Homes in ZIP Code 34786

/72
$2,500,000
- 5 Beds
- 5.5 Baths
- 5,696 Sq Ft
105 Pine St, Windermere, FL 34786

Extraordinary multigenerational living opportunity in the Town of Windermere, where mature oak trees and a quiet, established setting create a true sense of place just moments from the Butler Chain of Lakes. Set on an oversized, over half-acre corner lot in downtown Windermere, this custom home offers a rare blend of privacy, flexibility, and walkability to local dining, coffee shops, boutiques,

Tiffany Pantozzi

ALIGN REAL ESTATE LLC

(689) 334-1402

105 Pine St, 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

/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
/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

/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
/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
$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

/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
/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

/39
$1,460,000
- 4 Beds
- 3.5 Baths
- 3,844 Sq Ft
2509 Ridgewind Way, Windermere, FL 34786

Welcome to 2509 Ridgewind Way, a timeless Southern estate tucked inside the gates of The Estates at Windermere—one of Windermere’s most beloved communities known for its oak-lined streets, oversized lots, and quiet charm. Set on a rare .75-acre homesite, this beautifully updated residence blends classic architecture with the functionality today’s buyers are searching for. A wraparound front

Hilary Hall

COMPASS FLORIDA LLC

(689) 329-2224

2509 Ridgewind Way, 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
/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

/56
$595,000
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
6382 Golden Dewdrop Trail, Windermere, FL 34786

Ideally situated within WINDERMERE LANDINGS and in close proximity to highly rated schools, convenience stores, restaurants, golf courses & other amenities, this IMMACULATELY presented 3 bedroom and 2.5 bath property with 2 car garage and private driveway is a true GEM with its stunning curb appeal and TURNKEY presentation! On approach the front porch feels inviting with its welcoming entryway

Alice Anne Jackson

CORCORAN PREMIER REALTY

(689) 308-0830

6382 Golden Dewdrop Trail, 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

/61
$1,450,000
- 6 Beds
- 4.5 Baths
- 3,463 Sq Ft
11617 Camden Park Dr, Windermere, FL 34786

Welcome to one of Central Florida’s premier guard-gated golf communities. This impeccably maintained, move-in ready residence showcases refined finishes throughout, including tile and laminate flooring (no carpet), crown molding in every room, and upgraded designer lighting. An abundance of space with 6 bedrooms and 4 1/2 baths. The living room is enhanced by striking wood-look tiled accent

Carla Robles

WATSON REALTY CORP

(689) 329-3288

11617 Camden Park Dr, 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
/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

/98
$3,299,000 Pending
- 6 Beds
- 8 Baths
- 7,217 Sq Ft
4029 Isabella Cir, Windermere, FL 34786

Under contract-accepting backup offers. Experience an architectural masterpiece in the gated enclave of Casabella. Situated on a rare, oversized .85-acre lot, this estate has been transformed by the original owner with impeccable attention to detail. The interior features 6 beds, 6 full and 2 half baths, all the high-scratch-resistant flooring throughout the home comes in a beautiful white oak

Mauro Costa

VISTA CAY REALTY COMPANY

(407) 584-1756

4029 Isabella Cir, 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

/49
$755,000 Pending
- 4 Beds
- 3.5 Baths
- 2,628 Sq Ft
7519 Brofield Ave, Windermere, FL 34786

Under contract-accepting backup offers. Experience the best of Florida living in this home located in the sought-after Lake Sawyer community in Windermere. Offering a perfect blend of comfort, style, and functionality, this residence is ideal for both everyday living and entertaining.The first floor features a well-designed layout with separate formal and family room areas, while still

Carlos German

EXP REALTY LLC

(407) 479-4656

7519 Brofield Ave, Windermere, FL 34786
/10
$2,300 Per Month
- 3 Beds
- 2.5 Baths
- 1,460 Sq Ft
- House for Rent
8265 Maritime Flag St, Windermere, FL 34786

Now Leasing: 3BR/2.5BA Townhome in Amenity-Rich Lakeside Community - Just Minutes from Disney!This beautiful 3-bedroom, 2.5-bath townhome is officially on the market and won't last long. Located in the highly desirable, amenity-rich Lakeside community, this gated property offers the perfect blend of comfort, convenience, and lifestyle.The monthly rent includes water and access to

8265 Maritime Flag St, 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

/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
/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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