Windermere Property Search

Search All Windermere Real Estate

Windermere is a town in Orange County, Florida, known for its upscale neighborhoods and luxury real estate. The town is situated on the shores of Lake Butler and Lake Down, making it a popular destination for boating and water sports. The real estate market in Windermere is dominated by single-family homes, many of which are situated on large lots with waterfront views. Prices for these homes can range from the high hundreds of thousands to several million dollars, depending on the size and amenities of the property.

 

The history of Windermere dates back to the 1800s when the area was primarily used for cattle grazing and farming. The town was officially incorporated in 1925 and at that time, it was a small community with a population of less than 300 people.

 

In the early 1900s, a group of wealthy Northerners, known as the "Windermere Club," purchased land in the area and built a series of large, Victorian-style homes, which were primarily used as winter retreats. These homes were situated on large plots of land, many of which featured waterfront views on the town's many lakes.

 

During the 1950s and 1960s, Windermere experienced a population boom as the town began to attract more permanent residents. Many of these residents were drawn to the area's natural beauty and the town's many lakes, which offered opportunities for boating and water sports.

 

In recent years, Windermere has become known as one of the most affluent and desirable communities in Central Florida. The town is home to many upscale neighborhoods, and the real estate market is dominated by single-family homes, many of which are situated on large lots with waterfront views.

 

The town is also home to the Windermere Country Club, which features a golf course, tennis courts, and swimming pool for residents to enjoy. Additionally, the town has access to the West Orange Trail, a popular spot for biking, walking, and other outdoor activities. Today, Windermere is considered a high-end residential area, with a mix of older estates, and new, luxury developments, it's an exclusive and prestigious place to live.

 

Our website features the best Windermere real estate search for homes, condos, land and foreclosure 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. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Hot Windermere Properties

$529,900
3 Beds 2.5 Baths Enclave/Berkshire Park B G H I SubDv. 34786 Zip Code
MUST SEE! Here is a 3-bedroom, 2 1/2 bath home in sought-after Windermere, Florida with a large, FULLY FENCED back yard! This home is near A -rated Sunset Park Elementary school, Horizon West Middle School, and Windermere High School. This home is also one mile from popular grocery stores and a variety of restaurants and shops! An added convenience - Orlando International Airport is about 30 minutes away! Other features include the following: BRAND NEW STAINLESS STEEL KITCHEN APPLIANCES! FRESHLY PAINTED INTERIOR! Two-year old A/C, Downstairs Master Bedroom with large Master bath featuring dual separate sinks, a garden tub, separate shower, and master closet! BRAND NEW durable laminate flooring in both upstairs bedrooms and the study area! Roomy BONUS ROOM! Picture living in this comfortable home! There is a two-car garage! A half bath in the hallway. The kitchen has a cozy corner breakfast nook. The dining area features a new modern hanging light! After a meal, there are plenty of places to go - into the living room to watch TV, or upstairs to the bonus room, or the study and computer area, or outside to enjoy the partially covered patio! Just three blocks away is the sparkling community pool and play area overlooking a pond. Numerous biking and walking trails abound here! At night, watch the Disney fireworks! Residents say "why go away when you can stay and play here at home?!" Make plans now to see this home soon as there are very few homes available in this desirable area! Quick close OK!

13615 Riggs Way, Windermere

$650,000
4 Beds 2.5 Baths Creeks Run SubDv. 34786 Zip Code
**NEW ROOF & AC UNIT! Plus, renovated BATHROOMS & KITCHEN!!** If you want a stunning home that’s centrally located to just about everything here in Orlando, that’s within one of the most popular communities in Windermere then you can’t get better than this!! This beautifully updated home features 4 bedrooms and 2.5 bathrooms spread out over two stories with 2362 square feet of living space. As soon as you walk from the large front porch and through the front doors you're greeted with the foyer overlooking the formal dining room on your right. Towards the left you will find a beautiful office/den/library space with French doors perfect for some quiet reading time or work hours. Straight ahead is the main living room/kitchen combo. This main area includes a half bath which allows quick bathroom access when you have guests or the family is downstairs. The newly renovated (2021) kitchen/dinette combo includes a very large kitchen island which is a great prep space for large gatherings and family dinners. And you're going to love the updated appliances and touch activated faucet! From here, you can oversee the large living room and the pool area outside. You can beat those hot summer days by cooling off with a swim in your private saltwater HEATED POOL or hot tub! The living room is spacious and sits right next to the stairs that leads to the 2nd floor of the home. Between the kitchen and living room, you have the laundry room tucked away which provides access to the garage located in the rear of the home. Right under the stairs you have added storage and as we travel to the second floor, you will find all 4 bedrooms and 2 bathrooms. Once upstairs, you are greeted with 3 spacious bedrooms with lots of natural light, 1 full bath and you can't forget the 4th bedroom - the master bedroom/bathroom combo. The newly renovated (2023) bathrooms upstairs are simply stunning! The master bath makes for a great little getaway with a beautiful shower, large tub and separate sinks for shared spaces. The large master bedroom brings in lots of beautiful light and also has two walk in closets! This home is truly turnkey with all the major things taken care of. The home has a brand new roof and HVAC system that’s being installed this month and two brand new bathrooms that are simply stunning! The kitchen was recently remodeled to open up the space more for entertaining and enjoying large family gatherings. This community is surrounded by lakes so you’ll really enjoy the scenic walks around the neighborhood. And it truly is right in the center of it all. You're just 5 minutes to Winter Garden Village for the best shopping and restaurants in town! Only 15 minutes to Disney, 30 minutes to the airport, 20 minutes to downtown Orlando and you're just 4 minutes to 429 so you can quickly get to wherever you need to go! The Summerport community offers lots of activities for the whole family - monthly food truck events, movie nights, carnival days, and more. There's even a dog park for your fur babies! There is also a large clubhouse, community pool, and fitness center to enjoy. For the sports lovers, I'm sure you'll like playing on the basketball, tennis, and beach volleyball And you're going to love the multiple playgrounds nearby. Kings Crossing Elementary is also conveniently located within the community. What a dream house, right?! You’ve just got to come see it for yourself! Reach out to our team today to book your own private tour!

13839 Amelia Pond Drive, Windermere

$575,000
4 Beds 2.5 Baths Silver Woods Ph 04 SubDv. 34786 Zip Code
Located in the highly sought after neighborhood of Silver Woods sits this wonderful 4 bedroom 2.5 bathroom pool home. This home offers a split floor plan, vaulted ceilings, and over 2,000 square feet of living space. With it's close proximity to Dr. Phillips and Restaurant Row shopping, dining, and entertainment is at your fingertips. The sellers will offer the home fully furnished if the buyer offers full asking price. The home also offers a new roof installed on 3/2022. Collis Roof Owens Courning duration 5yr workmanship warranty, lifetime prorated product warranty, 130 mph strength. You will also enjoy the large .26 acre lot fully irrigated with mature landscaping. The community is also Zoned for Top Rated Schools, is close to the Dr. Phillips YMCA, and Bay Hill. With its $300 annual HOA fees, the home is a true gem. A rare find that comes with all these upgrades in the last 5 years. 3–5-year upgrades: Pool resurfacing, metallic blue granite finish Simonton PGT windows/doors; non-impact 120 mph strength Empire golden teak hardwood/laminate/carpet flooring 1–3-year upgrades: Bryant Carrier air conditioner - 4-ton unit Rheem H/W heater – 40 gallon Water sprinkler system – new zones/valves front/back PVC laminate privacy fence House painted - Behr brand (interior/exterior) Exterior lights front/back Interior doors throughout GE dishwashing machine Current – 1-year upgrades: Ameri pool pump motor 1.5hp Furnishings include: $12,000 French made hand carved leather pocket pool table. Dell intel 60 game arcade machine. 2 theater chairs 2-bedroom sets Pool patio furniture, grill, umbrella, games, and supplies. And much more. Schedule your showing today before it's sold to another family.

5124 Sun Palm Drive, Windermere

$2,350,000
4 Beds 3.5 Baths Lake Down Shores Rep SubDv. 34786 Zip Code
Welcome home to 2730 Midsummer Drive, arguably one of the most beautiful waterfront lots in all of Windermere if not all of Central Florida. Located on the Eastern Shores of Lake down 1 of 13 lakes in the highly sought-after Butler Chain of Lakes. Midsummer Drive is truly one of the most charming canopy oak covered roads you will find in Central Florida. With only 20 magnificent lakefront estate sized lots that rarely become available this is one opportunity you don’t want to pass up. This property provides incredible sunsets with panoramic views overlooking the large rear lawn that has currently over 145 feet of depth and over 130 feet of lakefront shoreline. The current property is over 350 feet deep on either side and provides more space and privacy than you will find in a traditional neighborhood. Currently there is a home on the property that could be remodeled but the true value is in the Land. With extensive soil samples completed and fairly recent survey you have the first steps needed to design and build your dream home. There is no other lot available on the butler chain with the views and potential that this lot provides. Minutes from I-4 , downtown Orlando, restaurant row, shopping, Orlando International Airport, Disney, and all the attractions without the down town Windermere traffic! Enjoy all your favorite water sports , great sunsets , and build your very own custom dream home.

2730 Midsummer Drive, Windermere

$11,995,000
5 Beds 7.5 Baths Reserve At Lake Butler Sound SubDv. 34786 Zip Code
Stunning modern masterpiece situated in Windermere's Reserve at Lake Butler Sound's most coveted lot. Known as "Overjoy" for its location on the sparkling waters of Lake Butler with unprecedented long lake views. Built by renowned builder Jones Clayton Construction and designed by coveted architect Mark Nasrallah, this collaboration is simply epic! The 14' glass double entry doors welcome you into this open floor plan, featuring 5 bedrooms, 7 full and 2 half baths with expansive unobstructed 140' lake views. This world class Aurora Award winning estate incorporates signature art deco design finishes and innovative architectural design. The main living area features a fireplace with Swarovski crystal insets, a Biazzi glass mosaic inset into the Benjamin grade Jerusalem limestone flooring, coffered ceiling with nine art deco-inspired custom chandeliers that complement the living room with extravagant floor to ceiling glass walls which offer inspiring views of the lake and 38' x 38' infinity edge pool and heated spa. The kitchen and family room are a work of art with cobalt blue ceiling insets that complement the blue Bahia granite countertops. Enjoy the efficiency of the kitchen and the clean lines of the Aigner cabinetry. The stunning first floor master suite offers Calcutta gold marble flooring, floor to ceiling glass walls, his and her two story dressing areas with a massage area, steam shower, sitting area, balcony and outdoor glass garden. A lovely private guest room is also conveniently located on the main floor. The floating glass 4 person elevator transports you to the second level where you'll enjoy the state of the art home theater with sueded walls and Kaleidescape media system. The third level provides three additional en suite bedrooms with views of the lake, plus a spacious loft and second laundry room. The expansive travertine driveway, air conditioned three car garage (not included in living SF amount), 2,800 feet of pool decking, and 1,000 feet of sun decking offers the ultimate in resort style living nestled among palm trees and endless vistas with panoramic views. This Central Florida estate is unmatched and perfectly located only 30 minutes to Orlando International Airport, 15 minutes to Disney, and just minutes from world famous golf courses, shopping & simply the best dining the Orlando area has to offer bar none!

11301 Bridge House Road, Windermere

$2,350,000
Lake Down Shores Rep SubDv. 34786 Zip Code
Welcome home to 2730 Midsummer Drive, arguably one of the most beautiful waterfront lots in all of Windermere if not all of Central Florida. Located on the Eastern Shores of Lake down 1 of 13 lakes in the highly sought-after Butler Chain of Lakes. Midsummer Drive is truly one of the most charming canopy oak covered roads you will find in Central Florida. With only 20 magnificent lakefront estate sized lots that rarely become available this is one opportunity you don’t want to pass up. This property provides incredible sunsets with panoramic views overlooking the large rear lawn that has currently over 145 feet of depth and over 130 feet of lakefront shoreline. The current property is over 350 feet deep on either side and provides more space and privacy than you will find in a traditional neighborhood. Currently there is a home on the property that could be remodeled but the true value is in the Land. With extensive soil samples completed and fairly recent survey you have the first steps needed to design and build your dream home. There is no other lot available on the butler chain with the views and potential that this lot provides. Minutes from I-4 , downtown Orlando, restaurant row, shopping, Orlando International Airport, Disney, and all the attractions without the down town Windermere traffic! Enjoy all your favorite water sports , great sunsets , and build your very own custom dream home.

2730 Midsummer Drive, Windermere

$5,300,000
4 Beds 4.5 Baths N/A SubDv. 34786 Zip Code
Sheer excitement exudes from this custom Element Home Builders lakefront home located directly on Lake Butler, of the famed Butler Chain of Lakes. INCLUDED IN THIS PRICE IS AN ADDITIONAL 1.16-ACRE HOMESITE ADJACENT TO THE HOME. Build your family compound, tennis court, or basketball court or keep it for privacy. This is one of the few properties available with over 2 acres on Lake Butler. With no HOA, this impressive home offers an open floor plan for entertaining, featuring wide plank hickory hardwood floors, 2 gas fireplaces, magnificent pocket glass doors opening to a covered lanai & beautiful pool with a cascading spa. For the Chef, there’s a Wolf cooktop, Sub-Zero ref/freezer, and Bosch dishwasher. The Kitchen also includes a working island, custom-built cabinets, custom granite tops and a hidden large walk-in pantry. For outdoor entertaining, the lanai, saltwater pool, and cascading spa are perfectly complimented by the summer kitchen and lounging area. The summer kitchen includes a Viking commercial grill, custom cabinets, built-in refrigerator, and an ice maker. This elevated living space has a serene Lakefront view with an amazing dock and boat lift. When the time comes to retreat to indoor living, you can retire in one of four en-suite bedrooms. The master bedroom includes a large walk-in closet. The spa-like master bath includes a vessel tub, walk-in shower, and double vanities highlighted by incredible lake views. The private office features wood-beamed tray ceilings. There is also an upstairs fun room with a second office option. Finally, there is no shortage of storage in the attached 3-car garage, private laundry & mud room. Other Smart House amenities include, 6 zone HVAC system, Nest thermostats, low E double paned windows, tankless hot water heaters, spray foam insulation, full home generator and security camera system. Stunning designer furnishings are included. You must see it to really appreciate all that this home has to offer.

12623 W Lake Butler Road, Windermere

$3,750,000
4 Beds 4.5 Baths N/A SubDv. 34786 Zip Code
The adjacent homesite, 1.16 acres, is also available for sale with the purchase of this home. This stunning custom-built Element Home Builders lakefront home is located directly on Lake Butler, of the famed Butler Chain of Lakes. With no HOA, this impressive home offers an open floor plan for entertaining, featuring wide plank hickory hardwood floors, 2 gas fireplaces, magnificent pocket glass doors opening to a covered lanai & beautiful pool with a cascading spa. For the Chef, there’s a Wolf cooktop, Sub-Zero ref/freezer, and Bosch dishwasher. The Kitchen also includes a working island, custom-built cabinets, custom granite tops, and a hidden sizeable walk-in pantry. The lanai, saltwater pool, and cascading spa are perfectly complimented by the summer kitchen and lounging area for outdoor entertaining. The summer kitchen includes a Viking commercial grill, custom cabinets, built-in refrigerator, and an ice maker. This elevated living space has a serene Lakefront view with an amazing dock and boat lift. When the time comes to retreat to indoor living, you can retire in one of four en-suite bedrooms. The master bedroom includes a large walk-in closet. The spa-like master bath includes a vessel tub, walk-in shower, and double vanities highlighted by incredible lake views. The private office features wood-beamed tray ceilings. There is also an upstairs fun room with a second office option. Finally, there is no shortage of storage in the attached 3-car garage, private laundry & mud room. Other Smart House amenities include 6 zone HVAC system, Nest thermostats, low E double-paned windows, tankless hot water heaters, spray foam insulation, full home generator and security camera system. Stunning designer furnishings are included. You must see it to really appreciate all that this home has to offer.

12623 W Lake Butler Road, Windermere

$1,295,000
4 Beds 4 Baths Estancia/Windermere SubDv. 34786 Zip Code
Location meets luxury in Estancia at Windermere! This stunning home boasts the fabulous Monte Carlo floorplan, complete with a lovely, courtyard entrance, four, ensuite bedrooms and an office with beautiful French doors. All of this, and situated on a cul de sac street! One step inside this beautiful home and you are greeted with soaring ceilings, and a living room with accordion sliders, looking onto the massive backyard of this home, sitting on over 1/3 acre! The chef's dream kitchen features stunning finishes, a gas cooktop, double-oven, wine refrigerator and an Insinkerator hot and cold water filtration system. The grand owner's suite has a large sitting area and a resort-style, master bath with large soaking tub and impressive, walk-in dressing room. Each of the four, spacious bedrooms feature custom closets in this well-thought-out, three-way split plan, ideal for privacy. One en-suite bedroom is just off the single car garage, and neighbors the office, making it an ideal spot for in-laws and guests. The motorized, retractable screens on the lanai make for a perfect spot to relax and enjoy your outdoor kitchen, and the massive backyard space, ready for your own backyard oasis! Your dining room features gorgeous, French doors opening onto your private courtyard, perfect for al fresco dining. The smart home features in this home are numerous, including smart thermostat, door lock, garage door opener and ring cameras in both the front and rear of the home. Estancia at Windermere is not only zoned for some of the best schools in Orange County, but is also conveniently located just a short bike ride to the food trucks and festivities in downtown Windermere, a mile from Publix grocery and less than 10 minutes to the everyday shopping of Winter Garden Village! Live here, and you are less than 30 minutes to Disney, Universal and famed Restaurant Row in Dr. Phillips. With easy access to the 429, the Florida Turnpike, and the 408, this luxurious home is perfectly situated, no matter where you want to go in Central Florida! Schedule your private showing of this special home today!

1152 Estancia Woods Loop, Windermere

$725,000
4 Beds 3 Baths Westover Club Ph 02 47/71 SubDv. 34786 Zip Code
This home is a sprawling 2,700 square feet with 4 bedrooms + office + a bonus room upstairs that could be a 5th bedroom! This is a highly desired 3-way split floorplan with large living spaces in the best location of Windermere. The kitchen offers modern custom bright cabinets that are sleek and contemporary, along with newer appliances including the low-profile built-in microwave. This space is open to the living room and breakfast nook overlooking the lanai. An incredible use of space has been added, transforming a portion of the lanai into more entertaining space. This conversion was done to perfection, and added an outdoor shower, a SAUNA for amazing health benefits and relaxation, and a summer kitchen complete with a built in mini-fridge, pizza oven, all enclosed with multiple gorgeous Pella sliding doors. There was absolutely no expense spared with this custom addition! Step outside of this entertainer's dream space to the sparkling blue pool that is heated by solar panels (completely paid off!) and there is STILL room for a great backyard all fenced-in with a classy vinyl fence. The master bedroom is complete with an ensuite updated bathroom and HUGE walk-in closet with custom built-in shelves & hanging space, and a built-in safe for extra protection. The upstairs bonus room has its own A/C unit and could double as a media room, 5th bedroom, mancave or in-law suite. The garage was extended 4' at time of construction making the garage an oversized 2-car garage. The community of Westover Club is a fantastic gated neighborhood with tennis courts, a playground, and conveniently located near the 408, Turnpike, shopping, dining, and Orlando attractions. This home is also zoned for top schools like Thornebrooke Elementary, Gotha Middle, and Olympia High - all incredible schools!

1949 Katie Hill Way, Windermere

$4,200,000
4 Beds 4.5 Baths Isleworth SubDv. 34786 Zip Code
Stunning Lake Louise views abound from this perfectly-sized Isleworth lakefront residence, perched above a protected cove on the famed Butler Chain of Lakes. Just unveiled with new flooring, new contemporary-style master bath retreat with added steam shower, sauna, soaking tub, and modern elegance – plus whole-home generator and new pool equipment and exterior paint. Enjoy the ease and convenience of direct access to the lakes from your private boat dock. This 4-bedroom, 4.5 bath residence boasts 5,752 square feet of grand living spaces - including soaring ceilings, stone and tile flooring, majestic columns, elegant stairs with wrought iron railings, wet bar with fridge, and a chef’s kitchen with island. Under a commanding balcony sits beveled glass and wood double doors that open to an elegant foyer. Picturesque windows fill the room with inviting lake scenes set behind a sparkling pool with a partial infinity edge. The first-floor master retreat features a large bedroom with private sitting room separated by a double-sided fireplace, creating a dramatic setting. A secondary master suite is conveniently located on the opposite end of the home, also on the first floor. Upstairs are two additional bedroom suites, a reading loft, and a large family room with theater screen and equipment. An optional enclosure of second-story open-air space over the family room would add more space for an additional bedroom or den, if desired, next to the balcony and outdoor terrace. Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf and Country Club is recognized as one of the Top 100 Platinum Clubs of the World offering the ultimate in amenities and concierge living.

6117 Louise Cove Drive, Windermere