Windermere Homes for Sale

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Lots And Land

4008 DOWNEAST LANE, WINDERMERE, Florida 34786

6Picture(s)
1.46Acre
Spectacular opportunity to own LAKE DOWN lakefront property on the Butler Chain of Lakes! With approximately 100 ft +/- of waterfront, this is a great chance to develop or build your dream home on Lake Down. Enjoy gorgeous western lakefront views and evening sunsets. Plus, this locale offers privacy and peacefulness as the property is tucked away on a quiet dead-end road.
$974,500

Single Family

1542 Belfiore Way, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
25Picture(s)
5,413Sqft
This majestic 2-story 5,413 sqft home features 5 BR/4.5 BA will impress you with magnificent views from the outdoor oasis !Decorative pavers lead up the oversized driveway to 3 car garage! Double door entry takes you into the formal living room with custom window treatments and formal dining with exquisite columns.
$949,000

Rental

8486 POWDER RIDGE TRAIL, WINDERMERE, Florida 34786

1Bedroom(s)
1Bathroom(s)
2Parking(s)
13Picture(s)
890Sqft
GOOD AND PRACTICE STUDIO WITH GARAGE. GREAT LOCATION. CHECK OUT.
$1,250

Single Family

5085 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
5Bathroom(s)
3Parking(s)
10Picture(s)
4,024Sqft
Nestled along the front nine of Isleworth’s renowned championship golf course, this lovely golf-front residence offers a backdrop of beautiful views of the 5th hole. The single-story home boasts an open and airy interior spanning more than 3,800 square feet of living space, with elegant stone and hardwood floors throughout.
$1,549,000

Lots And Land

MONTERREY CLUB COURT, WINDERMERE, Florida 34786

3Picture(s)
0.53Acre
Discover one of the last remaining home sites in the renowned community of Isleworth Golf & Country Club. Positioned on a cul-de-sac along the back nine of Isleworth's championship golf course, this 0.529-acre home site offers a peaceful setting and the perfect opportunity to build a custom dream home by Stonebridge Homes.
$694,800

Single Family

9648 MCCORMICK PLACE, WINDERMERE, Florida 34786

3Bedroom(s)
4Bathroom(s)
3Parking(s)
10Picture(s)
4,889Sqft
A fabulous golf and lakefront location and a beautifully updated interior are hallmarks of this elegant Isleworth estate. Nestled along the front nine along Isleworth’s 2nd fairway overlooking beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes and updates throughout.
$1,990,000

Single Family

9711 DEACON COURT, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
5Parking(s)
25Picture(s)
8,400Sqft
One or more photo(s) has been virtually staged. Isleworth living at its best! Live the good life in this sprawling mansion located on the shores of the famed Butler Chain in the main section of Isleworth. The private, gated estate has been extensively updated in 2020 with a brand new boat dock and a fully repainted interior and exterior – now in a fresh and modern white hue.
$3,995,000

Single Family

5097 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
2Parking(s)
25Picture(s)
6,215Sqft
Nestled along the front nine of Isleworth’s famed championship golf course, this immaculate estate has been extensively updated both inside and out, blending transitional style with a wealth of modern appointments to create a fabulous golf-front sanctuary.
$2,950,000

Single Family

13502 BELLARIA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
10Picture(s)
5,667Sqft
This elegant home is located at Bellaria, a guard-gated community on beautiful Windermere area. It features 5 bedrooms including a Master Suite downstairs, 5 full bathrooms and 2 half baths, plus a Media Room, an Office, upstairs Loft.
$1,299,900

Rental

8960 MATRIARCA ALLEY, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
21Picture(s)
1,556Sqft
Beautiful Front Pond View w/ Amazing views of Disney Fireworks every night! This exclusive 3 Bedroom/2.5 Bath Mattamy Town Home is the Amber floor plan - offering a two car garage with rear entry. The new tenant will love the light and bright open floor plan. There are Gorgeous designer options throughout including a full stainless steel kitchen appliance package plus washer and dryer.
$1,995

Single Family

13316 BELLARIA CIRCLE, WINDERMERE, Florida 34786

6Bedroom(s)
8Bathroom(s)
3Parking(s)
10Picture(s)
7,268Sqft
One or more photo(s) has been virtually staged. Luxury living and at home comfort come together at this stunning Mediterranean style property! This beautiful home sits on a 3/4 acre lot in the 24-hour guard gated community of Bellaria. Arrive and be in awe of the elegant exterior and landscaping, as well as the convenient large circular driveway.
$1,750,000

Single Family

13119 CASABELLA DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
4Parking(s)
25Picture(s)
6,855Sqft
Welcome to the best double waterfront lot at CASABELLA. A Luxury gated community in upscale Windermere. Offering only 79 single family homes on half-acre home sites.
$2,655,000

Single Family

6464 DEACON CIRCLE, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
10Picture(s)
6,605Sqft
Welcome to this gorgeous lake front home! Lake views compliment this spectacular Isleworth home that has a completely redesigned 2nd floor with world class finishes. As you step through the front entrance, you are led to a grand living area with floor to ceiling windows filling the space with natural light and giving you an amazing view of the lake.
$2,895,000

Single Family

5049 LATROBE DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,833Sqft
Majestic golf course views abound from this beautifully-crafted Isleworth estate.
$1,850,000

Single Family

5181 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
4Parking(s)
10Picture(s)
3,645Sqft
Set behind the manned gates of Central Florida’s most exclusive neighborhood and on the 4th hole of the Isleworth Golf Course, this executive pool home offers peace and privacy in a sought-after main phase location.
$1,395,000

Rental

5181 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
4Parking(s)
10Picture(s)
3,645Sqft
Set behind the manned gates of Central Florida’s most exclusive neighborhood and on the 4th hole of the Isleworth Golf Course, this executive pool home offers peace and privacy in a sought-after main phase location.
$9,800

Single Family

9927 GIFFIN COURT, WINDERMERE, Florida 34786

12Bedroom(s)
15Bathroom(s)
25Picture(s)
31,000Sqft
One or more photo(s) has been virtually staged. Situated within Isleworth Golf & Country Club - one of central Florida’s top gated golf communities. This home offers nearly four acres of western facing waterfront property with 700 feet of prime lake frontage and panoramic views of Lake Butler.
$19,500,000

Residential

14473 Yellow Butterfly Road, WINDERMERE, Florida 34786

5Bedroom(s)
3Bathroom(s)
25Picture(s)
3,211Sqft
NEW PRICE ADJUSTMENT! Take advantage today and live the Windermere Lifestyle! Here is your opportunity to own a Five (5) bedroom, Three (3) bathroom, 3,211 square foot, Two (2) car garage, pool home in Windermere for under 430k. The list price reflects the home’s current condition and it is being sold in AS IS.
$425,000

Townhouse

13459 Gorgona Isle Drive, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
25Picture(s)
1,788Sqft
Absolutely stunning townhome built December 2019. Completely remodeled and upgraded by interior designer finished April 10, 2020. Almost $45,000 in modern upgrades. Nothing else on the market compares to this incredible home. Minutes to Disney World. Situated just north of Magic Kingdom allowing for a prime location to watch nightly fireworks. Beautiful community pool and playground.
$399,900

Residential

5139 FAIRWAY OAKS DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
9Bathroom(s)
4Parking(s)
10Picture(s)
11,163Sqft
Seller Requirement: Buyer must produce proof of funds at full listing price. Nestled on a picturesque home site along the shores of Lake Bessie, this commanding waterfront residence blends a Spanish Mediterranean exterior with a modern transitional interior.
$4,745,000

Residential

953 LASCALA DR, WINDERMERE, Florida 34786

4Bedroom(s)
2Bathroom(s)
12Picture(s)
COME SEE THIS!!! Beautiful 2-story, 4-bedroom/2.5-bathroom home in the highly sought after, gated community of Belmere Village located in wonderful Windermere. The home features a double-door entry way, where you walk into a spacious living room that connects to the master bedroom, dining room, kitchen, and large family room.
$0

Single Family

225 FOREST STREET, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,289Sqft
Gorgeous custom home in downtown Windermere is perfectly located to enjoy all that the downtown Windermere lifestyle has to offer! It's a short walk to the tennis courts, play park, boat ramp, farmers market, food truck events, and shops and restaurants! The beautiful stone and copper accents perfectly compliment the wood doors, expansive front porch and architectural features to set the stage for
$925,000

Rental

1560 BELFIORE WAY, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
4,946Sqft
Move-in ready, this majestic and spacious executive home has a superb location with A-rated Olympia High School and enough room for everyone in the family to relax, play, entertain, work and rest! Enter handsome leaded glass front doors to a light filled foyer and living room with a soaring 2 story ceiling. Large windows throughout bring natural light. This 5 bedroom 4.
$5,500

Single Family

1560 BELFIORE WAY, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
10Picture(s)
4,946Sqft
https://tour.vht.com/433886424/IDXS From the moment you enter this majestic and spacious executive home with a superb location, A-rated Olympia High School and enough room for everyone in the family to relax, play, entertain, work and rest you'll know you're home! Enter handsome leaded glass front doors to a light filled home and living room with a soaring 2 story ceiling. This 5 bedroom 4.
$899,000

Single Family

10325 DOWN LAKEVIEW CIRCLE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
22Picture(s)
2,997Sqft
ENJOY the privacy and seclusion of this 1 acre home. Enjoy the access to the famous Butler Chain of Lakes. How about the desirable community of The Lakes, and within the community of Windermere with its charming small town feel.
$527,000

Rental

12754 GARRIDAN AVENUE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
25Picture(s)
1,970Sqft
Come live in this beautiful home in Windermere. Great floorplan, on the first floor you will find the kitchen with stainless steel appliances, 42" cabinets, granite countertops, a large island and eat in space; the dining area which opens to the great room; a 1/2 bathroom; and the master bedroom with 2 walk-in closets, and the master bathroom with garden tub and a separate shower.
$2,150

Single Family

11443 WATERSTONE LOOP DRIVE, WINDERMERE, Florida 34786

7Bedroom(s)
8Bathroom(s)
3Parking(s)
10Picture(s)
7,734Sqft
Windermere luxurious lakefront living at it’s best! This grand estate built in 2014 is perfectly sited along the shores of Lake Butler with unparalleled and unobstructed water views in the guard gated community of Waterstone.
$3,675,000

Rental

9742 GREEN ISLAND COVE, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
10Picture(s)
3,083Sqft
Nestled along the shores of beautiful Lake Louise within the gates of the renowned Isleworth Golf & Country Club, this charming golf villa offers a prime lakefront location in proximity to the Clubhouse. The interior boasts more than 3,000 square feet of living space, with an open floor plan set against a backdrop of picturesque water views.
$8,000

Single Family

5108 FAIRWAY OAKS DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
4Parking(s)
25Picture(s)
4,144Sqft
One or more photo(s) has been virtually staged. Nestled on a cul-de-sac within the gates of Isleworth, this elegant residence offers a lovely retreat in the famed golf club community. The interior spans 4,144 across a single-story floor plan, with stunning chandeliers and marble and wood floors throughout the home.
$1,550,000

Single Family

4705 JOANNA GARDEN COURT, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,060Sqft
One or more photo(s) has been virtually staged. Stunning Modern Mediterranean estate located in the Gardens of Isleworth within renowned Isleworth Golf & Country Club. This exquisite home has recently been re-painted to give it a bright, open, and airy feel. The home features 4 bedrooms, 4 full baths, 2 half baths, and a second floor sitting area.
$1,950,000

Single Family

0 DINGENS AVENUE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
3Parking(s)
10Picture(s)
4,000Sqft
Enjoy a tour any time, 24-hours a day - Pre-Construction. To be built. Energy Saving, Excellent location, and Custom made with Pride of Craftsmanship; that is what to expect when choosing to custom-build with a "hands-on" local builder. Located in the Olympia HS.
$900,000

Single Family

6385 SWANSON STREET, WINDERMERE, Florida 34786

6Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,499Sqft
Windermere Home situated within The Enclave neighborhood, newly built in 2015 by Meritage. The spacious Hawthorne floor plan features 4,499 square feet, 6 bedrooms, 4 full bathrooms, 1 half bathroom.
$740,000

Single Family

105 PALM STREET, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,268Sqft
Original one of a kind & sure to charm...from the waterfall courtyard entry, custom ironwork & enchanting brick paths. This Spanish style home was established in 1955 on one of the most desirable corner lots in old Windermere. Modifications over the years have built upon & enhanced the unique architecture.
$779,000

Townhouse

12361 VIA DERNA PLACE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
1,936Sqft
BACK ON MARKET. Make your appointment today to view this move-in ready end unit townhome with 4 bedrooms, 3 and 1/2 bathrooms. This home, features an abundance of windows, 2-car garage, 2 master bedroom suites and nightly views of Disney fireworks from the second floor balcony.
$309,900

Single Family

8051 WHITFORD CT, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
3Parking(s)
25Picture(s)
2,615Sqft
New Price! Custom built by Osprey Homes this "French Country Style Villa" on the 9th fairway of renowned Golden Bear Club private golf course is bound to impress. 3 way split bedroom suites with private bath access.
$765,000

Single Family

8333 BOWDEN WAY, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
3Parking(s)
24Picture(s)
2,455Sqft
**BRAND NEW ROOF MAY 2020!!**. THIS KEENES POINTE CHARMER HAS BEEN LOVINGLY MAINTAINED AND UPDATED THROUGHOUT THE YEARS. PERFECTLY FRAMED BY OAK TREES, YOU WILL BE IMPRESSED FROM THE MOMENT YOU PULL UP. THE OPEN FLOOR PLAN IS LIGHT AND BRIGHT. FORMAL LIVING AREAS ARE COMPLETE WITH HAND SCRAPPED WOOD FLOORS.
$519,000

Single Family

13285 PENSHURST LANE, WINDERMERE, Florida 34786

6Bedroom(s)
4Bathroom(s)
2Parking(s)
10Picture(s)
3,774Sqft
HUGE PRICE REDUCTION TO ENCOURAGE OFFERS! Exceptional enhanced luxurious executive estate private POOL home located in desirable Horizon West. Lennar's Smart Home Brewster Model with Craftsman Elevation. Many custom upgrades inside and out, including upgraded flooring, crown molding and wainscot in the formal dining room. Media room with Stadium Seating.
$599,000

Single Family

11910 WATERSTONE LOOP DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,181Sqft
***Must see custom built Silliman home in the desirable Windermere ‘Waterstone’ community*** This Mediterranean-style property, is like-new and upgraded with multiple designer features & improvements throughout. The exterior face of the home offers clean lines unbroken by a garage or by cars.
$1,045,000

Single Family

6205 GREATWATER DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
10Picture(s)
7,768Sqft
Luxury abounds in this exquisite lakefront estate on the Butler Chain of Lakes in Keene's Pointe. Beyond the circular driveway with fountain & porte-Cohere entry, a pair of wood French doors open to the stunning 2 story living room, with natural light while capturing the lake views & stone fireplace.
$3,150,000

Single Family

8806 CRESCENDO AVENUE, WINDERMERE, Florida 34786

6Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
4,353Sqft
Located at Windermere Trails community, this 4,353 ft² two story home provides ample living space for your family. This floor plan built by Meritage Homes boasts 6 bedrooms, 4 full bathrooms, 1 Office, 1 Loft, Formal Dining room and formal living room. This house also offer an outstanding outside area with a private pool, jacuzzi and outdoor kitchen so you can enjoy with the family.
$639,900

Rental

5731 W LAKE BUTLER ROAD, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
4Parking(s)
25Picture(s)
3,397Sqft
Spectacular home on Cypress Lake with stunning views. This property features hardwood floors, gas fire place, game room with bar, dining area, screened pool, and private boat ramp. With a four-car garage, inside utility room and beautiful maintained lawn.
$3,850

Single Family

5932 BLAKEFORD DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,699Sqft
Welcome to Keenes Point Community ! This luxurious 5 bedroom 5 bath is a dream home in a high-end community that's home to Golden Bear Golf Club. Spanning at 3700 SF, this magnificent residence graced by a beautiful layout is a haven for gazing at Golf Course views from multiple vantage points. The grand entryway with a voluminous layout made for entertaining.
$705,000

Single Family

9109 TINTORI LANE, WINDERMERE, Florida 34786

5Bedroom(s)
5Bathroom(s)
3Parking(s)
10Picture(s)
3,516Sqft
Opportunity awaits you at this Mediterranean inspired luxury executive home boasting over 3500 square feet with tile roof, brick paver driveway and oversized 3 car garage. Gorgeous gourmet kitchen with 42" maple cabinets, backsplash, 5 burner natural gas range with built in wine rack and wine cooler, and all complimented by a high end stainless steel appliance package.
$649,900

Single Family

2 1ST COURT, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,958Sqft
Recently appraised with in the last 30 days, this Windermere home sits next to the Butler Chain of Lakes with Access!!! Spectacular, This best describes this Olde Windermere home that has been completely renovated to today's style with so many extras you are sure to appreciate and love! Spacious floorplan with two master suites, one upstairs and one down.
$844,900

Single Family

17557 BLACK RAIL STREET, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
10Picture(s)
3,910Sqft
Welcome to this beautiful home located in The Enclave at Windermere Landing. Upon entry you are greeted by impressive 10ft ceilings leading onto a open floor-plan. This stunning 5 bed, 4 bath home has a spacious Gourmet kitchen with large center island, granite counter tops, 42" solid wood cabinet, Walk in pantry and Kitchen Aid Stainless Steel appliances.
$642,900

Single Family

3137 SEIGNEURY DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
6Parking(s)
25Picture(s)
5,643Sqft
GORGEOUS custom built Mediterranean style home nestled on over 1 acre of beautifully manicured landscaping within the desirable gated community of Harbor Isle.
$1,695,000

Single Family

6132 PAYNE STEWART DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
4Bathroom(s)
3Parking(s)
23Picture(s)
2,848Sqft
Positioned just steps away from Isleworth’s famed Clubhouse and amenities, this beautifully updated golf villa offers a prime location within the gates. Beautiful solid wood French doors reveal a designer-updated interior spanning 2,848 square feet. The single-story home has a fabulous layout featuring high ceilings, exposed wood beams, wood floors.
$1,325,000

Rental

9108 ISLEWORTH GARDENS DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
4Bathroom(s)
3Parking(s)
10Picture(s)
4,077Sqft
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful home offers a prime location within the Gardens of Isleworth – an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths. The garden villa offers a single-story floor plan spanning 4,077square feet, with beautiful views of the surrounding landscape.
$9,995
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