Homes In Orlando For Sale Search

Isleworth Homes for Sale

5199 Latrobe Dr, Windermere
$5,300,000
6 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set within the gates of renowned Isleworth, this beautifully reimagined golf-front estate presents an exceptional opportunity to experience refined Central Florida living at its finest. Perfectly positioned along Isleworth’s celebrated championship golf course, the residence captures sweeping views of the fourth fairway while offering the privacy, comfort, and sophistication synonymous with the community’s distinguished lifestyle.Thoughtfully renovated and impeccably maintained, the home encompasses more than 6,600 square feet of combined indoor living and covered outdoor space, where contemporary finishes, designer lighting, and warm architectural details create an atmosphere that is both elegant and inviting. Every space has been intentionally curated—from the centrally located gourmet kitchen to the well-appointed utility spaces, resulting in a residence designed for effortless everyday living and elevated entertaining alike.The flexible floor plan offers exceptional versatility to suit a variety of lifestyles, accommodating configurations of up to six bedrooms, or alternatively a combination of bedrooms, office space, fitness room, or additional gathering areas. Six full baths and one half bath are finished with timeless materials and meticulous attention to detail throughout.At the heart of the home, the designer kitchen features sleek white cabinetry, quartz countertops, stainless steel appliances, and seamless connectivity to the expansive family room and casual dining area. Large glass openings invite natural light indoors while providing direct access to the screened lanai and resort-style pool environment beyond.The private primary suite serves as a luxurious retreat, highlighted by porcelain plank flooring, a spa-inspired bath with freestanding soaking tub and walk-in shower, and an oversized custom walk-in closet. Additional guest suites provide comfort and flexibility for family and visitors, while the home’s four-car garage and expansive motor court offer abundant space for automobile enthusiasts and guests alike.Outdoors, the estate transforms into a true private sanctuary. A newly redesigned saltwater pool and spa are enclosed within a custom lanai structure and complemented by an expansive new pool deck, creating a year-round setting for relaxation and entertaining. Lush landscaping, a fenced rear lawn, and panoramic golf course vistas further enhance the sense of serenity and exclusivity.Blending timeless elegance with modern livability, this exceptional Isleworth residence offers a rare combination of spacious design, privacy, and premier golf-front surroundings within one of the finest golf club communities in the world.

5199 Latrobe Dr, Windermere
6462 Deacon Cir, Windermere
$6,595,000
5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Within the gates of Isleworth Golf & Country Club, along the shores of Lake Chase, this exceptional lakefront offers a refined and contemporary waterfront lifestyle. Ideally positioned near the driving range and just moments from Isleworth’s racquet center, clubhouse, fitness facilities, dining, and pool, the residence combines privacy with convenience.Designed by renowned architect Mark Nasrallah, the home spans more than 7,100 square feet and showcases sophisticated detailing and elevated finishes throughout. A grand foyer introduces the residence with a sweeping floating staircase and dramatic tiered crystal chandelier, leading into the formal living room where soaring ceilings, dual chandeliers, a fireplace, and expansive lake views create an impressive yet inviting setting.Marble flooring transitions seamlessly into the home’s primary living spaces, where rich hardwood floors enhance the warmth of the open-concept kitchen, casual dining area, and family room. The kitchen is both functional and elegant, featuring an oversized island, custom cabinetry, quarried quartz countertops, and professional-grade appliances by Wolf, Sub-Zero, and Bosch. A contemporary, temperature-controlled wine room accommodating over 100 bottles adds a distinctive touch. Architectural millwork in a diamond pattern defines the dining space, while custom media built-ins in the family room enhance the home’s cohesive design. Both areas open effortlessly to the lanai and pool deck.The primary suite serves as a private retreat, complete with a sitting area, designer lighting, and a spa-inspired bath featuring a soaking tub, expansive dual vanities, and a large walk-in shower. Additional interior highlights include a modern office with custom built-ins and private pool access, as well as a spacious game room with a full bar and captivating water views. Outdoors, the covered lanai extends to a resort-style pool and spa, surrounded by generous lounging areas and complemented by the private boat dock - creating an unparalleled setting for boating, entertaining, and year-round enjoyment in Florida's tropical climate.

6462 Deacon Cir, Windermere
5138 Fairway Oaks Dr, Windermere
$4,999,500
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

5138 Fairway Oaks Dr, Windermere
5151 Latrobe Dr, Windermere
$3,800,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s expansive wardrobe, featuring a central island, tiger wood floors, and cherry birch built-in displays—a true collector’s dream. The elegant foyer sets the tone, leading to formal living and dining spaces, and flowing effortlessly past a private office into the heart of the home: an open-concept kitchen, casual dining area, and family room designed for both entertaining and daily living. The gourmet kitchen is appointed with anigre wood cabinetry, a center island, dual sinks, a walk-in pantry, and professional appliances by Sub-Zero, Dacor, and Kitchenaid, marrying style and functionality in perfect harmony. A spacious game room with a wet bar provides an ideal space for recreation or hosting, while four luxurious bedrooms and 4.5 spa-inspired baths ensure comfort and privacy for family and guests alike. Seamlessly blending indoor and outdoor living, the estate features a sparkling open-air pool set against serene golf course vistas—an idyllic setting for year-round leisure and entertaining. Additional highlights include a circular driveway and motor court, a three-car garage, and a separate workshop. This is a rare opportunity to acquire a residence where world-class craftsmanship, refined design, and premier golf-front location converge, offering an unparalleled lifestyle in one of Central Florida’s most coveted enclaves.

5151 Latrobe Dr, Windermere
5145 Latrobe Drive, Windermere
$2,899,000
4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for entertaining. Providing access from all rooms to the outdoor living area, the thoughtfully designed floor plan blends elegance and functionality throughout. The kitchen is designed for both everyday living and entertaining, featuring Thermador appliances, including a cooktop, double ovens, warming drawer, microwave, dishwasher, icemaker, and beverage refrigerator. The space overlooks a generous dinette area with direct access to the patio, seamlessly connecting indoor and outdoor living. A formal dining room and a spacious great room provide additional gathering spaces for family and guests. The primary suite, located on the first floor, is a private retreat complete with three closets and a spa-inspired bath showcasing a large walk-in shower, soaking tub, and dual vanities. A second ensuite bedroom is also conveniently located on the main level, along with a well-appointed laundry room featuring built-in cabinetry. Upstairs, the travertine staircase with iron railing leads the way to a large game room with wet bar and French doors opening to an expansive balcony overlooking the pool and golf course. Two additional ensuite bedrooms complete the upper level. Throughout the home, you’ll find plantation shutters, travertine flooring, and hardwood floors, adding warmth and sophistication. The property also features an oversized three-car garage with storage and a large driveway for ample parking.Outdoor living is truly exceptional, with a large swimming pool, covered patio with half bath, and summer kitchen with beverage refrigerator—perfect for entertaining while enjoying serene golf course views. The oversized fenced backyard offers privacy and space to relax or play. Conveniently located to shopping, dining and expressways, as well as top-rated public and private schools, this home has it all!

5145 Latrobe Drive, Windermere
9323 Gladys Garden Court, Windermere
$11,900,000
6 Beds ⋅ 10 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door set a tone of understated elegance from the moment of arrival. Concrete tile roofing, four-car garage plus golf cart garage, and a friends-and-family entry with covered parking. Inside, discover Sierra Pacific casement windows with stained interior mullions flood the home with natural light, highlighting warm beams, wide-plank floors, and curated details. Lutron lighting, Sonos audio, and powered draperies enhance modern comfort without compromising design. The formal dining room features a stained white oak arched opening, classic dentil molding, and built-in wine display. The living room is anchored by a gas Isokern fireplace with precast surround, custom built-ins, stained beams, and sculptural custom one off lighting, while an interior glass breezeway subtly defines the transition to the private primary wing. The primary suite offers a serene retreat with custom arch detailing, a nickel joint ceiling, and stained beams. The spa-inspired bath includes a marble soaking tub and a dramatic solid limestone staircase leading to a hidden upper-level flex space, ideal for an office or gym, complete with beverage refrigeration and powered Roman shade. The boutique-style closet features dual islands and an integrated wash tower. At the heart of the home, the chef’s kitchen stuns with soaring 18-foot ceilings, exposed beams, a curved reeded island, and custom Urban Electric pendants designed specifically for the residence. Sub-Zero refrigeration, freezer, and wine column, a 60-inch Wolf range, dual integrated dishwashers, and a fully equipped back kitchen ensure effortless entertaining. Indoor and outdoor living connect seamlessly to a private courtyard-style retreat featuring a resort-inspired pool with copper scupper water features, a summer kitchen with Wolf grill, powered screens, and multiple lounging areas designed for year-round enjoyment. Additional highlights include four upstairs en-suite bedrooms, including a secondary primary suite, an upstairs laundry with linen towers and folding station, a third-level bonus floor with theater, bar, powder bath, and storage, elevator-ready construction, and an advanced security system with AI-enabled cameras and window vibration sensors. Designed with architectural intention, this home pairs refined craftsmanship with warmth, creating spaces that feel both elevated and deeply livable.

9323 Gladys Garden Court, Windermere
5074 Isleworth Country Club Drive, Windermere
$7,250,000
5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the two-story home features 5 bedrooms, 6.5 bathrooms, and a seamless blend of timeless modern design and resort-style living. A striking 10-foot custom pivot door welcomes you into light-filled interiors, where elegant European porcelain tile and expansive open living spaces create a bright, elevated ambiance. Designed for both entertaining and everyday living, the main living areas flow effortlessly through expansive sliding glass doors to a stunning outdoor retreat, complete with a fully retractable screen enclosure. The chef’s kitchen serves as the centerpiece of the home, appointed with top-of-the-line appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden chef’s pantry and temperature-controlled wine cellar enhance both functionality and style. The main-level primary suite offers a private, resort-inspired retreat, featuring a custom walk-in closet, a versatile bonus room ideal for fitness or wellness, and a dedicated in-home spa room. The spa-like primary bath includes a soaking tub, expansive walk-in shower, and a tropical outdoor shower, creating a tranquil escape. Upstairs, the newly constructed addition includes a secondary primary suite with a luxurious bath and walk-in closet, additional en-suite bedrooms, a spacious game room with access to a grand balcony overlooking panoramic golf course views, and a refined home theater. Outdoor living is equally impressive, featuring a sleek pool and heated spa, outdoor kitchen, wet bar, surround sound, and lush, manicured landscaping designed for privacy and enjoyment. Additional highlights include a fully integrated Crestron smart home system controlling lighting, audio, climate, and security, as well as a brand-new Generac generator for uninterrupted comfort. Fully remodeled and upgraded throughout, this residence presents a rare opportunity to own a like-new luxury estate in one of Central Florida’s most prominent communities.

5074 Isleworth Country Club Drive, Windermere
9725 Chestnut Ridge Drive, Windermere
$5,975,000
7 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Virtually Staged. Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Some photos have been virtually staged. Private showings are easily accommodated, including same-day requests.

9725 Chestnut Ridge Drive, Windermere
4819 Alexandra Garden Court, Windermere
$3,200,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa.  Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.

4819 Alexandra Garden Court, Windermere
Start Your Search

Orange County › Windermere › Isleworth

Isleworth, Windermere

Isleworth is a neighborhood in east Windermere, in the 34786 zip code, built most often in the 1990s. Homes are stucco and block. Most homes fall between about 3,600 and 10,200 square feet under air, and the median lot is about 0.60 acres.

Homes here carry an HOA, billed quarterly, typically around $1,659. Confirm the figure on a specific parcel before relying on it.

What the homes are

  • Built Most often built in the 1990s (47% of homes), with homes from 1986 to 2027.
  • Construction Stucco and block. Tile roofs are near universal.
  • Style Mediterranean, Custom, Other. Predominantly two story.
  • Size Most homes fall between about 3,600 and 10,200 square feet under air.
  • Bedrooms Four bedrooms is the most common plan, then five.
  • Lot The median lot is about 0.60 acres.
  • HOA Billed quarterly, typically around $1,659. Confirm on a specific parcel before relying on it.

Where Isleworth is

Isleworth, centered at 28.489079, -81.521294. Drag to explore.

Drive times below are measured on the road network from the center of Isleworth, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving toTimeMiles
Downtown Orlando25 min11.6
Walt Disney World26 min14.7
Orlando International Airport30 min19.8
Universal Orlando14 min5.2

Public schools nearby

  • Olympia High School 5 min, 1.5 mi
  • Palm Lake Elementary School 9 min, 2.9 mi
  • Windy Ridge K-8 School 8 min, 2.3 mi
  • Windermere Elementary School 8 min, 2.8 mi

Private schools nearby

  • Inspiring Minds Day School 5 min, 1.5 mi
  • Holy Family Catholic Church and School 6 min, 1.7 mi
  • New Academy Inc 5 min, 1.5 mi

Parks and recreation

  • Central Park 5 min, 1.4 mi
  • Fernwood Park 6 min, 1.6 mi
  • Palmer Park 7 min, 2.0 mi
  • R.D. Keene Park 10 min, 3.1 mi

Groceries and errands

  • Publix Super Market at The Grove 5 min, 1.2 mi
  • Horizon Foods 5 min, 1.4 mi
  • Walmart 5 min, 1.2 mi
  • Walmart Neighborhood Market 5 min, 1.3 mi

Nearest is not the same as zoned. The schools above are the closest ones to Isleworth by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Isleworth actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 14 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated November 2026.

What homes sold for in Isleworth

$4,093,750Median sale price
$712Median per square foot
38 daysMedian days to contract
14Homes sold in 12 months

Sale prices ran from $2,900,000 to $11,500,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home sizeSalesMedian priceMedian $/sq ftMedian days
3,000 sq ft and up13$3,900,000$70237 days

A price per foot taken from the whole neighborhood should never be applied straight to one house.

Seller concessions

7%Of sales included a seller credit
$48,682Typical credit when there was one
1 of 14Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Private 6 sales43%
Cash 5 sales36%
Conventional 3 sales21%

Cash was 36% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Isleworth, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Isleworth in Windermere, Orange County, covering closed sales from 7 November 2025 through 2 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. Data believed accurate but not guaranteed; listings and closings change daily.

How much is your home worth?

Get instant property value now!