AgentLogo

9731 CHESTNUT RIDGE DRIVE

WINDERMERE , FL 34786

MLS#: O6336655

$3,400,000

Status: Active
Listing number: O6336655
Listing provided by: ISLEWORTH REALTY LLC
Listing agent phone: None
Last update: 3 days ago
On site: 5 days ago
Browse Properties
ISLEWORTH - Residential

Property

Beds

4

Full Baths

4

1/2 Baths

None

Year Built

1986

Sq.Footage

4,877

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

Features & Amenities

Interior

  • Other Interior Features

    Cathedral Ceiling(s), Stone Counters, Walk-In Closet(s)

  • Total Bedrooms

    4

  • Bathrooms

    4

  • Cooling YN

    YES

  • Cooling

    Central Air, Zoned

  • Fireplace YN

    NO

  • Heating YN

    YES

  • Heating

    Central, Electric, Natural Gas

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    Block, Stucco

  • Other Exterior Features

    Balcony, Outdoor Grill, Rain Gutters

  • Parking

    Circular Driveway, Golf Cart Garage, Attached

  • Pool

    Yes

  • Pool Features

    Heated, In Ground, Private

  • Waterfront YN

    NO

  • View

    Pool

Area & Lot

  • Lot Features

    Landscaped, Near Golf Course, Paved

  • Lot Size(acres)

    0.54

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

Price

  • Sales Price

    $3,400,000

  • Tax Amount

    19866.86

  • Sq. Footage

    4, 877

  • Price/SqFt

    $697

HOA

  • Association

    YES

  • Association Fee

    $3,129

  • Association Fee Frequency

    Quarterly

  • Association Fee Includes

    N/A

School District

  • Elementary School

    Windermere Elem

  • Middle School

    Chain of Lakes Middle

  • High School

    Olympia High

Property Features

  • Stories

    2

  • Association Amenities

    Cable TV, Playground, Security

  • Foundation Details

    Block, Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Septic Tank

  • Tax Lot

    7

  • Water Source

    Public

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

Orange

Elementary School

Windermere Elem

Middle School

Chain of Lakes Middle

High School

Olympia High

Listing Courtesy of Monica Lochmandy , ISLEWORTH REALTY LLC

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent AshleyBaillio

FOUNDER

AshleyBaillio

Call Ashley today to schedule a private showing.

(561) 609-2391

franko+southflorida@init.hr


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below. Travertine floors flow seamlessly into the gourmet kitchen appointed with stainless steel appliances, a sunlit casual dining space, and direct access to both the intimate family room and an outdoor balcony for effortless indoor-outdoor living. Also on the primary level, the serene master suite offers a separate access to the terrace along with a luxuriously updated bath, and dual closets. Completing the primary level is a richly detailed wood-paneled office and a well-appointed laundry room, adding both warmth and function. The home’s thoughtful layout places the secondary bedrooms on the lower level, ensuring privacy and comfort for family or guests. Here, glass doors open to the multi-level terrace that gracefully surrounds the sparkling pool and spa, featuring generous deck space for year-round lounging and entertaining under the Florida sun. Offering an exceptional combination of timeless design, resort-inspired grounds, and a premier location within the gates, this remarkable residence is truly a sanctuary to call home.

9731 CHESTNUT RIDGE DRIVE

Message successfully sent.

What would you like to know?

Related Properties

Exquisitely appointed and elegantly packaged former model home, showcasing the pinnacle of perfection, from luxury home builder Element Homes. This masterpiece stands supreme for its high-quality fit and finish and a highly desirable floorplan – featuring a great room combination of family room, dining room, and kitchen – masterfully crafted to exhibit transitional style and function. A wall of glass sliders open to reveal a mammoth covered patio with roller screens, outdoor fireplace, saltwater pool, vanishing edge heated spa, summer kitchen, and detached Casita with bedroom, bath, and kitchenette. With 5 ensuite bedrooms and 4 and a half baths, plus a separate office, and media room with beverage center, rest assured there is room for all. Detailed ceiling beams add a touch of chic elegance. Other highlights include: engineered hard wood floors throughout, vinyl double pane windows and doors, decorative glass entry doors, tankless hot water heaters, spray foam insulation, over-sized circular paver driveway, insulated garage doors and epoxy finished garage floor, rooms individually Nest zoned, ship lap detailed ceilings, quartz countertops, cabinet grade pantry door leading to hide-a-way oversized built-in closet, refrigerator and dishwasher, Thermador appliances, custom shelving and drawers in all closets, great room gas fireplace, rain shower in master shower with beautiful glass enclosure. The Crestron smart wired home allows for Lutron lighting and sound throughout the home. Home sits in a quiet location with just 11 half-acre or larger homesites, walking distance to top-rated Thornebrooke Elementary, and steps away from the border of Windermere. Come experience why this home was the builder’s showcase address.
#O6333400

WINDERMERE

2012 BELLAMERE COURT

5 Beds

5 Baths

7,447 Sq.Ft.

$3,400,000

MLS#: O6333400

One or more photo(s) has been virtually staged. Stunning contemporary estate on over 1 acre in guard-gated Casabella. This 6-bedroom, 6 full bath, 2 half bath custom home offers over 7,500 sq ft of luxurious living. Open-concept design with soaring ceilings, walls of glass, and high-end finishes throughout. Gourmet kitchen with extended islands, premium appliances, and seamless flow into the great room and formal dining. First-floor primary suite with spa-like bath and custom closets. Each secondary bedroom includes an en-suite bath. Additional highlights include a home office, media room, and theatre room. Expansive backyard with resort style pool and outdoor kitchen. Smart home features, 4-car garage, and prime location near top-rated schools, golf, and amenities.
#O6333933

WINDERMERE

4077 ISABELLA CIRCLE

6 Beds

6 Baths

11,217 Sq.Ft.

$3,450,000

MLS#: O6333933

Under Construction. ***Showings only Wednesday after 5pm*** We present a luxury residence in Windermere, Florida, that combines modern design, spacious areas, and a prime location. Situated at 6208 Winter Garden Vineland Road, this property is strategically positioned in front of Windermere Preparatory School, one of the best private schools in Florida. With 5,441 sqft of climate-controlled living space and a total area of 8,091 sqft, this home impresses with its size and sophistication. It features 6 en-suite bedrooms, all with walk-in closets, plus a half bath and an additional full bathroom dedicated to the pool area, totaling 7.5 bathrooms. The modern architecture, a rare find in Orlando, stands out with its 12-foot ceilings, sliding doors in all bedrooms, and an open-concept social area that provides integration and elegance. The outdoor area is one of the highlights of this property. The swimming pool with a jacuzzi invites relaxation, while the spacious 880 sqft gourmet patio is perfect for entertaining friends and family. The property also features a tennis or pickleball court and a sand court, which can be used for beach volleyball, beach tennis, footvolley, or as a play area for children. To ensure maximum privacy, the entire 1.29-acre lot will be enclosed. The house is equipped with modern, energy-efficient Thermador appliances, 100% LED lighting, and infrastructure ready for surveillance systems and smart home automation, compatible with the leading platforms on the market. Another great feature is the four-car garage, which includes two electric vehicle chargers, offering convenience and sustainability for its residents. This property offers the perfect balance of luxury, technology, and comfort. Additionally, its location provides easy access to key points in the city, being approximately 30 minutes from Orlando International Airport (MCO), 19 minutes from Magic Kingdom, 18 minutes from Universal Studios, and 20 minutes from downtown Orlando. An added benefit is the absence of HOA fees, allowing total freedom to personalize and use the space as desired. This is a unique opportunity for those seeking an exclusive home in one of Florida's most sought-after areas. Schedule a visit and discover what makes this house truly special!
#O6330996

WINDERMERE

6208 WINTER GARDEN VINELAND ROAD

6 Beds

7 Baths

8,091 Sq.Ft.

$3,900,000

MLS#: O6330996

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.
#O6330108

WINDERMERE

4819 ALEXANDRA GARDEN COURT

4 Beds

4 Baths

6,461 Sq.Ft.

$3,200,000

MLS#: O6330108

A Masterpiece on the 4th Hole – Keene’s Pointe Luxury Living Perfectly poised on a premium golf-front lot in the gorgeous, guard-gated community of Keene’s Pointe, this custom-built residence by Unnerstall blends refined craftsmanship with thoughtful design and breathtaking views of the Golden Bear Club’s 4th hole and tranquil water features. Boasting over 6,100 square feet of impeccably designed living space, this home offers 5 en-suite bedrooms, two private offices, a dedicated fitness room, and a sunroom-style bonus/game room—all tailored for both comfortable daily living and elevated entertaining. From the moment you step through the grand double doors, you’re welcomed by travertine flooring, elegant architectural detail, and a sense of scale that is both impressive and inviting. The main-level primary suite is an expansive retreat featuring dual walk-in closets and an unforgettable two-story spa bath designed to inspire relaxation. A second bedroom suite on the first floor provides ideal accommodations for guests or multi-generational living. The heart of the home is the gourmet kitchen, beautifully appointed with custom cabinetry and open to the dramatic two-story great room, creating a seamless flow for entertaining. Upstairs, you’ll find three additional en-suite bedrooms, a flexible bonus room or office, and a private home gym. Step outside to your personal resort. A screened-in lanai leads to a lush, landscaped backyard with a copper-roofed gazebo, outdoor kitchen and bar, and a sparkling pool and spa—all perfectly positioned for enjoying Florida’s golden skies and outdoor lifestyle. Additional highlights include an oversized paver driveway, three-car garage plus separate golf cart entrance, Venetian plaster finishes, and designer touches throughout. Set within one of Windermere’s most exclusive communities, where majestic oaks, lakeside trails, and the Butler Chain of Lakes frame a lifestyle rich in privacy, recreation, and natural beauty—this is more than a home. It’s a statement.
#O6326947

WINDERMERE

11209 MACAW COURT

5 Beds

6 Baths

7,900 Sq.Ft.

$2,895,000

MLS#: O6326947

Experience Unmatched Lakeside Luxury in a Custom-Built Masterpiece Discover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined living. Step inside to a beautifully designed open-concept living space where the family room and gourmet kitchen seamlessly connect. The kitchen is a chef’s dream, featuring top-of-the-line appliances, a breakfast bar, an inviting eat-in nook, and a spacious butler’s pantry. A custom wine closet nearby provides a perfect display for your finest vintages. Adjacent to the kitchen, a well-appointed guest suite and a large laundry room enhance the home's convenience. The formal dining and living rooms, centered around a cozy shared fireplace, has stunning views of the lake—creating a warm and relaxed setting for entertaining. The first floor also features a private office, a full pool bathroom, and a luxurious primary suite. This expansive retreat includes a dedicated exercise room, while the spa-inspired en-suite bath boasts double vanities, dual walk-in closets, a garden tub, and a walk-through shower. A beautifully crafted wood and iron staircase leads to the second floor, where you'll find two spacious bedrooms, each with its own private bathroom. The expansive game room opens to a lake-view balcony, perfect for taking in serene sunsets. Movie nights are elevated in the state-of-the-art home theater, complemented by a convenient half bath. Step outside to your own private paradise—an entertainer’s dream. The large covered lanai includes a fireplace and a fully equipped summer kitchen. A sparkling pool and spa, along with a generous open patio, set the stage for unforgettable gatherings or peaceful evenings under the stars—complete with views of the nightly fireworks. Rounding out this extraordinary residence is a three-car garage, offering ample room for vehicles and recreational equipment. This is more than a home—it’s a lifestyle. Luxury, privacy, and breathtaking views await. Schedule your private tour today and experience the ultimate in lakeside living. Property can have a boat dock.
#V4943735

WINDERMERE

12812 JACOB GRACE COURT

4 Beds

4 Baths

9,150 Sq.Ft.

$3,799,000

MLS#: V4943735

Enjoy stunning sunsets from your private estate with expansive views, located on Lake Down, the prestigious Butler Chain of Lakes in Windermere. This well-appointed property features 2.78 acres with fully fenced terraced grounds, electric security gates, brick pavers, mature landscaping for privacy, and 130 feet of water frontage with a seawall, enclosed boat house, dock, and lift. The heated 7,363 square feet of living space includes the main home with 4 bedrooms and 5 bathrooms, as well as a lake guest house. Most rooms are graced with breathtaking views. Almost 10,000 square feet under roof, with a porte cochere, extensive balconies, walkways, outdoor kitchen, and multiple patios. The screened pool area has an inviting resort feel, complete with a waterfall, slide, and hot tub, all connected to the outdoor entertainment areas. Many quality upgrades, expansive ceilings with craftsman woodwork, wood and marble floors, formal dining with a music room, and fireplaces in the living, family room, and primary bedroom. The living room features a floor-to-ceiling window with remote-control blind, taking full advantage of the priceless view. The main staircase gives a dramatic vantage point to appreciate the open floor plan, ideal for entertaining. The well-appointed kitchen features a chef's prep kitchen, electric and Wolf gas double oven, two Sub-Zeros, double dishwashers, and a built-in espresso machine. All kitchen elements are set within rich wood custom cabinetry and granite countertops, with a breakfast room that leads to the pool area. The guest bathroom, laundry & family room are all conveniently located near the pool. The primary suite is downstairs and includes a private screened porch, remote-control blackout blind, custom cabinet with washer & dryer, and a large master bath with a soaking tub, walk-in shower all with elegant stonework. The suite is adjoined by a generous custom closet, safe for valuables, private gym with mirror, rubber floor, bonus storage, and a private staircase to the upstairs. Upstairs features large bedrooms with lots of closet space, balconies overlooking the water with Ipe decks and a secondary family room or playroom for the family. The lake cottage spells fun with balconies all around and views of the water and pool on three sides. Open beam ceilings, bamboo and new luxury vinyl wood floors, full kitchen & living room upstairs with a full bedroom and bath downstairs complete with a wet bar. The property has rear yard access down to the lake, great for boat parking or extra parking when you rally the team for a volleyball match on the court. You can also utilize the tennis courts & private boat ramp just a short walk down the street. There are too many low maintenance, cost saving features to list, but a few include; energy efficient solar power, metal roof, and three on demand propane powered gas water heaters. There are over $55,000 in solar panels that will save countless dollars over the years and is good for the environment. The electric bills are minimal. As I mentioned earlier Ipe hardwood is the best exotic hardwood the industry has to offer and it was used on the extensive decks for low maintenance. A new two horse sprinkler pump was recently installed that draws from the lake to maintain the exotic landscape. The durable easy to clean composite dock has two lifts & two boat slips. The owner will even throw in the $50,000 ski boat (approx Value) with an acceptable offer.
#O6324706

WINDERMERE

10545 DOWN LAKEVIEW CIRCLE

5 Beds

4 Baths

9,989 Sq.Ft.

$3,795,000

MLS#: O6324706

A Masterpiece of Design in Isleworth – 6186 Louise Cove Drive. Stunning, design magazine-worthy residence nestled behind the exclusive 24-hour guard-gated community of Isleworth, one of Central Florida’s most prestigious neighborhoods. This exquisite estate sits on a spacious 0.75-acre corner lot, surrounded by mature landscaping and a stately circular driveway that sets the tone for the luxury that awaits inside. No expense was spared in the recent $1 million designer remodel, which brought in California-based interior designers to source the finest materials from around the globe. Step through grand arched solid wood double doors into a soaring foyer where 16-foot ceilings and imported white French oak floors flow throughout the home. Walls were meticulously finished to level 5 smoothness a testament to the craftsmanship and attention to detail throughout. Designed for both entertaining and everyday living, the open-concept family room centers around a venetian plaster fireplace and effortlessly flows into a show-stopping double island kitchen. Imported German cabinetry is complemented by one piece quartzite slabs and backsplash, while high-end appliances include a 6-burner Wolf range with double ovens, a paneled Thermador refrigerator & freezer, venetian plastered hood, beverage fridge, and under counter microwave are all seamlessly integrated for a refined look. Retreat to the expansive primary suite, where comfort meets luxury. Enjoy access to a private study, Florida room, and a spa-inspired bathroom featuring a stand-alone soaking tub, oversized glass shower with handmade 4x4 Moroccan tile, French brass fixtures, and custom lighting. Primary suite also features a spacious walk-in closet offering custom built-ins, providing both elegance and functionality. The home’s Santorini-inspired full pool bath is a work of art in itself, with artisan stucco finishes adorning every surface. Each secondary bedroom is an en-suite, with marble or handcrafted tile finishes and ample closet space. Outdoors, your private fenced backyard oasis features a heated pool & spa, covered summer kitchen, and expansive lanai, perfect for enjoying Florida’s year-round sunshine. Additional highlights include a whole-house generator, tankless water heaters, four AC units, and a designer laundry room with imported German cabinetry. Live minutes from world-class attractions, dining, and elite schools, yet enjoy the serenity and security of one of the region’s most sought-after enclaves.
#O6324115

WINDERMERE

6186 LOUISE COVE DRIVE

4 Beds

5 Baths

6,261 Sq.Ft.

$3,250,000

MLS#: O6324115

NEW CONSTRUCTION Luxury Lakefront Estate | 6,202 Sq Ft a Private Guest House | 6 Beds + Office + Loft | Pool | No HOA | Boat Dock Experience unmatched lakeside living in this west-facing, 6,202 sq ft custom estate featuring 6 bedrooms with private en-suites, including a guest suite. Upstairs, the primary suite and three additional bedrooms each open to private balconies offering sweeping sunset views over the lake. A spacious loft/flex space and convenient upstairs laundry add extra versatility. The main level boasts a dedicated office, family room with fireplace, and a chef’s kitchen with eat-in space, large island, wine rack, and wet bar. The dining room can easily serve as a billiards or game area. Step outside to enjoy a resort-style pool, summer kitchen, and a newly built private boat dock—all overlooking tranquil lake waters and golden evening skies. Bonus Guest House: Complete with a full kitchen, private laundry, living room, and bedroom with walk-in closet, the guest house also features a loft space with its own balcony—offering uninterrupted panoramic lake views. The perfect private retreat.. NO HOA GATE WILL BE ADDED TO ENTRY
#O6312690

WINDERMERE

7706 FICQUETTE ROAD

6 Beds

6 Baths

8,693 Sq.Ft.

$3,950,000

MLS#: O6312690

- property

Send a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here