Deer Island estate tops Winter Garden home sales from April 27 to May 3

The home at 17737 Deer Isle Circle, Winter Garden, sold April 27, for $2,775,000.

By Michael Eng
| 7:30 a.m. May 8, 2026

West Orange Times & Observer
Real Estate

A Deer Island estate topped all Winter Garden residential real-estate transactions from April 27 to May 3.

The home at 17737 Deer Isle Circle, Winter Garden, sold April 27, for $2,775,000. Built in 2015, it has five bedrooms, three baths, two half-baths and 4,886 square feet of living area. Days on market: 32. The sellers were represented by Candace Cassidy, Premier Sotheby’s International Realty.

OAKLAND
LONGLEAF AT OAKLAND
The home at 2606 Bobcat Chase Blvd., Oakland, sold April 28, for $600,000. Built in 2019, it has four bedrooms, two-and-one-half baths and 2,473 square feet of living area. Days on market: 114.

TOWN OF OAKLAND
The home at 2135 Standing Rock Circle, Oakland, sold April 30, for $475,000. Built in 2020, it has three bedrooms, two-and-one-half baths and 2,078 square feet of living area. Days on market: 64.

WINTER GARDEN
AVALON WOODS
The home at 15274 Maritime Pine Drive, Winter Garden, sold April 28, for $1,039,538. Built in 2026, it has six bedrooms, four baths and 4,222 square feet of living area.

The home at 15261 Maritime Pine Drive, Winter Garden, sold April 30, for $1,1113,986. Built in 2026, it has six bedrooms, four baths and 4,222 square feet of living area.

COBBLESTONE AT WINTER GARDEN
The home at 224 Black Springs Lane, Winter Garden, sold April 27, for $485,000. Built in 2007, it has three bedrooms, two baths and 1,916 square feet of living area. Days on market: 39.

CYPRESS RESERVE
The home at 14170 Jomatt Loop, Winter Garden, sold May 1, for $770,000. Built in 2019, it has four bedrooms, three baths and 2,931 square feet of living area. Days on market: Seven.

DANIELS LANDING
The townhouse at 13335 Daniels Landing Circle, Winter Garden, sold May 1, for $324,000. Built in 2004, it has two bedrooms, two-and-one-half baths and 1,347 square feet of living area. Days on market: One.

DEER ISLAND
The home at 17737 Deer Isle Circle, Winter Garden, sold April 27, for $2,775,000. Built in 2015, it has five bedrooms, three baths, two half-baths and 4,886 square feet of living area. Days on market: 32.

EMERALD RIDGE
The home at 1818 Morning Sky Drive, Winter Garden, sold April 30, for $610,000. Built in 2004, it has four bedrooms, two-and-one-half baths and 2,943 square feet of living area. Days on market: Seven.

HERITAGE AT PLANT STREET
The townhouse at 628 Orange Belt Loop, Winter Garden, sold April 28, for $510,000. Built in 2018, it has three bedrooms, two-and-one-half baths and 1,850 square feet of living area. Days on market: 31.

LAKE COUNTY
The home at 11714 Flynn Court, Winter Garden, Lake County, sold April 27, for $1,240,000. Built in 1994, it has four bedrooms, three baths and 4,370 square feet of living area. Days on market: 142.

LAKEVIEW PRESERVE
The home at 3383 Current Ave., Winter Garden, Lake County, sold April 27, for $929,000. Built in 2021, it has five bedrooms, four-and-one-half baths and 3,975 square feet of living area. Days on market: 41.

OAKLAND HILLS
The home at 15198 E. Oakland Ave., Winter Garden, sold April 27, for $1,790,000. Built in 2023, it has four bedrooms, four baths and 3,616 square feet of living area. Days on market: Nine.

OAKLAND PARK
The home at 883 Tilden Oaks Trail, Winter Garden, sold April 30, for $1,075,000. Built in 2025, it has four bedrooms, three-and-one-half baths and 2,811 square feet of living area.

ORCHARD HILLS
The home at 4937 Wildwood Pointe Road, Winter Garden, sold May 1, for $800,000. Built in 2015, it has five bedrooms, four baths and 3,289 square feet of living area. Days on market: 59.

WESTSIDE TOWNHOMES
The townhouse at 1421 Fettler Way, Winter Garden, sold April 30, for $170,000. Built in 2004, it has two bedrooms, two baths and 1,076 square feet of living area. Days on market: One.

The townhouse at 1222 Westside Drive, Winter Garden, sold April 29, for $139,000. Built in 1987, it has one bedroom, one bath and 677 square feet of living area. Days on market: Four.

WINTERMERE POINTE
The home at 2425 Prairie View Drive, Winter Garden, sold April 30, for $641,000. Built in 2003, it has five bedrooms, three baths and 3,524 square feet of living area. Days on market: 65.

author

Michael Eng

As a child, Editor and Publisher Michael Eng collected front pages of the Kansas City Star during Operation Desert Storm, so it was a foregone conclusion that he would pursue a career in journalism. He holds a journalism degree from the University of Missouri — Columbia School of Journalism. When he’s not working, you can find him spending time with his wife and three children, or playing drums around town. He’s also a sucker for dad jokes.