Windermere Homes for Sale

Orange County has a stunning reputation for its high-end communities that provide exceptional amenities to its residents. The Orange County community of Windermere has a population of 2,500 and is located in the Orlando-Kissimmee Metropolitan area. Windermere has the appeal of being a small, safe, cozy town with convenient access to the big city. MAny Windermere residents use the neighborhood as a bedroom town, or in other words a place that residents typically travel outside of to work. Since the year 2000 Windermere has seen significant growth due to its ideal location.

The town of Windermere became established in the year 1925 and was approximately 1.57 square miles but after the annexed community of Butler Bay in 2007, Windermere became slightly larger. Windermere sees a ton of fluctuations in population due to the large number of tourists that travel through to visit Orlando, however, Windermere als benefits from tourists for several reasons. Reason number one: The beautiful historic buildings that line the streets in Windermere making it not only a picturesque place to live and visit but a historically fascinating place as well. For example, The Windermere Town Hall is located on Main street and is also known as the Old Windermere Women’s Club. Another place is the 1890 Windermere School also known as the Armstrong-Parramore House.

Wondering what types of homes are for sale in Windermere? Houses for purchase here vary in size, price, age etc. but come in all forms whether you are looking for a luxurious home or a small simple one. Homes in Windermere can range in price anywhere from $250,000 to over $1 million. The cozy town of Windermere is not only stunning but it is also a wonderful place to raise a family. The Orange County School District provides excellent educators and mentors to guide children through the challenges of a variety of subjects. There is much to be said on the quality and appearance of Windermere but another noteworthy subject is recreation. There are so many community events like art shows and parades that residents are encouraged to attend but there are also a wide variety of activities that all residents and visitors alike can take advantage of. Windermere is extremely close to Butler Bay Recreational Area where visitors may hike, bike, swim and so much more! If you would like more information or help finding a home in Windermere, Florida, please don’t hesitate to contact us today!

Latest Windermere Homes and Condos for Sale

8486 Powder Ridge Trail, Windermere image

8486 Powder Ridge Trail, Windermere $375,000

GREAT house and amazing location. The house has 4 bedrooms 3 full baths and 1 half bath. In attached also has a Mother law house (loft), good size for family room or gues...

4 Beds
3.5 Baths
Windermere Trails SubDv.
34786 Zip Code

6228 Lecco Way, Windermere $850,000

Located on a beautiful water view lot in the gated community of Waterstone, this Silliman built home shows like a model and has numerous upgrades. The kitchen is a cooks ...

4 Beds
3 Baths
Waterstone A D E F G H J L SubDv.
34786 Zip Code

535 Oakdale Street, Windermere $697,000

It is rare today to find the perfect house in the perfect place! Fully renovated and upgraded gem in the heart of downtown Windermere. Walk amongst beautiful oak trees o...

5 Beds
3 Baths
Windermere Rep SubDv.
34786 Zip Code

8179 Maritime Flag Street Unit 202, Windermere image

8179 Maritime Flag Street Unit 202, Windermere — Lakeside At Lakes Of Windermer $214,900

Beautiful Lakeside at Lakes of Windermere 3 bedroom "Aruba model" condo with open floor plan, large master walk-in closet, crown molding, 1st floor corner unit with, pri...

3 Beds
2 Baths
Lakeside/Lks/Windermere SubDv.
34786 Zip Code

6564 Lagoon Street, Windermere $399,000

Beautiful LAKE FRONT 1.21 acres of vacant land with NO HOA. You are hidden away, yet located in desirable Windermere conveniently located near shopping at The Groves, res...

Sawyer Shores Sub SubDv.
34786 Zip Code

12724 Westside Village Loop, Windermere image

12724 Westside Village Loop, Windermere $620,000

This former Meritage model home is now for sale! The Barrett floorplan features an open-concept design, including a first floor in-law suite, study, hobby room and bonus ...

4 Beds
3.5 Baths
Westside Village SubDv.
34786 Zip Code

1816 Westover Reserve Boulevard, Windermere image

1816 Westover Reserve Boulevard, Windermere $649,000

UPDATED HOME. One of a kind luxurious home with many UPGRADED items! Gated Community. Oversized island granite kitchen with deep custom cabinets, pull out drawers. *Extra...

5 Beds
4 Baths
Westover Reserve SubDv.
34786 Zip Code

325 Magnolia Street, Windermere $1,997,000

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 ...

4 Beds
3 Baths
Windermere Town SubDv.
34786 Zip Code

6186 Louise Cove Drive, Windermere image

6186 Louise Cove Drive, Windermere $1,500,000

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 doo...

4 Beds
5.5 Baths
Isleworth West SubDv.
34786 Zip Code

5005 Down Point Lane, Windermere $1,799,000

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...

6 Beds
5.5 Baths
Sunset Bay SubDv.
34786 Zip Code

11655 Black Rail Street, Windermere image

11655 Black Rail Street, Windermere $359,000

BEAUTIFUL 3 BEDROOM HOME + BONUS ROOM -- Home in Windermere off of Chase Road in Windermere Landing! Enter through the wood door just beyond the inviting front porch. **A...

3 Beds
2.5 Baths
Windermere Lndgs Ph 02 SubDv.
34786 Zip Code

7319 Colbury Avenue, Windermere $359,900

CURTAIN RISING! Beautiful 3 Bedroom 2 Bathroom house on a greenbelt with NO DIRECT rear neighbors is ready for YOU to call it HOME! This home features a lovely covered fr...

3 Beds
2 Baths
Enclave/Berkshire Park B G H I SubDv.
34786 Zip Code

12749 Westside Village Loop, Windermere image

12749 Westside Village Loop, Windermere $635,000

It’s a Beautiful and Charming Hayden model home!!! It has lots of builder upgrades such as; open floor plan with hight ceiling, wood floors on almost all the rooms down s...

5 Beds
4.5 Baths
Westside Village SubDv.
34786 Zip Code

6038 Golden Dewdrop Trail, Windermere image

6038 Golden Dewdrop Trail, Windermere $585,000

This absolutely immaculate smart home is not only upgraded in almost every way possible, and on an amazing lot, but also runs off of SOLAR keeping the owner's power bill ...

4 Beds
3.5 Baths
Windermere Lndgs Fd-1 SubDv.
34786 Zip Code

2630 Park Royal Dr, Windermere $1,075,000

One acre Windermere estate home with unique charm and character offering an incredible lifestyle. Almost 6,000 sf living area with 5/6 bedrooms, 5 bathrooms, bonus/media ...

5 Beds
5 Baths
Windsor Hill SubDv.
34786 Zip Code

11548 Claymont Circle, Windermere $735,000

Short Sale. Short sale great location, great home, great opportunity.

4 Beds
5 Baths
Keenes Pointe Ut 04 Sec 31 48 82 SubDv.
34786 Zip Code

12708 Langstaff Drive, Windermere — 27 $255,000

Beautiful 3/2.5 townhome in the peaceful Lake Reams Townhome Community in Windermere! This property features a split floor plan with kitchen and family living room sharin...

3 Beds
2.5 Baths
Lakes/Windermere-Lk Reams Twnh SubDv.
34786 Zip Code

12712 Bideford Avenue, Windermere $434,900

WOW, owner spares no expense with this beautiful amazing home. It’s a 5BR/3BA two story home, with workspace and storage in the attached two car garage. Fenced back yard,...

5 Beds
3 Baths
Lakes Of Windermere Ph 02a SubDv.
34786 Zip Code

13531 Gorgona Isle Drive, Windermere image

13531 Gorgona Isle Drive, Windermere $530,000

Must see 3D Tour and Video! This gorgeous, one-story home is situated in a prime location just behind Disney’s Magic Kingdom Theme Park. You will simply fall in love wit...

4 Beds
3 Baths
Windermere Isle SubDv.
34786 Zip Code

7676 Brofield Avenue, Windermere $500,000

4-bedroom, 3.5-bath pool home with a pond in the front and conservation area behind. No rear or front neighbors so you can enjoy your newly built pool with peace and priv...

4 Beds
3.5 Baths
Lake Sawyer South Ph 04 SubDv.
34786 Zip Code

5310 Segari Way, Windermere — 5310 $319,000

RARE opportunity to get one of the ONLY three-bedroom CORNER TOWNHOMES for sale right now in popular Summerport! NEW ROOF! NEW A/C. The HOA pays for the exterior structur...

3 Beds
2.5 Baths
Summerport SubDv.
34786 Zip Code

4333 Isabella Circle, Windermere $2,193,000

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 ent...

6 Beds
7 Baths
Casabella SubDv.
34786 Zip Code

6532 Helmsley Circle, Windermere — 6532 $321,500

LOCATION, LOCATION, LOCATION!!!! Gorgeous townhouse located at the coziest community Preston Square in Windermere! This property offers a beautiful layout throughout with...

4 Beds
3 Baths
Preston Square SubDv.
34786 Zip Code

5724 Somersby Road, Windermere — 5724 $264,900

Looking for a low maintenance home with a relaxed lifestyle surrounded by incredible community amenities that include trails surrounded by nature – mature trees, ponds, l...

3 Beds
2.5 Baths
Tennyson Pk/Summerport SubDv.
34786 Zip Code

12300 Montalcino Circle, Windermere image

12300 Montalcino Circle, Windermere $660,000

Rare opportunity to build your dream home on a lakefront Windermere lot! One of the last county-approved gated communities in Windermere, Casa del Lago ownership will of...