Back 17737 Deer Isle Circle
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17737 Deer Isle Circle

Winter Garden FL 34787

5
5
3
7790 sq. ft.
44593 sq. ft.
Single-Family
Last sold for $2,775,000
Candace CassidyCandace Cassidy, last sold this property on 27 April 2026 after 60 days on market.

Overview

Experience over an acre of elevated direct sunset lakefront luxury living on the naturally spring-fed waters of John’s Lake. Offered publicly for the first time, this fully custom estate represents a rare convergence of beauty, privacy and enduring design. Nearly 5,000 square feet of interior living space unfold effortlessly into an additional 1,000 square feet of exceptionally well-appointed enclosed outdoor living, creating seamless indoor to outdoor living. Positioned within the private gated enclave of Deer Island and presented in impeccable condition since its 2015 construction, the home reflects meticulous care and pride of ownership. Thoughtfully designed for a life well lived by owners and guests alike, every detail was executed with intention. Arrival is elegant and memorable, welcomed by a central fountain and expansive motor court leading to an oversized three-car garage, while two bedrooms on the main level, including the primary and guest suite, provide comfort, privacy and effortless livability for generations. Designed for entertaining, walls of fully retractable sliding glass doors dissolve the boundary between indoors and out, allowing the living and great rooms to open to the terrace beyond. The covered outdoor lounge, finished with a wood-paneled ceiling, gas fireplace and fully equipped outdoor kitchen, extends daily living outdoors. The infinity pool and spa, framed by gas fire bowls, merge seamlessly with the lake view itself, while a dedicated pool access bath enhances convenience. Privately positioned to capture sweeping lake views, the primary suite opens directly to the lanai and features dual walk-in closets. Its bath is anchored by a freestanding copper soaking tub, hammered copper sinks set within custom vanities, and a full stone walk-in shower with multiple showerheads and built-in bench. The kitchen features custom wood cabinetry, oversized island, induction cooktop, separate built-in refrigerator and freezer, professional-grade appliances, and walk in pantry. Architectural details include travertine flooring, coffered and tray ceilings, refined millwork and wrought iron staircase. All closets feature custom built-ins. The second-floor media room may also serve as a spacious fifth bedroom with private balcony overlooking the lake. Beyond the terrace, tiered gardens descend toward the shoreline, where Four Seasons marble statuary is thoughtfully placed throughout the grounds, like a work of art set within the landscape. A private putting green, fire pit and manicured lawn enhance the setting. The composite dock includes dual lifts for boat and jet ski, water and electric service, and upper level sun deck positioned for sunset views. John’s Lake spans over 2,500 acres and is known for exceptional clarity, ideal for skiing, boating, water sports and fishing. Deer Island offers gated entry with waterside tennis, pickleball and basketball courts. The home is serviced by a private well. Less than one mile from the Florida Turnpike and 25 minutes to downtown Orlando. Contact for your private viewing.

Features

5 bedrooms
5 bathrooms
3 carspaces
3 garage spaces
7790 sq. ft. floor area
44593 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 5 bedroom single-family properties sold in Winter Garden over the last 12 months, the estimated median property value of 17737 Deer Isle Circle is $842.5k.

Median value
$842.5k
Estimated value range
$479k - $3.8m
Median days on market
48
Estimated value trend
3%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Winter Garden. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 17737 Deer Isle Circle

2026
Sold
$2,775,000
27 Apr 2026 by Candace Cassidy, of PREMIER SOTHEBY'S INTL. REALTY
2012
Sold
$185,000
04 May 2012 by BOB BEAUMONT, of Valbridge Property Advisors

Happy sellers in Winter Garden

86%
86% of sellers in Winter Garden reported that their sale price either exceeded or met their price expectations.

Winter Garden stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 48 reviews in Winter Garden over the last 12 months.

Local market activity for 5 bedroom single-family properties in Winter Garden

In the last 12 months, 383 five-bedroom single-family properties similar to 17737 Deer Isle Circle, have been sold.

This represents a 1% decrease in five-bedroom single-family properties sales when compared to the previous 12 months.

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