Windermere Homes under $400,000

Welcome to Windermere, Florida, a picturesque town nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and charming small-town vibe, Windermere offers a unique blend of tranquility and community spirit. With its rich history and a commitment to preserving its natural beauty, this delightful locale is perfect for families, professionals, and retirees alike.

One of the most appealing aspects of Windermere is its diverse real estate market, which includes a selection of beautiful homes priced under $400,000. Whether you’re a first-time homebuyer or looking to downsize, you’ll find a variety of options that cater to your lifestyle. From cozy single-family homes with spacious yards to modern townhouses with contemporary finishes, Windermere offers something for everyone.

Living in Windermere means enjoying a wealth of outdoor activities. With numerous parks and recreational areas, residents can indulge in everything from hiking and biking to fishing and boating on the stunning Butler Chain of Lakes. The town's strong sense of community is evident in its local events, farmers' markets, and festivals, providing ample opportunities to connect with neighbors and make lasting friendships.

Moreover, Windermere is conveniently located near major highways, making it easy to access the vibrant attractions of Orlando while still enjoying the peaceful charm of suburban life. With a strong school system and a family-friendly atmosphere, Windermere is not just a place to live; it's a place to thrive. Explore your options today and discover the perfect home in this enchanting Florida town!

Newest Windermere Homes under $400,000

8276 Maritime Flag St Unit 1204, Windermere image

8276 Maritime Flag St Unit 1204, Windermere — 8276 $324,900

Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combina...

3 Beds
2 Baths
Lakeside/Lk/Windermere Ph 12 SubDv.
34786 Zip Code

8179 Maritime Flag Street Unit 206, Windermere image

8179 Maritime Flag Street Unit 206, Windermere — 8179 $350,000

Enjoy easy Florida living in this beautifully maintained first-floor, 3-bedroom, 2-bathroom condo in Windermere. The split floor plan offers privacy, while premium upgrad...

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

8168 Boat Hook Loop Unit 302, Windermere image

8168 Boat Hook Loop Unit 302, Windermere — 8168 $299,997

Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated ...

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

11446 Jasper Kay Terrace Unit 202, Windermere image

11446 Jasper Kay Terrace Unit 202, Windermere — 14466 $295,000

Welcome to easy Florida living in the desirable Lakeside community of Windermere! This beautifully maintained 2-bedroom, 2-bathroom condo offers a comfortable open-concep...

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

12934 Vennetta Way, Windermere — Venetta Way $369,000

Virtually Staged. Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath end-unit townhome in one of Windermere’s most sought-after communities. Offering the adde...

3 Beds
3 Baths
Lake Sawyer South Ph 03 SubDv.
34786 Zip Code

8608 Brookvale Drive, Windermere — 8 $379,900

LIVE IN OR INVEST WHERE OTHERS DREAM OF VACATIONING!!! Amazing opportunity in Windermere, one of Central Florida’s most desirable locations, just minutes from the magic o...

3 Beds
3 Baths
Lakes/Windermere Lake Reams Twnh SubDv.
34786 Zip Code

12417 Cruxbury Drive, Windermere — 12417 $359,000 ▼

Welcome to the peaceful townhome community of The Lakes of Windermere, conveniently nestled just behind Walt Disney World’s Magic Kingdom! Enjoy beautiful green space out...

2 Beds
3 Baths
Lakes/Windermere-Lk Reams Twhm SubDv.
34786 Zip Code

8168 Boat Hook Loop Unit 303, Windermere image

8168 Boat Hook Loop Unit 303, Windermere — 7 $320,000

Welcome to 8168 Boat Hook Loop, Unit 303, a beautifully maintained condominium offering comfortable, low-maintenance living in a desirable community. This move-in ready r...

3 Beds
2 Baths
Lakeside At Lakes Of Windermere SubDv.
34786 Zip Code

7430 Bentonshire Avenue, Windermere image

7430 Bentonshire Avenue, Windermere — 7430 $354,900

Virtually Staged. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. MOVE-IN READY and listed below recent appraisal - ideally located in the highly desirable Wickham Park community...

2 Beds
3 Baths
Wickham Park 04 05 06 09 10 11 12 01 SubDv.
34786 Zip Code

8860 Herencia Alley, Windermere — 8860 $398,000 ▼

Priced to sell! Great location and highly desired community! This beautifully maintained two-level townhome in the charming Legado community of Windermere offers 1,578 sq...

3 Beds
3 Baths
Legado 95/47 Lot 99 SubDv.
34786 Zip Code

7752 Rigby Street, Windermere — 7752 $395,000 ▼

Virtually Staged. Welcome home to this beautiful 3 bedroom, 2.5 bath townhome in one of Windermere’s most sought after communities. Offering a private courtyard, this ho...

3 Beds
3 Baths
Whickham Park SubDv.
34786 Zip Code

12744 Langstaff Drive, Windermere — Na $394,900 ▼

Price Improvement! Recently reduced.Located in one of Windermere’s most desirable communities, this beautifully updated 3-bedroom, 2.5-bath townhouse offers the perfect b...

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