AVENUE
Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie.
Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere. Imagine waking up to shimmering water views, paddle-boarding before b
Living Area:
3805 Sqft.
|
5
Beds,
4
Baths
|
$1,660,000 |
9731 CHESTNUT RIDGE DRIVE
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers a
Living Area:
4877 Sqft.
|
4
Beds,
4
Baths
|
$3,400,000 |
10545 DOWN LAKEVIEW CIRCLE
Enjoy stunning sunsets from your private estate with expansive views, located on Lake Down, the prestigious Butler Chain of Lakes in Windermere. This well-appointed property features 2.78 acres with fully fenced terraced grounds, electric security gates, brick pavers, mature landscaping for privacy,
Living Area:
7263 Sqft.
|
5
Beds,
7
Baths
|
$3,795,000 |
109 E 12TH AVENUE
Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida
Living Area:
2791 Sqft.
|
4
Beds,
4
Baths
|
$1,237,000 |
3417 BAY MEADOW COURT
RARE 1-ACRE LOT living awaits in this fully renovated modern residence, ideally situated on a quiet CUL-DE-SAC close to Windermere Town. The unparalleled space allows you to PARK YOUR RV/VESSELS IN YOUR BACKYARD and BUILD YOUR OWN ENTERTAINMENT AREA. Inside, the home is move-in-ready, featuring a br
Living Area:
2681 Sqft.
|
4
Beds,
4
Baths
|
$1,280,000 |
111 MAIN STREET
Prime Windermere Location! Fully Renovated and Move-In Ready!
Don’t miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms—perfe
Living Area:
2272 Sqft.
|
3
Beds,
2
Baths
|
$949,000 |
11923 LAKE BUTLER BOULEVARD
Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with s
Living Area:
2238 Sqft.
|
3
Beds,
2
Baths
|
$1,630,000 |
3443 WILD MYRTLE COURT
Welcome to 3443 Wild Myrtle Court, a beautifully renovated executive home nestled on a serene 1.2-acre cul-de-sac lot in the esteemed Lake Butler Estates of Windermere, Florida. This expansive 5-bedroom, 3-bathroom residence offers 2,918 square feet of thoughtfully designed living space, combining m
Living Area:
2918 Sqft.
|
5
Beds,
3
Baths
|
$1,200,000 |
2828 MARQUESAS COURT
Gorgeous Private Lakefront Custom Brick Estate over 10,000 sq ft under roof, just under 7,000 sq ft under HVAC. First Time Ever on Market! Step thru the Gorgeous Leaded Glass Doors into this Magnificent Estate the Entry made for Royalty Custom Magnolia Curved Staircase with custom Italian Marble Fl
Living Area:
6819 Sqft.
|
6
Beds,
6
Baths
|
$2,995,000 |
11056 CLIPPER COURT
Professional Pictures Coming Soon * Huge 5 Bedroom 6 Bath Multi-Generational Pool Home Has 1 Full Suite on 1st Floor & 2 Spacious Suites on the 2nd Floor * Open Floorplan * The Marina Bay Community Includes a Waterfront Marina for your boat that is directly connected to Lake Down and the Butler Chai
Living Area:
6375 Sqft.
|
5
Beds,
6
Baths
|
$1,600,000 |
225 MAGNOLIA STREET
LAKEFRONT GRANDEUR IN WINDERMERE | A MASTERPIECE ON LAKE DOWN
Unveiling a rare opportunity to own an architectural masterpiece on the famed Butler Chain of Lakes—a residence that redefines lakefront luxury in the exclusive town of Windermere. Custom-built in 2019, this Mediterranean-inspired esta
Living Area:
5935 Sqft.
|
7
Beds,
11
Baths
|
$4,899,000 |
801 W 2ND AVENUE
Experience the epitome of lakefront living on the Butler Chain of Lakes with this exceptional Windermere estate. On one of the area’s desirable streets, this home offers over $350,000 of recent luxurious upgrades, including a new kitchen and fireplace, new windows and doors, landscape lighting, ne
Living Area:
5639 Sqft.
|
5
Beds,
7
Baths
|
$4,250,000 |
409 W 2ND AVENUE
Step inside this beautifully updated home where clean lines, soaring ceilings, and two-story windows fill every corner with natural light. A floating staircase makes a stunning first impression, while the spacious family room with its cozy fireplace is the perfect spot to gather with friends and fam
Living Area:
4688 Sqft.
|
5
Beds,
5
Baths
|
$2,399,000 |
647 RIDGEWOOD DRIVE
One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Wind
Living Area:
2681 Sqft.
|
3
Beds,
3
Baths
|
$2,150,000 |
11113 LAKE BUTLER BOULEVARD
Welcome to this beautiful, unique and modern home, built less than 3 years ago. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much
Living Area:
4094 Sqft.
|
5
Beds,
6
Baths
|
$2,499,000 |