Windermere, FL Homes

/51
Est $638,679 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,236 Sq Ft
13786 Summer Harbor Ct, Windermere, FL 34786

13786 Summer Harbor Ct, Windermere, FL 34786

/15
$510,000
- 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
/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
Last Listing Agent Jeffrey Funk EXP REALTY LLC

12860 Penshurst Ln, Windermere, FL 34786

/36
Est $881,090 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,051 Sq Ft
7242 Rambling Water Way, Windermere, FL 34786

7242 Rambling Water Way, Windermere, FL 34786

/81
$2,970,000
- 5 Beds
- 4 Baths
- 3,737 Sq Ft
10203 Trout Rd, Orlando, FL 32836

Discover this exquisite lakefront property nestled on over 1.9 acres with more than 100 feet of water frontage on LAKE TIBET and part of the Butler Chain of Lakes. This home offers breathtaking views and absolutely stunning sunsets. As you drive onto the winding paver circular driveway with lovely fountain and beautiful landscaping, you will notice the terracotta tile roof and the undeniable

Darlene O'Hara HOMEVEST REALTY

10203 Trout Rd, Orlando, FL 32836
/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 $643,919

Last Listing Agent Leila Ferrara WRA BUSINESS & REAL ESTATE

7036 Mapperton Dr, Windermere, FL 34786

/55
Est $580,033 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,126 Sq Ft
6820 Merrick Landing Blvd, Windermere, FL 34786

6820 Merrick Landing Blvd, Windermere, FL 34786

/100
$14,250,000
- 5 Beds
- 5.5 Baths
- 9,511 Sq Ft
5525 Isleworth Country Club Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over

Monica Lochmandy ISLEWORTH REALTY LLC

5525 Isleworth Country Club Dr, 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 $8,776,111

Last Listing Agent Dianna Desboyaux DOUGLAS ELLIMAN

9832 Laurel Valley Dr, Windermere, FL 34786

/2
Est $425,872 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,722 Sq Ft
11866 Water Run Aly, Windermere, FL 34786

11866 Water Run Aly, Windermere, FL 34786

/24
$440,000 Pre-Foreclosure
- 3 Beds
- 2.5 Baths
- 1,948 Sq Ft
7411 Ripplepointe Way, Windermere, FL 34786

Welcome to this impeccably maintained Windermere townhome that perfectly combines modern finishes, elegant design, and an unbeatable location. Step inside to a grand entryway that opens to a flexible space, ideal for a home office, reading nook, or even a fourth bedroom. The spacious kitchen features ample cabinetry, a generous island with seating, and a cozy built in dining area perfect for

John Cunningham KELLER WILLIAMS CLASSIC

7411 Ripplepointe Way, 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 $2,357,177

Last Listing Agent Ursula Garcia Moraes PRISTINE INTERNATIONAL REALTY LLC

10121 Lone Tree Ln, Orlando, FL 32836

/23
Est $570,786 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,950 Sq Ft
11486 Misty Oak Aly, Windermere, FL 34786

11486 Misty Oak Aly, Windermere, FL 34786

/44
$1,599,000
- 5 Beds
- 5 Baths
- 3,520 Sq Ft
6001 Caymus Loop, Windermere, FL 34786

Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect blend of elegance and modern convenience.

Stella Freeman QUATTRO R E SOLUTIONS LLC

6001 Caymus Loop, 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 $1,735,770

Last Listing Agent Jay Martin CORCORAN PREMIER REALTY

830 Oakdale St, Windermere, FL 34786

/28
Est $434,539 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,441 Sq Ft
13303 Gorgona Isle Dr, Windermere, FL 34786

13303 Gorgona Isle Dr, Windermere, FL 34786

/43
$327,000
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
8179 Maritime Flag St Unit 202-108, Windermere, FL 34786

Welcome to Lakeside at Lakes of Windermere! This beautifully updated first-floor condo combines comfort, style, and convenience?located just minutes from the Disney parks and directly across the street from Lakeside Village Center, offering shopping, dining, and everyday amenities. Step inside to find luxury vinyl flooring in all bedrooms with no carpet, fresh interior paint, and elegant crown

Naf Zaman THE FIRM RE

8179 Maritime Flag St Unit 202-108, 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 $379,378

Last Listing Agent Rafael Fernandez AGENT TRUST REALTY CORPORATION

8612 Brookvale Dr, Windermere, FL 34786

/2
Est $442,589 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,881 Sq Ft
11405 Brownstone St, Windermere, FL 34786

11405 Brownstone St, Windermere, FL 34786

/28
$2,175,000 New Construction
- 4 Beds
- 5 Baths
- 3,136 Sq Ft
436 E 7th Ave, Windermere, FL 34786

Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full

DENILEY VALDES TALENT REALTY SOLUTIONS

436 E 7th Ave, 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
Last Listing Agent Dan Palmer TEAM DONOVAN

7417 Lake Albert Dr, Windermere, FL 34786

/2
Est $480,852 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,212 Sq Ft
7653 Ripplepointe Way, Windermere, FL 34786

7653 Ripplepointe Way, Windermere, FL 34786

/26
$4,395,000
- Land
- 1 Acre
- $4,395,000 per Acre
12418 Park Ave, Windermere, FL 34786

WELCOME TO PARK AVENUE. An extraordinary opportunity awaits on 1 acre of prime lakefront with coveted southeastern exposure and sweeping panoramic views. Perfectly positioned along the pristine shoreline of Lake Butler on the renowned Butler Chain of Lakes, this exclusive homesite is located within one of Windermere’s most desirable gated enclaves—Chaine Du Lac. Offering the rare distinction of

Michael Julian JULIAN PROPERTIES, INC.

12418 Park Ave, Windermere, FL 34786
/2
$355,000 Sold Jun 13, 2025

8933 Newmarket Dr, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,336 Sq Ft
- Built 2006
Last Sold Summary
- 10% Below List Price
- $266/SF
- 74 Days On Market
Current Estimated Value $349,963

Last Listing Agent Jenna Palmero COLDWELL BANKER REALTY

8933 Newmarket Dr, Windermere, FL 34786

/61
Est $1,054,977 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 4,176 Sq Ft
8361 Torcello Isle Dr, Windermere, FL 34786

8361 Torcello Isle Dr, Windermere, FL 34786

/45
$912,000
- 4 Beds
- 3.5 Baths
- 3,315 Sq Ft
8724 Peachtree Park Ct, Windermere, FL 34786

Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designed home in one of Windermere’s most sought-after hidden gems. With bonus spaces including a loft, mudroom, screened outdoor patio that goes around the house and a well-appointed this residence offers both refined living and everyday practicality. Experience the magic of Windermere living at Peachtree Park, a

Marcelo Machado LA ROSA REALTY LLC

8724 Peachtree Park Ct, Windermere, FL 34786
/2
$710,000 Sold Nov 25, 2025

9631 Hollyglen Place, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,854 Sq Ft
- Built 1979
Last Sold Summary
- 5% Below List Price
- $249/SF
- 14 Days On Market
Last Listing Agent Hilary Hall COMPASS FLORIDA LLC

9631 Hollyglen Place, Windermere, FL 34786

/40
Est $529,326 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,107 Sq Ft
13856 Summerport Trail Loop, Windermere, FL 34786

13856 Summerport Trail Loop, Windermere, FL 34786

/46
$585,000 Open Sat 1PM - 4PM
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
6442 Golden Dewdrop Trail, Windermere, FL 34786

Come see this beautiful place. This immaculate home features include over 2,100 square feet of living space, a desirable Kitchen with 42" Cabinets and Granite, Stainless Steel Appliances, Beautiful Backsplash, engineered hardwood flooring on the first floor, vinyl on the second floor, ceramic tile in bathrooms and laundry, screened-in patio porch with a ceiling fan, an elegant courtyard, and much

Yindy Reyes EMPIRE NETWORK REALTY

6442 Golden Dewdrop Trail, Windermere, FL 34786
/2
$435,000 Sold Jan 01, 2026

13775 Bressler Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,001 Sq Ft
- Built 2019
Last Sold Summary
- 7% Below List Price
- $217/SF
- 84 Days On Market
Last Listing Agent Sonia Frederick BAHIA INTERNATIONAL REALTY

13775 Bressler Aly, Windermere, FL 34786

/43
Est $772,976 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,419 Sq Ft
8711 Lookout Pointe Dr, Windermere, FL 34786

8711 Lookout Pointe Dr, Windermere, FL 34786

/35
$444,000
- 3 Beds
- 2.5 Baths
- 1,589 Sq Ft
13366 Abuela Aly, Windermere, FL 34786

Welcome to this pristine, like-new residence at 13366 Abuela Aly, Windermere. This home is impeccably maintained and features no carpeting: ceramic tile spans the entire first floor, while the staircase and second floor are finished with elegant laminate or hardwood flooring. The property boasts quartz countertops, numerous premium upgrades by the owner, and stainless steel appliances, including

Alexandra Mateu BAHIA INTERNATIONAL REALTY

13366 Abuela Aly, Windermere, FL 34786
/2
$819,500 Sold Jun 13, 2025

2151 Tillman Ave, Winter Garden, FL 34787
- 5 Beds
- 4 Baths
- 3,506 Sq Ft
- Built 2007
Last Sold Summary
- 4% Below List Price
- $234/SF
- 41 Days On Market
Current Estimated Value $817,083

Last Listing Agent Andy Neal THE AGENCY FL

2151 Tillman Ave, Winter Garden, FL 34787

/37
Est $457,050 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,756 Sq Ft
13477 Gorgona Isle Dr, Windermere, FL 34786

13477 Gorgona Isle Dr, Windermere, FL 34786

/53
$1,025,000 Pending
- 4 Beds
- 3.5 Baths
- 2,971 Sq Ft
1804 Maple Leaf Dr, Windermere, FL 34786

Experience refined living at 1804 Maple Leaf Drive, an impeccably maintained corner-lot residence nestled in the highly sought-after community of Windermere Downs. Offering nearly 3,000 square feet of thoughtful design, this light-filled home features hardwood floors, solid wood cabinetry, and an inviting layout perfect for both entertaining and everyday comfort. With 4 spacious bedrooms, 3.5

Anna McIntyre LAKESIDE REALTY WINDERMERE INC

1804 Maple Leaf Dr, Windermere, FL 34786
/2
$835,000 Sold Jul 03, 2025

2538 Carter Grove Cir, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,523 Sq Ft
- Built 1996
Last Sold Summary
- 3% Below List Price
- $331/SF
- 8 Days On Market
Current Estimated Value $839,358

Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

2538 Carter Grove Cir, Windermere, FL 34786

/95
Est $866,785 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,407 Sq Ft
11947 Otterbrooke Trail, Windermere, FL 34786

11947 Otterbrooke Trail, Windermere, FL 34786

/66
$3,699,000
- 3 Beds
- 5 Baths
- 4,262 Sq Ft
4812 Alexandra Garden Ct, Windermere, FL 34786

Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a private courtyard

Rob Rahter STOCKWORTH REALTY GROUP

4812 Alexandra Garden Ct, Windermere, FL 34786
/2
$1,349,000 Sold May 02, 2025

11748 Waterstone Loop Dr, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,235 Sq Ft
- Built 2012
Last Sold Summary
- 10% Below List Price
- $417/SF
- 59 Days On Market
Current Estimated Value $1,365,997

Last Listing Agent Immu Korvenmaa ALIGN REAL ESTATE LLC

11748 Waterstone Loop Dr, Windermere, FL 34786

/42
Est $730,246 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,935 Sq Ft
11813 Cave Run Ave, Windermere, FL 34786

11813 Cave Run Ave, Windermere, FL 34786

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