Windermere Real Estate Search
Windermere Properties for Sale
What I Love About Windermere
Windermere is a small area of natural beauty just north of Disney, called the Windermere Chain of Lakes. In downtown Windermere, it feels like walking into history and upscale living. Large oak trees, roundabouts, and mature landscaping give the downtown a historic and sophisticated feel.
One of the smallest downtowns among all the Orlando suburbs is situated in downtown Windermere. There are only 4 or 5 shops in the area and you can walk through the area in 15 minutes or so. Although one may pass through here, it is a beautiful drive. In addition to the coffee shops, another spa, café, and a few other shops, there are a few professional stores.
The Windermere moniker has become familiar for being one of the most desirable neighborhoods in Orlando. But if that doesn’t do anything for you, then you need to realize the proximity to the parks. Driving to Disney is a 15- to 20-minute journey from Windermere, with many routes accessible by back roads!
Many of the most desired homes in Orlando and Central Florida can be found in Windermere. A chain of lakes situated in West Orange County is actually one of the most beautiful chains in the country.
There are eleven pristine lakes that are connected by canals in the Butler Chain of Lakes. Boaters flock to the historic Bird Island in Windermere, a paradise for boaters. There is a small island with sandbars within Lake Butler called Bird Island.
Windermere real estate is full of great home choices if you want to buy a home. Whether you want to live in Keene’s Pointe, Isleworth Country Club, or Lake Butler Sound or you want a home in classic Windermere along beautiful sand roads, you can find a home there.
There are many communities and areas within Windermere that offer direct access to the Butler Chain of Lakes, one of Windermere’s major attractions.
From historic single-story homes to lakefront mega-mansions, downtown Windermere has a wide range of real estate for sale.
There are still many homes built on sand roads in Downtown Windermere, Windermere’s original neighborhood.
Orlando homes do not have this unique charm, making Windermere homes stand out from the rest. 2nd Avenue and Pine Street are two of the most sought-after streets for living in Downtown Windermere. They both have access to tarmac roads.
Windermere condominiums range from just under $1 million to more than $25 million; lots and small homes are available for under $1 million.
Does Windermere offer family-friendly amenities?
It is one of the family-friendly communities in Central Florida, with one of the most beautiful and peaceful settings. Many top schools in Orlando are located in Windermere including Windermere Prep.
Children’s parks are spread throughout downtown Windermere, including swings and slides.
In addition to basketball courts and tennis courts in the neighborhood, there are many safe places to walk along the back streets of Windermere or around the lake.
Distance from Windermere to Disney World in Orlando
The neighborhood of Windermere is situated just north of Disney World, making it one of the closest communities to Disney World.
What is it like to live in Windermere, Florida?
There are few places in Orlando that are as desirable as Windermere. There are only three communities that can match Windermere in terms of proximity to Disney World: Winter Park, Winter Garden, and Lake Nona.
Windermere is one of the safest neighborhoods in Orlando, but if you’re looking for even more safety, check out Keenes Pointe or Isleworth. A number of fairly larger churches are also found in the Windermere area, the most prominent of which is Family Church, Windermere Campus, which is located directly in Downtown Windermere.
Our website features the best Windermere real estate search for homes, condo, and land properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.
You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.
- Windermere Properties between $350,000 and $400,000 for Sale
- Windermere Properties between $400,000 and $450,000 for Sale
- Windermere Properties between $450,000 and $500,000 for Sale
- Windermere Properties between $500,000 and $600,000 for Sale
- Windermere Properties between $600,000 and $700,000 for Sale
- Windermere Properties between $700,000 and $800,000 for Sale
- Windermere Properties between $800,000 and $900,000 for Sale
- Windermere Properties between $900,000 and $1,000,000 for Sale
- Windermere Properties between $1,000,000 and $1,500,000 for Sale
- Windermere Properties between $1,500,000 and $2,000,000 for Sale
Curious about what’s happening in the Windermere real estate market? Sign up for a Windermere Real Estate Market Report to see what’s active, under contract, and sold!
Newest Windermere Properties for Sale
Keene's Pointe - Gated/24-hour attended community centered around The Golden Bear Club, an 18-hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, ...
- 5 Beds
- 4 Baths
- Keenes Pointe Ut 04 Sec 31 48 82 SubDv.
- 34786 Zip Code
Keene's Pointe - 24-hr gated/attended community in Windermere, Florida, featuring The Golden Bear Club. An 18-hole golf course designed by Jack Nicklaus offering golf, t...
- 3 Beds
- 3 Baths
- Keenes Pointe SubDv.
- 34786 Zip Code
This house is a gorgeous two-story home with 5 bedrooms, 3.5 baths, and a two-car garage. This home offers an open floor plan with a family room and dining area connected...
- 5 Beds
- 3.5 Baths
- Windstone SubDv.
- 34786 Zip Code
Welcome to this stunning residence in the sought-after community of The Sanctuary At Lakes Of Windermere! Nestled in an AMAZING LOCATION, this spacious home offers five b...
- 5 Beds
- 4.5 Baths
- Sanctuary/Lks/Windermere SubDv.
- 34786 Zip Code
Discover this hidden luxurious Mediterranean inspired custom estate nestled behind a private double iron gate leading to a wide circular paved driveway on a 1.21 acre lot...
- 5 Beds
- 6 Baths
- Lake Down Cove SubDv.
- 34786 Zip Code
Welcome to your dream retreat in the highly sought-after Keenes Pointe neighborhood of Windermere, FL! This exquisite residence boasts five spacious en suite bedrooms, en...
- 5 Beds
- 5 Baths
- Keenes Pointe SubDv.
- 34786 Zip Code
Welcome to your FULLY FURNISHED AND DECORATED dream home, a stunning 3,390 sq. ft. oasis of elegance and comfort, nestled in the prestigious Windermere Trails community. ...
- 4 Beds
- 3.5 Baths
- Windermere Trls Ph Ia SubDv.
- 34786 Zip Code
GORGEOUS RECENTLY RENOVATED TOWN-HOME!!!!! . The property is a corner unit in the highly desirable Vineyards community in Windermere. Upon entry, you will notice the ope...
- 3 Beds
- 2.5 Baths
- Vineyards/Horizons West Ph 2a SubDv.
- 34786 Zip Code
... Move in ready custom home in the 24 hours guarded community... This is a 6 bedroom suites, 7 baths, 2 1/2 baths, and 4 car garage custom home that offers over 10,000 ...
- 6 Beds
- 7.5 Baths
- Isleworth SubDv.
- 34786 Zip Code
One or more photo(s) has been virtually staged. Introducing your new home nestled in the heart of Windermere! This beautiful 3 bed 2.5 bath townhome is located in the pic...
- 3 Beds
- 2.5 Baths
- Carrington SubDv.
- 34786 Zip Code
A beautiful home located in the heart of downtown Windermere offering 4-bedrooms, 3-bathrooms, with a perfect blend of comfort and convenience. The house features hardwo...
- 5 Beds
- 4 Baths
- Windermere Town SubDv.
- 34786 Zip Code
Exquisite custom LAKEFRONT POOL HOME in desirable WINDERMERE on Lake Sawyer. This stunning beauty has 4 bedrooms and 3.5 baths, a separate office, a bonus room with a spe...
- 4 Beds
- 3.5 Baths
- Lakes Windermere Ph 01 49 108 SubDv.
- 34786 Zip Code
Here is your opportunity to own a single-story fully remodeled pool home on a corner lot in the desirable downtown Windermere with NO HOA on county water! At first glance...
- 3 Beds
- 2 Baths
- Windermere Town SubDv.
- 34786 Zip Code
Welcome to 6811 Helmsley Circle, a modern 4-bedroom, 3-bathroom single-family home with an extra-large upstairs office, located in the charming community of Windermere. B...
- 4 Beds
- 3 Baths
- Preston Square SubDv.
- 34786 Zip Code
Fantastic 3-bedroom, 2.5-bath townhouse in the desirable Wickham Park community. The kitchen features solid surface countertops, stainless steel appliances, an island, an...
- 3 Beds
- 2.5 Baths
- Wickham Park 66/28 Lot 261 SubDv.
- 34786 Zip Code
Welcome to this breathtaking Mediterranean-inspired custom home in the prestigious Lake Butler Sound community. From the moment you arrive at the circular driveway, you'l...
- 4 Beds
- 5.5 Baths
- Reserve At Lake Butler Sound SubDv.
- 34786 Zip Code
Don’t miss the opportunity to make this beautiful 3 bedroom townhome your own! The sought out Windermere Lakeside Villas Community offers resort-style amenities including...
- 3 Beds
- 2.5 Baths
- Lakeside Villas SubDv.
- 34786 Zip Code
Keene’s Pointe Beauty – Spectacular Custom Home located on one of the best lots on the 9th fairway of this Jack Nicklaus Signature Course with panoramic golf views, sunse...
- 5 Beds
- 5.5 Baths
- Keene's Pointe SubDv.
- 34786 Zip Code
Located in the heart of Windermere, this charming 3-bedroom, 2.5-bathroom townhouse is truly the perfect place to call home. A bright and spacious main living area greets...
- 3 Beds
- 2.5 Baths
- Edens Hammock SubDv.
- 34786 Zip Code
This luxurious estate sits on an amazing lakefront lot on a private 187-acre spring-fed lake, offering breathtaking water views from every corner. Set on a spacious .64-a...
- 5 Beds
- 4.5 Baths
- Butler Bay SubDv.
- 34786 Zip Code
WELCOME HOME TO THE MANORS AT BUTLER BAY! This STUNNING Pool home is located in the HEART of Windermere and BOASTS 5 Bedrooms, 4 FULL/2 HALF Baths, an OVER-SIZED .65-acre...
- 5 Beds
- 4.5 Baths
- Manors At Butler Bay Ph 02 SubDv.
- 34786 Zip Code
This amazing residence in Keene’s Pointe overlooking the picturesque 4th fairway of the Golden Bear Club has everything you could want or need in a custom home. This fle...
- 6 Beds
- 5 Baths
- Keenes Pointe SubDv.
- 34786 Zip Code
Amazing 1acre corner lot on Lake Cypress in the community Kelso on Lake Butler. Just down the street is the private community boat ramp on Lake Butler. Beautiful lot to b...
- Kelso On Lake Butler SubDv.
- 34786 Zip Code
Discover an incredible opportunity to bring your vision to life on this amazing and great located vacant land. Nestled in a prime Windermere location, this blank canvas i...
- Sawyer Shores Sub SubDv.
- 34786 Zip Code
Welcome home to this beautifully renovated, villa-style retreat located in renowned guard gated Isleworth Golf & Country Club. This home exudes the ideal balance of unwav...
- 4 Beds
- 4.5 Baths
- Isleworth SubDv.
- 34786 Zip Code
Beautiful Lakeside at Lakes of Windermere condominium - Third floor corner unit with screened balcony. This unit features an open floor plan that combines kitchen, living...
- 3 Beds
- 2 Baths
- Lakeside At Lakes Of Windermre Condominium SubDv.
- 34786 Zip Code
Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. Location! Location! Location! This well maintained home is located on the 11th fairway of The G...
- 4 Beds
- 4 Baths
- Keenes Pointe SubDv.
- 34786 Zip Code
WINDERMERE LAKEFRONT - PRIVATE LAKE CRESCENT IN WINDERMERE CLUB!! Beautiful 4 Bedroom, 3 Bath Pool home on Premium Half Acre+ Lot with approximately 200 Feet Water Front...
- 4 Beds
- 3 Baths
- Butler Bay/Windermere Club SubDv.
- 34786 Zip Code
Welcome to 9111 Outlook Rock Trail, Windermere, FL in Windermere Trails! Walkable to Lakeside Village Center with Publix, great local restaurants, and small businesses. Y...
- 5 Beds
- 3.5 Baths
- Windermere Trails SubDv.
- 34786 Zip Code
Beautifully Maintained 3-Bedroom Townhome in Lakeside Village, Windermere! This meticulously kept 3-bedroom, 2.5-bath townhome is located in the highly desirable Lakesid...
- 3 Beds
- 2.5 Baths
- Lakeside Villas SubDv.
- 34786 Zip Code
Location, Location. Location! Welcome to **Windermere, Florida**,and the desirable Summerport Community. Nestled in a vibrant, family-friendly neighborhood, this home off...
- 3 Beds
- 2 Baths
- Summerport Ph 02 SubDv.
- 34786 Zip Code
Perfectly located on a corner lot in the highly sought-after, 24-hour guard-gated community of Keene's Pointe, this luxury property offers an incredible investment opport...
- 4 Beds
- 4 Baths
- Keenes Pointe Ut 06 50 95 SubDv.
- 34786 Zip Code
Welcome to this fully renovated 4-bedroom, 3-bathroom home in Windermere, offering stunning Lake Down views and the bonus of no HOA. Step into the open and inviting layou...
- 4 Beds
- 3 Baths
- Down Acres Estates SubDv.
- 34786 Zip Code
WOW!! Location location location! Come and enjoy this great light and bright pool home in great school district. Fenced 1/3 acre lot with no rear neighbors . BRAND NEW R...
- 4 Beds
- 4 Baths
- Westover Club Ph 02 47/71 SubDv.
- 34786 Zip Code
Welcome to Central Florida's Resort-Style living on this fresh water private canal front property,90' wide lot with direct access to Lake Butler (chain of lakes) and no H...
- 5 Beds
- 3 Baths
- Sandy Shores SubDv.
- 34786 Zip Code
One of only a few built in Keene’s Pointe, this Annandale model by Morrison Homes, presents a floor plan that feels like a custom home; so different that what you typical...
- 4 Beds
- 4 Baths
- Keene's Pointe SubDv.
- 34786 Zip Code
LAKEFRONT! Gorgeous 4 BR, 3.5 BA TWO STORY, POOL HOME on a wide LAKEFRONT lot on LAKE Speer in WINDERMERE. This gorgeous lake front home is a rear and wonderful opportuni...
- 5 Beds
- 3.5 Baths
- Edens Hammock SubDv.
- 34786 Zip Code
Stunning 3-Bedroom Home with Modern Upgrades! This beautifully renovated 3-bedroom, 3-bathroom home is ideally located across from Bay Lake Elementary school and park, ju...
- 3 Beds
- 2.5 Baths
- Windermere Trls Prcl 3 SubDv.
- 34786 Zip Code
Welcome to this exquisite two-story residence situated on a spacious corner lot, blending luxury with everyday convenience. Boasting 5 bedrooms and 5.5 bathrooms, this be...
- 5 Beds
- 5.5 Baths
- Lake Sawyer South Ph 1 SubDv.
- 34786 Zip Code
This beautiful ENERGY STAR Certified home in Windermere, located just 2 miles from Disney attractions, now includes even more exceptional features. In addition to the 5 b...
- 5 Beds
- 3.5 Baths
- Windermere Trls Ph 4b SubDv.
- 34786 Zip Code
Welcome to your dream home! This spacious 4-bedroom, 3.5-bathroom residence offers the perfect blend of luxury and comfort. Nestled on a desirable corner lot, this proper...
- 4 Beds
- 3.5 Baths
- Lakes/Windermere-Peachtree SubDv.
- 34786 Zip Code
The Lakehouse.....Built in 1966 and kept in original condition this mid-century modern home embodies timeless design and a seamless connection with nature. Set on over an...
- 5 Beds
- 4.5 Baths
- Summerport Beach SubDv.
- 34786 Zip Code
Once upon a time a Disney Executive fell in love with the beautiful Snow White and built a home that dreams are made of on the shores of the Butler Chain of Lakes. The ...
- 5 Beds
- 7.5 Baths
- Isleworth SubDv.
- 34786 Zip Code
Discover luxury living in the heart of Keene's Pointe, Windermere. Home to the renowned Golden Bear Golf Club. This meticulously designed 4-bedroom, 3-bathroom , 3-car g...
- 4 Beds
- 3 Baths
- Keenes Pointe SubDv.
- 34786 Zip Code
This beautiful home, built by Toll Brothers in 2019, is located within CASABELLA, one of the more sought-after communities in Central Florida Located in Windermere, this ...
- 5 Beds
- 5.5 Baths
- Casabella Ph 2 SubDv.
- 34786 Zip Code
Welcome to 9106 Panzani Place! This beautiful 5-bedroom, 4-bathroom home located in the charming community of Windermere. This stunning home sits on a corner lot and feat...
- 5 Beds
- 4 Baths
- Tuscany Ridge 50 141 SubDv.
- 34786 Zip Code
One or more photo(s) has been virtually staged. Receiving Offers.. Beautiful home in Lakes of Windermere Exceptional Opportunity! Act Now! Step into this gorgeous home—t...
- 4 Beds
- 3.5 Baths
- Lakes/Windermere Ph 04 SubDv.
- 34786 Zip Code
Ready to start you own business!!!! This is a prime location location and location This franchise is getting sales everyday healthy food , great attentions and the best ...
- 34786 Zip Code
Don’t miss your opportunity to own this peaceful corner unit townhome on a quiet street with beautiful park views in the front and preserve views behind your home. When ...
- 3 Beds
- 2.5 Baths
- Lake Sawyer South Ph 03 SubDv.
- 34786 Zip Code
Luxury living in one of Central Florida's most sought-after neighborhoods, Windermere Grande. This 5 bedroom, 3.5 bath single-family home offers .85 acres of land and a s...
- 4 Beds
- 3.5 Baths
- Windermere Grande SubDv.
- 34786 Zip Code
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