Windermere, FL Homes

/35
$1,399,000 Pending
- 5 Beds
- 4.5 Baths
- 3,082 Sq Ft
106 Palm St, Windermere, FL 34786

Under contract-accepting backup offers. Set on a large, tree-lined lot just moments from historic downtown Windermere, this fully reimagined residence blends modern luxury with timeless charm—delivering a level of craftsmanship and detail that truly stands out. Every inch of this home has been thoughtfully redesigned, including a newly configured floor plan, all new interior doors and trim, and

Jill Healey KELLER WILLIAMS WINTER PARK

106 Palm St, Windermere, FL 34786
/60
$4,400 Per Month
- 4 Beds
- 2.5 Baths
- 2,236 Sq Ft
- House for Rent
11745 Via Lucerna Cir, Windermere, FL 34786

Experience luxury living in this beautifully updated 4-bedroom, 2.5-bathroom single-story home located in the 24/7 gated camera surveillance Belmere community in Windermere. This home has been completely and tastefully remodeled with luxury finishes throughout, transforming it into a modern sanctuary of comfort and elegance. Every detail has been upgraded with intention, blending sophistication,

Margaret Marambio LPT REALTY, LLC

11745 Via Lucerna Cir, Windermere, FL 34786
/2
$619,000 Sold Oct 31, 2025

13260 Penshurst Ln, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,076 Sq Ft
- Built 2015
Last Sold Summary
- 1% Below List Price
- $298/SF
- 6 Days On Market
Current Estimated Value $607,678

Last Listing Agent Nadia Eggers FUTURE HOME REALTY INC

13260 Penshurst Ln, Windermere, FL 34786

/2
Est $385,522 Not Listed For Sale

12202 Langstaff Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,545 Sq Ft
- Built 2012
12202 Langstaff Dr, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $254/SF
- 8 Days On Market
- Last Sold Price $393,000
- Mar 24, 2025
Last Listing Agent Milagros Agostini-Prado LPT REALTY, LLC

/57
$1,490,000
- 4 Beds
- 4 Baths
- 3,487 Sq Ft
12718 Windermere Isles Place, Windermere, FL 34786

Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an exceptional blend of privacy, space, and elegance. Enjoy serene views of the expansive backyard and picturesque koi pond from the spacious shaded patio or the screened rear porch. The

Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

12718 Windermere Isles Place, Windermere, FL 34786
/25
$2,150 Per Month
- 2 Beds
- 2.5 Baths
- 1,200 Sq Ft
- Townhouse for Rent
12654 Langstaff Dr, Windermere, FL 34786

Charming and specious 2 bedroom Townhouse in Windermere! Introducing the highly sought after Windermere Townhouse in Windermere, FL! This charming townhouse features 2 bedrooms and 2.5 bathrooms, spacious layout filled with natural light, and ceramic tiles in common areas downstairs.The kitchen boasts an island, plenty of storage and dining room a step away, perfect for cooking and

Jacob Hara TRANSCEND REALTY

12654 Langstaff Dr, Windermere, FL 34786
/2
$375,000 Sold Sep 22, 2025

13730 Lensdale Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 1,640 Sq Ft
- Built 2007
Last Sold Summary
- $229/SF
- 10 Days On Market
Current Estimated Value $374,802

Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

13730 Lensdale Ln, Windermere, FL 34786

/2
Not Listed For Sale

0 Westover Roberts Rd Unit MFRO6286777, Windermere, FL 34786
0 Westover Roberts Rd Unit MFRO6286777, Windermere, FL 34786

Last Sold Summary
- 6 Days On Market
- Last Sold Price $1,150,000
- Mar 26, 2025
Last Listing Agent Christopher Lyons AGILE GROUP REALTY

/61
$1,425,000
- 4 Beds
- 3.5 Baths
- 3,660 Sq Ft
1125 Kelso Blvd, Windermere, FL 34786

This is a must see!!! Offering four bedrooms and three and one half baths, this home sits on a beautifully landscaped, estate-sized 1 acre lot! The floor plan is flexible and allows for multiple entertaining options. The kitchen is a cook's dream with an abundance of wood cabinetry, expansive granite counters, a huge center island and built in appliances. It is light and bright and open to the

Ken Teixeira WEICHERT REALTORS HALLMARK PROPERTIES

1125 Kelso Blvd, Windermere, FL 34786
/35
$5,500 Per Month
- 4 Beds
- 3 Baths
- 3,030 Sq Ft
- House for Rent
11917 Camden Park Dr, Windermere, FL 34786

This stunning single-story home in the guard-gated community of Keene’s Pointe offers 4 bedrooms, 3 bathrooms, and 3,030 square feet of beautifully designed living space. The open-concept floorplan is enhanced by soaring ceilings and an abundance of windows, filling the home with natural light.Upon entry, you’re welcomed by elegant formal spaces—including a foyer, living room, dining room,

Brynn Munro CORCORAN PREMIER REALTY

11917 Camden Park Dr, Windermere, FL 34786
/2
$689,000 Sold Jul 08, 2025

1412 Glenwick Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
- Built 2002
Last Sold Summary
- 2% Below List Price
- $332/SF
- 63 Days On Market
Current Estimated Value $672,592

Last Listing Agent Chris Bunnell EXP REALTY LLC

1412 Glenwick Dr, Windermere, FL 34786

/2
Est $1,148,499 Not Listed For Sale

3302 Just-A-mere Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,450 Sq Ft
- Built 1986
3302 Just-A-mere Ct, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $482/SF
- 18 Days On Market
- Last Sold Price $1,180,000
- Mar 25, 2025
Last Listing Agent Sue Webb WATSON REALTY CORP.

/39
$1,359,999 Pending
- 5 Beds
- 4.5 Baths
- 4,257 Sq Ft
11044 Hawkshead Ct Unit 2, Windermere, FL 34786

Under contract-accepting backup offers. Stunning home in the Reserve at Lake Butler Sound-Windermere. This luxury living at its finest located in the prestigious 24 hour guarded community. The property features 5 bedrooms, 4.5 bathrooms, a 3-car garage, and a private heated pool, perfect for relaxing or entertaining. The owner has invested more than $100,000 upgrades..... newly renovated kitchen

Jennie Ho MAY HO REALTY

11044 Hawkshead Ct Unit 2, Windermere, FL 34786
/37
$3,400 Per Month
- 4 Beds
- 2.5 Baths
- 3,011 Sq Ft
- House for Rent
12761 Bideford Ave, Windermere, FL 34786

Beautiful 4-bedroom 2.5 bath home located in the desirable Lakes of Windermere community. This two-story corner lot home has everything you can ask for, formal living and dining rooms, kitchen with granite countertops, stainless steel appliances, and a breakfast bar that opens to a large family room, on the first floor you also have a massive master bedroom suite, with a large closet and the

Paul Moscoso Donoso SHINING OAK REALTY

12761 Bideford Ave, Windermere, FL 34786
/2
$960,000 Sold Feb 23, 2026

11550 Delwick Dr, Windermere, FL 34786
- 5 Beds
- 3 Baths
- 2,843 Sq Ft
- Built 2004
Last Sold Summary
- 4% Below List Price
- $338/SF
- 6 Days On Market
Current Estimated Value $954,767

Last Listing Agent Constantino Trimarcchi TRIMARCHI REALTY CORP

11550 Delwick Dr, Windermere, FL 34786

/2
Est $484,046 Not Listed For Sale

13805 Bressler Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,093 Sq Ft
- Built 2019
13805 Bressler Aly, Windermere, FL 34786

Last Sold Summary
- $232/SF
- 34 Days On Market
- Last Sold Price $485,000
- Mar 28, 2025
Last Listing Agent Kenneth Wilder CREEGAN GROUP

/36
$1,349,000 Pending
- 4 Beds
- 3 Baths
- 2,937 Sq Ft
5837 Caymus Loop, Windermere, FL 34786

Under contract-accepting backup offers. Completely renovated and thoughtfully reconfigured in 2023, this stunning 4-bedroom, 3-bath home is located in the highly sought-after, 24-hour gated and guarded community of Keene’s Pointe. Designed for modern living, the home features an open and refreshed layout with new flooring throughout and elegant paneling details that elevate the interior design.

Jay Stewart SOUTHERN REALTY GROUP LLC

5837 Caymus Loop, Windermere, FL 34786
/25
$2,450 Per Month
- 3 Beds
- 2.5 Baths
- 1,446 Sq Ft
- Townhouse for Rent
8253 Maritime Flag St Unit 109, Windermere, FL 34786

One or more photo(s) has been virtually staged. 3-bedroom, 2.5-bath townhome located in the desirable Lakeside Village community in Windermere. This spacious home features an open-concept layout with tile flooring on the first floor and carpet upstairs, offering a functional and comfortable living space. The kitchen includes granite countertops, stainless steel appliances, and ample cabinet

Priscila Policarpo Attuy de Albuqu WRA BUSINESS & REAL ESTATE

8253 Maritime Flag St Unit 109, Windermere, FL 34786
/2
$460,000 Sold Dec 01, 2025

7673 Ripplepointe Way, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,212 Sq Ft
- Built 2015
Last Sold Summary
- 2% Below List Price
- $208/SF
- 19 Days On Market
Current Estimated Value $465,310

Last Listing Agent Mahmoud Mango DALTON WADE INC

7673 Ripplepointe Way, Windermere, FL 34786

/15
Est $1,071,500 Not Listed For Sale

14428 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,199 Sq Ft
- Built 2025
14428 Crest Palm Ave, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $358/SF
- 0 Days On Market
- Last Sold Price $1,144,870
- Mar 12, 2025
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/26
$1,396,000
- 6 Beds
- 4.5 Baths
- 3,794 Sq Ft
13596 Gorgona Isle Dr, Windermere, FL 34786

Stunning Two-Story Pool Home in Prime Windermere LocationWelcome to this exceptional two-story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space, and comfort. With 6 generously sized bedrooms and an open, airy design, this home is ideal for families seeking both elegance and functionality.The primary suite is a true retreat, featuring a

Jennifer Olmeda WRA BUSINESS & REAL ESTATE

13596 Gorgona Isle Dr, Windermere, FL 34786
/25
$2,800 Per Month
- 3 Beds
- 2.5 Baths
- 1,822 Sq Ft
- Townhouse for Rent
11807 Vermillion Ave, Windermere, FL 34786

A Rate School Zone and Beautiful brand like NEW TOWNHOUSE in Windermere Trails Community! This stunning 3 bedrooms, 2.5 bathrooms, and 2 car garage end of unit townhouse comes with high-end upgrades. he gourmet-style kitchen has new stainless steel appliances, neutral tile throughout the first floor MASTER BEDROOM DOWNSTAIRS!! The Private Courtyard provides lots of space for entertaining guests

Huimei Yang HANG SENG REALTY , INC

11807 Vermillion Ave, Windermere, FL 34786
/2
$1,143,000 Sold May 16, 2025

2008 Water Key Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,273 Sq Ft
- Built 2000
Last Sold Summary
- 4% Below List Price
- $349/SF
- 29 Days On Market
Current Estimated Value $1,131,613

Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

2008 Water Key Dr, Windermere, FL 34786

/3
Est $1,111,500 Not Listed For Sale

14410 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
- Built 2025
14410 Crest Palm Ave, Windermere, FL 34786

Last Sold Summary
- 10% Below List Price
- $398/SF
- 0 Days On Market
- Last Sold Price $1,233,197
- Mar 14, 2025
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/45
$1,199,000 Pending
- 3 Beds
- 3.5 Baths
- 3,368 Sq Ft
8350 Bowden Way, Windermere, FL 34786

Under contract-accepting backup offers. Gated/24-hour attended Keene's Pointe. Home of The Golden Bear Club, a private membership club offering golf, tennis, fitness, dining and swimming. This thoughtfully designed home offers both space and functionality for modern living. Upon entry, you’re welcomed by a spacious formal dining room, formal living room, and a private office featuring classic

Teresa Stewart SOUTHERN REALTY GROUP LLC

8350 Bowden Way, Windermere, FL 34786
/28
$6,750 Per Month
- 4 Beds
- 4 Baths
- 2,886 Sq Ft
- House for Rent
11531 Claymont Cir, Windermere, FL 34786

This 4BR/4 FULL Bath PLUS BONUS ROOM home located right next to a beautiful park in Keene’s Pointe is calling your name! Enjoy the serenity of this guard gated, golf course and country club community. This flexible split floor plan features all 4 bedrooms downstairs with the primary suite on one side of the house and on the other side you will find a deluxe, Jack and Jill bedroom layout with

Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

11531 Claymont Cir, Windermere, FL 34786
/2
$6,000,000 Sold May 06, 2026

1002 Down Reserve Ct, Windermere, FL 34786
- 6 Beds
- 5.5 Baths
- 6,706 Sq Ft
- Built 2021
Last Sold Summary
- 13% Below List Price
- $895/SF
- 42 Days On Market
Current Estimated Value $6,480,052

Last Listing Agent Jennifer Olmeda WRA BUSINESS & REAL ESTATE

1002 Down Reserve Ct, Windermere, FL 34786

/2
Est $1,132,500 Not Listed For Sale

14262 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,404 Sq Ft
- Built 2025
14262 Crest Palm Ave, Windermere, FL 34786

Last Sold Summary
- 8% Below List Price
- $363/SF
- 0 Days On Market
- Last Sold Price $1,236,498
- Mar 21, 2025
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/18
$408,000
- 3 Beds
- 2.5 Baths
- 1,584 Sq Ft
11636 Water Run Aly, Windermere, FL 34786

This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a

Jose Jimenez EXP REALTY LLC

11636 Water Run Aly, Windermere, FL 34786
/23
$3,000 Per Month
- 4 Beds
- 3.5 Baths
- 1,793 Sq Ft
- Townhouse for Rent
8602 Via Tavoleria Way, Windermere, FL 34786

An exquisite, maintenance-free townhome is available for rent in the highly sought-after Carrington community of Windermere. This spacious 4-bedroom, 3.5-bathroom residence offers an ideal and flexible floor plan.The main level features a convenient guest bedroom with a full bathroom. Upstairs, you will find a bright loft and the remaining bedrooms, including the private primary suite. The

Yukey Hoo U KEY REALTY

8602 Via Tavoleria Way, Windermere, FL 34786
/2
$1,060,000 Sold Sep 11, 2025

76 Oakdale St, Windermere, FL 34786
- 3 Beds
- 1.5 Baths
- 2,011 Sq Ft
- Built 1957
Last Sold Summary
- 18% Below List Price
- $527/SF
- 82 Days On Market
Current Estimated Value $1,021,956

Last Listing Agent Bill Martini BHHS FLORIDA REALTY

76 Oakdale St, Windermere, FL 34786

/2
Est $1,097,488 Not Listed For Sale

14291 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 4,222 Sq Ft
- Built 2024
14291 Crest Palm Ave, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $256/SF
- 0 Days On Market
- Last Sold Price $1,080,813
- Feb 28, 2025
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/45
$3,499,999
- 5 Beds
- 4.5 Baths
- 4,417 Sq Ft
5001 Latrobe Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Traditional five-bedroom four and a half bath pool home with an open layout in Isleworth Golf & Country Club. Perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features two primary suites downstairs with private

Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

5001 Latrobe Dr, Windermere, FL 34786
/28
$2,450 Per Month
- 3 Beds
- 2 Baths
- 1,332 Sq Ft
- Condo for Rent
11564 Mizzon Dr Unit 304, Windermere, FL 34786

Welcome to Lakeside of Windermere!!! This Luxury Lifestyle Community is conveniently located across from shopping plazas which provide Publix Grocery, restaurants and shops. Enjoy top quality amenities including resort swimming pool, fitness center, clubhouse, playground, outdoor beach volleyball, and fishing pier on Lake Burden. This condo is in a highly desirable area of Windermere, just

Alex Lukavsky CENTURY 21 CARIOTI

11564 Mizzon Dr Unit 304, Windermere, FL 34786
/2
$1,000,000 Sold Sep 03, 2025

1947 Broadleaf Ct, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,646 Sq Ft
- Built 1989
Last Sold Summary
- 20% Below List Price
- $274/SF
- 64 Days On Market
Current Estimated Value $987,092

Last Listing Agent Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

1947 Broadleaf Ct, Windermere, FL 34786

/2
Est $1,097,312 Not Listed For Sale

14237 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,687 Sq Ft
- Built 2025
14237 Crest Palm Ave, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $423/SF
- 0 Days On Market
- Last Sold Price $1,137,874
- Feb 28, 2025
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/26
$1,000,000
- Land
- 21,780 Sq Ft
- $2,000,000 per Acre
2504 Windermere Reserve Ct, Windermere, FL 34786

Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

Carolina Dumit CORCORAN PREMIER REALTY

2504 Windermere Reserve Ct, Windermere, FL 34786
/16
$2,700 Per Month
- 3 Beds
- 3 Baths
- 1,891 Sq Ft
- Townhouse for Rent
12349 Via Derna Place, Windermere, FL 34786

Beautiful large townhome in desirable Windermere/Carrington community. Brand-new flooring! 3 beds/3 full baths with one bedroom and bath on first floor. Granite kitchen with stainless steel appliances. Fenced patio and covered lanai with private garage access. Community pool and cabana just steps away. Enjoy nightly Disney fireworks from the neighborhood. Minutes to Disney Parks, Disney Springs,

Ying Lee WORLD REALTY USA, INC

12349 Via Derna Place, Windermere, FL 34786
/2
$840,000 Sold Oct 17, 2025

4509 Indian Deer Rd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,412 Sq Ft
- Built 2006
Last Sold Summary
- 1% Below List Price
- $348/SF
- 10 Days On Market
Current Estimated Value $818,010

Last Listing Agent Clementine Costantini KELLER WILLIAMS REALTY AT THE LAKES

4509 Indian Deer Rd, Windermere, FL 34786

/2
Est $413,120 Not Listed For Sale

11740 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,569 Sq Ft
- Built 2016
11740 Water Run Aly, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $269/SF
- 26 Days On Market
- Last Sold Price $422,000
- Feb 23, 2025
Last Listing Agent Bryan Burns RE/MAX

Showing Results 281 - 320, Page 8 of 18

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