loading

16 Homes For Sale in The Neighborhood Of Isleworth In Windermere, FL

Sort by:
New
$2,590,000Est. Payment
3 Beds | 4 Baths | 4,225 Sqft
5056 Isleworth Country Club Drive, Windermere, FL 34786
House For Sale

World Famous Isleworth Golf and Country Club! Located on the 6th hole this sensational Transitional masterpiece is just what you are looking for! Rebuilt from the ground up! Be the first to live in this sensational house. Watch your favorite Golfers pass by from one of your spacious Artistic Paver lanais. Two gourmet kitchens. One inside the other out. Featuring top of the line Thermador stainless steel appliances. Including A fee standing 100 bottle Thermador wine cooler! Luxurious Master suite with breakfast bar walk in closets, free standing tub and shower you will not want to get out of ! Master wing has an office or den and a private lanai with fire pit. Two on suites with full baths for family or guests. The large open floor plan has a formal dinning room and living room . Vaulted Ceilings with authentic wooden beams! The Great room off the kitchen has a gas fireplace for our occasional chilly Florida nights! This house was finished with the finest of everything including" ADT Sonos get Secured " Security system, surround sound throughout and 85 inch flat screen. Luxurious over sized heated pool and spa area to relax in while watching the sunset over the golf course. Now is the time to move to a vacation life style at home!!!

$1,840,000Est. Payment
3 Beds | 3 Baths | 3,942 Sqft
5139 Latrobe Drive, Windermere, FL 34786
House For Sale

Set along the front nine of Isleworth's famed championship golf course, this beautiful estate is a true golf-front paradise overlooking the 4th fairway. The interior spans nearly 4,000 square feet and has been updated extensively throughout with new flooring, finishes and modern appointments. The foyer opens to the formal living room with an elegant custom fireplace recently added to the home along with an elevated ceiling and direct access to the screened, covered lanai. Beautiful wood floors continue into the well-appointed kitchen which features beautiful cabinetry, black granite countertops and professional stainless steel appliances. This large gathering space overlooks a casual dining area as well as the warm and inviting family room. The master suite is a true gem within the home and features dual closets, a large bath that has been completely renovated with an exquisite walk-in shower, vanities and new flooring, and the best in indoor-outdoor living with doors that fully open to the resort-style backyard. This exceptionally private area is a breathtaking menagerie replete with a sparkling pool, sundeck, expansive detached cabana and outdoor kitchen and a number of winding walkways through the lush, tropical greenery and an extraordinary collection of koi fish. The grounds come to life at night with beautifully lit lounging areas and everything needed to enjoy Central Florida's warm climate all year round.

$2,700,000Est. Payment
7 Beds | 8 Baths | 6,933 Sqft
5127 Latrobe Drive, Windermere, FL 34786
House For Sale

Contemporary vision inside Isleworth Country Club. Welcome to this modern golf front estate, featuring high quality craftsmanship and built. Perfectly situated on the 5th hole of Isleworth's world-renowned golf course, the inviting outdoor living space includes a pool bordered with stone, oversized spa, fire pit, summer kitchen, entertainment areas and plenty of dining space. Brand new roof installed in January 2021, interior/exterior paint job and new landscape completed in February of 2021. On the first floor you will find the spacious master suite and an additional bedroom or office space. Dining room is complimented by the glass and wood climate controlled wine cellar. The home features gourmet kitchen, oversized walk in pantry and opens into the spacious family room. Upstairs, you will find the spacious game room, wet bar and movie theater and an 5 additional bedrooms, to which could be used as guest suites, exercise room or home office. Home interior is staged by Saccaro Furniture and exterior furniture staged by Elementar Outdoor.

$2,250,000Est. Payment
4 Beds | 6 Baths | 4,512 Sqft
5145 Latrobe Drive, Windermere, FL 34786
House For Sale

Nestled along Isleworth's famed championship golf course overlooking Hole 4, this beautiful golf-front estate spans more than 4,500 square feet and has been updated with modern finishes creating a true golfer's paradise. Beyond the motor court, French entry doors reveal an open foyer with volume ceiling leading past the formal dining room and wine bar to the formal living room. Light pours into this elegant gathering space where a soaring ceiling and modern fireplace are a perfect complement to the marble floors and neutral, light gray hues. The kitchen showcases dark wooden cabinetry paired with smooth granite countertops and professional stainless steel appliances. Adjacent to the kitchen, a casual dining space and family room both offer plenty of windows and direct access to the pool. Offering beautiful hardwood floors, a sitting area, multiple closets and an exquisite bath with two vanities, a walk-in shower and separate garden tub, the main-level master suite is the ideal spot to start and end the day. Three additional en-suite bedrooms, a bonus room and a three-car garage complete the interior. Enjoy stunning views down the 4th fairway from the balcony or descend to the fenced grounds where the covered lanai, sparkling pool and ample deck space deliver a tropical oasis to be enjoyed all year round.

$1,549,000Est. Payment
4 Beds | 5 Baths | 4,024 Sqft
5085 Latrobe Drive, Windermere, FL 34786
House For Sale

Nestled along the front nine of Isleworth's renowned championship golf course, this lovely golf-front residence offers a backdrop of beautiful views of the 5th hole. The single-story home boasts an open and airy interior spanning more than 3,800 square feet of living space, with elegant stone and hardwood floors throughout. Beyond the circular motor court, exquisite French doors open to the formal living and dining rooms - each with custom ceiling detail and views of the lanai and open-air swimming pool. The center-island kitchen offers custom cabinetry, stainless steel appliances and smooth granite countertopsall overlooking a large family room with built-in media center and direct access to the lanai and pool. The spacious master suite boasts a sitting area with French doors that open to the lanai, as well as an expansive bath with dual sinks, a garden tub, walk-in shower and open closet with built-in display shelves. Three additional bedroom, a powder bath and laundry room complete the interior. The fenced yard surrounds the open-air pool, spa and sundeck overlooking Hole 5.

$3,990,000Est. Payment
6 Beds | 8 Baths | 9,762 Sqft
5501 Isleworth Country Club Dr, Windermere, FL 34786
House For Sale

Perfectly sited on approximately one acre on the 14th hole of renown Isleworth Golf and Country Club this Transitional style estate presents a 21st century translation;completely renovated in 2017. The residence opens up at the foyer visually connecting interior spaces with dramatic results. The focus is on symmetry of design from the stunning walnut floors to the elegant designer finishes. Abundant natural light in the grand room adds a sense of the outdoors and activates the openness of the plan. The thoroughly new modern kitchen features Quartz counters,top of the line stainless appliances (including large 6 burner Wolf range)and is complete with rich custom cabinetry. A stunning 1000 bottle climate controlled wine room is impressive. The family space transitions naturally to the outdoor resort style covered loggia, warm and relaxing with natural brick flooring and massive fireplace with retractable screens. Perfect for entertaining family and friends the outdoor areas are a delight featuring a sparkling climate controlled salt pool and spa overlooking golf views. The impressive master suite offers an intimate space to rest. The master suite is linked to the completely redone Master Bath with outdoor shower. Separate guest suite has small kitchen, living room and bedroom. This gracious estate has been completely repainted and features new Crestron AV system, Lutron lighting, Reverse Osmosis whole house water system, and whole house generator. Secondary bedrooms are spacious and ensuite.

$8,300,000Est. Payment
5 Beds | 9 Baths | 11,229 Sqft
6432 Deacon Circle, Windermere, FL 34786
House For Sale

This stunning Georgian manor located within the gates of the renowned Isleworth community tastefully intertwines timeless old world charm with modern style. Upon entry, you will be welcomed by the grand staircase while you gaze past the wall of seamless glass overlooking your infinity pool as it appears to flow into Lake Chase; a sand bottom, spring fed ski lake. From the four French limestone fireplaces and custom pillars to the intricate carvings and cappuccino marble flooring, this home has been flawlessly updated and maintained. All five bedrooms share the same floor with their own en suite bath and private balcony. The master bedroom also has a private lounge with morning kitchen. Isleworth offers unparalleled security with 24 hour manned gates. The home offers privacy while still being close to Isleworth Golf Course and Clubhouse. The tennis center, driving range and putting green are all a few hundred feet away. Convenient to shopping, Orlando International Airport and Attractions. Optional Country Club membership offers exceptional golf, tennis, dining and many social activities. Situated on Lake Chase in the Butler Chain of Lakes, known for its water quality and wildlife habitat. Isleworth is one of the most sought after communities in Central Florida.

$3,400,000Est. Payment
4 Beds | 5 Baths | 6,738 Sqft
5284 Isleworth Country Club Drive, Windermere, FL 34786
House For Sale

Poised on Isleworth Country Club Drive overlooking Eagle Pond and the 11th tee, this exquisite estate offers exceptional golf and water views within the gates of Central Florida's most iconic golf and country club community. Adjacent to the beautiful "Cloister Conspiracy" sculpture by Philip Jackson, the residence features an interior spanning more than 6,700 square feet with picture-perfect views of the surrounding landscape. Oversized wood, glass and wrought-iron French doors reveal a gallery entry where smooth marble floors sprawl beneath meticulously detailed ceilings adorned with chiseled millwork and dotted with stone columns. Presenting traditional architecture and design, the formal living and dining rooms with custom coffered ceilings lead seamlessly to the center-island kitchen and family room with an abundance of light. A range of impressive professional appliances and custom cabinets serve the kitchen, as well as a beautiful built-in bar and custom brick-lined wine cellar. On the first floor, two generous master retreats feature exquisite baths complete with dual vanities, garden tubs and walk-in showers with beautiful stone surrounding stained glass windows. The second floor is complete with two additional guest rooms and an office. The outdoor living area, which features a multi-level terrace and sundeck surrounding the sparkling pool, spa and water feature. Blending the finest finishes with an exceptionally beautiful setting, the estate offers the best in golf-front living.

$849,000Est. Payment
3 Beds | 2 Baths | 2,196 Sqft
656 E 6th Ave, Windermere, FL 34786
House For Sale

Unique lakefront property within the town limits of Olde Windermere. A perfect fit for someone wanting to downsize and yet enjoy the lake lifestyle. This lovely home sits on a beautiful oversized lot and overlooking the sunrises and sunsets on fabulous Lake Bessie, which is perfect for boating, skiing and great fishing. Lake Bessie is only open to property owners and town residents, and it is famous for its big bass. Great shopping area nearby with gym, pharmacy, restaurants, grocery store and much more. The incorporated town of Windermere offers a full police force, 13 parks, tennis courts, coffee shop, ice cream shop, eatery, wine shop and more and no HOA for original residents.

$6,300,000Est. Payment
5 Beds | 8 Baths | 10,843 Sqft
9838 Laurel Valley Drive, Windermere, FL 34786
House For Sale

Capturing majestic sunset views of beautiful Lake Butler, this fabulous lakefront estate is perfectly set between Lake Butler's shoreline and the 15th hole of Isleworth's renowned championship golf course. The three-story estate offers a nod to Mizner-inspired architecture and is stunning in both scale and contemporary style. With fresh, white interiors, a wealth of modern accents and an array of exciting living spaces, the estate is a lakefront paradise. Marble floors with onyx inlays lead from the grand two-story foyer and curved, floating staircase to the open gathering area featuring a distinctive three-story spiral staircase, formal dining room, center-island kitchen and two living areas offering volume windows with automatic shades that perfectly frame the lake views. The main master suite presents an impressive, oversized bed outfitted specifically for this estate along with a large bath featuring a jetted tub, walk-in shower and multiple vanities. The lower level comes fully equipped with game room, fitness room with sauna, swim-in pool, full bar and custom home theater with a box office and snack stand. Ascend to the upper level via elevator where a second gaming area and numerous bedrooms create the ultimate venue for entertaining family and friends. Offering an unforgettable setting, the spectacular grounds boast a sparkling, open-air pool and spa with plenty of space for sunbathing and dining al fresco. A private boat dock offering direct access to the famed Butler Chain of Lakes invites year-round water recreation, from boating to jet skiing to paddle boarding and more.

$2,350,000Est. Payment
4 Beds | 4 Baths | 3,957 Sqft
5427 Monterrey Club Court, Windermere, FL 34786
House For Sale

A one-of-a-kind residence within the gates of the renowned Isleworth Golf & Country Club, this remarkable estate offers impeccably designed interiors spanning more than 3,900 square feet. A contemporary masterpiece showcasing the pinnacle of modern styling, the property offers an ideal layout for stylish living and entertaining. The home embraces its perfect setting surrounding a lovely courtyard pool with carefully conceived finishes at every turn. The formal living room showcases 24" granite floors, a 12' Ebony Macassar paneled wall and console and 12' floor-to-ceiling windows with views of the courtyard. Beyond the dining room, the gourmet kitchen overlooks the family room and features Leicht "Highline" cabinetry imported from Germany - a perfect complement to the professional appliances including the Thermador refrigerator and freezer, Miele oven, built-in Miele coffee maker, microwave, steam oven, convection oven and dishwasher. The spacious master suite offers a private foyer with 12' floor-to-ceiling cabinets, a built-in console and matching paneled walls. Pocket doors lead to the beautiful master bath which features white paneled walls, double vanities, electric shades, a soaking tub with air jets, separate walk-in shower and a master closet with built-ins. The estate also offers a guest house with lovely views of the courtyard pool, plenty of custom built-ins including a desk, wardrobes and queen-sized bed, as well as Leicht floor-to-ceiling paneled walls and 12' electric drapes. The custom office features custom glass doors, a stainless steel wall accent, a 12' built-in desk and suspended cabinetry with six built-in computer monitors. Stainless architectural lighting, granite floors and baseboards, LED lighting and a three-car garage add to the many pleasures of this pristine Isleworth estate.

$500,000
$6,100,000Est. Payment
6 Beds | 10 Baths | 12,298 Sqft
5318 Isleworth Country Club Drive, Windermere, FL 34786
House For Sale

NEW PRICE! MOTIVATED SELLER OFFERS A $500,000. PRICE REDUCTION! WONDERFUL OPPORTUNITY TO PURHASE IN EXCLUSIVE GATED GOLF AND COUNTRY CLUB COMMUNITY, FULL-TIME GUARD-GATEHOUSE. CUSTOM BUILT! Stunning entrance. Pristine condition. Dramatic interior includes an interior custom designed swimming pool, in a temperature-controlled entertainment, two-story Pavilion with stone flooring, skylights, a heated pool and spa, a bar, grilling/cooking area, dining area and lounging area - all of which is the absolute focal point of this dramatic interior! Imagine entertaining your family and friends here, with the moonlight streaming through the skylights. This dream home could be the fulfillment of your dream of owning a home in one of Florida's most amenity-rich, gated communities. Sited on almost 2 acres embraced by mature, manicured landscape and golf course frontage in rear. The front porte-cochere leads to a double door entry, and opens to a wide two-story, marble Foyer with winding staircase gracefully ascending to 2nd floor balcony. From the grand marble foyer you are looking through the 12,000 square foot interior and the two-story living room, out to the Pavilion and the pool and then out to the sprawling landscaped gardens with reflecting pond and fountain, and the golf course! A dramatic "first impression"! The interior is the embodiment of quality craftsmanship, where formal and casual areas are perfectly blended for comfort and privacy. The 1st floor features 2 Master suites (one is currently purposed as a family room), a grand two-story living room, dining room, custom fitted home office/study with computer station, custom Kitchen, and a 2nd Master Suite, on opposing side of floor plan, featuring a series of French doors opening to the Pavilion - imagine the moonlight in here! Two balconies span the width of the 2nd floor, affording exciting views looking down on to the Pavilion. The 2nd floor features 6 spacious bedroom suites, located on op

$7,495,000Est. Payment
6 Beds | 8 Baths | 12,778 Sqft
9288 Blanche Cove Drive, Windermere, FL 34786
House For Sale

Under Construction. Under construction, with a small window of time to still make it your own. Nestled behind the famed gates of Isleworth, one of the most exclusive private Golf and Country Club communities in the world, situated on one of the last waterfront lots you will find this gorgeous homesite with construction well underway! Offering serene views of Lake Blanche and towering Cypress trees framing a canvas of sunsets, you will be hard pressed to find a more picturesque setting. Transitional style mixed with more modern elements sets the stage for this one-of-a kind estate with a skybox that overlooks the indoor half basketball court. Upon entering the home, you are ushered into the spacious great room that overlooks the pool area and lake. A gallery connects the home's primary living spaces, including the warm and inviting family room, kitchen, and family dining area, which are the perfect entertaining spaces. The truly custom kitchen will feature state of the art appliances and of course, since it is the heart of the home, beautiful stone counters and the latest in designer touches. Located downstairs off the gallery is the luxurious master suite, including his and her walk-in closets with plenty of room for any shoe collection, and a luxurious spa like master bathroom. Additionally, across from the master suite, is the stately office with a glass wall overlooking the air-conditioned collector's showroom garage. The split floor plan also offers 2 downstairs guest suites which is ideal for multi-generational families as well as young children. Whether you choose the stairs or the elevator to reach the second level, you will be greeted by a large loft area that can be used as a game room. You will also find the second Master suite, perfectly suited for in laws, a nanny or long term guests. There are two additional bedrooms upstairs, each with their own generously sized en-suite bathrooms that are finished with exquisite finishes. Showcasing the latest tre

$5,959,000Est. Payment
5 Beds | 9 Baths | -- Sqft
5507 Worsham Ct, Windermere, FL 34786
House For Sale

Immaculate custom estate perfectly situated on the 14th green of the Isleworth Country Club. This Isleworth mansion features an exquisite transitional, contemporary and timeless interior, beautiful golf views and plenty of space for perfect family gatherings. The unparalleled grand open floor plan greets you with a massive soaring two-story foyer and living room featuring floor-to-ceiling windows with spectacular golf front views. Entertain friends and family in the fully equipped theatre or the generous summer kitchen area complemented by an expansive private pool and spa. Retreat and relax in the elaborate main floor master suite complete with a spectacular marble bathroom featuring deluxe spa, extensive his and hers vanity, multiple showers, a very generous closet and a private terrace to the spa. Create the ultimate atmosphere for entertaining in the formal dining room or al fresco dining in the covered lanai and extensive terraces. This magnificent home and its unique hand-selected finishes include: artisan-crafted cabinetry, grand marble stairs, wood and marble floors, exquisite door frames, unique chandeliers, a formal study with custom fireplace, a spectacular home office, an additional second floor master bedroom, a five-car garage: two of which have been converted to flex study/office/play room areas (can be converted back), elevator, plenty of private outdoor space and basketball hoop. This picturesque home site is move-in ready!

$1,950,000Est. Payment
0.7 Acres
9736 Chestnut Ridge Drive, Windermere, FL 34786
Lots Land For Sale

Claim your piece of Isleworth lakefront paradise today. This remarkable property is located on picturesque Lake Bessie and is one of the last lakefront lots in Isleworth. It provides 131 feet of lake frontage and is nestled among beautiful old Florida foliage. From the elevated home site you can enjoy watercolor sunsets and golf course views across the lake. Amenities in the neighborhood include a marina, an 18 hole golf course designed by Arnold Palmer and an spacious clubhouse featuring restaurants, a pool with splash pad, and cutting edge fitness center. This rare opportunity won't last long. Call today to schedule your private showing.

$28,000,000Est. Payment
12 Beds | 11 Baths | 31,000 Sqft
9927 Giffin Ct, Windermere, FL 34786
House For Sale

Private Grandeur Embodied Isleworth Estate - Situated on 3 acres overlooking tranquil panoramic Lake Butler sunset views. This magnificent custom estate is comprised of approximately 31,000 square feet of living space, which includes a 6,000 square foot indoor basketball court. Beautiful double, curved stair cases greet you in the two-story foyer and guides you to the estate's magnificent great room. The great room boasts approximately 1,170 square feet, built-in sofas, 2 story marble fireplace, wood beams with large corbels then complimented by a wall of glass showcasing the serene views of Lake Butler. Experience deep rich color tones, large open doorways, and beautiful hand-crafted wood paneling and moldings throughout majority of the home. The astonishing estate was designed with lake views in mind for almost every room. Other highlights include gated entry, full house Crestron technology, 17 plus car garages with showroom details, 3 fireplaces, walk-in humidor and wine storage, two story ceilings, 15 feet in depth pool with rock wall water feature, summer kitchen, custom chef's kitchen, covered cabana and 10-foot privacy wall.

version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >