Isleworth, FL homes for sale & real estate

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ABOUT THIS HOME
Isleworth, FL Homes for Sale
Tucked within the gates of Isleworth Golf Community and Country Club lies a residence that feels more like a private lakeside retreat than a home. Here, more than 7,000 square feet of elegance unfolds across a premium homesite on the shores of Lake Butler, where the water is clear, the sandy beach is pristine, and the sunsets spill across the horizon in dazzling color every evening. The moment you step inside, the story begins with a grand foyer — ceilings soaring high above, delicate moldings tracing every line, and crystal chandeliers casting a warm, inviting glow. From there, each room flows gracefully into the next: a formal living space framed by expansive windows that draw your

$5,900,000

5 beds5 baths7,491 sq ft

9826 Laurel Valley Dr, Windermere, FL 34786

Sandy beach • Premium homesite • Grand foyer

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Presenting a magnificent Isleworth golf front estate with sweeping lake views, perched above holes #2 and #9 and Lake Chase, combining a completely reimagined interior with designer elegance and modern grand style. With no neighbors on three sides, this stunning home offers a unique combination of privacy mixed with rare golf and water vistas. Home recently underwent a major “spare no expense” remodel by McNally Construction and design by Debby Dearth of McNally Design using the highest quality materials combining the latest designs with timeless Mediterranean architecture. Enter to an impressive foyer and Great Room with soaring 20-foot ceilings above and basket weaved marble a

$5,325,000

4 beds5.5 baths6,424 sq ft

5243 Isleworth Country Club Dr, Windermere, FL 34786

Lake views • Major remodel • Vaulted ceilings

3D & VIDEO TOUR

ABOUT THIS HOME
Isleworth, FL Homes for Sale
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 the last three years to deliver exceptional comfort, sophistication and panache at every turn. The two-story estate is set on a pristine 1.02-acre golf-front home site along Isleworth's famed championship golf course and from the moment you enter, you'll be captivated by the artistry in design and mo

$14,250,000

5 beds5.5 baths9,511 sq ft

5525 Isleworth Country Club Dr, Windermere, FL 34786

Golf front home site • Custom swimming pool • Putting green

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Stunning golf and lake views and beautifully updated grounds are hallmarks of this elegant Isleworth estate. Nestled along the front nine overlooking Isleworth’s 2nd fairway and beautiful Lake Chase, this two-story home spans more than 4,800 square feet and features modern finishes throughout. Beautiful porcelain tile travels throughout the main level from the spacious living room with an oversized modern built-in featuring slate stonework and lit shelves. The spacious master suite features a large sitting area and an en-suite bathroom with dual vanities, a walk-in closet, modern soaking tub and separate walk-in shower. Completing the main level are the home office, formal dining room

$3,800,000

3 beds3.5 baths4,751 sq ft

9648 Mccormick Pl, Windermere, FL 34786

Golf views • Lake views • Modern finishes

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two e

$4,900,000

5 beds4.5 baths5,548 sq ft

5036 Latrobe Dr, Windermere, FL 34786

Spacious kitchen • Lakefront estate • Oversized windows

Property at 9731 Chestnut Ridge Dr, Windermere, FL 34786, 4 beds, 4 baths

$3,400,000

4 beds4 baths4,877 sq ft

9731 Chestnut Ridge Dr, Windermere, FL 34786

Property at 6120 Payne Stewart Dr, Windermere, FL 34786, 4 beds, 4.5 baths

$2,700,000

4 beds4.5 baths3,636 sq ft

6120 Payne Stewart Dr, Windermere, FL 34786

Property at 5199 Latrobe Dr, Windermere, FL 34786, 5 beds, 6.5 baths

$5,494,000

5 beds6.5 baths4,665 sq ft

5199 Latrobe Dr, Windermere, FL 34786

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3D WALKTHROUGH

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Modern sophistication and timeless Windermere charm come together in this fully reimagined residence located just steps from Lake Bessie and the heart of Windermere Town. Set on a beautifully landscaped corner lot with no HOA, this home offers a rare blend of luxury comfort and walkable small town living in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated to provide both style and peace of mind, including a new roof, new air conditioning system, new plumbing, new flooring, new drainfield and a new water filtration system along with fresh interior and exterior paint. Inside, light filled living and dining spaces flow effortlessly across ma

$1,224,000

4 beds3.5 baths2,791 sq ft

109 E 12th Ave, Windermere, FL 34786

New plumbing • New flooring • New roof

3D WALKTHROUGH

ABOUT THIS HOME
Isleworth, FL Homes for Sale
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, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are

$2,285,000

6 beds5 baths5,513 sq ft

713 Main St, Windermere, FL 34786

Chef kitchen • Beautiful library • Walk-in pantry

ABOUT THIS HOME
Isleworth, FL Homes for Sale
One or more photo(s) has been virtually staged. Welcome to 9107 Ivey Hill. Nestled in the heart of Dr. Phillips, sitting between the prestigious Bay Hill Golf Course and beautiful Butler Chain of lakes, You will find this North Bay Semi-custom residence to be the best opportunity to live in one of Orlando’s most desirable communities! This 4-bedroom, 3-bath + Office, one-story, pool home blends luxury, comfort and the perfect Florida lifestyle. You will be amazed by the high ceilings throughout, a functional/flexible floor plan, and the exquisite outdoor living features found in this well cared for home. Expansive, dedicated formal living and dinning areas, as well as pool views, w

$895,000

4 beds3 baths3,055 sq ft

9107 Ivey Hill Ct, Orlando, FL 32819

Bay hill golf course • Pool views • 0.35 acre lot

ABOUT THIS HOME
Isleworth, FL Homes for Sale
One or more photo(s) has been virtually staged. Welcome to an exceptional opportunity in the heart of Bay Hill, situated directly on the green of Hole 4—one of the community’s most sought-after golf course locations. This homesite offers sweeping views of manicured fairways, mature trees, and pristine landscape, delivering the privacy, prestige, and scenery that define the Bay Hill lifestyle. This spacious single-story, 4-bedroom, 3-bath home features 2,528 sq ft of living space and a smart, well-designed layout centered around golf views and indoor-outdoor living. High ceilings, large architectural windows, and multiple sets of French doors fill the home with natural light and

$1,275,000

4 beds3 baths2,528 sq ft

5709 Masters Blvd, Orlando, FL 32819

Golf course location • Sweeping views • Natural light

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Welcome to North Bay, one of the most coveted pockets of Bay Hill and Dr Phillips, where golf cart living, lakeside beauty, and world-class convenience define everyday life. This is the first time ever this waterfront home has been offered for sale, giving you a rare opportunity to live in one of Central Florida’s most iconic communities. Step through the double glass doors and feel the openness created by 12 foot ceilings and streams of natural light. The layout includes both a formal living room and a formal dining room, perfect for holiday gatherings, special occasions, or simply enjoying a little extra space in your daily routine. The family room offers a warm gas fireplace and te

$800,000

4 beds3 baths2,544 sq ft

9179 Dollanger Ct, Orlando, FL 32819

Waterfront home • Ample cabinetry • Gas fireplace

3D WALKTHROUGH

ABOUT THIS HOME
Isleworth, FL Homes for Sale
MOVE IN FOR THE HOLIDAYS! Don’t miss this Silver Woods jewel box in a super central location! Large corner lot on quiet cul-de-sac. Featuring a FANTASTIC 55x10 screened porch with custom summer kitchen - PERFECT for relaxing and entertaining. Sunny and bright great room plan with vaulted ceilings and hardwood floors is freshly painted and ready for your personal touches. Updated kitchen with granite counters, stainless steel appliances and breakfast bar open to living area. Split bedroom plan features large primary suite with privacy barn door to vanity area and large walk in closet. 2 generous additional bedrooms with updated hall bath and great closets. BRAND NEW A/C, Newer roof 20

$535,000

3 beds2 baths1,492 sq ft

4818 Breezy Palms Ct, Windermere, FL 34786

Large corner lot • Screened porch • Updated kitchen

Property at 4711 Joanna Garden Ct, Windermere, FL 34786, 3 beds, 3.5 baths

$3,250,000

3 beds3.5 baths4,089 sq ft

4711 Joanna Garden Ct, Windermere, FL 34786

Property at 5558 Brookline Dr, Orlando, FL 32819, 5 beds, 4.5 baths

$2,797,000

5 beds4.5 baths5,822 sq ft

5558 Brookline Dr, Orlando, FL 32819

Property at 6047 Blakeford Dr, Windermere, FL 34786, 4 beds, 4 baths

$1,979,000

4 beds4 baths4,156 sq ft

6047 Blakeford Dr, Windermere, FL 34786

Property at 1003 Down Reserve Ct, Windermere, FL 34786, 6 beds, 7 baths

$4,999,999

6 beds7 baths6,816 sq ft

1003 Down Reserve Ct, Windermere, FL 34786

Property at 5110 Pine Top Pl, Orlando, FL 32819, 5 beds, 4 baths

$908,000

5 beds4 baths3,248 sq ft

5110 Pine Top Pl, Orlando, FL 32819

Property at 6064 Masters Blvd, Orlando, FL 32819, 4 beds, 3.5 baths

$1,575,000

4 beds3.5 baths3,766 sq ft

6064 Masters Blvd, Orlando, FL 32819

Property at 436 E 7th Ave, Windermere, FL 34786, 4 beds, 5 baths

$2,275,000

4 beds5 baths3,136 sq ft

436 E 7th Ave, Windermere, FL 34786

Property at 2 Chase Rd, Windermere, FL 34786, 4 beds, 4.5 baths

$3,200,000

4 beds4.5 baths3,889 sq ft

2 Chase Rd, Windermere, FL 34786

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

$1,485,000

5 beds4 baths4,186 sq ft

101 Lee St, Windermere, FL 34786

Property at 5311 Bay Side Dr, Orlando, FL 32819, 5 beds, 4 baths

$920,000

5 beds4 baths3,207 sq ft

5311 Bay Side Dr, Orlando, FL 32819

Property at 4812 Alexandra Garden Ct, Windermere, FL 34786, 3 beds, 4 baths

$3,699,000

3 beds4 baths4,262 sq ft

4812 Alexandra Garden Ct, Windermere, FL 34786

Property at 4819 Alexandra Garden Ct, Windermere, FL 34786, 4 beds, 4.5 baths

$3,200,000

4 beds4.5 baths3,745 sq ft

4819 Alexandra Garden Ct, Windermere, FL 34786

Property at 311 E 8th Ave, Windermere, FL 34786, 5 beds, 4 baths

$1,660,000

5 beds4 baths3,805 sq ft

311 E 8th Ave, Windermere, FL 34786

Property at 5727 Emerington Cres, Orlando, FL 32819

$1,995,000

— beds— baths— sq ft

5727 Emerington Cres, Orlando, FL 32819

Based on information submitted to the MLS GRID as of Tue Dec 30 2025. 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.

Average home prices near Isleworth, FL

Cities

Clermont homes for sale
$449,900
Altamonte Springs homes for sale
$192,500
Windermere homes for sale
$1,630,000
Longwood homes for sale
$397,000
Celebration homes for sale
$470,000
St. Cloud homes for sale
$418,500
Maitland homes for sale
$350,000
Sanford homes for sale
$355,000
Orlando homes for sale
$325,000
Kissimmee homes for sale
$342,450
Winter Garden homes for sale
$617,450
Apopka homes for sale
$459,990
Davenport homes for sale
$329,900
Lake Mary homes for sale
$545,000
Winter Park homes for sale
$950,000

Neighborhoods

Lake Reams homes for sale
$869,000
Little Sand Lake homes for sale
$710,000
Metro West homes for sale
$225,000
Sand Lake Hills homes for sale
$544,450
Reserve at Lake Butler Sound homes for sale
$1,387,000
Florida Center homes for sale
$302,000
South Bay homes for sale
$1,150,000
International Drive Area homes for sale
$229,999
Lake Sawyer homes for sale
$625,000
Keenes Pointe homes for sale
$2,600,000

Isleworth, FL real estate trends

All Home Types trends in Isleworth, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$3,525,000

+36.6% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Isleworth, FL

$3,525,000

+36.6%

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