Homes with Pools for Sale in Windermere, FL

187 homes

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ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
A rare architectural statement on Lake Down, this extraordinary contemporary waterfront estate redefines luxury living in the heart of Windermere. Positioned on the prestigious Butler Chain of Lakes, this stunning residence offers 5 bedrooms, 5 full baths, 2 half baths, and a private elevator, seamlessly blending sophisticated design with effortless lakefront living. Constructed to Miami coastal specifications, the home was engineered with exceptional attention to quality, durability, and structural integrity while maintaining its striking modern aesthetic. Floor-to-ceiling glass walls frame breathtaking water views and flood the home with natural light, while soaring ceilings and open-conc

$6,900,000

5 beds6 baths6,300 sq ft

Waterfront estate • Private elevator • Spectacular pool

9061 Ron Den Ln, Windermere, FL 34786

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Luxury Living in the Heart of Windermere! Welcome to this beautifully maintained 4 bedrooms and 2.5 bathrooms, single family home, located in the highly desirable community of Windermere. Situated on a charming alley-style streetscape, this elegant property offers the perfect blend of comfort, style, and convenience in one of Central Florida’s most sought-after locations. This spacious home features an open and functional floor plan with abundant natural light, generous living and dining areas, and thoughtfully designed spaces ideal for both everyday living and entertaining. Enjoy a fresh updated feel with NEW interior paint and NEW exterior paint, enhancing both the beauty and curb

$509,000

4 beds2.5 baths2,221 sq ft

Ample cabinetry • New exterior paint • Private patio

7867 Berkshire Oak Aly, Windermere, FL 34786

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Welcome to effortless Florida living in this move-in ready, light-filled first-floor condo located in the heart of Windermere. Perfectly positioned, this beautifully maintained residence offers the ideal combination of comfort, convenience, and resort-style amenities just minutes from Disney, Winter Garden Village, & directly across from Lakeside Village Center with shopping, dining, and everyday conveniences. Designed with a desirable split-bedroom floor plan, this spacious home features an inviting open-concept layout that seamlessly c

$295,000

2 beds2 baths1,161 sq ft

Gated community • First-floor condo • Open-concept layout

8180 Boat Hook Loop #102, Windermere, FL 34786

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throu

$1,450,000

4 beds4 baths3,997 sq ft

Custom cabinetry • Designer finishes • Half-acre lot

9548 Crown Prince Ln, Windermere, FL 34786

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Windermere, FL:
Welcome to one of the best opportunities in Windermere's highly sought-after Lakes of Windermere community! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, convenience, and the Florida lifestyle buyers are searching for. Step inside to discover a thoughtfully designed floor plan featuring spacious living areas, abundant natural light, and stylish updates throughout. The well-appointed kitchen opens seamlessly to the main living spaces, creating an ideal setting for everyday living and entertaining. Upstairs, the generous primary suite provides a private retreat, while three additional bedrooms offer flexibility for family, guests, a home offic

$624,994

4 beds2.5 baths2,053 sq ft

Community pool • Front balcony • Upgraded kitchen

13013 Overstreet Rd, Windermere, FL 34786

Property at 8168 Boat Hook Loop #724, Windermere, FL 34786, 3 beds, 2 baths

$325,000

3 beds2 baths1,455 sq ft

8168 Boat Hook Loop #724, Windermere, FL 34786

Property at 9119 Balmoral Mews Sq, Windermere, FL 34786, 4 beds, 4 baths

$1,399,000

4 beds4 baths4,052 sq ft

9119 Balmoral Mews Sq, Windermere, FL 34786

Property at 9349 Tibet Pointe Cir, Windermere, FL 34786, 5 beds, 7 baths

$6,995,000

5 beds7 baths7,529 sq ft

9349 Tibet Pointe Cir, Windermere, FL 34786

Property at 6560 Lake Burden View Dr, Windermere, FL 34786, 4 beds, 4 baths

$1,799,000

4 beds4 baths3,687 sq ft

6560 Lake Burden View Dr, Windermere, FL 34786

Property at 9648 Weatherstone Ct, Windermere, FL 34786, 6 beds, 4 baths

$2,395,000

6 beds4 baths4,482 sq ft

9648 Weatherstone Ct, Windermere, FL 34786

Property at 4301 Down Point Ln, Windermere, FL 34786, 5 beds, 4 baths

$2,950,000

5 beds4 baths7,153 sq ft

4301 Down Point Ln, Windermere, FL 34786

Property at 5199 Latrobe Dr, Windermere, FL 34786, 6 beds, 6.5 baths

$5,300,000

6 beds6.5 baths4,665 sq ft

5199 Latrobe Dr, Windermere, FL 34786

Property at 9110 Palm Tree Dr, Windermere, FL 34786, 3 beds, 2 baths

$635,000

3 beds2 baths1,819 sq ft

9110 Palm Tree Dr, Windermere, FL 34786

Property at 11545 Brickyard Pond Ln, Windermere, FL 34786, 8 beds, 8.5 baths

$2,200,000

8 beds8.5 baths4,735 sq ft

11545 Brickyard Pond Ln, Windermere, FL 34786

Property at 5138 Fairway Oaks Dr, Windermere, FL 34786, 4 beds, 5 baths

$4,999,500

4 beds5 baths4,330 sq ft

5138 Fairway Oaks Dr, Windermere, FL 34786

Property at 2958 Marquesas Ct, Windermere, FL 34786, 5 beds, 4.5 baths

$1,830,000

5 beds4.5 baths4,716 sq ft

2958 Marquesas Ct, Windermere, FL 34786

Property at 11035 Schooner Way, Windermere, FL 34786, 4 beds, 3 baths

$1,500,000

4 beds3 baths3,517 sq ft

11035 Schooner Way, Windermere, FL 34786

Property at 7723 Fairgrove Ave, Windermere, FL 34786, 3 beds, 2.5 baths

$380,000

3 beds2.5 baths1,680 sq ft

7723 Fairgrove Ave, Windermere, FL 34786

Property at 13786 Summer Harbor Ct, Windermere, FL 34786, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths2,236 sq ft

13786 Summer Harbor Ct, Windermere, FL 34786

Property at 1407 Hempel Ave, Windermere, FL 34786, 4 beds, 3 baths

$1,090,000

4 beds3 baths2,842 sq ft

1407 Hempel Ave, Windermere, FL 34786

Property at 7330 Brightland St, Windermere, FL 34786, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,881 sq ft

7330 Brightland St, Windermere, FL 34786

Property at 7327 Millstone St, Windermere, FL 34786, 3 beds, 2.5 baths

$449,000

3 beds2.5 baths1,531 sq ft

7327 Millstone St, Windermere, FL 34786

Property at 9057 Balmoral Mews Sq, Windermere, FL 34786, 6 beds, 5.5 baths

$1,849,000

6 beds5.5 baths5,430 sq ft

9057 Balmoral Mews Sq, Windermere, FL 34786

Property at 9575 Westover Roberts Rd, Windermere, FL 34786, 7 beds, 8 baths

$4,850,000

7 beds8 baths8,931 sq ft

9575 Westover Roberts Rd, Windermere, FL 34786

Property at 11429 Brownstone St, Windermere, FL 34786, 4 beds, 2.5 baths

$448,000

4 beds2.5 baths1,910 sq ft

11429 Brownstone St, Windermere, FL 34786

Property at 13519 Bicton Ln, Windermere, FL 34786, 4 beds, 3.5 baths

$695,000

4 beds3.5 baths2,594 sq ft

13519 Bicton Ln, Windermere, FL 34786

Property at 5070 Down Point Ln, Windermere, FL 34786, 6 beds, 6.5 baths

$4,995,000

6 beds6.5 baths7,349 sq ft

5070 Down Point Ln, Windermere, FL 34786

Property at 9725 Chestnut Ridge Dr, Windermere, FL 34786, 7 beds, 6 baths

$5,975,000

7 beds6 baths8,000 sq ft

9725 Chestnut Ridge Dr, Windermere, FL 34786

Property at 12264 Montalcino Cir, Windermere, FL 34786, 4 beds, 5.5 baths

$5,390,000

4 beds5.5 baths7,872 sq ft

12264 Montalcino Cir, Windermere, FL 34786

Property at 14442 Desert Haven St #4305, Windermere, FL 34786, 3 beds, 2.5 baths

$359,900

3 beds2.5 baths1,534 sq ft

14442 Desert Haven St #4305, Windermere, FL 34786

Property at 11339 Camden Park Dr, Windermere, FL 34786, 5 beds, 4 baths

$1,490,000

5 beds4 baths3,492 sq ft

11339 Camden Park Dr, Windermere, FL 34786

Property at 4906 Aviva Garden Ct, Windermere, FL 34786, 3 beds, 4.5 baths

$3,990,000

3 beds4.5 baths6,236 sq ft

4906 Aviva Garden Ct, Windermere, FL 34786

Property at 9343 Tibet Pointe Cir, Windermere, FL 34786, 7 beds, 9 baths

$7,695,000

7 beds9 baths8,362 sq ft

9343 Tibet Pointe Cir, Windermere, FL 34786

Property at 7060 Ventnor Dr, Windermere, FL 34786, 3 beds, 2.5 baths

$444,900

3 beds2.5 baths1,642 sq ft

7060 Ventnor Dr, Windermere, FL 34786

Property at 12405 Cruxbury Dr, Windermere, FL 34786, 2 beds, 2.5 baths

$399,000

2 beds2.5 baths1,429 sq ft

12405 Cruxbury Dr, Windermere, FL 34786

Property at 6130 Grosvenor Shore Dr, Windermere, FL 34786, 4 beds, 4.5 baths

$2,950,000

4 beds4.5 baths4,676 sq ft

6130 Grosvenor Shore Dr, Windermere, FL 34786

Property at 12357 Via Derna Pl, Windermere, FL 34786, 3 beds, 2.5 baths

$430,000

3 beds2.5 baths1,919 sq ft

12357 Via Derna Pl, Windermere, FL 34786

Property at 11410 Rapallo Ln, Windermere, FL 34786, 6 beds, 5.5 baths

$745,000

6 beds5.5 baths3,336 sq ft

11410 Rapallo Ln, Windermere, FL 34786

Property at 5151 Latrobe Dr, Windermere, FL 34786, 4 beds, 4.5 baths

$3,900,000

4 beds4.5 baths5,301 sq ft

5151 Latrobe Dr, Windermere, FL 34786

Property at 5145 Latrobe Dr, Windermere, FL 34786, 4 beds, 4.5 baths

$2,999,999

4 beds4.5 baths4,512 sq ft

5145 Latrobe Dr, Windermere, FL 34786

Property at 9323 Gladys Garden Ct, Windermere, FL 34786, 6 beds, 8 baths

$11,900,000

6 beds8 baths9,770 sq ft

9323 Gladys Garden Ct, Windermere, FL 34786

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Based on information submitted to the MLS GRID as of Mon Sep 07 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Homes with Pools for Sale in Windermere

There are currently 187 homes with pools for sale in Windermere at a median listing price of $1.83M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windermere stay on the market for 112 days. Popular neighborhoods include Windsor Landing, and Isleworth. This map is refreshed with the newest listings in Windermere every 15 minutes.

In the past month, 6 homes have been sold in Windermere. In addition to houses in Windermere, there were also 2 condos, 1 townhouse, and 0 multi-family units for sale in Windermere last month. Find your dream home in Windermere using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Windermere are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windermere. Our Windermere real estate stats and trends will give you more information about home buying and selling trends in Windermere. If you're looking to sell your home in the Windermere area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windermere with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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