Windermere Town Real Estate

Windermere Town Real Estate

Welcome to Windermere Town, a charming subdivision nestled in the heart of Windermere, Orange County, Florida. This picturesque community offers residents a peaceful and serene atmosphere, perfect for those seeking a tranquil place to call home.

Windermere Town is known for its beautiful tree-lined streets, well-maintained properties, and close-knit community feel. The neighborhood boasts a variety of architectural styles, from cozy bungalows to spacious modern homes, providing options for every taste and preference.

Residents of Windermere Town enjoy easy access to a range of amenities, including top-rated schools, parks, shopping centers, and dining options. The neighborhood is conveniently located near major highways, making it a breeze to explore all that the vibrant city of Windermere has to offer.

Whether you're looking to raise a family, retire in a peaceful setting, or simply enjoy the beauty of Florida living, Windermere Town has something for everyone. Come and experience the laid-back lifestyle and warm sense of community that make this subdivision a truly special place to live.

Newest Listings in Windermere Town

$4,850,000
4 Beds ⋅ 4.5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
This property includes an Incredibly Rare Air Conditioned Boathouse that is completely renovated with Apartment, Kitchen and Bathroom. A Custom Platform Boat Lift with overhead garage door lends security and privacy that other boathouses do not offer....................... The home has all the latest state of the art technology allowing you to control everything from the convenience of your phone from the best Brands like Lutron Smart House Electronics to control Lighting, Nest for A/C, Schlage for Exterior Doors and MyQ for Overhead Garage Doors. The Whole House Generac Generator brings comfort and peace of mind to your family during the worst weather...................... The whole property has been completely remodeled with the finest materials. The Miele Kitchen Appliances boast a Free Standing Fridge & Freezer with Furniture Grade Cabinet Doors. The Steam Oven wall unit brings a whole new dimension to Gourmet meals with a 6 Burner Gas Range and separate Oven makes large parties a breeze........................................... The wall unit Convection Oven / Microwave gives a 3rd option for meal prep. An Ice Maker and Bar Sink in the Island gives the Mixologist a great place to Host friends & family. The Stainless Farmhouse Sink overlooks the Lake & Pool and provides another easy area for clean-up................................... This Home is the Entertainers Dream with a Huge Flagstone Pool Deck featuring a Covered Porch and Automatic Screens that make it the perfect place to enjoy amazing sunsets. Continue the fun indoors with a Luxurious Theatre complete with stadium seating, a Concession Stand with mini fridge, sink & Ticket Booth. It is the perfect place to host a birthday or weekend Slumber Party............................... The Resort like Primary Suite with Shower and Soaking Tub Inside a Bay Window Overlooking the Lake & Pool provides the most Romantic place to enjoy the Sunset and release the stress from your busy day. The Entrance Foyer Elevator opens up on the 2nd floor to a large mezzanine making it easy to get to the 3 upstairs Ensuite Bedrooms, Theatre & Office/Study................................ Each Bedroom has a private bath and oversized closet. All 3 Bedrooms have direct access to the huge balcony that overlooks the Pool & Lake................................ The 3 Car Garage is equipped with 2 Tesla Chargers. There is a separate 8 spot parking area for 8 Guests, perfect for larger gatherings........................ If you want to have a place where all of the kids and their friends want to hang out and create lasting memories this is it!..................... Windermere is a Golf Cart friendly community. The Brewery, Cafe, Pizza & Coffee shop is a short walk down Main Street. The Butler Chain has 13 interconnected lakes giving you over 5,000 acres of endless boating and fishing options

904 Main Street, Windermere
$3,148,000
4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Boasting a prime location in the Town of Windermere on Lake Down with access to the Butler Chain of Lakes, enjoy the perks of town and lake living being in the heart of Windermere. Less than half a mile from your front door and in walking distance is Windermere Main Street, hosting Paloma Coffee, shops and the new redevelopment of the 500 block in Downtown Windermere where there will be retail and restaurants. Enjoy the Farmer's Market every Friday morning where local farmers, food trucks and craftsman come to sell goods in addition to many events the Town of Windermere hosts throughout the year. Dixie Cream, a popular breakfast and lunch restaurant and the Windermere Brewing Company are equally as close. All the best of Windermere living within .4 miles of your front door. NO carpet, the home features travertine throughout and new luxury vinyl planking in the second and third bedrooms. The kitchen has a gas range with vented exhaust fan and a brand new top of the line, all-in-one convection oven/microwave and air fryer. Step into the Florida room and imagine yourself enjoying your morning cup of coffee or evening glass of wine looking over your pool onto the lake. Come experience what living in Windermere is about!

325 Magnolia Street, Windermere
$679,000
Windermere Town SubDv. ⋅ 34786 Zip Code
This is a rare opportunity to own a two-home parcel in the highly sought-after community of Windermere. This property is ideal for use as a rental or to tear down and make the lot the new location of your custom-built dream home! As rental units, these bungalow-style homes are ideally located close to the center of downtown Windermere and Lake Bessie. Both homes offer 2 bedrooms,1 bathroom, plus a 450 square foot shed on .38 acres. Each are full of character and style with stainless steel appliances, Shaker-style cabinets and other designer touches. Or if you have been searching for the absolute perfect location to build, this is it! The lot allows for an ample-sized home that is just steps from beautiful Lake Bessie and the boat ramp to the lake. The area is a truly picturesque setting with towering mature live oaks and just a short golf cart ride to all of downtown Windermere's amenities which include shops, dining, wine market, brewery, basketball courts, tennis, pickleball, multiple boat ramps, playgrounds and so much more. Don't miss the opportunity to own this rare piece of beautiful Windermere. Schedule your property tour today!

721 Magnolia Street, Windermere
$679,000
4 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
This is a rare opportunity to own a two-home parcel in the highly sought-after community of Windermere. This property is ideal for use as a rental or to tear down and make the lot the new location of your custom-built dream home! As rental units, these bungalow-style homes are ideally located close to the center of downtown Windermere and Lake Bessie. Both homes offer 2 bedrooms,1 bathroom, plus a 450 square foot shed on .38 acres. Each are full of character and style with stainless steel appliances, Shaker-style cabinets and other designer touches. Or if you have been searching for the absolute perfect location to build, this is it! The lot allows for an ample-sized home that is just steps from beautiful Lake Bessie and the boat ramp to the lake. The area is a truly picturesque setting with towering mature live oaks and just a short golf cart ride to all of downtown Windermere's amenities which include shops, dining, wine market, brewery, basketball courts, tennis, pickleball, multiple boat ramps, playgrounds and so much more. Don't miss the opportunity to own this rare piece of beautiful Windermere. Schedule your property tour today!

721 Magnolia Street, Windermere
$950,000
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Welcome to Historic Downtown Windermere. This stunning, fully remodeled mid-century-modern home is ready to welcome its new owner into a life like none other. Located in the golf cart district, you have convenient access to a private boat ramp and two public boat ramps, community parks, tennis courts, and a downtown district that boasts charm and exclusivity. Besides an idyllic lifestyle, this home offers something that many do not, completely renovated and move in ready. With no detail forgotten, every aspect of this home has been masterfully updated and upgraded. Upon entering you are greeted by immaculate new landscaping, new sod, new trees, and shrubbery - giving fantastic curb appeal. This concrete block home has been completely repainted, along with the addition of a new garage door. Your smart front door swings open to towering high Ceilings, floor to ceiling windows, and a stunning bright home. Centered in the middle of the home is a mid-century fireplace with dark porcelain tile offsetting your bright porcelain tile flooring and new interior paint. This chef's kitchen has been completely remodeled, and redesigned. With designer cabinets, beautiful quartz countertops, luxury cafe appliances, and a beautiful butcher block island, your hosting desires are a reality with additional bar top seating. From your kitchen you have a large open family room, walk in pantry and walk in laundry room. In your main living space, you have an optional formal sitting area along with a potential formal dining room that leads to a covered outdoor patio. This home offers several different potential room layouts depending on your needs. Off of this space you have two guest rooms with new lighting, new fans, and a completely new bathroom. Up the new staircase, you have your private master suite. Complete with new lighting, new fans, new his and her vanities, new shower, new stand-alone tub, and new walk-in closet. The theme of this home is modern mid-century modern with the added convenience brand new finishes, technology, and features. Apart from the brand-new interior, this home offers a new AC, new electrical fuses, a new well tank, a new well pump, new irrigation, new gravel, a 2022 roof, and new hot water heater. Windermere is a town nestled along the lakes. Peace and tranquility at every turn, 4 Chase Road is the perfect home for anyone looking for luxury living in this historic waterfront town.

4 Chase Road, Windermere
$3,350,000
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Incredible Sunsets & Disney Fireworks Every Night - Open Water View of Lake Butler & the Pristine & Quiet Side of Bird Island - White Sand Beach - Crystal Clear Water - 3 Bedroom - 2 Bath - Open Floor Plan - 2 Car Garage - Remodeled Kitchen & Baths - Wood Floors - Sea Wall - Enclosed Storage Room on Dock - Automatic Canvas Boat Cover - Concrete Block 2 Story - New Energy Efficient Windows - Massive Windows Overlooking The Lake - Golf Cart Friendly Community - Deeded 40 x 80 Vacant Lot Buffer on Main St - Natural Gas - Excellent Schools - Community Tennis & Pickle Ball Courts within Walking Distance

884 Main Street, Windermere
$3,100,000
4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Just like brand new, fully renovated by Davila Homes, this gorgeous home on Wauseon Bay in the Lake Butler Chain is taking shape. Featuring 4 bedrooms and 3 bathrooms, this home offers an amazing lakefront view and everything BRAND NEW plumbing, AC, electrical, septic system, top-of-the-line appliances and more. The modern, sophisticated design extends to the stunning backyard, which includes a fire pit, outdoor kitchen, and ample space for entertainment and relaxation. Master bedroom downstairs with an supersize walking custom built closet. Enjoy the boat dock and breathtaking sunsets on the Lake Butler Chain. Conveniently located in downtown Windermere, walk to the coffee shop and farmers market. No HOA.

7 1st Court, Windermere
$2,250,000
4 Beds ⋅ 4.5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
***AVAILABLE FOR SALE OR RENT. SELLER FINANCING AND LEASE TO PURCHASE WILL BE CONSIDERED.*** Stunning new LAKEFRONT construction in the heart of Downtown Windermere completed in July 2024. This exquisite single-story home spans 2,868 sq ft with an open-concept design, featuring white oak hardwood floors and contemporary style throughout. Highlights include 4 bedrooms, each with its own en-suite bathroom, living room with expansive lake views, European-style kitchen, home office, and laundry room. Indulge in top-tier amenities including a luxury heated pool and spa, quartz countertops and smart appliances. Enjoy cool lake breezes and sunrises from your front porch overlooking the lake and finished in Nordic travertine. Located on the highly desirable Lake Bessie, famed for its boating and fishing, the property has 100’ of lakefront with the option to build your own private dock. Downtown Windermere is just a short walk or golf cart ride away - enjoy the weekly farmers market, tennis courts, brewery, restaurants and parks this charming town has to offer. This home offers the ultimate in contemporary lakefront living at an unbeatable price. Don’t miss your chance! Be sure to click on the virtual tour links. <iframe width='853' height='480' src=https://my.matterport.com/show/?m=UpoSG6KDFjw&mls=1></iframe>

Windermere
$599,000
3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
**Price improvement! Sellers motivated!** Now is your chance to live the true Windermere lifestyle, "Among the Lakes"! Make this charming 3/2 home your haven for all that the Town Windermere has to offer. No HOA restrictions, well maintained, and move-in ready, this home sits on an impressive 95 ft X 150 ft corner lot in the very heart of the Town of Windermere. Located just a few blocks from the quaint Town square, weekly farmers markets, shops, eateries, brewery, coffee shop, wine shop, monthly food truck nights, resident-only special events, public library, churches, and so much more. Enjoy boating on the famous Butler Chain of Lakes and Lake Bessie through exclusive, deeded boat ramp access, relax and watch the sunset from one of numerous parks and playgrounds, or swim and fish from one of several town docks! Home features original hardwood flooring throughout the living spaces and bedrooms, with ceramic tile in the kitchen and bathrooms. Roof and A/C replaced in 2018, septic in 2019, electric upgraded in 2021 (see attachments for full list of upgrades). Other features include attached carport (pre-wired for EV wall connector port) and separate laundry room/workshop space with plenty of extra storage space. This is a RARE opportunity to make your Windermere dream come true! With A-rated schools and plenty of outdoor activities available, this unique, golf-cart friendly community make this home a must-see. Don't miss out on your chance to live "Among the Lakes”!

133 Main Street, Windermere
Start Your Search