Windermere, FL Homes

/29
$650,000 Pending
- 4 Beds
- 2 Baths
- 2,063 Sq Ft
9426 Palm Tree Dr, Windermere, FL 34786

Under contract-accepting backup offers. This is it! Welcome home to this updated, showstopper in Windermere with an oversized pool. From the moment you walk in the door, you will be impressed with how open and expansive the home feels- the kitchen, dining, family and living areas are included in one great space. The family and living room share a double-sided wood burning fireplace and both

Richard Alpizar IRON VALLEY REAL ESTATE CENTRAL FLORIDA

9426 Palm Tree Dr, Windermere, FL 34786
/70
$6,000 per month
- 5 Beds
- 4 Baths
- 3,659 Sq Ft
- House for Rent
11539 Brickyard Pond Ln, Windermere, FL 34786

A truly gorgeous and meticulously maintained lakefront residence located in the highly desirable Lake Burden community in Windermere, this stunning home is completely move-in ready and offers an exceptional Florida lifestyle. Wake up every morning to breathtaking lake views and peaceful sunrises from your backyard, while enjoying nightly views of Disney fireworks right from the front of the home

Jonathan Casique PM ELITE REALTY LLC

11539 Brickyard Pond Ln, Windermere, FL 34786
/2
$390,000 Sold May 02, 2025

7752 Rigby St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,335 Sq Ft
- Built 2012
Last Sold Summary
- 2% Below List Price
- $292/SF
- 22 Days On Market
Current Estimated Value $382,507

Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

7752 Rigby St, Windermere, FL 34786

/2
Est $907,718 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,226 Sq Ft
8243 Procida Isle Ln, Windermere, FL 34786

8243 Procida Isle Ln, Windermere, FL 34786

/53
$650,000 Pending
- 4 Beds
- 2 Baths
- 2,555 Sq Ft
6139 Andreozzi Ln, Windermere, FL 34786

Under contract-accepting backup offers. Here is your chance to own this spacious well-maintained one-story 4-bedroom waterfront home on a pond located in the desirable Providence neighborhood of Windermere. As you enter through the front porch and foyer you will immediately notice the high 10’ ceilings and inviting rooms to your well-thought-out floor plan. The living room is spacious with an

Simon Simaan THE SIMON SIMAAN GROUP

6139 Andreozzi Ln, Windermere, FL 34786
/20
$3,595 per month
- 3 Beds
- 2.5 Baths
- 2,400 Sq Ft
- House for Rent
11602 Ashlin Park Blvd, Windermere, FL 34786

Property Id: 904398Welcome to this charming three-bedroom, two-and-a-half-bathroom rental property in the desirable Windermere area. Set on a spacious corner lot, this home features a generous three-car garage and ample outdoor space. Inside, you'll find brand-new carpet(not pictured) and fresh paint throughout, complemented by upgraded kitchen and bathrooms for a modern touch.The

11602 Ashlin Park Blvd, Windermere, FL 34786
/2
$1,194,000 Sold Aug 25, 2025

6720 Winter Garden Vineland Rd, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,554 Sq Ft
- Built 2003
Last Sold Summary
- 8% Below List Price
- $336/SF
- 32 Days On Market
Current Estimated Value $1,234,269

Last Listing Agent Rita Schoeffler BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

6720 Winter Garden Vineland Rd, Windermere, FL 34786

/37
Est $1,645,455 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,396 Sq Ft
1214 Estancia Woods Loop, Windermere, FL 34786

1214 Estancia Woods Loop, Windermere, FL 34786

/14
$1,054,990 New Construction
- 4 Beds
- 3.5 Baths
- 3,074 Sq Ft
Griffin Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

The Griffin is a two-story home offering four bedrooms, three full bathrooms, one half bathroom, and a two-car garage. The kitchen opens to a dramatic two-story family room, creating a bright and inviting living space. The second-floor primary suite offers privacy and comfort, while a conveniently located laundry room and optional butler’s pantry enhance everyday functionality. Additional

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932783, Windermere, FL 34786
/41
$13,500 per month
- 7 Beds
- 5.5 Baths
- 5,221 Sq Ft
- House for Rent
6219 Tiroco Way, Windermere, FL 34786

Rare Opportunity to lease in Exclusive and Gated Waterstone Subdivision in Windermere! This home is furnished and has 7 total bedrooms and 5.5 Baths although some bedrooms are currently being used as Media/Office. As you enter the home you will see the expansive Living room with sky high ceilings and view of the stunning pool area. Primary Bedroom is downstairs and offers a large primary bath

Billy Cannon, Jr BHHS FLORIDA REALTY

6219 Tiroco Way, Windermere, FL 34786
/2
$1,450,000 Sold Aug 13, 2025

8430 Woburn Ct, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,319 Sq Ft
- Built 1999
Last Sold Summary
- 3% Below List Price
- $437/SF
- 64 Days On Market
Current Estimated Value $1,420,991

Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

8430 Woburn Ct, Windermere, FL 34786

/62
Est $2,540,692 Not Listed For Sale
- 5 Beds
- 7 Baths
- 5,734 Sq Ft
13334 Bellaria Cir, Windermere, FL 34786

13334 Bellaria Cir, Windermere, FL 34786

/62
$1,390,000
- 4 Beds
- 3.5 Baths
- 3,809 Sq Ft
8375 Bowden Way, Windermere, FL 34786

"Price Improvement". This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm, inviting, and beautifully curated.The highlight of this home is its backyard oasis — a peaceful retreat overlooking the sparkling pool and

Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

8375 Bowden Way, Windermere, FL 34786
/12
$3,230 per month
- 4 Beds
- 2.5 Baths
- 3,115 Sq Ft
- House for Rent
14479 Yellow Butterfly Rd, Windermere, FL 34786

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3374.90. That covers your base rent, $3230.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

14479 Yellow Butterfly Rd, Windermere, FL 34786
/2
$670,000 Sold Nov 14, 2025

2015 Woody Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,042 Sq Ft
- Built 1978
Last Sold Summary
- 4% Below List Price
- $328/SF
- 28 Days On Market
Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

2015 Woody Dr, Windermere, FL 34786

/80
Est $2,510,203 Not Listed For Sale
- 5 Beds
- 7 Baths
- 5,161 Sq Ft
11628 Waterstone Loop Dr, Windermere, FL 34786

11628 Waterstone Loop Dr, Windermere, FL 34786

/100
$3,500,000 Open Sat 11AM - 2PM
- 4 Beds
- 3.5 Baths
- 5,273 Sq Ft
10577 Down Lakeview Cir, Windermere, FL 34786

Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with

Simon Simaan THE SIMON SIMAAN GROUP

10577 Down Lakeview Cir, Windermere, FL 34786
/29
$4,200 per month
- 4 Beds
- 3 Baths
- 2,521 Sq Ft
- House for Rent
13333 Zori Ln, Windermere, FL 34786

Welcome to this beautifully designed one-story home in the highly sought-after Windermere community! With 4 spacious bedrooms and 3 full bathrooms, this home offers the perfect blend of comfort and style. Featuring modern finishes throughout, you’ll immediately notice the sleek, no-carpet flooring that flows seamlessly across the open-concept floor plan. The gourmet kitchen is a chef’s dream,

Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

13333 Zori Ln, Windermere, FL 34786
/2
$550,000 Sold Sep 30, 2025

5238 Beach River Rd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,414 Sq Ft
- Built 2004
Last Sold Summary
- $228/SF
- 3 Days On Market
Current Estimated Value $550,127

Last Listing Agent Liza Farzati SERHANT

5238 Beach River Rd, Windermere, FL 34786

/40
Est $744,640 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,988 Sq Ft
9150 Outlook Rock Trail, Windermere, FL 34786

9150 Outlook Rock Trail, Windermere, FL 34786

/39
$550,000
- 4 Beds
- 2 Baths
- 2,159 Sq Ft
11322 Rapallo Ln, Windermere, FL 34786

One or more photo(s) has been virtually staged. ***Back on Market due to Buyer not depositing Escrow*** “Mortgage savings may be available for buyers of this listing.” Located in the gated Windermere community of Belmere Village, this beautifully maintained 4-bedroom, 2-bathroom home offers both comfort and convenience. Residents enjoy low HOA fees and a wealth of amenities including a clubhouse,

John Callahan REDFIN CORPORATION

11322 Rapallo Ln, Windermere, FL 34786
/20
$3,305 per month
- 5 Beds
- 2.5 Baths
- 2,389 Sq Ft
- House for Rent
13450 Sunkiss Loop, Windermere, FL 34786

Special security deposit offer: Pay just 50% of your base rent as your security deposit (taxes and fees not included), valid for new applicants who sign a 12-month lease by February 28, 2026. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company.

13450 Sunkiss Loop, Windermere, FL 34786
/2
$2,625,000 Sold Feb 07, 2025

5379 Isleworth Country Club Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,872 Sq Ft
- Built 1989
Last Sold Summary
- 12% Below List Price
- $678/SF
- 363 Days On Market
Current Estimated Value $2,615,582

Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

5379 Isleworth Country Club Dr, Windermere, FL 34786

/2
Est $1,345,284 Not Listed For Sale
- 5 Beds
- 4 Baths
- 4,908 Sq Ft
17550 Black Rail St, Windermere, FL 34786

17550 Black Rail St, Windermere, FL 34786

/60
$795,000 Pending
- 4 Beds
- 2.5 Baths
- 2,766 Sq Ft
12905 Strode Ln, Windermere, FL 34786

Under contract-accepting backup offers. Completely remodeled in 2021! Welcome home to your stunning 4-bedroom craftsman with contemporary finishes in the highly sought after community of Windermere Sound. This well-maintained waterfront home with no rear neighbors has it all. At first glance you will immediately notice the amazing curb appeal with its charming architecture, manicured landscaping,

Simon Simaan THE SIMON SIMAAN GROUP

12905 Strode Ln, Windermere, FL 34786
/27
$2,700 per month
- 3 Beds
- 2.5 Baths
- 1,920 Sq Ft
- Townhouse for Rent
7605 Ripplepointe Way, Windermere, FL 34786

Move in ready!! Exterior of building just painted. 3-Bedroomm, 2.5-Bath, family room open to kitchen, separate dining room that can be an office. Fenced in patio between townhome and garage. Ceramic tile downstairs in general areas, new washer and dryer, new interior paint, and new vinyl on stairs, hallway, and bedrooms. Lake Burden is a sought-after community offering tennis courts, playgrounds,

Brigitte Elzarki COLDWELL BANKER REALTY

7605 Ripplepointe Way, Windermere, FL 34786
/2
$2,404,000 Sold Jan 15, 2026

1724 Windermeredown Place, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,000 Sq Ft
- Built 1995
Last Sold Summary
- 4% Below List Price
- $401/SF
- 46 Days On Market
Last Listing Agent Chad Going SERHANT

1724 Windermeredown Place, Windermere, FL 34786

/34
Est $534,226 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
13335 Overstreet Rd, Windermere, FL 34786

13335 Overstreet Rd, Windermere, FL 34786

/22
$399,900 Pending
- 3 Beds
- 2.5 Baths
- 1,468 Sq Ft
7361 Brightland St, Windermere, FL 34786

Under contract-accepting backup offers. New Price! Nestled in the heart of Windermere, this two-story townhome is a perfect blend of charm, comfort, and modern living. As you approach, the cute front porch entrance welcomes you, hinting at the warmth that lies within. The exterior is adorned with stone columns and crowned with a stylish barrel-tiled roof, adding character to this inviting abode.

Peter Luu REAL BROKER, LLC

7361 Brightland St, Windermere, FL 34786
/17
$3,595 per month
- 4 Beds
- 3 Baths
- 3,058 Sq Ft
- House for Rent
11530 Vicolo Loop, Windermere, FL 34786

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3739.90. That covers your base rent, $3595.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

11530 Vicolo Loop, Windermere, FL 34786
/2
$1,655,000 Sold Aug 15, 2025

1424 Kelso Blvd, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 3,104 Sq Ft
- Built 1975
Last Sold Summary
- 12% Below List Price
- $533/SF
- 112 Days On Market
Current Estimated Value $1,716,592

Last Listing Agent Carmen Aridas RE/MAX PRIME PROPERTIES

1424 Kelso Blvd, Windermere, FL 34786

/22
Est $1,053,572 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,117 Sq Ft
12525 Montalcino Cir, Windermere, FL 34786

12525 Montalcino Cir, Windermere, FL 34786

/50
$1,129,990 New Construction
- 4 Beds
- 3.5 Baths
- 3,692 Sq Ft
14354 Crest Palm Ave, Windermere, FL 34786

The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,692 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a

Dream Finders Homes Builder

14354 Crest Palm Ave, Windermere, FL 34786
/25
$3,899 per month
- 5 Beds
- 4 Baths
- 3,256 Sq Ft
- House for Rent
8931 Lookout Pointe Dr, Windermere, FL 34786

$3999 month for a 1 year lease$3,899 for an 18 month lease This 5/4 2 story home with a Bonus room located in Windemere Trails is just over 3200 sq ft. Downstairs is one bedroom and one full bathroom, separate dining and living room, and large eat-in kitchen. The upgraded kitchen has gorgeous granite counters with, lots of counter space, solid wood tall cabinets, and high-end stainless steel

Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

8931 Lookout Pointe Dr, Windermere, FL 34786
/2
$718,000 Sold Oct 20, 2025

12755 Westside Village Loop, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,064 Sq Ft
- Built 2018
Last Sold Summary
- 12% Below List Price
- $234/SF
- 142 Days On Market
Current Estimated Value $715,166

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12755 Westside Village Loop, Windermere, FL 34786

/40
Est $540,051 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,184 Sq Ft
12160 Canyon Sun Trail, Windermere, FL 34786

12160 Canyon Sun Trail, Windermere, FL 34786

/15
$959,990 New Construction
- 3 Beds
- 2.5 Baths
- 2,226 Sq Ft
Plant at Lake Cawood Cove - Traditional, Windermere, FL 34786

The Plant is a one-story home offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The spacious kitchen features a large island and flows seamlessly into the dining and family rooms. A private primary suite includes a walk-in closet, while a generously sized den and covered lanai provide versatile living spaces for work, relaxation, and outdoor enjoyment. Modern

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932781, Windermere, FL 34786
/18
$3,345 per month
- 4 Beds
- 3.5 Baths
- 2,628 Sq Ft
- House for Rent
7623 Colbury Ave, Windermere, FL 34786

Special security deposit offer: Pay just 50% of your base rent as your security deposit (taxes and fees not included), valid for new applicants who sign a 12-month lease by February 28, 2026. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company.

7623 Colbury Ave, Windermere, FL 34786
/2
$3,100,000 Sold Apr 01, 2025

2812 Marquesas Ct, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 5,624 Sq Ft
- Built 1984
Last Sold Summary
- 2% Below List Price
- $551/SF
- 55 Days On Market
Current Estimated Value $3,010,243

Last Listing Agent Kari Fleck THE REAL ESTATE COLLECTION LLC

2812 Marquesas Ct, Windermere, FL 34786

/40
Est $649,450 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,208 Sq Ft
7230 Rambling Water Way, Windermere, FL 34786

7230 Rambling Water Way, Windermere, FL 34786

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