Windermere Homes for Sale

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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

Single Family

9927 GIFFIN COURT, WINDERMERE, Florida 34786

12Bedroom(s)
15Bathroom(s)
16Picture(s)
31,000Sqft
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.
$16,500,000

Townhouse

13459 Gorgona Isle Drive, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
25Picture(s)
1,788Sqft
PRICE IMPROVEMENT! 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 compares15358556 to this incredible home. Minutes to Disney World. Situated just north of Magic Kingdom allowing for a prime location to watch nightly fireworks.
$385,000

Single Family

13455 BELLARIA CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
4Parking(s)
25Picture(s)
5,825Sqft
Stunning Custom-Built Home in the luxurious gated community of Bellaria! This 5 Bedroom, 7 Bathroom home is sure to impress. Upon entering the home, you are greeted by the formal living room and dining room, featuring a wine cellar, beautiful tray ceiling, and polished travertine that runs throughout the downstairs living areas.
$1,600,000

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

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.
$1,685,000

Single Family

5085 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(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

Single Family

9648 MCCORMICK PLACE, WINDERMERE, Florida 34786

3Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(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

11327 WINDERMERE ROAD, WINDERMERE, Florida 34786

6Bedroom(s)
6Bathroom(s)
4Parking(s)
25Picture(s)
4,681Sqft
Don't miss out on this beautiful 6 bedroom 5.5 bathroom Windermere home! In addition to the 6 bedrooms there are 2 office/den spaces. This one of a kind home is located with the TOWN OF WINDERMERE limits. With a wide open floor  plan this home has it all. Enjoy your gourmet kitchen with granite counter tops, Kitchenaid & Bosch appliances, double oven & huge pantry.
$985,000

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

Townhouse

5209 SEGARI WAY, WINDERMERE, Florida 34786

2Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,155Sqft
SUPER RARE ONE STORY END UNIT WINDERMERE TOWNHOME WITH 2 CAR GARAGE !!! For sale for the first time by the original owner. These units are extremely coveted since they are the ONLY ONE STORY townhomes in the entire zipcode.
$238,800

Single Family

5181 LATROBE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
4Parking(s)
25Picture(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.
$1,295,000

Townhouse

5318 KUMQUAT LOOP, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,461Sqft
Luxury Windermere townhome with DOWNSTAIRS OWNERS SUITE, fresh interior paint and carpet , ALL APPLIANCES ...even washer and dryer ! COVERED Fishing pier to spring fed pond a minute walk from your front door !!! Granite counters, open kitchen and great room plan with covered and screened rear lanai and 2 car garage.
$273,500

Condominium

11446 Jasper Kay Terrace, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,455Sqft
Windermere Condo, Vacant, Clean, and ready for new owners! 3 Bedroom, 2 Bathroom Condo in Windermere with ceramic tile, Crown Moulding and Inside Laundry with washer/dryer and all appliances included! 1455 Square Feet,split plan, screened porch.
$219,900

Single Family

5427 MONTERREY CLUB COURT, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,957Sqft
A one-of-a-kind residence within the gates of the renowned Isleworth Golf & Country Club, this remarkable estate offers impeccably designed interiors spanning more than 3,900 square feet. A contemporary masterpiece showcasing the pinnacle of modern styling, the property offers an ideal layout for stylish living and entertaining.
$2,350,000

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

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

11467 CLAYMONT CIRCLE, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
10Picture(s)
3,400Sqft
THIS IS A MUST SEE HOME Located in the desirable Keene's Pointe Neighbor with 24 hour guard attended gated community in Beautiful Windermere The home of the Golden Bear Club an 18-hole Golf Course designed by Jack Nicklaus. This Gorgeous home has been completely renovated with stunning custom upgrades throughout.
$724,900

Single Family

4282 MCKINNON ROAD, WINDERMERE, Florida 34786

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,869Sqft
Two Story Custom 6 Bedrooms / 6 Baths, 1 Acre Estate Home in Windermere. As you enter the 8' French Doors of the property you are greeted by a Foyer that features a 21' Ceiling, Double Chandeliers, Double Crown Molding, and Wooden Staircase. The property has 10'-12' Ceilings and Crown Molding and 8' Doors throughout.
$1,260,000

Single Family

325 MAGNOLIA STREET, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,975Sqft
Best value on one of the largest lakefront properties on famed The Butler Chain of Lakes within The Town of Windermere. Watch the most beautiful sunrise and sunsets over lake Down, surrounded by the mature landscaping spread out over almost 3 acres. Be ready for all of your water sport activities. Major extensive renovations from the ground up in 2001 made this home like new construction.
$1,997,000

Townhouse

14077 ANCILLA BOULEVARD, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,642Sqft
Beautiful Summerport Townhouse move-in ready condition. First floor Master bedroom, brand new A/C unit, brand new maintenance-free quartz countertops in kitchen. Wood flooring throughout first floor except for master bedroom and bathrooms. Completely redone first floor half-bath. Sit on the front porch and watch the sunset over Ancilla Pond. Rear driveway with access road.
$265,000

Single Family

325 MAGNOLIA STREET, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,975Sqft
Best value on one of the largest lakefront properties on famed The Butler Chain of Lakes within The Town of Windermere. Watch the most beautiful sunrise and sunsets over lake Down, surrounded by the mature landscaping spread out over almost 3 acres. Be ready for all of your water sport activities. Major extensive renovations from the ground up in 2001 made this home like new construction.
$1,997,000

Single Family

1535 DINGENS AVENUE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,495Sqft
Live the Country Life in the heart of Town! French Farmhouse in the middle of Florida! Follow tree lined Dingens Ave in Gotha/Windermere all the way down to the cul de sac where you will find this European style custom home. Found on a large 1/2 acre lot this is the quiet country life everyone is dreaming of right now. This home welcomes you in with double front doors.
$799,900

Single Family

6890 TRELLIS VINE LOOP, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,463Sqft
Superbly maintained two story home in Windermere! Built in 2015, this 3,463 square foot home has 5 bedrooms, 3.5 baths, and an open floor plan. The gourmet kitchen features 42" cabinets, double ovens, a large center island, granite countertops, stainless steel appliances, and a walk-in pantry.
$579,000

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

12220 GRANDMERE COURT, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
3,156Sqft
Welcome to your new home, This beautiful home offers 5 bedrooms, 3.5 bath, meticulously maintained home inside and out, perfectly built on over an half acre lot and on cul-de-sec, backed to greenbelt.
$799,000

Single Family

9304 ISLEWORTH GARDENS DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,840Sqft
Stately elegance and exceptional craftsmanship define luxury living from inside this graceful waterfront villa with 3-bedroom suites, Executive office, and private movie theater situated in the secluded Gardens of Isleworth.
$1,895,000

Single Family

8459 WOBURN COURT, WINDERMERE, Florida 34786

5Bedroom(s)
4Bathroom(s)
3Parking(s)
23Picture(s)
3,688Sqft
Roof and 1 AC less than 2 years old! Updated 5 bedroom with home office, high ceilings and pool home located in the highly desirable, guard gated Keenes Pointe community. This move-in ready home sits on an oversized cul-de-sac lot with a screened in pool with spa, fenced in back yard overlooking Tibet Butler Preserve, and a 3 car garage with storage room.
$739,000

Single Family

13113 PENSHURST LN, WINDERMERE, Florida 34786

3Bedroom(s)
2Bathroom(s)
25Picture(s)
1,948Sqft
Wow! Don't miss this incredible home in highly sought after Lakes of Windermere at a nearly impossible-to-find price point! Conveniently located near majorroadways, shopping in Winter Gardens, and Windermere's best rated schools, this single story ranch home boasts a split bedroom, open floor plan with plenty of room to entertain.
$365,000

Townhouse

8625 VIA TAVOLERIA WAY, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,919Sqft
Beautiful Like-New Luxury Townhome at Carrington. Popular Lucea model. 1,946 sq. ft., 3 bed, 2.5 bath with FLEX room! Open layout for entertaining. With only 78 townhomes, Carrington is an exclusive community in Windermere.
$284,900

Townhouse

14447 BLUEBIRD PARK ROAD, WINDERMERE, Florida 34786

3Bedroom(s)
3Bathroom(s)
2Parking(s)
21Picture(s)
1,712Sqft
This immaculate house is presented pristinely offering an open floor plan with 3 bedrooms and 2.5 bathrooms. Freshly painted throughout the house, combo family/dining area. Large master bedroom with tray ceilings with built in wardrobe in master closet, master bath has a garden tub & separate shower. The other 2 bedrooms are spacious with built in shelves in the closets.
$279,000

Single Family

7319 ELLA LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
15Picture(s)
2,282Sqft
Beautiful 4 bedroom 3.5 bathroom full of upgrades. The house has two master suites - one in the first floor and one in the second floor with level 2 laminate floor. Two bedrooms with a convenient Jack & Jill bathroom and a mezzanine in the second floor. The kitchen is equipped with stainless steel appliances, granite counter tops and back splash.
$385,900

Single Family

5861 CAYMUS LOOP, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
2,928Sqft
Come live the Keene's Pointe lifestyle! This fabulously updated 4 bedroom, 4 bath, golf front estate home is located on the 15th tee, just a stone's throw from the signature Jack Nicklaus Golden Bear Club. The oversized, quiet, lot is located at the end of Caymus Loop and just under a half acre in size, a rare find.
$764,900

Single Family

520 HALEY DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
4,883Sqft
Don't miss out on this gorgeous, fully remodeled home located in the Crescent Lakes Estates! This 4 bedrooms, 3.5 bathroom compound sits on a well manicured 1 acre lot with complete privacy. The home has received a full facelift with additions added plus top of the line finishes. You cannot beat this desired open floor plan with a kitchen/dining/family & game room combo.
$1,199,000

Single Family

12866 LAKE SAWYER LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
3Parking(s)
10Picture(s)
3,458Sqft
WINDERMERE LAKEFRONT and NO HOA! Take advantage of the incredible opportunity to own this custom 4/3 home on huge lot with 100' of Little Lake Sawyer shoreline. Room to roam inside and out, it's the perfect combination of Olde Florida style complementing the comforts of today's lifestyle. This Cape Cod features block construction, inviting front porch, 3-car garage, and plenty of parking.
$829,000

Single Family

6207 CYPRESS CHASE DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
6,085Sqft
*** One of the BEST values in the neighborhood under 2M with its low price per square foot!! *** Welcome to ISLEWORTH, one of the most exclusive GATED communities in the WORLD! Private, luxurious, & inviting, known for its championship GOLF course. Access the renowned Butler Chain of Lakes for a day of boating & entertainment, or enjoy the amenities the Club has to offer.
$1,850,000

Single Family

8462 ABBOTSBURY DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,343Sqft
Welcome to gated community at the Lakes of Windermere. This immaculate 4 bedroom 3 bathroom home offers an open floor plan and gorgeous direct views of the Preserve. It is impeccably maintained by the current owners. Amazing floor plan from the entry greets to a living room with formal dining. Kitchen overlooks family room opening to breathtaking views of the Preserve.
$369,900

Single Family

11035 SCHOONER WAY, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
2Parking(s)
6Picture(s)
3,517Sqft
Nestled among the Butler Chain of Lakes in the Town of Windermere, find tranquility in Marina Bay living. This homes warmth truly enhances the family experience and features many upgrades, a spacious floor plan and oversized lot. Home has no HOA with an added plus of RV/Boat station with electricity and water.
$785,000

Single Family

5005 DOWN POINT LANE, WINDERMERE, Florida 34786

6Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,191Sqft
Absolutely stunning, completely remodeled Windermere home with a detached remodeled guest or in-law suite. Covered breezeway to garage and guest house. This 6 bedroom and 5 ½ bath home sits on .87 acre with spectacular lake views. Located in Sunset Bay, a community of upscale, custom built homes with deeded access to Lake Down.
$1,799,000

Single Family

2114 GROVE POINT LANE, WINDERMERE, Florida 34786

4Bedroom(s)
3Bathroom(s)
3Parking(s)
25Picture(s)
2,805Sqft
Located in one of the most beautiful gated communities in Windermere, this fully remodeled Mediterranean style home sits on a gorgeous private 1.22 acre lot. As soon as you step foot into this beautiful home you can see that it is perfect for a family or large scale entertaining. This 4 Bedroom/3 Bath home has been fully renovated.
$750,000

Single Family

5318 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

6Bedroom(s)
10Bathroom(s)
4Parking(s)
25Picture(s)
12,298Sqft
MOTIVATED SELLER! YOUR OFFER MAY BUY THIS STUNNING GOLF-FRONT ESTATE IN ISLEWORTH - SELLER CONSIDERING ALL OFFERS! Dramatic interior includes an interior custom designed, temperature-controlled, grand two-story Pavilion with stone flooring, skylights, a heated pool and spa, a bar, grilling/cooking area, dining area and lounging area - all of which is the absolute focal point of this stunning in
$6,600,000

Residential

4812 LEWIS GARDEN COURT, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,505Sqft
One or more photo(s) has been virtually staged. Under Construction. Completion May 2020. With a Spanish style and modern design, The Georgia by Goehring & Morgan combines open spaces with beautiful finishes for a breathtaking retreat within the Gardens of Isleworth. Beyond the circular motor court, an arched wooden door reveals the foyer with groin vault leading into the two-story home.
$2,649,000

Single Family

5305 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
7Bathroom(s)
5Parking(s)
25Picture(s)
7,463Sqft
GOLF AND LAKEFRONT! Situated on the 18th green at Isleworth Country Club and boasting stunning views of Lake Louise in the Butler Chain of Lakes, this Isleworth mansion is perfectly positioned in every way imaginable. Whether you want to lounge poolside and watch the golfers hit in or relax in the covered lanai and enjoy the summer kitchen while taking in the lake view, this home has it all.
$3,700,000

Single Family

9508 WINDY RIDGE ROAD, WINDERMERE, Florida 34786

6Bedroom(s)
14Bathroom(s)
18Picture(s)
51,000Sqft
This 18-acre private walled and gated compound is one of the most exceptional properties in Central Florida, unrivaled by its sheer size, ideal shape, remarkable topography and high elevation. The property offers over 600 feet of unobstructed views and access to one of Lake Bulter's cleanest lakes.
$30,000,000

Single Family

5372 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

8Bedroom(s)
9Bathroom(s)
3Parking(s)
10Picture(s)
13,230Sqft
Discover the very best in Isleworth living through this spectacular estate overlooking the serene waters of Hourglass Lake. The estate is a rich and fascinating masterpiece that inspires superior craftsmanship and exudes both sophistication and panache at every turn.
$7,400,000

Single Family

6186 LOUISE COVE DRIVE, WINDERMERE, Florida 34786

4Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,849Sqft
Within the gates of Isleworth West, this elegant estate is nestled on a large corner home site and spans more than 4,800 square feet of living space. Beautiful custom doors reveal a lovely formal living room with an expansive bay window that frames the sparkling open-air pool, spa and lush landscaping.
$1,500,000

Single Family

5056 ISLEWORTH COUNTRY CLUB DRIVE, WINDERMERE, Florida 34786

3Bedroom(s)
4Bathroom(s)
3Parking(s)
25Picture(s)
4,225Sqft
Offering a prime location within the gates of the renowned Isleworth Golf & Country Club, this beautifully updated golf-front estate sits along the front nine overlooking the 6th fairway. Completely reimagined both inside and out, the estate boasts exquisite, quality finishes at every turn.
$2,700,000

Single Family

8288 TIBET BUTLER DRIVE, WINDERMERE, Florida 34786

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
6,745Sqft
Live like Rock star Royalty in this elegantly designed Rick Watson custom home on the shores of Lake Burden. Designed with timeless elegance this luxurious home was meant for entertaining . From the moment you walk up to the huge carved front entry doors with its iron mullions , you will be dazzled by this home, that immediately welcomes you in with dramatic water views that will blow you away.
$2,599,999
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