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.
$2,193,000
4333 ISABELLA CIRCLE
WINDERMERE, Florida
6Bedroom(s)
7Bathroom(s)
49Picture(s)
6,857Sqft
Your DREAM HOME awaits! This Toll Brothers executive home is situated on a generous 2/3 acre lot, ample parking, with a magnificent outdoor entertainment area. As you enter the home the dramatic ceiling and natural light give the home an airy, luxurious feel. The chef’s kitchen features Wolf appliances, a Sub-Zero refrigerator, along with its extra-large island.
$318,000
6532 HELMSLEY CIRCLE
WINDERMERE, Florida
4Bedroom(s)
3Bathroom(s)
14Picture(s)
1,935Sqft
LOCATION, LOCATION, LOCATION!!!! Gorgeous townhouse located at the coziest community Preston Square in Windermere! This property offers a beautiful layout throughout with 4 bedrooms, one being downstairs to use it as a guest room or an office, freshly painted, all laminate flooring in the first floor and brand new carpet on the second.
$1,895,000
8336 BOYLA COURT
WINDERMERE, Florida
5Bedroom(s)
4Bathroom(s)
49Picture(s)
5,520Sqft
Come home to this Lakefront Mediterranean Mansion w/ French Moroccan flare built by Campbell Custom Homes. This incredible estate is situated on a ¾ acre lot on a quiet cul-de-sac in Keene’s Pointe, a guard gated golf course and lakefront community in Windermere, Florida.
$219,900
11446 JASPER KAY TERRACE
WINDERMERE, Florida
3Bedroom(s)
2Bathroom(s)
44Picture(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.
$328,990
7665 RIPPLEPOINTE WAY
WINDERMERE, Florida
4Bedroom(s)
3Bathroom(s)
40Picture(s)
2,212Sqft
Beautiful 4Bed/3 Bath. New Carpet!!!! New Paint!!!! LAKE BURDEN COMMUNITY , Windermere . rnFirst Floor with Tile, Excellent Floor Plant Bedroom and Bathroom on the first floor. Three spacious rooms on the second floor. A -Rated schools, shopping centers, restaurants.
$274,994
7616 BILLINGHAM STREET
WINDERMERE, Florida
3Bedroom(s)
2Bathroom(s)
27Picture(s)
1,563Sqft
IMPECCABLE maintenance free living in Windermere! Just minutes away from highly rated schools, shopping and dining and Disney World parks. This immaculate CORNER unit features an open floor plan full of natural lighting. The downstairs features a living room, dining room, half bath, and kitchen including granite countertops, stainless steel appliances and 42"cabinets.
$2,677,000
4260 ISABELLA CIRCLE
WINDERMERE, Florida
4Bedroom(s)
5Bathroom(s)
103Picture(s)
7,971Sqft
*** EASY TO CONVERT BACK TO 6 BEDROOMS, 7 1/2 BATHS ***rn rnWelcome to 4260 Isabella Circle, a contemporary masterpiece located at Casabella. This exquisite residence features unparalleled details and upgrades throughout, from the art inspired custom light fixtures, to the hand scraped hardwood floors, marble tiled bathrooms, and a one of a kind custom wine cellar.
$639,000
12507 MONTALCINO CIRCLE
WINDERMERE, Florida
4Bedroom(s)
3Bathroom(s)
96Picture(s)
3,024Sqft
Welcome home to your gated lakefront community of Casa Del Lago. This community has only 88 home sites and is nestled on the west side of Windermere's Lake Burden. Living here your family is zoned for incredible schools such as Sunset Park Elementary, Horizon West Middle School, and Windermere High School.
$965,000
1572 LAKE RHEA DRIVE
WINDERMERE, Florida
5Bedroom(s)
4Bathroom(s)
48Picture(s)
4,490Sqft
NEW PRCE! OWNER MOTIVATED! LAKE FRONT, WINDERMERE, GUARD GATED COMMUNITY, GREAT LOCATION, UNDER $1MM ! ! ! rnThis well maintained and recently updated Lakefront, Executive Home is located in the exclusive gated Reserve at Belmere. The 5 BR/4BA home offers an excellent floor plan, designed to maximize its' views of the lake and outdoors.
$1,489,000
11448 WATERSTONE LOOP DRIVE
WINDERMERE, Florida
5Bedroom(s)
4Bathroom(s)
26Picture(s)
4,199Sqft
Where YOU were meant to be. A Place where dreams come true.rnrn*Truly unique, warm, cozy details...rn*Amazing location with wonderful views...rn*Welcoming feel, sense of Peace...rn*Paradise waiting, make your memories...rn*Brierhill Custom Home, Standards of Excellence...rnrnSchedule your private tour of this one of a kind, breathtaking Brierhill Custom Home. Paradise Found...
$1,799,000
12101 CRESCENT COVE COURT
WINDERMERE, Florida
4Bedroom(s)
5Bathroom(s)
62Picture(s)
6,315Sqft
Windermere's "Zen House" is the answer to getting away from the daily hustle. This incredible 1+ acre lot is laced with whimsical paths within an immaculate garden interspersed with fruit trees, tranquil water fountains, a koi pond and a boardwalk stretching along approximately 230' of canal frontage.
$2,700,000
5056 ISLEWORTH COUNTRY CLUB DRIVE
WINDERMERE, Florida
3Bedroom(s)
3Bathroom(s)
35Picture(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.
$3,495,000
9313 TIBET POINTE CIRCLE
WINDERMERE, Florida
6Bedroom(s)
7Bathroom(s)
56Picture(s)
8,393Sqft
Beautifully sited on close to three acres and located in prestigious guard gated Keene’s Pointe Country Club this Butler Chain of Lakes, lakefront home exudes a spirit of elegance derived from it’s European architectural influences. This stunning plan is perfect for family living and entertaining. The extended drive and mature landscaping create a refined entry.
$2,350,000
2608 MIDSUMMER DRIVE
WINDERMERE, Florida
5Bedroom(s)
4Bathroom(s)
106Picture(s)
5,536Sqft
Walk through the doors and you will never want to leave! Arguably, one of the most beautiful waterfront lots in all of Windermere if not all of Central Florida. This Custom home features sensational waterfront views from almost every room in the house. First floor master suite with private porch.
$1,674,900
6429 LAKE BURDEN VIEW DRIVE
WINDERMERE, Florida
5Bedroom(s)
5Bathroom(s)
47Picture(s)
6,293Sqft
Just Listed! Custom Rick Watson estate situated on a premium golf frontage lot inside the exclusive 24 hour man gated famed Jack Nicklaus designed Golden Bear Country Club community in Windermere. This 6,293 sqft home includes 5 bedroom, 5 bath (all en-suite) with 4 additional half baths, 2 separate his and her home offices, movie theater and game room.
$2,350,000
5427 MONTERREY CLUB COURT
WINDERMERE, Florida
4Bedroom(s)
3Bathroom(s)
37Picture(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.
$385,000
13459 GORGONA ISLE DRIVE
WINDERMERE, Florida
3Bedroom(s)
2Bathroom(s)
39Picture(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 compares to this incredible home. Minutes to Disney World. Situated just north of Magic Kingdom allowing for a prime location to watch nightly fireworks.
$579,000
6890 TRELLIS VINE LOOP
WINDERMERE, Florida
5Bedroom(s)
3Bathroom(s)
47Picture(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.
$3,150,000
12516 PARK AVENUE
WINDERMERE, Florida
6Bedroom(s)
6Bathroom(s)
102Picture(s)
8,172Sqft
Experience Butler Chain living at its finest in this stunning Akers custom home, situated on a quiet cove of Lake Butler, within the gated community of Chaine du Lac! This home is filled with recent updates, such as a newly resurfaced pool, fresh paint throughout, refinished wood floors, and so much more! The stately curb appeal of this 6 bedroom, 6/2 bathroom, 8,887 sqft home sets high expectatio
$1,199,000
12056 SANDY SHORES DRIVE
WINDERMERE, Florida
2Bedroom(s)
2Bathroom(s)
33Picture(s)
1,488Sqft
Your Dream Lakefront home is here! This single family home is located on the highly coveted and prestigious Lake Butler of the Butler Chain of Lakes in Windermere. You will be swept away by the gorgeous view, big lot size, and the serene nature and wildlife.
$360,000
4962 WINDERMERE AVENUE
KISSIMMEE, Florida
4Bedroom(s)
3Bathroom(s)
30Picture(s)
1,914Sqft
BEAUTIFUL TOWNHOME NEAR THE ATTRACTIONS, EXCELLENT OPPORTUNITY TO INVEST...This is a 4 Bedroom, 3 Bath townhome with pool is located in the desired & gated "Storey Lake" Resort. A few minutes away from Walt Disney World, Universal Studios, Sea world, shops and restaurants. Professionally decorated, with open floor plan , great room and dining area...
$539,000
606 MAGNOLIA STREET
WINDERMERE, Florida
4Bedroom(s)
2Bathroom(s)
39Picture(s)
2,327Sqft
Awesome opportunity to own this Beautiful 4/2 one story home located in downtown Windermere with No HOA!!! This split plan Ranch style home has been completely renovated. Upon entering one is immediately impressed with the open and airy floor plan enhanced with skylights and highlighted with a wood burning fireplace.
$2,450,000
11126 BRIDGE HOUSE ROAD
WINDERMERE, Florida
5Bedroom(s)
5Bathroom(s)
57Picture(s)
7,263Sqft
Sited within the guard gated community of Sanctuary at Lake Butler Sound, the Palazzo de Cortile by Jim Akers Homes delivers an unforgettable living experience of exceptional quality throughout. You are welcomed to this palace of the courtyard by its impressive marble fountain and motor court with twin adjoining two car garages.
$7,495,000
9288 BLANCHE COVE DRIVE
WINDERMERE, Florida
5Bedroom(s)
4Bathroom(s)
24Picture(s)
12,778Sqft
Under Construction.

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