Windermere, FL Homes

/54
$959,900
- 5 Beds
- 4 Baths
- 3,070 Sq Ft
13858 Caywood Pond Dr, Windermere, FL 34786

JUST REMODELED! Stunning lakefront pool home located in the heart of Windermere, offering 5 bedrooms, 4 full bathrooms, and nearly 3,100 square feet of beautifully updated living space. Perfectly positioned between downtown Windermere and Winter Garden Village, this exceptional property is nestled within the highly desirable Summerport community and features pristine waterfront views. This is

Chun Cai SPRING REALTY ONE LLC

13858 Caywood Pond Dr, Windermere, FL 34786
/18
$2,750 per month
- 3 Beds
- 2.5 Baths
- 1,748 Sq Ft
- Townhouse for Rent
12813 Gracehill Ln, Windermere, FL 34786

This beautifully maintained townhouse offers 3 bedrooms and 2.5 bathrooms with a peaceful pond view. The kitchen features granite countertops, 42-inch wood cabinets, stainless steel appliances, and a pantry, providing both functionality and style. The first floor includes spacious living, dining, and family areas, along with a convenient laundry room. The entire second floor features brand new

Melquisedec Martins NOVA REAL ESTATE SERVICES INC

12813 Gracehill Ln, Windermere, FL 34786
/2
$520,000 Sold Jun 26, 2025

12880 Holdenbury Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 3,103 Sq Ft
- Built 2006
Last Sold Summary
- 13% Below List Price
- $168/SF
- 67 Days On Market
Current Estimated Value $685,990

Last Listing Agent Jacquie Sosa EXP REALTY LLC

12880 Holdenbury Ln, Windermere, FL 34786

/17
Est $856,878 Not Listed For Sale

1348 Lake Olivia Ln, Windermere, FL 34786
- Built 2018
1348 Lake Olivia Ln, Windermere, FL 34786

Last Sold Summary
- 28% Above List Price
- $132/SF
- 530 Days On Market
Last Sold Price $669,000

Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

/31
$990,000 New Construction
- 4 Beds
- 4 Baths
- 3,100 Sq Ft
Arlington w/ Bonus Plan at Palms at Windermere, Windermere, FL 34786

Welcome to the Arlington with Bonus! This stunning 3,099 square foot, two-story floor plan boasts 4 bedrooms, 4 bathrooms, and a spacious 2-car garage. Experience the ultimate in open-concept living on the main level, perfect for entertaining family and friends. The garage includes an extra hobby/work space for all your creative projects. Step outside and unwind under the inviting covered patio,

Dream Finders Homes Builder

14207 Crest Palm Ave Unit 36493225, Windermere, FL 34786
/31
$12,500 per month
- 3 Beds
- 3 Baths
- 3,535 Sq Ft
- House for Rent
9701 Lake Isleworth Ct, Windermere, FL 34786

Within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and living room with a

Michelle Corbin ISLEWORTH REALTY LLC

9701 Lake Isleworth Ct, Windermere, FL 34786
/2
$650,000 Sold May 05, 2025

4801 Breezy Palms Ct, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 1,996 Sq Ft
- Built 1986
Last Sold Summary
- $326/SF
- 1 Day On Market
Current Estimated Value $654,920

Last Listing Agent Luana Oliveira ORANGE SLICE PROPERTIES

4801 Breezy Palms Ct, Windermere, FL 34786

/2
Est $500,871 Not Listed For Sale

6315 Golden Dewdrop Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
- Built 2012
6315 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- $252/SF
- 46 Days On Market
Last Sold Price $500,000

Last Listing Agent Sandy Jones CLOCK TOWER REALTY

/47
$989,989 New Construction
- 4 Beds
- 3.5 Baths
- 3,239 Sq Ft
14377 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 3,239 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

14377 Crest Palm Ave, Windermere, FL 34786
/24
$3,500 per month
- 4 Beds
- 2.5 Baths
- 2,981 Sq Ft
- House for Rent
12925 Holdenbury Ln, Windermere, FL 34786

Located in a highly sought-after top-rated school zone, this beautifully designed two-story home offers the perfect blend of space, privacy, and functionality. Featuring four spacious bedrooms and 2.5 bathrooms, the home is thoughtfully laid out to accommodate modern living. The showpiece of the home is the oversized gourmet kitchen, complete with abundant cabinet and counter space and two large

Jing Yue INTEREALTY SERVICE

12925 Holdenbury Ln, Windermere, FL 34786
/2
$8,500,000 Sold Sep 05, 2025

5271 Isleworth Country Club Dr, Windermere, FL 34786
- 7 Beds
- 13 Baths
- 11,403 Sq Ft
- Built 2013
Last Sold Summary
- 3% Below List Price
- $745/SF
- 206 Days On Market
Current Estimated Value $8,282,222

Last Listing Agent Monica Lochmandy ISLEWORTH REALTY LLC

5271 Isleworth Country Club Dr, Windermere, FL 34786

/8
Est $827,000 Not Listed For Sale

1330 Lake Olivia Ln, Windermere, FL 34786
- Built 2018
1330 Lake Olivia Ln, Windermere, FL 34786

Last Sold Summary
- 16% Above List Price
- $160/SF
- 196 Days On Market
Last Sold Price $710,000

Last Listing Agent Heather Berrios EXP REALTY LLC

/13
$1,129,990 New Construction
- 5 Beds
- 4.5 Baths
- 3,542 Sq Ft
Duval Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

The Duval is a two‐story home offering five bedrooms, four full bathrooms, one half bathroom, and a two‐car garage. A bright kitchen with breakfast nook anchors the open main floor, while a second‐floor loft overlooks the family room below. The private second‐floor primary suite, optional butler’s pantry, and centrally located laundry room add convenience and luxury to this spacious plan.

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932788, Windermere, FL 34786
/31
$2,500 per month
- 2 Beds
- 2 Baths
- 1,155 Sq Ft
- Townhouse for Rent
5317 Keenes Pheasant Dr, Windermere, FL 34786

SINGLE-STORY, END-UNIT TOWNHOME WITH BRAND NEW CARPET AND PAINT! Step into this updated townhome, ready for immediate occupancy! As you enter, you are greeted by a large open concept living and dining space with tons of natural light. The kitchen connects seamlessly to the living area, and features tons of cabinetry, stainless steel appliances, pantry, bar top seating, and additional eat-in

Matthew Gordon COLDWELL BANKER REALTY

5317 Keenes Pheasant Dr, Windermere, FL 34786
/2
$480,000 Sold Sep 26, 2025

13715 Bressler Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- Built 2019
Last Sold Summary
- 9% Below List Price
- $224/SF
- 215 Days On Market
Current Estimated Value $475,335

Last Listing Agent Irene Fort PREFERRED REAL ESTATE BROKERS

13715 Bressler Aly, Windermere, FL 34786

/2
Est $3,143,544 Not Listed For Sale

4124 Isabella Cir, Windermere, FL 34786
- 6 Beds
- 8 Baths
- 6,842 Sq Ft
- Built 2016
4124 Isabella Cir, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $490/SF
- 59 Days On Market
Last Sold Price $3,350,000

Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

/77
$1,200,000
- 3 Beds
- 2 Baths
- 2,521 Sq Ft
414 E 5th Ave, Windermere, FL 34786

CHARMING LAKEVIEW HOME IN THE HEART OF WINDERMERE! Enjoy unobstructed views of Lake Down from this beautifully located 3-bedroom, 2-bath home in the Town of Windermere. A stunning 44-foot-wide front porch provides the perfect place to relax and take in the peaceful lake scenery, morning sunrises, and evening breezes. Inside, the home offers comfortable living spaces designed for everyday living

Kathie Glass BHHS FLORIDA REALTY

414 E 5th Ave, Windermere, FL 34786
/31
$2,700 per month
- 3 Beds
- 2.5 Baths
- 1,570 Sq Ft
- Townhouse for Rent
11619 Water Run Aly, Windermere, FL 34786

Located in the desirable Ashlin Park neighborhood of Windermere, this well-maintained 3-bedroom, 2.5-bath townhome features a bright, open floor plan with an abundance of natural light. The kitchen features quartz countertops, stainless steel appliances, and espresso cabinetry. The primary suite includes a walk-in closet and a private bath. Enjoy a private interior courtyard connecting the home

Cristiane Carneiro Spfndola Rocha L WRA BUSINESS & REAL ESTATE

11619 Water Run Aly, Windermere, FL 34786
/2
$930,000 Sold Nov 10, 2025

5141 Autumn Ridge Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,390 Sq Ft
- Built 1990
Last Sold Summary
- 2% Below List Price
- $389/SF
- 91 Days On Market
Current Estimated Value $914,727

Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

5141 Autumn Ridge Ln, Windermere, FL 34786

/43
Est $522,255 Not Listed For Sale

11650 Black Rail St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- Built 2012
11650 Black Rail St, Windermere, FL 34786

Last Sold Summary
- $243/SF
- 1 Day On Market
Last Sold Price $520,000

Last Listing Agent Julie Fernandez OAK AVENUE REAL ESTATE LLC

/2
$999,989 New Construction
- 4 - 6 Beds
- 3.5 Baths
- 3,199 Sq Ft
Tidewater w/ Bonus Plan at Palms at Windermere, Windermere, FL 34786

The Tidewater with Bonus floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 3.5 bathrooms. Spanning 3,199 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

14207 Crest Palm Ave Unit 36498094, Windermere, FL 34786
/20
$3,100 per month
- 4 Beds
- 3 Baths
- 2,345 Sq Ft
- House for Rent
5019 Blue Major Dr, Windermere, FL 34786

Welcome home to this beautifully maintained property in Windermere’s sought-after Summerport community. Enjoy a chef-inspired kitchen complete with solid countertops, updated stainless steel appliances, and a gas range—perfect for everyday living and entertaining. New interior paint, stylish flooring throughout, and upgraded lighting and bathroom fixtures make this home the perfect rental!

Alex Sadowski KELLER WILLIAMS REALTY AT THE PARKS

5019 Blue Major Dr, Windermere, FL 34786
/2
$518,000 Sold May 14, 2025

5014 Wise Bird Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,342 Sq Ft
- Built 2004
Last Sold Summary
- 13% Below List Price
- $221/SF
- 102 Days On Market
Current Estimated Value $522,275

Last Listing Agent Hong Lu CHARLES RUTENBERG REALTY ORLANDO

5014 Wise Bird Dr, Windermere, FL 34786

/59
Est $2,701,867 Not Listed For Sale

13340 Bellaria Cir, Windermere, FL 34786
- 6 Beds
- 8 Baths
- 6,803 Sq Ft
- Built 2015
13340 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 6% Above List Price
- $375/SF
- 5 Days On Market
Last Sold Price $2,550,000

Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY

/98
$1,400,000 Pending
- 5 Beds
- 5.5 Baths
- 3,383 Sq Ft
1625 Down Lake Dr, Windermere, FL 34786

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. A rare opportunity in Windermere's established Lakes / Lake Down neighborhood — an exceptional builder's home offering the quality & finishes typically found at much higher price points. Set on a beautifully manicured ONE-ACRE LOT with BOAT ACCESS to the BUTLER CHAIN OF LAKES, this residence blends comfort,

Cindy Rosenbloom THE ROSENBLOOM TEAM

1625 Down Lake Dr, Windermere, FL 34786
/35
$2,450 per month
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Condo for Rent
11562 Amidship Ln Unit 114, Windermere, FL 34786

Beautiful 3-bedroom, 2-bath condo located in the desirable Lakeside at Lakes of Windermere community. This freshly painted unit features an open layout, spacious living area, and private screened balcony. Water included in rent. Enjoy community amenities including pool, fitness center, playground, and gated entry. Conveniently located near shopping, dining, and just minutes from Walt Disney

Alvaro Molina TWIN HOMES REALTY

11562 Amidship Ln Unit 114, Windermere, FL 34786
/2
$745,000 Sold Jul 28, 2025

9676 Wild Oak Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,856 Sq Ft
- Built 1977
Last Sold Summary
- 21% Below List Price
- $261/SF
- 102 Days On Market
Current Estimated Value $774,254

Last Listing Agent Hardy Edwards, III BHHS FLORIDA REALTY

9676 Wild Oak Dr, Windermere, FL 34786

/64
Est $794,633 Not Listed For Sale

12851 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,694 Sq Ft
- Built 2018
12851 Westside Village Loop, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $213/SF
- 94 Days On Market
Last Sold Price $785,000

Last Listing Agent Torey Eisenman BENCHMARK REAL ESTATE GRP INC

/87
$2,300,000
- 5 Beds
- 4.5 Baths
- 4,284 Sq Ft
81 Oakdale St, Windermere, FL 34786

Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step

David Warzycha COLDWELL BANKER REALTY

81 Oakdale St, Windermere, FL 34786
/36
$4,275 per month
- 6 Beds
- 3.5 Baths
- 3,841 Sq Ft
- House for Rent
7403 Fairgrove Ave, Windermere, FL 34786

Spacious 6-bedroom, 3.5-bath unfurnished home offering 3,841 sq ft in the desirable Windermere Sound community. This well-designed floor plan features a downstairs primary bedroom, a large upstairs loft, generously sized bedrooms with walk-in closets, an office area and an expansive kitchen complete with a walk-in butler pantry and ample cabinet space—perfect for entertaining and everyday living.

Sunny Pabla PABLA PROPERTIES

7403 Fairgrove Ave, Windermere, FL 34786
/2
$585,000 Sold Aug 19, 2025

8359 Lookout Pointe Dr, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 2,604 Sq Ft
- Built 2016
Last Sold Summary
- 1% Below List Price
- $225/SF
- 3 Days On Market
Current Estimated Value $581,248

Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

8359 Lookout Pointe Dr, Windermere, FL 34786

/56
Est $2,402,066 Not Listed For Sale

13352 Bellaria Cir, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 5,524 Sq Ft
- Built 2014
13352 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $425/SF
- 149 Days On Market
Last Sold Price $2,350,000

Last Listing Agent Llin Lu PREMIER SOTHEBYS INT'L REALTY

/56
$600,000
- 3 Beds
- 3.5 Baths
- 2,720 Sq Ft
6626 Bridgewater Village Rd, Windermere, FL 34786

**Corner-Lot Home Across from Park in The Vineyards of Horizon West** Perfectly positioned on a corner lot directly across from a peaceful green space, this bright and beautifully upgraded home is located in one of Horizon West’s most sought-after communities. With park views, walkable streets, and a true neighborhood feel, this home offers the ideal blend of comfort, style, and location. The

David Dorman CENTURY 21 CARIOTI

6626 Bridgewater Village Rd, Windermere, FL 34786
/16
$2,500 per month
- 3 Beds
- 2.5 Baths
- 1,540 Sq Ft
- Townhouse for Rent
7843 Hardenton St, Windermere, FL 34786

Townhome Windermere area 3 Bedroom and 2.5 Bathroom, 2 car garage, 2 story unit. The kitchen cabinets 42", with quartz counters, island/breakfast bar, and stainless steel appliances, open private patio. Wickham Park has a community pool, clubhouse and parks. Great location, close to street mall and supermarket, Close to Disney, Winter Garden Village and major highways (529, turnpike, I4). Close

Franca Troisi MY REALTY GROUP, LLC.

7843 Hardenton St, Windermere, FL 34786
/2
$2,700,000 Sold Feb 09, 2026

9151 Tibet Pointe Cir, Windermere, FL 34786
- Land
- 2.21 Acres
- $1,221,719 per Acre
Last Sold Summary
- 16% Below List Price
- 341 Days On Market
Current Estimated Value $4,002,770

Last Listing Agent Janet Allen PREMIER SOTHEBYS INT'L REALTY

9151 Tibet Pointe Cir, Windermere, FL 34786

/23
Est $440,407 Not Listed For Sale

13736 Bravante Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
- Built 2017
13736 Bravante Aly, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $238/SF
- 6 Days On Market
Last Sold Price $455,000

Last Listing Agent Kristine McKinley RE/MAX

/63
$999,998
- 4 Beds
- 3 Baths
- 2,743 Sq Ft
2125 Kane Park Way, Windermere, FL 34786

Welcome to this beautifully updated single-story pool home on a rare 0.71-acre cul-de-sac lot in Windermere’s Willows at Lake Rhea, zoned for A-rated schools and offering exceptional privacy between homes. Surrounded by mature landscaping, the property provides a peaceful setting rarely found in newer communities while still offering convenient access to major roads, shopping, dining, and area

Deb Schroeder INFINITY REALTY GROUP LLC

2125 Kane Park Way, Windermere, FL 34786
/32
$2,650 per month
- 2 Beds
- 2.5 Baths
- 1,239 Sq Ft
- Townhouse for Rent
12623 Langstaff Dr, Windermere, FL 34786

ONE OF A KIND, EXECUTIVE WINDERMERE 2 BEDROOM 2.5 BATHROOMS TOWNHOME FURNISHED & DECORATED! This recently renovated home is in the sought-after Lake Reams Community only a minute drive to the backside of Disney! As you open the front door you are drawn to Upscale Interior, filled with Upgrades & a Warm Family Décor. The eating area overlooks an Enclosed Custom-Made Courtyard leading to a Detached

Ernesto Cisneros ELITE REALTY ENTERPRISES LLC

12623 Langstaff Dr, Windermere, FL 34786
/2
$380,000 Sold Nov 13, 2025

5219 Keenes Pheasant Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,461 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $260/SF
- 6 Days On Market
Current Estimated Value $376,602

Last Listing Agent Roland Cotardo THE SIMON SIMAAN GROUP

5219 Keenes Pheasant Dr, Windermere, FL 34786

/36
Est $1,522,099 Not Listed For Sale

1146 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,374 Sq Ft
- Built 2018
1146 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 5% Above List Price
- $332/SF
- 42 Days On Market
Last Sold Price $1,450,000

Last Listing Agent Alice Anne Jackson CORCORAN PREMIER REALTY

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