Windermere, FL Homes

/19
$4,276,160 Pending
- 5 Beds
- 6.5 Baths
- 6,401 Sq Ft
1821 Windermere Rd, Windermere, FL 34786

Pre-Construction. To be built. Discover an unparalleled opportunity to acquire a sovereign 1.16-acre estate homesite in the heart of Windermere. This meticulously positioned property, oriented east-west for optimal light, is ensconced within a private setting and borders a permanent conservation area, ensuring absolute privacy and serene, unimpeded vistas. The absence of an HOA affords complete

Matt Matthews ORLANDO TBI REALTY LLC

1821 Windermere Rd, Windermere, FL 34786
/2
$837,000 Sold Jun 05, 2025

6550 Crestmont Glen Ln Unit 1, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 3,282 Sq Ft
- Built 2002
Last Sold Summary
- 8% Below List Price
- $255/SF
- 14 Days On Market
Current Estimated Value $844,143

Last Listing Agent Cheryl Roda-Wu CENTURY 21 BE3

6550 Crestmont Glen Ln Unit 1, Windermere, FL 34786

/2
Est $545,903 Not Listed For Sale

8797 Peachtree Park Ct, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,710 Sq Ft
- Built 2017
8797 Peachtree Park Ct, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $327/SF
- 30 Days On Market
Last Sold Price $560,000

Last Listing Agent Cliff Glansen FLATFEE.COM

/57
$3,400,000
- 4 Beds
- 4 Baths
- 4,877 Sq Ft
9731 Chestnut Ridge Dr, Windermere, FL 34786

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

Monica Lochmandy ISLEWORTH REALTY LLC

9731 Chestnut Ridge Dr, Windermere, FL 34786
/2
$704,000 Sold Sep 18, 2025

1220 Glenheather Dr, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,695 Sq Ft
- Built 2002
Last Sold Summary
- 3% Below List Price
- $261/SF
- 22 Days On Market
Current Estimated Value $707,674

Last Listing Agent Dominick Florio RE/MAX TOWN & COUNTRY REALTY

1220 Glenheather Dr, Windermere, FL 34786

/2
Est $2,345,798 Not Listed For Sale

3992 Isabella Cir, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,339 Sq Ft
- Built 2018
3992 Isabella Cir, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $527/SF
- 114 Days On Market
Last Sold Price $2,287,500

Last Listing Agent Nicole Dege REDFIN CORPORATION

/65
$3,200,000
- 6 Beds
- 6.5 Baths
- 6,308 Sq Ft
13448 Bellaria Cir, Windermere, FL 34786

Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting

Shawn Kennedy KENNEDY REALTY GROUP LLC

13448 Bellaria Cir, Windermere, FL 34786
/2
$4,475,000 Sold Mar 25, 2026

6474 Deacon Cir, Windermere, FL 34786
- 6 Beds
- 5.5 Baths
- 5,853 Sq Ft
- Built 1989
Last Sold Summary
- $765/SF
Current Estimated Value $4,419,224

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

6474 Deacon Cir, Windermere, FL 34786

/2
Est $784,490 Not Listed For Sale

6884 Trellis Vine Loop, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,409 Sq Ft
- Built 2019
6884 Trellis Vine Loop, Windermere, FL 34786

Last Sold Summary
- 5% Below List Price
- $242/SF
- 6 Days On Market
Last Sold Price $825,000

Last Listing Agent Jennifer Mitchell CLOCK TOWER REALTY

/52
$532,000
- 4 Beds
- 2.5 Baths
- 2,048 Sq Ft
8243 Bryce Canyon Ave, Windermere, FL 34786

Beautiful and cozy residence located in the desirable WINDERMERE area. This single-family - bungalow style home offers four bedrooms, two-and-a-half baths and a two-car garage. There's a LOFT UPSTAIRS, perfect for a TV or office/study room. With an open floor plan and ENERGY-EFFICIENT built, the kitchen features stainless steel appliances, overlooking the family room. All bedrooms and family

Cristian Cen Chen SIMPSON REALTY LLC

8243 Bryce Canyon Ave, Windermere, FL 34786
/2
$2,460,000 Sold Dec 18, 2025

11019 Ullswater Ln, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 5,916 Sq Ft
- Built 2006
Last Sold Summary
- 2% Below List Price
- $416/SF
- 23 Days On Market
Current Estimated Value $2,440,826

Last Listing Agent Ken Pozek REAL BROKER, LLC

11019 Ullswater Ln, Windermere, FL 34786

/2
Est $660,403 Not Listed For Sale

7201 Rambling Water Way, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,432 Sq Ft
- Built 2015
7201 Rambling Water Way, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $280/SF
- 8 Days On Market
Last Sold Price $680,000

Last Listing Agent Jacquie Sosa EXP REALTY LLC

/81
$1,620,000
- 4 Beds
- 3.5 Baths
- 4,437 Sq Ft
13734 Lake Cawood Dr, Windermere, FL 34786

NEW PRICE - SELLER MOTIVATED!Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious, thoughtfully designed living with a

Angela Schifano CHARLES RUTENBERG REALTY ORLANDO

13734 Lake Cawood Dr, Windermere, FL 34786
/2
$880,000 Sold Mar 16, 2026

11314 Ledgement Ln Unit 1, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,080 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $286/SF
- 125 Days On Market
Current Estimated Value $919,894

Last Listing Agent Mark Vescio MARK SPAIN REAL ESTATE

11314 Ledgement Ln Unit 1, Windermere, FL 34786

/53
Est $1,084,756 Not Listed For Sale

8799 Crescendo Ave, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,502 Sq Ft
- Built 2015
8799 Crescendo Ave, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $244/SF
- 19 Days On Market
Last Sold Price $1,100,000

Last Listing Agent Karen Costa FLORIDA CAPITAL REALTY

/91
$3,725,000
- 4 Beds
- 4.5 Baths
- 6,054 Sq Ft
12812 Jacob Grace Ct, Windermere, FL 34786

Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined

Alireza Partovi EXP REALTY LLC

12812 Jacob Grace Ct, Windermere, FL 34786
/2
$315,000 Sold Apr 30, 2025

11564 Mizzon Dr Unit 309, Windermere, FL 34786
- 2 Beds
- 2 Baths
- 1,161 Sq Ft
- Built 2006
Last Sold Summary
- 3% Below List Price
- $271/SF
- 135 Days On Market
Current Estimated Value $308,455

Last Listing Agent Matthew DeClue BROKER BRYANT REALTY

11564 Mizzon Dr Unit 309, Windermere, FL 34786

/42
Est $885,706 Not Listed For Sale

11859 Gold Creek Trail, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 3,804 Sq Ft
- Built 2012
11859 Gold Creek Trail, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $239/SF
- 8 Days On Market
Last Sold Price $910,000

Last Listing Agent Flavio Melo BB GROUP REALTY CORP

/23
$399,000
- 3 Beds
- 2.5 Baths
- 1,565 Sq Ft
12879 Emersondale Ave, Windermere, FL 34786

Welcome home to this beautiful END-UNIT 3-bedroom, 2.5-bath townhome, thoughtfully designed to maximize space, comfort, and natural light. With abundant windows throughout, the home is filled with sunshine, creating a bright and inviting atmosphere from the moment you step inside. The open-concept floor plan is ideal for both everyday living and entertaining. Enjoy tile flooring in the kitchen,

Kyle Li UNIONE REALTY INC

12879 Emersondale Ave, Windermere, FL 34786
/2
$508,000 Sold Jan 30, 2026

12860 Penshurst Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
- Built 2003
Last Sold Summary
- 6% Above List Price
- $207/SF
- 3 Days On Market
Current Estimated Value $495,602

Last Listing Agent Jeffrey Funk EXP REALTY LLC

12860 Penshurst Ln, Windermere, FL 34786

/2
Est $445,207 Not Listed For Sale

8673 Coventry Park Way, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,760 Sq Ft
- Built 2016
8673 Coventry Park Way, Windermere, FL 34786

Last Sold Summary
- 5% Below List Price
- $267/SF
- 101 Days On Market
Last Sold Price $470,000

Last Listing Agent Yogini Bhave CHARLES RUTENBERG REALTY ORLANDO

/49
$709,999 Pending
- 4 Beds
- 3.5 Baths
- 2,699 Sq Ft
13912 Darchance Rd, Windermere, FL 34786

Beautifully updated home with peaceful pond views from the front creates an idyllic setting to call home. High end finishes can be found throughout including: engineered white oak hardwood floors, designer light fixtures, fully remodeled transitional kitchen with quartz counters and stainless steel appliances, luxuriously updated baths, laundry room, and family room with custom built ins and

Hojin Chang RE/MAX PRIME PROPERTIES

13912 Darchance Rd, Windermere, FL 34786
/2
$650,000 Sold Jun 16, 2025

7036 Mapperton Dr, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 2,777 Sq Ft
- Built 2003
Last Sold Summary
- 14% Below List Price
- $234/SF
- 209 Days On Market
Current Estimated Value $645,088

Last Listing Agent Leila Ferrara WRA BUSINESS & REAL ESTATE

7036 Mapperton Dr, Windermere, FL 34786

/2
Est $3,404,559 Not Listed For Sale

5006 Sawyer Cove Way, Windermere, FL 34786
- 4 Beds
- 7 Baths
- 5,727 Sq Ft
- Built 2018
5006 Sawyer Cove Way, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $611/SF
- 1 Day On Market
Last Sold Price $3,500,000

Last Listing Agent Shawna Tree MEGAN DOWDY REALTY, LLC

/31
$565,000 Pending
- 4 Beds
- 2 Baths
- 2,063 Sq Ft
9056 Woodbreeze Blvd, Windermere, FL 34786

One or more photo(s) has been virtually staged. Stop searching and start living in your private Windermere oasis at 9056 Woodbreeze Blvd. Nestled on a premium lot in the sought-after Silver Woods community, this home offers a rare level of privacy with no rear neighbors, a peaceful pond backdrop, and only one adjacent neighbor. From the moment you enter, soaring vaulted ceilings and sleek,

Ryan Solberg MAXLIFE REALTY LLC

9056 Woodbreeze Blvd, Windermere, FL 34786
/2
$9,000,000 Sold Oct 06, 2025

9832 Laurel Valley Dr, Windermere, FL 34786
- 6 Beds
- 10 Baths
- 11,100 Sq Ft
- Built 2004
Last Sold Summary
- 3% Below List Price
- $811/SF
- 0 Days On Market
Current Estimated Value $8,751,145

Last Listing Agent Dianna Desboyaux DOUGLAS ELLIMAN

9832 Laurel Valley Dr, Windermere, FL 34786

/21
Est $768,319 Not Listed For Sale

8736 Peachtree Park Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,775 Sq Ft
- Built 2017
8736 Peachtree Park Ct, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $284/SF
- 172 Days On Market
Last Sold Price $789,000

Last Listing Agent Michael Velasquez THE SIMON SIMAAN GROUP

/47
$900,000 Open Sat 2PM - 4PM
- 3 Beds
- 2 Baths
- 2,386 Sq Ft
4 Chase Rd, Windermere, FL 34786

FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge.Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to

Matthew Hughes REAL BROKER, LLC

4 Chase Rd, Windermere, FL 34786
/2
$2,350,000 Sold Oct 21, 2025

10121 Lone Tree Ln, Orlando, FL 32836
- 3 Beds
- 2 Baths
- 2,348 Sq Ft
- Built 1968
Last Sold Summary
- 6% Below List Price
- $1,001/SF
- 0 Days On Market
Current Estimated Value $2,360,845

Last Listing Agent Ursula Garcia Moraes PRISTINE INTERNATIONAL REALTY LLC

10121 Lone Tree Ln, Orlando, FL 32836

/2
Est $521,576 Not Listed For Sale

6322 Golden Dewdrop Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,136 Sq Ft
- Built 2012
6322 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $247/SF
- 64 Days On Market
Last Sold Price $527,500

Last Listing Agent James Martinez CHARLES RUTENBERG REALTY ORLANDO

/91
$3,950,000
- 6 Beds
- 7 Baths
- 5,709 Sq Ft
12132 Montalcino Cir, Windermere, FL 34786

Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.The gourmet kitchen features custom dark cabinetry, quartz

Caroline Perotti BELLA VIEW REALTY LLC

12132 Montalcino Cir, Windermere, FL 34786
/2
$1,700,000 Sold Oct 10, 2025

830 Oakdale St, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,670 Sq Ft
- Built 2019
Last Sold Summary
- 13% Below List Price
- $463/SF
- 320 Days On Market
Current Estimated Value $1,709,019

Last Listing Agent Jay Martin CORCORAN PREMIER REALTY

830 Oakdale St, Windermere, FL 34786

/2
Est $1,237,039 Not Listed For Sale

6020 Golden Dewdrop Trail, Windermere, FL 34786
- 8 Beds
- 5 Baths
- 4,740 Sq Ft
- Built 2012
6020 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- 8% Above List Price
- $243/SF
- 30 Days On Market
Last Sold Price $1,150,000

Last Listing Agent Rick Brown KELLER WILLIAMS ADVANTAGE 2 REALTY

/39
$449,980 Open Fri 4PM - 6PM
- 3 Beds
- 2.5 Baths
- 1,767 Sq Ft
13369 Gorgona Isle Dr, Windermere, FL 34786

Back on the Market! The Buyer was not able to obtain financing; you now have a new opportunity to own this gorgeous Townhome! Wow! Gorgeous, newly updated three-bedroom luxury townhome with a scenic water and fountain view. This spacious, light-filled home is open, bright, clean and move-in ready. This home features a new HVAC system with programmable thermostat, new flooring, trim and fresh

Wendy Fischer PREMIER SOTHEBYS INT'L REALTY

13369 Gorgona Isle Dr, Windermere, FL 34786
/2
$387,000 Sold May 15, 2025

8612 Brookvale Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,516 Sq Ft
- Built 2013
Last Sold Summary
- 3% Below List Price
- $255/SF
- 28 Days On Market
Current Estimated Value $376,436

Last Listing Agent Rafael Fernandez AGENT TRUST REALTY CORPORATION

8612 Brookvale Dr, Windermere, FL 34786

/2
Est $557,990 Not Listed For Sale

8014 Jailene Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,322 Sq Ft
- Built 2012
8014 Jailene Dr, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $250/SF
- 5 Days On Market
Last Sold Price $580,000

Last Listing Agent Tina St Clair ST. CLAIR REALTY GROUP, LLC

/83
$7,595,000
- 5 Beds
- 6.5 Baths
- 6,937 Sq Ft
5074 Isleworth Country Club Dr, Windermere, FL 34786

Luxury living perfectly positioned along the 6th fairway in the world-renowned guard-gated community of Isleworth. This exceptional estate offers over 6,900 square feet of completely remodeled space which includes over 2,400 square foot addition upstairs thoughtfully reimagined by acclaimed architect Mark Nasrallah. Featuring 5 bedrooms and 6.5 bathrooms, the home sits on over half an acre and

Armaan Memarpouri MEMARPOURI REALTY LLC

5074 Isleworth Country Club Dr, Windermere, FL 34786
/2
$1,710,000 Sold Jan 16, 2026

7417 Lake Albert Dr, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 5,006 Sq Ft
- Built 2014
Last Sold Summary
- 1% Above List Price
- $342/SF
- 80 Days On Market
Current Estimated Value $1,668,442

Last Listing Agent Dan Palmer TEAM DONOVAN

7417 Lake Albert Dr, Windermere, FL 34786

/2
Not Listed For Sale

8136 Serenity Spring Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
- Built 2013
8136 Serenity Spring Dr, Windermere, FL 34786

Last Sold Summary
- $207/SF
- 63 Days On Market
Last Sold Price $380,000

Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

/15
$490,000
- 3 Beds
- 2.5 Baths
- 1,977 Sq Ft
6310 Golden Dewdrop Trail, Windermere, FL 34786

Windermere Landings, Highly desirable community, only five minutes from downtown Windermere, and great school district. Beautiful two story home, Three bedroom Two and half bath with upstairs loft space for a home office. The Kitchen has overlooking the great family room and dining room.wood cabinets, granite countertops, an island, and counter height bar seating. A/C unit was replaced in 2019

Mengshi Lu JOY ESTATE ENTERPRISE INC

6310 Golden Dewdrop Trail, Windermere, FL 34786

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Windermere, FL Homes

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