Windermere Real Estate - Search All Windermere Homes & Condos for sale

A highly sought after place to live, Windermere, FL is steeped in a rich history that helps give the town its modern charm.

Founded in 1887, Windermere prides itself on many of its historical sites, from its Town Hall (built from 1922-1924), which began as The Women's Club, to Cal Palmer's office Building (completed in 1911), to the Parramore House, also known as the Historic 1890 Windermere Schoolhouse, which became the first school in the Town of Windermere.

2782 Park Royal Drive, Windermere $595,000

This beautiful 2 story traditional home is located in the exclusive community of Windsor Hill in the heart of Windermere. Situated on a full 1/2 acre lot with no rear nei...

4 Beds
4.5 Baths
Windsor Hill SubDv.
34786 Zip Code

8231 Procida Isle Lane, Windermere image

8231 Procida Isle Lane, Windermere $480,000

UNDER CONSTRUCTION until mid-July. Second image depicts actual color scheme. Located close to 429, Disney and Hamlin Shops, this inviting ENERGY STAR Certified home featu...

5 Beds
4 Baths
Windermere Isle SubDv.
34786 Zip Code

8045 Tibet Butler Drive, Windermere image

8045 Tibet Butler Drive, Windermere $949,000

Rare 5 bedroom single story home in country club neighborhood of Keene's Pointe. This home features a master suite split open floor plan, gourmet kitchen, wood floors, pl...

5 Beds
6 Baths
Keenes Pointe SubDv.
34786 Zip Code

11409 Cranebrook Court, Windermere image

11409 Cranebrook Court, Windermere $1,599,900

QUALITY & LOCATION x3! Osprey 5-bed 5/2 bath custom home with Covered Dock and Boat Lift set in a quiet cul-de-sac. Access Lake Burden for jet and water skiing and fishin...

5 Beds
5.5 Baths
Keene's Pointe Unit 8 SubDv.
34786 Zip Code

3453 Bay Meadow Court, Windermere $630,000

Location, Location,Location! Beautiful Windermere home on 1+ acre lot. Home sits off a cul de sac and has a long paved drive giving any owner a nice sense of security. Th...

4 Beds
3.5 Baths
Lake Butler Estates SubDv.
34786 Zip Code

2137 Westover Reserve Boulevard, Windermere image

2137 Westover Reserve Boulevard, Windermere $699,750

Custom quality Windermere home in one of SW Orange Countys premier gated communities " Westover Reserve ", with ornate decorator touches thru-out. Unique and refreshing ...

4 Beds
4 Baths
Westover Reserve Ph 02 SubDv.
34786 Zip Code

6238 Lake Burden View Drive, Windermere image

6238 Lake Burden View Drive, Windermere $899,900

Remarkable home built by Brentwood Custom Homes in gated/attended Keene's Pointe. Nestled among The Golden Bear Club, an 18-hole golf course designed by Jack Nicklaus fea...

4 Beds
4 Baths
Keenes Pointe Un 07 SubDv.
34786 Zip Code

11033 Hawkshead Court, Windermere $1,050,000

This estate home is beautifully appointed and located on a quiet cul-de-sac in the sought-after Lake Butler Sound subdivision. Situated on just under half an acre, This e...

4 Beds
4 Baths
Reserve At Lake Butler Sound SubDv.
34786 Zip Code

1169 Estancia Woods Loop, Windermere image

1169 Estancia Woods Loop, Windermere $914,000

UNDER CONSTRUCTION. Orlando home builder presents palatial living at its finest. The Monte Carlo in Windermere, FL leaves no detail untouched in search of true luxury arc...

4 Beds
4 Baths
Estancia At Windermere SubDv.
34786 Zip Code

2405 Ridgewind Way, Windermere $825,000

Gorgeous 6 bedroom PLUS office PLUS bonus 6.5 bath home on a fenced acre of land in the highly sought after gated community of Estates at Windermere! Upon first entry the...

6 Beds
6.5 Baths
Estates At Windermere SubDv.
34786 Zip Code

4442 Begonia Court, Windermere $699,000

A stunning home in a magnificent community. Magnolia Park of Windermere is prestigious gated community consisting of 32 custom designed homes all on ½+ acre lots. Homes h...

5 Beds
4.5 Baths
Magnolia Park Windermere SubDv.
34786 Zip Code

5306 Nagami Drive, Windermere $828,000

YOU MUST SEE THIS PROPERTY! LOCATION, LOCATION, LOCATION! Imagine your life living on lake front Windermere property. Enjoy all the boating, fishing and spectacular Ma...

7 Beds
5 Baths
Summerport Ph 03 SubDv.
34786 Zip Code

11628 Waterstone Loop Drive, Windermere image

11628 Waterstone Loop Drive, Windermere $1,599,000 ▼

Former Brierhill Homes Model in Windermere’s most upscale neighborhood, the Guard-Gated Waterstone community. This home has 5 bedrooms, 5.5 baths, an oversized 3-car gara...

5 Beds
5.5 Baths
Waterstone SubDv.
34786 Zip Code

2309 Ridgewind Way, Windermere $999,000

Beautiful waterfront pool home on Lake Bass in gated and highly sought after Estates of Windermere, which includes tennis, parks and playgrounds. Home is nestled on .71 a...

5 Beds
4 Baths
Estates At Windermere SubDv.
34786 Zip Code

2127 Lilypad Lane, Windermere $650,000

SIMPLY STUNNING! The FANTASTIC brick pavered pool/spa feels like your very own PRIVATE RESORT! Plenty of room for seating, lounging and your hammock. Buy the s’mores supp...

4 Beds
3 Baths
Willows At Lake Rhea SubDv.
34786 Zip Code

8453 Woburn Court, Windermere $549,000

Keene's Pointe - 24-hour gated/attended golf community. This home offers 4 bedrooms, 2 baths, formal dining room and upstairs bonus room. Situated on a premium conserva...

4 Beds
2 Baths
Keenes Pointe Unit 01 SubDv.
34786 Zip Code

1950 Hempel Avenue, Windermere $698,800

This is your chance to own one of the most iconic homes in Windermere. Set on treed acre lot with NO HOA , this custom Victorian dream home could be yours ! You will fall...

5 Beds
4 Baths
Windermere SubDv.
34786 Zip Code

11050 Coniston Way, Windermere $829,900

Wow. Check out this amazing Country French style estate home in the luxurious community of "The Reserve at Lake Butler Sound". The home has 4 bedrooms, office / study, 4 ...

4 Beds
4.5 Baths
Reserve At Lake Butler Sound SubDv.
34786 Zip Code

2601 Midsummer Drive, Windermere $550,000

This home is located in the highly desirable community of Lake Down Shores. Quite cul-de-sac lot on 1.22 acres. Neighborhood boat ramp access to the Butler chain of lakes...

3 Beds
2.5 Baths
Lake Down Shores Rep SubDv.
34786 Zip Code

9352 Sir Lawrence Court, Windermere image

9352 Sir Lawrence Court, Windermere $525,000

Amazing opportunity to own a Custom-Built pool home on 1 acre in Windermere! This family friendly floor plan features **NEW ROOF installed MAY 2018, **4 bedrooms **3 full...