Windermere, FL Homes

/40
$3,390,000
- 4 Beds
- 4.5 Baths
- 3,365 Sq Ft
5050 Isleworth Country Club Dr, Windermere, FL 34786

Situated on the 6th fairway along the course of Isleworth Golf & Country Club, this updated golf front sparkles with new porcelain tile throughout and modern chandeliers. This single-story residence was renovated in 2020 featuring a new tile roof, fresh paint inside and out, all bathrooms updated and a fully renovated kitchen. Spanning over 3,300 square feet, the 4-bedroom, 4.5-bath is nestled in

Toni Marie Cafferty

COMPASS FLORIDA LLC

(407) 807-6191

5050 Isleworth Country Club Dr, 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
$670,000 Sold Nov 14, 2025

2015 Woody Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,042 Sq Ft
- Built 1978
Last Sold Summary
- 4% Below List Price
- $328/SF
- 28 Days On Market
Current Estimated Value $679,631

Last Listing Agent Darrell Nunnelley VINTAGE REALTY GROUP LLC

2015 Woody Dr, Windermere, FL 34786

/40
Est $528,909 Not Listed For Sale

12160 Canyon Sun Trail, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,184 Sq Ft
- Built 2015
12160 Canyon Sun Trail, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $259/SF
- 2 Days On Market
- Last Sold Price $565,000
- May 23, 2024
Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

/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
/45
$2,795 Per Month
- 3 Beds
- 2.5 Baths
- 2,203 Sq Ft
- House for Rent
13040 Overstreet Rd, Windermere, FL 34786

Beautiful 3-Bedroom Home in Windermere Sound – Prime Location with Top-Rated Schools. Owner spent more than 10K to upgrade and add a screened porch! Welcome to this gorgeous 3-bedroom single-family home located in the highly desirable Windermere Sound community, known for its top-rated schools and exceptional lifestyle. This home offers the perfect blend of comfort, convenience, and community

Amanda Yuan MULTI CHOICE REALTY LLC

13040 Overstreet Rd, Windermere, FL 34786
/2
$680,000 Sold Feb 20, 2026

4825 Palm Tree Ct, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,100 Sq Ft
- Built 1985
Last Sold Summary
- $324/SF
- 9 Days On Market
Current Estimated Value $673,829

Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

4825 Palm Tree Ct, Windermere, FL 34786

/2
Est $590,733 Not Listed For Sale

11560 Ashlin Park Blvd, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,270 Sq Ft
- Built 2015
11560 Ashlin Park Blvd, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $262/SF
- 32 Days On Market
- Last Sold Price $595,000
- Apr 14, 2025
Last Listing Agent Matt Allen MATT ALLEN REAL ESTATE LLC

/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
/24
$2,900 Per Month
- 4 Beds
- 3 Baths
- 2,362 Sq Ft
- Elegant 4-bedroom 3-bathroom Home in Windermere
4835 Blue Major Dr, Windermere, FL 34786

Discover refined Florida living in this elegant 4-bed, 3-bath home ( 2,362 sq ft) in Windermere. Built in 2005 on a nearly 8,000 sq ft lot, this residence features hardwood flooring, a detached 2-car garage, and an open, sunlit floor plan. Nestled in the highly desirable 34786 zip code, it offers both the charm of suburban tranquility and the convenience of top-rated nearby schools. Your

4835 Blue Major Dr, Windermere, FL 34786
/2
$550,000 Sold Sep 30, 2025

5238 Beach River Rd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,414 Sq Ft
- Built 2004
Last Sold Summary
- $228/SF
- 3 Days On Market
Current Estimated Value $550,813

Last Listing Agent Liza Farzati SERHANT

5238 Beach River Rd, Windermere, FL 34786

/67
Est $1,607,870 Not Listed For Sale

1220 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 4,007 Sq Ft
- Built 2018
1220 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 5% Above List Price
- $381/SF
- 72 Days On Market
- Last Sold Price $1,525,000
- Jan 26, 2024
Last Listing Agent Angela Rodriguez DREAM FINDERS REALTY GROUP CORP

/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
/29
$2,400 Per Month
- 2 Beds
- 2.5 Baths
- 1,510 Sq Ft
- Townhouse for Rent
12335 Cruxbury Dr, Windermere, FL 34786

Discover this spacious 2-bedroom, 2.5-bath end-unit townhome nestled in a charming Windermere community known for itstree-lined streets, sidewalks, and beautiful canopied trees. Step inside to find brand new carpet throughout and a functional layout featuring alarge kitchen and great room, plus an additional flex space at the front of the home—perfect for a home office or playroom. The

Andy Neal THE AGENCY FL

12335 Cruxbury Dr, Windermere, FL 34786
/2
$620,000 Sold Apr 24, 2026

6846 Helmsley Cir, Windermere, FL 34786
- 5 Beds
- 3 Baths
- 2,555 Sq Ft
- Built 2009
Last Sold Summary
- 11% Below List Price
- $243/SF
- 154 Days On Market
Last Listing Agent Nickolas Amburgey COMPASS FLORIDA LLC

6846 Helmsley Cir, Windermere, FL 34786

/17
Est $652,640 Not Listed For Sale

1348 Lake Olivia Ln, Windermere, FL 34786
- Built 2018
1348 Lake Olivia Ln, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $132/SF
- 530 Days On Market
- Last Sold Price $669,000
- Sep 25, 2023
Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

/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
/30
$2,450 Per Month
- 3 Beds
- 2 Baths
- 1,332 Sq Ft
- Condo for rent
8277 Maritime Flag St Unit 1315, Windermere, FL 34786

Lakeside At Lakes Of Windermere Community: 3/2 condo for rent located in the desirable Windermere, Florida area. This beautifully maintained second-floor condo offers 3 spacious bedrooms and 2 full bathrooms, providing plenty of room for comfortable living. The open-concept layout features a bright and airy living space, perfect for relaxing or entertaining. The kitchen is

8277 Maritime Flag St Unit 1315, Windermere, FL 34786
/2
$1,318,000 Sold May 01, 2026

1625 Down Lake Dr, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 3,383 Sq Ft
- Built 1984
Last Sold Summary
- 6% Below List Price
- $390/SF
- 48 Days On Market
Current Estimated Value $1,374,479

Last Listing Agent Cindy Rosenbloom THE ROSENBLOOM TEAM

1625 Down Lake Dr, Windermere, FL 34786

/2
Est $513,410 Not Listed For Sale

6315 Golden Dewdrop Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
- Built 2012
6315 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $252/SF
- 46 Days On Market
- Last Sold Price $500,000
- Aug 30, 2024
Last Listing Agent Sandy Jones CLOCK TOWER REALTY

/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
/39
$2,600 Per Month
- 3 Beds
- 2 Baths
- 1,706 Sq Ft
- Townhouse for Rent
5513 Somersby Rd, Windermere, FL 34786

Available June 10, 2026! Schedule a showing for this charming 3 bed 2 bath with a loft today!2 car garage and wonderfully maintained!Located in the beautiful town of Windermere in SummerPort; this community features lake access, beautiful tree lined streets, fitness center, playground, pool, tennis courts, basketball courts, park and clubhouse!Lawn care included in rent.Tenant

Jennifer Linton METRO CITY REALTY

5513 Somersby Rd, Windermere, FL 34786
/2
$2,404,000 Sold Jan 15, 2026

1724 Windermeredown Place, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,000 Sq Ft
- Built 1995
Last Sold Summary
- 4% Below List Price
- $401/SF
- 46 Days On Market
Current Estimated Value $2,336,797

Last Listing Agent Chad Going SERHANT

1724 Windermeredown Place, Windermere, FL 34786

/2
Est $3,103,363 Not Listed For Sale

4124 Isabella Cir, Windermere, FL 34786
- 6 Beds
- 8 Baths
- 6,842 Sq Ft
- Built 2016
4124 Isabella Cir, Windermere, FL 34786

Last Sold Summary
- 7% Below List Price
- $490/SF
- 59 Days On Market
- Last Sold Price $3,350,000
- Aug 05, 2024
Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

/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
/27
$2,500 Per Month
- 3 Beds
- 2.5 Baths
- 1,480 Sq Ft
- Townhouse for Rent
12965 Langstaff Dr, Windermere, FL 34786

Welcome to this stunning 3-bedroom, 2.5-bathroom townhome in a serene community near a conservation area. Enjoy the beauty of all-flooring living, a renovated kitchen with stainless steel appliances, and a charming courtyard. With a two-space garage, quiet neighborhood, and proximity to excellent schools and central location, this townhome offers both tranquility and convenience.

12965 Langstaff Dr, Windermere, FL 34786
/2
$1,655,000 Sold Aug 15, 2025

1424 Kelso Blvd, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 3,104 Sq Ft
- Built 1975
Last Sold Summary
- 12% Below List Price
- $533/SF
- 112 Days On Market
Current Estimated Value $1,745,337

Last Listing Agent Carmen Aridas RE/MAX PRIME PROPERTIES

1424 Kelso Blvd, Windermere, FL 34786

/43
Est $530,466 Not Listed For Sale

11650 Black Rail St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- Built 2012
11650 Black Rail St, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $243/SF
- 1 Day On Market
- Last Sold Price $520,000
- Jun 10, 2024
Last Listing Agent Julie Fernandez OAK AVENUE REAL ESTATE LLC

/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
/48
$2,900 Per Month
- 4 Beds
- 2.5 Baths
- 1,638 Sq Ft
- Condo for Rent
14200 Oasis Cove Blvd Unit 3301, Windermere, FL 34786

Amazing opportunity to live in the exclusive and highly desirable Windermere area! This stunning corner townhouse in the sought-after gated community of Oasis Cove features 4 spacious bedrooms and 2.5 bathrooms, offering an abundance of natural light and a functional layout. The home boasts a beautiful lake view that provides a serene backdrop for daily living, complemented by a private fenced

Carola Garcia De Montenegro AGENT TRUST REALTY CORPORATION

14200 Oasis Cove Blvd Unit 3301, Windermere, FL 34786
/2
$718,000 Sold Oct 20, 2025

12755 Westside Village Loop, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,064 Sq Ft
- Built 2018
Last Sold Summary
- 12% Below List Price
- $234/SF
- 142 Days On Market
Current Estimated Value $721,142

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12755 Westside Village Loop, Windermere, FL 34786

/59
Est $2,706,745 Not Listed For Sale

13340 Bellaria Cir, Windermere, FL 34786
- 6 Beds
- 8 Baths
- 6,803 Sq Ft
- Built 2015
13340 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 6% Above List Price
- $375/SF
- 5 Days On Market
- Last Sold Price $2,550,000
- Dec 18, 2023
Last Listing Agent Matt Tomaszewski CORCORAN PREMIER REALTY

$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
/2
$2,100 Per Month
- 2 Beds
- 2.5 Baths
- 1,250 Sq Ft
- Townhouse for Rent
13014 Langstaff Dr, Windermere, FL 34786

COMING SOON! Beautiful 2 bed 2.5 Bath Townhouse, Living Room Area, Breakfast Area. Make an Offer! Apply Today!MORE PHOTOS COMING SOON!If you would like to view this home, and TO SCHEDULE A SHOWING PLEASE EMAIL US AT FOR AVAILABLE SHOW TIMES. Please send us your Name, Phone Contact and Email Address. All Showings are done on Monday thru Friday between 10am & 4pm.HOW TO

13014 Langstaff Dr, Windermere, FL 34786
/2
$825,000 Sold Feb 11, 2026

1735 Maple Leaf Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,771 Sq Ft
- Built 1989
Last Sold Summary
- 3% Below List Price
- $298/SF
- 3 Days On Market
Current Estimated Value $822,871

Last Listing Agent Frank Del Toro REVEL REALTY LLC

1735 Maple Leaf Dr, Windermere, FL 34786

/64
Est $795,700 Not Listed For Sale

12851 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,694 Sq Ft
- Built 2018
12851 Westside Village Loop, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $213/SF
- 94 Days On Market
- Last Sold Price $785,000
- Jul 01, 2024
Last Listing Agent Torey Eisenman BENCHMARK REAL ESTATE GRP INC

/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
/31
$12,500 Per Month
- 3 Beds
- 3 Baths
- 3,535 Sq Ft
- House for Rent
9701 Lake Isleworth Ct, Windermere, FL 34786

Within the gates of Isleworth Golf and Country Club on a lovely cul-de-sac, you will discover this Golf Villa, boasting over 3,500 square feet of space. With 3 bedrooms plus an office, which could easily be used as a 4th bedroom, this charming villa has a spacious master suite with a garden view step-down shower, a notable kitchen with breakfast nook, formal dining room, and living room with a

Michelle Corbin ISLEWORTH REALTY LLC

9701 Lake Isleworth Ct, Windermere, FL 34786
/2
$1,500,000 Sold Apr 29, 2026

11821 Waterstone Loop Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,447 Sq Ft
- Built 2012
Last Sold Summary
- 3% Below List Price
- $435/SF
- 7 Days On Market
Current Estimated Value $1,519,409

Last Listing Agent Mauricio Penha VOLKE REAL ESTATE LLC

11821 Waterstone Loop Dr, Windermere, FL 34786

/2
Est $517,669 Not Listed For Sale

6054 Roseate Spoonbill Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
- Built 2011
6054 Roseate Spoonbill Dr, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $258/SF
- 26 Days On Market
- Last Sold Price $512,500
- Apr 30, 2025
Last Listing Agent Aline Oliveira META ONE REALTY GROUP LLC

Showing Results 81 - 120, Page 3 of 18

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