Homes with Pools for Sale in Isleworth, FL

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ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is ac

$8,500,000

4 beds5 baths7,100 sq ft

5092 Isleworth Country Club Dr, Windermere, FL 34786

Custom cabinetry • Breathtaking views • Travertine floors

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden pa

$19,500,000

6 beds9 baths13,494 sq ft

5192 Vardon Dr, Windermere, FL 34786

Outdoor shower • Lakefront estate • Summer kitchen

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ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence with contemporary interiors and expansive views across the course. Beyond the private entry gate to the property, a long, dramatic drive leads to the circular motor court anchored by a distinctive tiered fountain, creating an impressive arrival to this beautifully reimagined Isleworth estate. Inside, soaring ceilings and a dramatic two-story foyer introduce beautifully updated living spaces, where new flooring, refined architectural details and distinctive backlit feature walls create a fresh, elevated aesthetic. Prim

$4,395,000

6 beds6 baths4,739 sq ft

5186 Vardon Dr, Windermere, FL 34786

Tiered fountain • Private entry gate • Circular motor court

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, each with its own full bathroom, plus a powder room for guests. Soaring ceilings and an open floor plan bring a sense of space to the main living areas, where travertine floors and new doors complement the recent renovations. The gourmet kitchen features a 10-ft center island and top of the line appliances. The primary suite includes a recently renovated bathroom with a generously sized shower and soaking tub. Outside, a fully fenced garden setting surrounds the pool and spa. A summer kitchen and fireplace make the space inv

$3,250,000

3 beds3.5 baths2,848 sq ft

6126 Payne Stewart Dr, Windermere, FL 34786

Renovated bathroom • Fully fenced garden • Summer kitchen

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ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Virtually Staged. Pre-Construction. To be built. Poised on a remarkable . 69-acre homesite along the shores of Lake Bessie, this exceptional new residence offers a rare opportunity to create a substantial private estate in one of Isleworth’s most coveted lakefront settings. Designed and to be built by Supreme International Construction, the residence will encompass approximately 15,337 square feet of living space across three levels, with six bedrooms, including two private primary suites, an elevator and a four-car garage accommodating up to eight vehicles with lifts. Created for both grand entertaining and effortless everyday living, the main level will feature a dramatic great hall

$18,750,000

6 beds8 baths15,337 sq ft

5036 Latrobe Dr, Windermere, FL 34786

Formal dining room • Expansive kitchen • Lakefront estate

Property at 5373 Isleworth Country Club Dr, Windermere, FL 34786, 5 beds, 5.5 baths

$7,200,000

5 beds5.5 baths5,993 sq ft

5373 Isleworth Country Club Dr, Windermere, FL 34786

Property at 9832 Laurel Valley Dr, Windermere, FL 34786, 6 beds, 8.5 baths

$11,750,000

6 beds8.5 baths11,100 sq ft

9832 Laurel Valley Dr, Windermere, FL 34786

Property at 5524 Worsham Ct, Windermere, FL 34786, 4 beds, 6 baths

$3,500,000

4 beds6 baths7,669 sq ft

5524 Worsham Ct, Windermere, FL 34786

Property at 9921 Lake Louise Dr, Windermere, FL 34786, 5 beds, 6 baths

$6,650,000

5 beds6 baths6,970 sq ft

9921 Lake Louise Dr, Windermere, FL 34786

Property at 5050 Isleworth Country Club Dr, Windermere, FL 34786, 4 beds, 4.5 baths

$3,189,000

4 beds4.5 baths3,365 sq ft

5050 Isleworth Country Club Dr, Windermere, FL 34786

Property at 6462 Deacon Cir, Windermere, FL 34786, 5 beds, 5 baths

$6,595,000

5 beds5 baths7,178 sq ft

6462 Deacon Cir, Windermere, FL 34786

Property at 5073 Latrobe Dr, Windermere, FL 34786, 4 beds, 5 baths

$2,800,000

4 beds5 baths4,706 sq ft

5073 Latrobe Dr, 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 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 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 5145 Latrobe Dr, Windermere, FL 34786, 4 beds, 4.5 baths

$2,949,000

4 beds4.5 baths4,512 sq ft

5145 Latrobe Dr, Windermere, FL 34786

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

$3,800,000

4 beds4.5 baths5,301 sq ft

5151 Latrobe Dr, Windermere, FL 34786

Property at 5074 Isleworth Country Club Dr, Windermere, FL 34786, 5 beds, 6.5 baths

$7,250,000

5 beds6.5 baths7,099 sq ft

5074 Isleworth Country Club Dr, Windermere, FL 34786

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ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Welcome to Valhalla Way, an absolutely turn-key home, in the highly sought-after guard-gated community of Keene’s Pointe. Timeless in character yet fully updated for modern living, this stunning pool home offers a golf-course view of the 14th hole at the renowned Golden Bear–designed Keene’s Pointe Country Club, a beautifully renovated kitchen, soaring ceilings, and more than 5,000 square feet of thoughtfully designed space. Step through the ornate yet fitting front door and the foyer opens into a formal living area, where cathedral ceilings create a bright, open feel and French doors lead to one of the home’s covered lanais. The formal dining room is an inviting spa

$2,790,000

5 beds6 baths5,225 sq ft

6850 Valhalla Way, Windermere, FL 34786

Formal living area • Covered lanais • Golf course view

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Foreclosure Auction Ends October 26, 2026 at 11:00 AM EST. Discover this spacious 4-bedroom, 4.5-bathroom single-family home, offering a unique opportunity in a desirable Windermere neighborhood. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa.

$5,000

4 beds4.5 baths4,243 sq ft

6418 Cartmel Ln, Windermere, FL 34786

3 garage spots • Pool • Built 2005

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, formal living and dining and an office/den. As you enter this one level home you will find 3-way split functional plan. Boasting the primary ensuite separate from the three additional bedrooms with a spacious bath and TWO WALK-IN CLOSETS, and access to the covered/screened lanai. Spacious kitchen with an abundance of cabinetry, convenient desk area and island. Newer stainless Steel appliances. The kitchen, dinette and great room feature two sets of French doors that give way to the covered screened lanai and back yard. Beyond the screened lanai is an over

$1,050,000

4 beds3 baths2,984 sq ft

5944 Caymus Loop, Windermere, FL 34786

Primary ensuite • Gated golf community • Two walk-in closets

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Welcome to Villa Cartmel, where privacy lives beautifully. Set behind the gates of Lake Butler Sound, this exceptional Windermere residence offers a rare combination of privacy, tranquility, and effortless Florida living. With 4.185 sqf (check remarks), 5 bedrooms, 4.5 bathrooms, and a 3-car garage, the home has been thoughtfully designed for everyday comfort, elegant entertaining, and the relaxed lifestyle that makes Central Florida so desirable. From the moment you enter, beautifully appointed living spaces flow naturally from one to the next, creating an atmosphere that feels luxury yet welcoming. Expansive windows bring abundant natural light into the interiors while framing the lush gr

$2,390,000

5 beds4.5 baths4,185 sq ft

6544 Cartmel Ln, Windermere, FL 34786

Lush landscaping • 0.56 acre lot • 3 garage spots

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Set on 0.54 acre at the end of a quiet cul-de-sac in the Reserve at Lake Butler Sound, 6533 Cartmel Lane offers single-story living within one of Windermere’s established guard-gated communities. Mature landscaping, a paver driveway and a substantial architectural entry frame the residence, while the private pool opens to an expansive backyard that gives the property a notable sense of space and privacy. Inside, high ceilings and generous natural light shape a thoughtfully arranged split-bedroom floor plan. The primary suite is positioned apart from the secondary bedrooms, creating a more private retreat within the home. Just beyond the bedroom, a bonus room offers a flexible extensio

$1,598,000

4 beds3.5 baths3,751 sq ft

6533 Cartmel Ln, Windermere, FL 34786

Private pool • Bonus room • Screened lanai

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Isleworth, FL:
Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pan

$3,595,000

3 beds4 baths4,333 sq ft

9310 Isleworth Gardens Dr, Windermere, FL 34786

Wolf appliances • Double islands • Gas range

Property at 101 Lee St, Windermere, FL 34786, 5 beds, 4 baths

$1,395,000

5 beds4 baths4,186 sq ft

101 Lee St, Windermere, FL 34786

Property at 9142 Bayway Dr, Orlando, FL 32819, 5 beds, 7 baths

$2,799,000

5 beds7 baths5,343 sq ft

9142 Bayway Dr, Orlando, FL 32819

Property at 9130 Dollanger Ct, Orlando, FL 32819, 5 beds, 2.5 baths

$700,000

5 beds2.5 baths2,914 sq ft

9130 Dollanger Ct, Orlando, FL 32819

Property at 6055 Louise Cove Dr, Windermere, FL 34786, 5 beds, 5.5 baths

$6,850,000

5 beds5.5 baths7,158 sq ft

6055 Louise Cove Dr, Windermere, FL 34786

Property at 6719 Valhalla Way, Windermere, FL 34786, 5 beds, 6 baths

$4,495,000

5 beds6 baths6,159 sq ft

6719 Valhalla Way, Windermere, FL 34786

Property at 800 W 2nd Ave, Windermere, FL 34786, 5 beds, 4.5 baths

$5,600,000

5 beds4.5 baths5,511 sq ft

800 W 2nd Ave, Windermere, FL 34786

Property at 9316 Gladys Garden Ct, Windermere, FL 34786, 5 beds, 6.5 baths

$6,500,000

5 beds6.5 baths5,471 sq ft

9316 Gladys Garden Ct, 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 5646 Masters Blvd, Orlando, FL 32819, 4 beds, 4.5 baths

$1,620,000

4 beds4.5 baths4,265 sq ft

5646 Masters Blvd, Orlando, FL 32819

Property at 11051 Hawkshead Ct, Windermere, FL 34786, 5 beds, 5 baths

$1,795,000

5 beds5 baths3,728 sq ft

11051 Hawkshead Ct, Windermere, FL 34786

Property at 9011 Chapman Oak Ct, Windermere, FL 34786, 4 beds, 2 baths

$584,900

4 beds2 baths2,050 sq ft

9011 Chapman Oak Ct, Windermere, FL 34786

Property at 9144 Galleon Ct, Orlando, FL 32819, 4 beds, 2.5 baths

$800,000

4 beds2.5 baths2,556 sq ft

9144 Galleon Ct, Orlando, FL 32819

Property at 9144 Isleworth Gardens Dr, Windermere, FL 34786, 3 beds, 4 baths

$4,100,000

3 beds4 baths5,004 sq ft

9144 Isleworth Gardens Dr, Windermere, FL 34786

Property at 8734 Crestgate Cir, Orlando, FL 32819, 4 beds, 4 baths

$1,490,000

4 beds4 baths3,998 sq ft

8734 Crestgate Cir, Orlando, FL 32819

Based on information submitted to the MLS GRID as of Sat Oct 24 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 Isleworth

There are currently 18 homes with pools for sale in Isleworth at a median listing price of $4.7M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Isleworth stay on the market for 76 days. Popular neighborhoods include Metro West, Sand Lake Hills, Eagle Pointe, International Drive Area, and Keenes Pointe. This map is refreshed with the newest listings in Isleworth every 15 minutes.

In the past month, 1 home has been sold in Isleworth. Find your dream home in Isleworth 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 Isleworth are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Isleworth. If you're looking to sell your home in the Isleworth area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Isleworth with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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