Windermere, FL Homes

/65
$1,495,000
- 4 Beds
- 4.5 Baths
- 3,399 Sq Ft
12411 Montalcino Cir, Windermere, FL 34786

A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite throughout the home a

Mauro Costa

VISTA CAY REALTY COMPANY

(689) 334-2915

12411 Montalcino Cir, Windermere, FL 34786
/20
$3,960 Per Month
- 4 Beds
- 3 Baths
- 2,970 Sq Ft
- House for Rent
9042 Arbors Edge Trail, Windermere, FL 34786

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

(689) 225-0584

9042 Arbors Edge Trail, Windermere, FL 34786
/2
$580,000 Sold Apr 13, 2026

7451 Fairgrove Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,092 Sq Ft
- Built 2017
Last Sold Summary
- $277/SF
- 51 Days On Market
Current Estimated Value $571,485

Last Listing Agent Lorraine da Silva Andrade TALENT REALTY SOLUTIONS

7451 Fairgrove Ave, Windermere, FL 34786

/2
Est $659,361 Not Listed For Sale

13772 Ingelnook Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,750 Sq Ft
- Built 2013
13772 Ingelnook Dr, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $247/SF
- 4 Days On Market
- Last Sold Price $680,000
- Dec 20, 2024
Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

/54
$717,000
- 4 Beds
- 3.5 Baths
- 2,594 Sq Ft
13519 Bicton Ln, Windermere, FL 34786

Welcome to one of Windermere's most sought-after gated communities — where luxury living meets unbeatable Central Florida convenience. This impeccably maintained 4-bedroom, 3-bathroom home offers nearly 3,000 square feet of thoughtfully designed living space, a 3-car garage, and a brand-new roof and windows, giving buyers peace of mind and long-term value from day one.DISNEY VIEWS & OUTDOOR

Tiphany Weeks

DIAMOND REAL ESTATE GROUP

(407) 974-7651

13519 Bicton Ln, Windermere, FL 34786
/59
$3,900 Per Month
- 4 Beds
- 3.5 Baths
- 2,696 Sq Ft
- House for Rent
13544 Riggs Way, Windermere, FL 34786

Welcome to this beautifully updated home in the highly desirable Enclave at Berkshire Park in Windermere. Situated on an oversized corner lot of approximately .25 acres, this spacious residence offers the perfect combination of comfort, functionality, and curb appeal. Recently refreshed with brand-new interior paint and new carpet throughout, the home also features a newer roof and a spacious

Evan Caulfield STOCKWORTH REALTY GROUP

13544 Riggs Way, Windermere, FL 34786
/2
$1,000,000 Sold Oct 27, 2025

5235 W Lake Butler Rd, Windermere, FL 34786
- Land
- 29,620 Sq Ft
- $1,470,588 per Acre
Last Sold Summary
- 53% Below List Price
- 211 Days On Market
Current Estimated Value $1,035,451

Last Listing Agent Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

5235 W Lake Butler Rd, Windermere, FL 34786

/2
Est $886,183 Not Listed For Sale

8243 Procida Isle Ln, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,226 Sq Ft
- Built 2018
8243 Procida Isle Ln, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $282/SF
- 81 Days On Market
- Last Sold Price $910,000
- Dec 23, 2024
Last Listing Agent Mariana Haddad LA ROSA REALTY LLC

/43
$1,225,000
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
109 E 12th Ave, Windermere, FL 34786

Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to include roof (2018), a/c (2016), plumbing, flooring, drain field

Judy Black

UPSIDE REAL ESTATE INC

(689) 262-5600

109 E 12th Ave, Windermere, FL 34786
/26
$1,399 Per Month
- 1 Bed
- 1 Bath
- 320 Sq Ft
- MOVE IN MAY-Water & electricity included 1x1 above garage apartment!! Full kitchen & bathroom!! W...
14252 Confetti Dr, Windermere, FL 34786

1X1 above garage apartment! Electricity & water included!! MOVE IN MAY!! Call or text Joanne Bracero to schedule a tour! 1x1 apartment above garage offers - 380 sq ft of living space under AC with private entrance. Wonderful full kitchen, full bath, spacious living area, and 1 private bedroom. Washer & dryer in laundry closet. Garage/apartment is detached from the main house. Tenants

14252 Confetti Dr, Windermere, FL 34786
/2
$735,000 Sold Oct 23, 2025

12821 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
- Built 2018
Last Sold Summary
- 2% Below List Price
- $199/SF
- 15 Days On Market
Current Estimated Value $742,335

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12821 Westside Village Loop, Windermere, FL 34786

/37
Est $1,644,412 Not Listed For Sale

1214 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,396 Sq Ft
- Built 2019
1214 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 6% Above List Price
- $353/SF
- 39 Days On Market
- Last Sold Price $1,550,000
- Aug 17, 2023
Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

/82
$2,235,000
- 6 Beds
- 6 Baths
- 5,031 Sq Ft
713 Main St, Windermere, FL 34786

Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove,

Kari Fleck

THE REAL ESTATE COLLECTION LLC

(407) 494-6941

713 Main St, Windermere, FL 34786
/47
$9,999 Per Month
- 3 Beds
- 3 Baths
- 3,255 Sq Ft
- House for Rent
5243 W Lake Butler Rd, Windermere, FL 34786

Experience Lakefront Luxury Living - where every day feels like a vacation. Prepare to be captivated by this fully renovated three-bedroom, three-bath lakefront home on the highly sought-after Lake Butler. Part of the Butler Chain of Lakes, featuring 13 connected lakes. A true retreat that blends resort-style amenities with refined design. Nestled on pristine waterfront, this property offers

Steve Simpson 407 PROPERTIES

5243 W Lake Butler Rd, Windermere, FL 34786
/2
$1,274,000 Sold Mar 27, 2026

12779 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
- Built 2018
Last Sold Summary
- $345/SF
- 5 Days On Market
Current Estimated Value $1,208,859

Last Listing Agent Ramon Brandão WEBB FLORIDA REALTY LLC

12779 Westside Village Loop, Windermere, FL 34786

/62
Est $2,389,847 Not Listed For Sale

13334 Bellaria Cir, Windermere, FL 34786
- 5 Beds
- 7 Baths
- 5,734 Sq Ft
- Built 2014
13334 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $427/SF
- 189 Days On Market
- Last Sold Price $2,450,000
- Jun 27, 2024
Last Listing Agent María Gabriela Lara CENTURY 21 CARIOTI

/32
$1,390,000
- 6 Beds
- 4.5 Baths
- 4,522 Sq Ft
17538 Black Rail St, Windermere, FL 34786

Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage. Located in a desirable

Elaine Garcia

GARCIA REALTY GROUP

(689) 312-9273

17538 Black Rail St, Windermere, FL 34786
/15
$2,100 Per Month
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Townhouse for Rent
8256 Maritime Flag St, Windermere, FL 34786

3 Bedroom 2 Bath First Floor Condo in the gated community of Lakeside at Windermere. Large open Floor plan with Dinning Room, Family Room and Kitchen. Screened in patio. Master Bedroom has attached Bathroom with double vanity, large soaking tub and walk in closet. Club House with Fitness Center, 2 Pools, Sand Volleyball Court and outdoor BBQ areas. 2 Additional Bedrooms with large closets share a

8256 Maritime Flag St, Windermere, FL 34786
/2
$350,000 Sold Feb 04, 2026

7462 Bentonshire Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,480 Sq Ft
- Built 2007
Last Sold Summary
- 9% Below List Price
- $236/SF
- 185 Days On Market
Current Estimated Value $355,334

Last Listing Agent Ivan Petkov FLORIDA REALTY INVESTMENTS

7462 Bentonshire Ave, Windermere, FL 34786

/80
Est $2,517,137 Not Listed For Sale

11628 Waterstone Loop Dr, Windermere, FL 34786
- 5 Beds
- 7 Baths
- 5,161 Sq Ft
- Built 2015
11628 Waterstone Loop Dr, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $475/SF
- 9 Days On Market
- Last Sold Price $2,450,000
- Nov 30, 2023
Last Listing Agent Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

$1,039,091 New Construction
- 4 Beds
- 3 Baths
- 2,740 Sq Ft
14353 Crest Palm Ave, Windermere, FL 34786

Welcome to the Arlington! This single-story floor plan features 4 bedrooms, 3 bathrooms, and a 2-car garage, offering 2,740 square feet of spacious living. Enjoy an open-concept design that seamlessly connects the dining, kitchen, and living areas. The garage also includes an extra hobby/work space. Relax on the large covered patio or create culinary masterpieces in the chef's kitchen. The

Cindy Sapp

OLYMPUS EXECUTIVE REALTY INC

14353 Crest Palm Ave, Windermere, FL 34786
/42
$15,950 Per Month
- 6 Beds
- 8 Baths
- 6,881 Sq Ft
- House for Rent
3999 Isabella Cir, Windermere, FL 34786

Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort. Situated on an expansive half acre lot, this

Lucas DeSouza DELUCA REAL ESTATE SERVICES CORP

3999 Isabella Cir, Windermere, FL 34786
/2
$2,400,000 Sold May 05, 2026

8402 Lake Burden Cir Unit 2, Windermere, FL 34786
- 5 Beds
- 6.5 Baths
- 6,248 Sq Ft
- Built 2004
Last Sold Summary
- 16% Below List Price
- $384/SF
- 163 Days On Market
Current Estimated Value $2,611,181

Last Listing Agent Toni Marie Cafferty COMPASS FLORIDA LLC

8402 Lake Burden Cir Unit 2, Windermere, FL 34786

/2
Est $854,542 Not Listed For Sale

6926 Trellis Vine Loop, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,124 Sq Ft
- Built 2018
6926 Trellis Vine Loop, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $282/SF
- 26 Days On Market
- Last Sold Price $880,000
- Apr 21, 2025
Last Listing Agent DENILEY VALDES TALENT REALTY SOLUTIONS

/44
$489,999 Pending
- 3 Beds
- 2.5 Baths
- 1,996 Sq Ft
13755 Bravante Aly, Windermere, FL 34786

Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 13755 Bravante Aly, Windermere, FL 34786, a charming two story home featuring 3 bedrooms and 2 bathrooms located in a desirable Windermere community. This home offers a

Thomas Nickley

KELLER WILLIAMS REALTY AT THE PARKS

(689) 399-2513

13755 Bravante Aly, Windermere, FL 34786
/21
$2,800 Per Month
- 3 Beds
- 2.5 Baths
- 1,881 Sq Ft
- Townhouse for Rent
7652 Ripplepointe Way, Windermere, FL 34786

Brand new Windermere townhome for rent: 7652 Ripplepointe Way, 3BR/2.5BA...1,881 s/f...$2800moAvailable: NOWFully-equipped, upgraded kitchen offers an island, granite counters and good wood cabinetry and storage space. All major appliances are included (stainless)- and an inside laundry room has a washer/dryer combination for your convenience.Please call with information

7652 Ripplepointe Way, Windermere, FL 34786
/47
$1,069,989 Sold Jan 22, 2026

14427 Crest Palm Ave, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,571 Sq Ft
- Built 2026
Move in Ready Sold Summary
- $234/SF
- 15 Days On Market
Current Estimated Value $1,052,136

Dream Finders Homes Palms at Windermere

14427 Crest Palm Ave, Windermere, FL 34786

/31
Est $407,849 Not Listed For Sale

14237 Desert Haven St, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 1,861 Sq Ft
- Built 2012
14237 Desert Haven St, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $223/SF
- 71 Days On Market
- Last Sold Price $415,000
- Mar 10, 2025
Last Listing Agent Pam Eddy COLDWELL BANKER HUBBARD HANSEN

/30
$1,595,000
- Land
- 2.12 Acres
- $752,358 per Acre
10948 Down Park Ln, Windermere, FL 34786

LAST REMAINING LOT OF THE FOUR IN THIS EXCLUSIVE PRIVATE ESTATE LAKEFRONT COMMUNITY! Rare opportunity to build your dream home in the highly sought after Town of Windermere. This exceptional vacant homesite offers over 2.12 acres and is the largest buildable lot within this private gated enclave of only four estate properties, providing exceptional privacy and generous spacing between homes. The

Andrew Kincaid

BHHS FLORIDA REALTY

(689) 588-0828

10948 Down Park Ln, Windermere, FL 34786
/21
$14,000 Per Month
- 5 Beds
- 5.5 Baths
- 5,507 Sq Ft
- House for Rent
4326 Isabella Cir, Windermere, FL 34786

Welcome to your private luxury retreat in the exclusive gated community of Casabella in Windermere. This exceptional fully furnished estate offers over 5,400 square feet of thoughtfully designed living space, featuring 5 bedrooms, 5.5 bathrooms, and a 3-car garage—perfectly blending elegance, comfort, and functionality. From the moment you arrive, the circular driveway and lush, manicured

Timothy Schmidt RIGHTHOUSE REALTY LLC

4326 Isabella Cir, 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 $1,240,411

Last Listing Agent Rita Schoeffler BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

6720 Winter Garden Vineland Rd, Windermere, FL 34786

/2
Est $1,351,261 Not Listed For Sale

17550 Black Rail St, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 4,908 Sq Ft
- Built 2015
17550 Black Rail St, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $272/SF
- 44 Days On Market
- Last Sold Price $1,335,000
- Dec 09, 2024
Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

/24
$750,000
- 5 Beds
- 4 Baths
- 3,597 Sq Ft
13145 Zori Ln, Windermere, FL 34786

One or more photo(s) has been virtually staged. Priced right and move-in ready! Situated in the Windermere community of Providence, this home offers spacious living across two floors. Upon entering, you are greeted by the formal living and dining rooms. The family room is open to the kitchen for easy entertaining. The primary suite along with three other bedrooms are on the first floor. On the

Toni Marie Cafferty

COMPASS FLORIDA LLC

(689) 265-3814

13145 Zori Ln, Windermere, FL 34786
/22
$4,950 Per Month
- 3 Beds
- 2 Baths
- 2,056 Sq Ft
- Keenes Point - Windermere
8447 Bowden Way, Windermere, FL 34786

Welcome to Keenes Point - Windermere, a stunning 3-bedroom, 2-bathroom home located in the desirable Windermere, FL. This property is nestled within a secure gated community, offering an added layer of peace and security. The home boasts a private pool, perfect for cooling off during those hot Florida summers. The private backyard provides ample space for outdoor activities or simply enjoying the

8447 Bowden Way, Windermere, FL 34786
/2
$975,000 Sold Apr 01, 2026

7545 Lake Albert Dr, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 3,425 Sq Ft
- Built 2008
Last Sold Summary
- 11% Below List Price
- $285/SF
- 158 Days On Market
Current Estimated Value $1,051,472

Last Listing Agent Nicole Mickle OLYMPUS EXECUTIVE REALTY INC

7545 Lake Albert Dr, Windermere, FL 34786

/34
Est $518,823 Not Listed For Sale

13335 Overstreet Rd, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- Built 2013
13335 Overstreet Rd, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $258/SF
- 6 Days On Market
- Last Sold Price $530,000
- Feb 16, 2024
Last Listing Agent Ryan Langley FLORIDA REALTY INVESTMENTS

/81
$2,125,000
- 4 Beds
- 4.5 Baths
- 3,751 Sq Ft
12699 Hawkstone Dr, Windermere, FL 34786

Welcome to Chalet du Lac, set on the exclusive and private Lake Sawyer chain of lakes in Windermere—where mornings are welcomed by sunrise over glistening waters dancing through a veil of Cypress trees and Spanish moss. Nestled along the western shoreline of Lake Sawyer within an enclave of custom-built lakefront homes, Chalet du Lac features 4 bedrooms and 5 baths, lives large at 3751 sq ft

Drew Ross

LAKEFIELD REALTY GROUP LLC

(407) 676-7612

12699 Hawkstone Dr, Windermere, FL 34786
/16
$3,300 Per Month
- 4 Beds
- 2.5 Baths
- 2,439 Sq Ft
- House for Rent
12803 Holdenbury Ln, Windermere, FL 34786

AVAILABLE MAY 7th 2026! House is getting new carpet, new appliances and full interior painting job. Spacious 4-bedroom, 2.5-bath home in the desirable Lakes of Windermere community. This well-designed floor plan features all bedrooms upstairs, with the main floor offering a large living room, formal dining room, office/reading room, and a convenient half bath for guests. The primary suite

Silvia Odebrecht ICON REALTY ASSOCIATES INC

12803 Holdenbury Ln, 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 $1,406,553

Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

8430 Woburn Ct, Windermere, FL 34786

/22
Est $1,031,847 Not Listed For Sale

12525 Montalcino Cir, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,117 Sq Ft
- Built 2013
12525 Montalcino Cir, Windermere, FL 34786

Last Sold Summary
- 4% Above List Price
- $317/SF
- 20 Days On Market
- Last Sold Price $989,000
- Aug 03, 2023
Last Listing Agent MELANIE BIGIO OLYMPUS EXECUTIVE REALTY INC

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