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Windermere Real Estate Search

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About Windermere, Florida in Orlando Fl.

For those who are ready to settle down in a quiet, beautiful, and charming place to live, there is nowhere else to be outside of Windermere, FL. Founded in 1880 this small town provides all the scenery, safety, and luxury a buyer could be seeking. From lake front living along the beautiful Butler Chain of Lakes to a starter home located on one of the old roads covered in Windermere’s famous old trees, there is a house for every buyer and budget. This little town has gotten quite the affluent make over in the last 25 years and is known to now contain some of the most desirable real estate in Florida.

Spanning just 1.57 square miles with only 2,580 residents, Windermere has the small town feel so many people desire. The estimated median household income is around $109,000, a significant increase from 2000, when the number was $88,000. As local businesses continue to thrive and grow, Windermere homes are not staying on the market very long. With the average home value increasing some 42% in the last decade, buyers can be confident their home will be more than just a great place to live; it will be a solid investment for the future. With homes ranging from the low $300Ks to $5 million or more there is a house for any taste, size, and budget. Windermere is divided into three areas, each with their own character and charm. From downtown Windermere, to the golf communities of Keene’s Pointe and Isleworth, and even the community style based Berkshire Park and Summerport, there are plenty of areas for a buyer to find their perfect home.

Location is everything when choosing a new town to move to and Windermere is no exception. Windermere is conveniently located 15 minutes away from Disney World and the bustling city of Orlando. It’s always an easy, quick commute to work because the convenience of Windermere’s location. Living so close to all these popular attraction means Windermere residents always have something at their fingertips to do and see. Multiple theme parks, nightlife, recreation, and entertainment are all a short drive away but when the day is over they can easily return to the quiet relaxation of their Windermere home.

Why Consider Buying a Home in Windermere, FL?

Many of Windermere’s residents choose Windermere for one thing: Lake Living. With 11 connected lakes provided on the Butler Chain many residents spend their evenings and weekends boating, fishing, exploring the waterways and relaxing along these lake's crystal clear water. Don’t think lake living is in your budget but owning a boat to take out is? No problem! The City of Windermere has 2 free boat ramps for boat access year-round. With so many lakes, communities, and homes located along these perfect shorelines we guarantee you can find your own piece of waterfront paradise in no time!

Six Star Realty Group can help you find the most ideal Windermere home within our portfolio of homes. With agents, always available at your fingertips, we guarantee you will find the home of your dreams in just a short amount of time. Call today to speak to an agent and start the search for your perfect home in Windermere, Florida! 

 

Windermere Homes For Sale | Newest Listings

1484 Hempel Avenue, Windermere image
1484 Hempel Avenue, Windermere $599,000

Welcome to this cozy, beautiful single-family home across the street from Lake Olivia in Windermere, FL. This one-story home features three bedrooms, two bathrooms, a go...

  • 3 Beds
  • 2 Baths
  • Gotha Town SubDv.
  • 34786 Zip Code
13596 Gorgona Isle Dr, Windermere image
13596 Gorgona Isle Dr, Windermere $1,715,000

This two-story ENERGY STAR Certified affluent home inspired in Mediterranean Tuscan style with beautiful stones walls, grand foyer with stunning hardwood floors, Spanish ...

  • 6 Beds
  • 4.5 Baths
  • Windermere Isle SubDv.
  • 34786 Zip Code
12712 Water Point Boulevard, Windermere image
12712 Water Point Boulevard, Windermere $1,850,000

This magnificent acre estate is a must see! Coupled with the stately 4,705sqft FIVE bedroom and FOUR bath residence sits a true unicorn: a SINGLE-STORY 1BR/1.5BA (1,107s...

  • 6 Beds
  • 5.5 Baths
  • Waterford Pointe SubDv.
  • 34786 Zip Code
7431 Lake Albert Drive, Windermere image
7431 Lake Albert Drive, Windermere $2,380,000

Welcome to the IMMACULATE 7431 Lake Albert drive on a "ONE OF A KIND" 1.1 ACRE LOT with tons of upgrades throughout, stunning pool with jacuzzi spa and fenced patio for l...

  • 6 Beds
  • 6.5 Baths
  • Lake Burden South Ph 2 SubDv.
  • 34786 Zip Code
9133 Palm Tree Drive, Windermere image
9133 Palm Tree Drive, Windermere $549,900

WINDERMERE ~ SILVER WOODS! Rare offering in this highly desired community in Windermere. This 3 bedroom 2 bath POOL home is nicely appointed on a full 1/4 acre lot and ...

  • 3 Beds
  • 2 Baths
  • Silver Woods Ph 02 SubDv.
  • 34786 Zip Code
8168 Boat Hook Loop Unit 107, Windermere image
8168 Boat Hook Loop Unit 107, Windermere — 8180 $380,000

A beautiful 3 bedroom ground floor condo located conveniently opposite the clubhouse which has all the luxury amenities you could ask for. Inside you'll be impressed by t...

  • 3 Beds
  • 2 Baths
  • Lakeside/Lks/Windermere SubDv.
  • 34786 Zip Code
11410 Rapallo Lane, Windermere image
11410 Rapallo Lane, Windermere $800,000

Welcome Home. This beautiful home built by Park Square will take your breath away upon entering. From its turret-style architectural exterior design to the beautiful wi...

  • 6 Beds
  • 5.5 Baths
  • Belmere Village G2 48 65 SubDv.
  • 34786 Zip Code
6379 Swanson Street, Windermere image
6379 Swanson Street, Windermere $1,150,000

Beautiful single-family Mediterranean home with 4 bedrooms and a Flex Room, 4 bathrooms, and a 2/1 split car garage layout in the desirable gated community of Enclave in ...

  • 5 Beds
  • 4 Baths
  • Enclave SubDv.
  • 34786 Zip Code
7229 Still Pond Lane, Windermere image
7229 Still Pond Lane, Windermere $795,000

The soaring two-story bonus room is perfect for a 4th bedroom w/ spacious closet & private 1/2 bath. This Ashton Woods-Manchester design pool home (w/ heated spa) provide...

  • 3 Beds
  • 2.5 Baths
  • Ashlin Park Ph 2 SubDv.
  • 34786 Zip Code
6373 Swanson Street, Windermere image
6373 Swanson Street, Windermere $825,000

Beautiful one-story single-family home with 4 bedrooms, 2.5 bathrooms, and 2/1 split car garage layout in the desirable gated community of Enclave in Windermere. This hom...

  • 4 Beds
  • 2.5 Baths
  • Enclave SubDv.
  • 34786 Zip Code
12724 Langstaff Drive, Windermere image
12724 Langstaff Drive, Windermere $399,000

Light and bright, meticulously kept, end unit townhome in Windermere. Spacious family room and living room on the first floor with expansive brick paver private patio, pe...

  • 3 Beds
  • 2.5 Baths
  • Lakes/Windermere-Lk Reams Twnh SubDv.
  • 34786 Zip Code
13615 Riggs Way, Windermere image
13615 Riggs Way, Windermere $529,900

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...

  • 3 Beds
  • 2.5 Baths
  • Enclave/Berkshire Park B G H I SubDv.
  • 34786 Zip Code
13839 Amelia Pond Drive, Windermere image
13839 Amelia Pond Drive, Windermere $650,000

**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...

  • 4 Beds
  • 2.5 Baths
  • Creeks Run SubDv.
  • 34786 Zip Code
5124 Sun Palm Drive, Windermere image
5124 Sun Palm Drive, Windermere $575,000

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 ceiling...

  • 4 Beds
  • 2.5 Baths
  • Silver Woods Ph 04 SubDv.
  • 34786 Zip Code
9802 6th Street, Windermere image
9802 6th Street, Windermere $450,000

Corner building lot. Small town charm with easy access to major roads. Short distance to Town of Windermere, desirable schools, parks, hospitals and more. Home on pro...

  • Gotha Town SubDv.
  • 34786 Zip Code
1403 Dingens Avenue, Windermere image
1403 Dingens Avenue, Windermere $450,000

Corner building lot in Gotha. Small Town charm convenient to major roadways. Near Town of Windermere and desirable schools. No HOA. Adjacent lot also available.

  • Gotha Town SubDv.
  • 34786 Zip Code
11301 Bridge House Road, Windermere image
11301 Bridge House Road, Windermere $11,995,000

Stunning modern masterpiece situated in Windermere's Reserve on Lake Butler Sound's most coveted waterfront lot. Known as "Overjoy" for its location on the sparkling wate...

  • 5 Beds
  • 7.5 Baths
  • Reserve At Lake Butler Sound SubDv.
  • 34786 Zip Code
11226 Macaw Court, Windermere image
11226 Macaw Court, Windermere $1,599,999

Welcome home to this custom built Bill Sauerwine Courtyard pool home. As you enter the double wrought iron gates. you will see the inviting salt water pool and spa, summ...

  • 4 Beds
  • 4.5 Baths
  • Keenes Pointe Ut 06 50 95 SubDv.
  • 34786 Zip Code
8179 Maritime Flag St Unit 203, Windermere image
8179 Maritime Flag St Unit 203, Windermere — 2 $377,000

Lakeside at Lakes of Windermere, second floor condominium unit. This home has been well maintained by the original owner and offers 3 bedrooms and 2 baths. The split fl...

  • 3 Beds
  • 2 Baths
  • Lakeside At Lakes Of Windermere SubDv.
  • 34786 Zip Code
4667 Indian Deer, Windermere image
4667 Indian Deer, Windermere $660,000

Wonderful pool home in the desiirable community of Summerport in Windermere! 4 bedrooms, and 3 baths with a 2-car garage. The yard is fenced for privacy so you can enjoy...

  • 4 Beds
  • 3 Baths
  • Summerport Phase 5 58/124 Lot 125 SubDv.
  • 34786 Zip Code
6731 Valhalla Way, Windermere image
6731 Valhalla Way, Windermere $2,250,000

Keene's Pointe - gated/24-hour attended golf course community featuring The Golden Bear Club. A members-only 18-hole golf course offering golf, tennis, fitness, dining an...

  • 6 Beds
  • 7.5 Baths
  • Keenes Pointe 46/104 SubDv.
  • 34786 Zip Code
12623 W Lake Butler Road, Windermere image
12623 W Lake Butler Road, Windermere $5,300,000

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 ...

  • 4 Beds
  • 4.5 Baths
  • N/A SubDv.
  • 34786 Zip Code
12623 W Lake Butler Road, Windermere image
12623 W Lake Butler Road, Windermere $3,750,000

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 d...

  • 4 Beds
  • 4.5 Baths
  • N/A SubDv.
  • 34786 Zip Code
12577 Foynes Avenue, Windermere image
12577 Foynes Avenue, Windermere $649,000

Welcome to 12577 Foynes Ave! This is the house your buyer has been looking for! Large, 1 story with bonus room on second floor has been totally renovated!!! Let's start...

  • 5 Beds
  • 3.5 Baths
  • Lakes/Windermere Ph 04 SubDv.
  • 34786 Zip Code
11365 Evesham Drive, Windermere image
11365 Evesham Drive, Windermere — Na $359,900

A rare opportunity for a single story, end unit townhome in the heart of Lakeside Village, Windermere. This home is wonderfully maintained with a recently installed HVAC ...

  • 2 Beds
  • 2 Baths
  • Preston Square SubDv.
  • 34786 Zip Code
5332 Water Creek Drive, Windermere image
5332 Water Creek Drive, Windermere $765,000

Rare acre lot in highly sought-after area of Windermere with NO hoa fees and NO builder ties, buy and build your dream home. Level and cleared lot on private maintained r...

  • Lake Davis Estates SubDv.
  • 34786 Zip Code
1949 Katie Hill Way, Windermere image
1949 Katie Hill Way, Windermere $725,000

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 wi...

  • 4 Beds
  • 3 Baths
  • Westover Club Ph 02 47/71 SubDv.
  • 34786 Zip Code
2505 Windermere Reserve Court, Windermere image
2505 Windermere Reserve Court, Windermere $605,000

Build your custom home on the last remaining home site in the Reserve of Windermere. Element Home Builders will build the home designed to compliment the building envelo...

  • Reserve At Windermere SubDv.
  • 34786 Zip Code
6117 Louise Cove Drive, Windermere image
6117 Louise Cove Drive, Windermere $4,200,000

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 unveile...

  • 4 Beds
  • 4.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
11948 Provincial Way, Windermere image
11948 Provincial Way, Windermere $1,799,900 ▼

HUGE PRICE REDUCED TO SELL!!!Exquisite Arthur Rutenberg customized Calais model home is sought after in Reserve at Belmere. This lakefront, 4bed/5bath/den/bonus room hous...

  • 4 Beds
  • 5 Baths
  • Reserve At Belmere Ph4 SubDv.
  • 34786 Zip Code
9143 Woodbreeze Boulevard, Windermere image
9143 Woodbreeze Boulevard, Windermere $568,000

In desirable Siver Woods community with a Windermere address, close to everything. Beautiful house completely renovated in 2022: 24"x48" porcelain tile throughout the hou...

  • 3 Beds
  • 2 Baths
  • Silver Woods Ph 02 SubDv.
  • 34786 Zip Code
8264 Maritime Flag Street Unit 1420, Windermere image
8264 Maritime Flag Street Unit 1420, Windermere — 14 $375,000

Move-in-ready or a great investment, located in the Resort style community-Lakeside Windermere. Elevator provides easy access. 3 bedroom/2 bath end unit is located on the...

  • 3 Beds
  • 2 Baths
  • Lakeside At Lakes Of Windermere Condominium Phase SubDv.
  • 34786 Zip Code
1330 Lake Olivia Lane, Windermere image
1330 Lake Olivia Lane, Windermere $895,500

Build your dream home on this waterfront lot. The gated community of Lake Olivia Reserve is home to only 12 lots and the perfect place to build your luxury home. Bring th...

  • Lake Olivia Reserve Rep SubDv.
  • 34786 Zip Code
11036 Schooner Way, Windermere image
11036 Schooner Way, Windermere $1,895,000 ▼

*** REMODELED HOME ON 1 ACRE LOT with CHAIN OF LAKE ACCESS under 2MM.*** Custom Windermere home on over an acre of land, with private 40+ ft dock on a wide canal to Lak...

  • 4 Beds
  • 3.5 Baths
  • Marina Bay Estates SubDv.
  • 34786 Zip Code
9736 Chestnut Ridge Drive, Windermere image
9736 Chestnut Ridge Drive, Windermere $7,388,000

Pre-Construction. To be built. Featuring an exceptional setting along the shores of beautiful Lake Bessie with gorgeous sunset views, this five-bedroom estate will be bui...

  • 5 Beds
  • 5.5 Baths
  • Isleworth SubDv.
  • 34786 Zip Code
13335 Bellaria Circle, Windermere image
13335 Bellaria Circle, Windermere $2,790,000

Unparalleled luxury living in this elegant 5 bedroom, 6/1 bath home with over 6,300 sq.ft. of stylish living space. Officially known as Maison du Parc, this sprawling sin...

  • 5 Beds
  • 6.5 Baths
  • Bellaria SubDv.
  • 34786 Zip Code
225 Magnolia Street, Windermere image
225 Magnolia Street, Windermere $4,500,000

Elegantly designed and custom-built in 2019, this Mediterranean-style home is located on the famed Butler Chain of Lakes. This beautiful property is for the discriminatin...

  • 7 Beds
  • 10.5 Baths
  • Windermere Rep SubDv.
  • 34786 Zip Code
12030 Via Caselli Lane, Windermere image
12030 Via Caselli Lane, Windermere — 5 $498,000

The brand new beautiful townhouse at Royal Estate Luxury Townhomes is located in the premier community of Windermere with an excellent school district. Its unbeatable loc...

  • 4 Beds
  • 3 Baths
  • Royal Estates SubDv.
  • 34786 Zip Code
9119 Balmoral Mews Sq, Windermere image
9119 Balmoral Mews Sq, Windermere $1,290,000

Welcome to Balmoral and your new highly sought after Windermere address! An exclusive gated community containing only 32 custom homes. This spacious residence boasts lush...

  • 4 Beds
  • 4 Baths
  • Balmoral SubDv.
  • 34786 Zip Code
13754 Ingelnook Drive, Windermere image
13754 Ingelnook Drive, Windermere $630,000

Welcome to The Vineyards at Horizon West, an exceptional community located in Windermere. Make yourself at home with this magnificent KB-built home featuring all the amen...

  • 4 Beds
  • 2.5 Baths
  • Vineyards/Horizons West Ph 1b SubDv.
  • 34786 Zip Code
6230 Golden Dewdrop Trail, Windermere image
6230 Golden Dewdrop Trail, Windermere $519,000

Welcome home! Nested in the heart of Windermere. Fantastic layout with all spaces we want to have in a "homey" HOME. Master Bedroom features coffered ceiling, walk-in cl...

  • 3 Beds
  • 2.5 Baths
  • Windermere Lndgs Ph 02 SubDv.
  • 34786 Zip Code
9155 Outlook Rock Trail, Windermere image
9155 Outlook Rock Trail, Windermere $814,900

This beautiful, fully upgraded, and private home in Windermere is the perfect place to call home. Every bedroom in this family retreat has its own bedroom attached! This...

  • 5 Beds
  • 4.5 Baths
  • Windermere Trls Ph 5b SubDv.
  • 34786 Zip Code
415 W 3rd Avenue, Windermere image
415 W 3rd Avenue, Windermere $2,000,000 ▼

Consider this NEW…. totally renovated to the highest standards. Experience breathtaking LAKE VIEWS, SUNSETS and Disney FIREWORKS from the wide wrap around porch. This i...

  • 3 Beds
  • 2.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
811 Main Street, Windermere image
811 Main Street, Windermere $600,000

This home in the heart of downtown Windermere is waiting just for you! Located on a spacious double lot, with a fenced in backyard and NO HOA, this property will surely b...

  • 2 Beds
  • 1.5 Baths
  • Windermere Town SubDv.
  • 34786 Zip Code
Gladys Garden Court, Windermere image
Gladys Garden Court, Windermere $635,000

Within the gates of Isleworth, this beautiful home site is positioned within the Gardens of Isleworth – an intimate enclave of custom homes surrounded by lush gardens, wa...

  • Isleworth SubDv.
  • 34786 Zip Code
Gladys Garden Court, Windermere image
Gladys Garden Court, Windermere $620,000

Within the gates of Isleworth, this beautiful home site is positioned within the Gardens of Isleworth – an intimate enclave of custom homes surrounded by lush gardens, wa...

  • Isleworth SubDv.
  • 34786 Zip Code
Gladys Garden Court, Windermere image
Gladys Garden Court, Windermere $620,000

Within the gates of Isleworth, this beautiful home site is positioned within the Gardens of Isleworth – an intimate enclave of custom homes surrounded by lush gardens, wa...

  • Isleworth SubDv.
  • 34786 Zip Code
8637 Coventry Park Way, Windermere image
8637 Coventry Park Way, Windermere — 3 $435,000 ▲

Great opportunity to own this 3 Bedrooms, 2 Bathroom and 1 Half bathroom. kitchen includes 42 inches cabinets, stone counters, kitchen island, butlers pantry. Large maste...

  • 3 Beds
  • 2.5 Baths
  • Windermere Trails Parcel 3 SubDv.
  • 34786 Zip Code
4302 Isabella Circle, Windermere image
4302 Isabella Circle, Windermere $3,499,000

Sensationally Luxurious and Fully Furnished Home with Outdoor Poolside Oasis! Nestled on a spacious 0.88-acre lot in an exclusive gated community, this 5BR/6.5BA, 5,362sq...

  • 5 Beds
  • 6.5 Baths
  • Casabella SubDv.
  • 34786 Zip Code
5909 Caymus Loop, Windermere image
5909 Caymus Loop, Windermere $1,090,000

A fantastic Keene’s Pointe golf course home that is move-in ready. This 4 Bedroom, 3 Full Bath home with an Office, has been updated so you can move in today without the...

  • 4 Beds
  • 3 Baths
  • Keenes Pointe SubDv.
  • 34786 Zip Code
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Windermere Communities

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