Isleworth, FL homes for sale & real estate

9 homes

Sort:

Recommended

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

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
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

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

$7,995,000

5 beds6.5 baths6,937 sq ft

5074 Isleworth Country Club Dr, Windermere, FL 34786

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 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

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

$2,799,000

4 beds4.5 baths3,636 sq ft

6120 Payne Stewart Dr, Windermere, FL 34786

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

3D WALKTHROUGH

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Step into a storybook cottage tucked in the heart of Windermere, where history whispers through every room and morning light dances across original 1915 details. Part of the early homestead still remains, giving this home a charm that simply can’t be recreated. The family room feels like a cozy tale come to life with its high ceilings, original wood floors, beadboard ceiling, and brick fireplace—the kind of spot that begs for gatherings, laughter, and quiet evenings by the fire. Sunlight pours through an abundance of windows, making every corner feel warm and cheerful. A sunny dinette awaits weekend breakfasts, while the formal living room offers a refined space for hosting or u

$885,000

2 beds1.5 baths2,115 sq ft

416 Magnolia St, Windermere, FL 34786

0.38 acre lot • Garage • Car-dependent

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

0.28 acre lot • $51 HOA • 2 garage spots

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

0.24 acre lot • $30 HOA • 2 garage spots

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Nestled within the exclusive Gardens of Isleworth enclave within Isleworth Golf & Country Club, this exquisite residence exemplifies refined Florida living. Crafted by Pellegrini Homes with professionally designed interiors, the single-story home seamlessly blends architectural sophistication with inviting comfort. A brick paver motor court introduces the residence, where a gracious custom arched French entry door sets the tone for the elegance within. The formal foyer makes a lasting impression with its soaring octagonal ceiling accented in tongue-and-groove woodwork. Inside, the formal living room—currently styled as a music salon—showcases a faux-painted garden ceiling

$3,250,000

3 beds3.5 baths4,089 sq ft

4711 Joanna Garden Ct, Windermere, FL 34786

0.26 acre lot • $2,142 HOA • 3 garage spots

ABOUT THIS HOME
Isleworth, FL Homes for Sale
Welcome to this beautifully maintained 4-bedroom, 2-bath home in the highly sought-after Dr. Phillips community! Nestled in a quiet, well-established neighborhood, this residence offers stunning curb appeal and a thoughtfully designed split-bedroom layout. Inside, you'll find an upgraded kitchen with rich wood cabinetry, granite countertops, and newer stainless steel appliances, perfect for cooking and entertaining. Three of the bedrooms feature brand-new vinyl flooring, adding modern style and comfort. Step outside to enjoy the private, fenced-in backyard with a screened and covered lanai, ideal for relaxing or hosting gatherings year-round. This is a rare opportunity to own a charming, mo

$499,900

4 beds2 baths1,849 sq ft

6135 Hardrock Cir, Orlando, FL 32819

0.28 acre lot • 2 garage spots • Car-dependent

ABOUT THIS HOME
Isleworth, FL Homes for Sale
This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around a charming wood-burning fireplace, surrounded by newly installed windows (2020) that fill the space with natural light. French doors open to a large screened porch — an ideal spot fo

$895,000

4 beds3 baths2,410 sq ft

299 W 4th Ave, Windermere, FL 34786

0.38 acre lot • 3 garage spots • Car-dependent

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

$5,499,999

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

$2,425,000

4 beds5 baths3,136 sq ft

436 E 7th Ave, Windermere, FL 34786

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

$1,550,000

5 beds4 baths4,186 sq ft

101 Lee St, 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 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 6018 Tarawood Dr, Orlando, FL 32819, 6 beds, 7 baths

$2,850,000

6 beds7 baths5,825 sq ft

6018 Tarawood 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 5329 Foxshire Ct, Orlando, FL 32819, 4 beds, 3 baths

$899,900

4 beds3 baths3,189 sq ft

5329 Foxshire Ct, Orlando, FL 32819

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 6533 Cartmel Ln, Windermere, FL 34786, 4 beds, 3.5 baths

$1,398,888

4 beds3.5 baths3,751 sq ft

6533 Cartmel Ln, Windermere, FL 34786

Based on information submitted to the MLS GRID as of Mon Nov 24 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
$450,000
Altamonte Springs homes for sale
$200,000
Windermere homes for sale
$1,862,500
Longwood homes for sale
$395,000
Celebration homes for sale
$507,500
St. Cloud homes for sale
$415,000
Maitland homes for sale
$375,000
Sanford homes for sale
$352,000
Orlando homes for sale
$330,000
Kissimmee homes for sale
$344,900
Winter Garden homes for sale
$655,000
Apopka homes for sale
$444,245
Davenport homes for sale
$330,000
Lake Mary homes for sale
$479,000
Winter Park homes for sale
$962,500

Neighborhoods

Lake Reams homes for sale
$765,000
Little Sand Lake homes for sale
$599,900
Metro West homes for sale
$220,000
Sand Lake Hills homes for sale
$549,950
Florida Center homes for sale
$309,000
South Bay homes for sale
$1,150,000
Signature Lakes homes for sale
$615,000
International Drive Area homes for sale
$229,900
Windsor Landing homes for sale
$799,000
Keenes Pointe homes for sale
$2,340,000

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)

$4,925,000

-6.2% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Isleworth, FL

$4,925,000

-6.2%

See more Isleworth, FL market insights

More to explore in Isleworth, FL

How to buy a house in Isleworth, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.