39$650,000
4 bd · 4 ba · 2,533 sqft
1105 Shadowbrook Trl, Winter Springs, FL
Amy Phillips · CALL IT CLOSED INTL REALTY
Homes with a Pool in Winter Springs, FL
Hide MapHomes with a Pool in Winter Springs, FL
24 of 34 Listings
39$650,000
4 bd · 4 ba · 2,533 sqft
1105 Shadowbrook Trl, Winter Springs, FL
Amy Phillips · CALL IT CLOSED INTL REALTY
30$380,000
3 bd · 2 ba · 1,168 sqft
417 Holly Ct, Winter Springs, FL
Colleen Kahl · RE/MAX TOWN & COUNTRY REALTY
44$925,000
5 bd · 4 ba · 3,521 sqft
609 Viana Ct, Winter Springs, FL
Jenny Wemert · WEMERT GROUP REALTY LLC
37$559,000
3 bd · 2 ba · 2,292 sqft
1008 Forest Cir, Winter Springs, FL
Dean Erlandson · LIVE FLORIDA NOW LLC
51$670,000
4 bd · 3 ba · 2,729 sqft
4161 Aldergate Pl, Winter Springs, FL
Karen Arbutine · RE/MAX CENTRAL REALTY
57$849,900
4 bd · 4 ba · 2,597 sqft
1522 Eagle Nest Cir, Winter Springs, FL
Jennifer Christ · THE AGENCY FL
42$1,080,000
5 bd · 5 ba · 4,001 sqft
149 Cherry Creek Cir, Winter Springs, FL
Denise McKinley · RE/MAX TOWN & COUNTRY REALTY
Price Reduced42$698,000
4 bd · 3 ba · 2,701 sqft
992 Sleeping Rock Ct, Winter Springs, FL
Wilfred Sierra Sosa, PA · RE/MAX PRIME PROPERTIES
2$499,900
3 bd · 2 ba · 1,947 sqft
1013 Walnut Creek CV, Winter Springs, FL
Julie Bailey · HOME SOLD NETWORK LLC
Price ReducedOpen house Sun, Oct 18 · 12:00 PM40$574,900
4 bd · 3 ba · 1,917 sqft
632 Tuskawilla Point Ln, Winter Springs, FL
Ingrid Jimenez Calvo · AXEN REALTY, LLC
100$2,500,000
6 bd · 6 ba · 6,132 sqft
1447 Bird Rd, Winter Springs, FL
Robert Sassos · SIMPLICITY: A RE BROKERAGE CO
75$525,000
4 bd · 3 ba · 2,181 sqft
4038 Biscayne Dr, Winter Springs, FL
Caroline Van Den Berg · VAN DEN BERG REAL ESTATE GROUP
35$499,000
4 bd · 3 ba · 2,268 sqft
855 Benchwood Dr, Winter Springs, FL
Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS
Price Reduced73$969,000
5 bd · 4 ba · 3,014 sqft
1041 Northern Way, Winter Springs, FL
Mariann Torres · LPT REALTY, LLC
Price Reduced37$410,000
3 bd · 2 ba · 1,748 sqft
205 Inkwood Ct, Winter Springs, FL
Travous Dever · THE KEYES COMPANY
Price Reduced60$569,999
4 bd · 2 ba · 1,985 sqft
943 March Hare Ct, Winter Springs, FL
Kristin Dobo · SCHMITT REALTY PLLC
70$550,000
3 bd · 2 ba · 1,735 sqft
766 Andover Cir, Winter Springs, FL
Alex Jerez · MILLENIUM REALTY GROUP
Price Reduced46$599,000
3 bd · 3 ba · 2,272 sqft
116 Partridge Cir, Winter Springs, FL
Christine Schneider · RE/MAX TOWN & COUNTRY REALTY
67$785,000
5 bd · 4 ba · 3,660 sqft
337 Twelve Oaks Dr, Winter Springs, FL
Virginia Bellhorn · WATSON REALTY CORP
Price Reduced58$679,000
4 bd · 3 ba · 2,272 sqft
864 Bentley Green Cir, Winter Springs, FL
Patrick Calathes · REAL BROKER, LLC
Price Reduced35$497,500
4 bd · 3 ba · 2,256 sqft
909 Devon Creek Rd, Winter Springs, FL
David DeCristo · MARK SPAIN REAL ESTATE
37$439,900
3 bd · 3 ba · 1,730 sqft
625 Pearl Rd, Winter Springs, FL
Jack Luiz · LANDSHARK REALTY
43$515,000
4 bd · 2 ba · 1,931 sqft
699 N Endeavour Dr, Winter Springs, FL
Dominick Florio · RE/MAX TOWN & COUNTRY REALTY
Price Reduced30$595,000
4 bd · 3 ba · 2,840 sqft
248 Huntridge Way, Winter Springs, FL
Heather Unger, PA · ACME REAL ESTATE FLORIDA LLC
Homes with a Pool in Winter Springs, FL: 34 active listings as of .
Stellar MLSSource: HJN community data
September 2026 · This period is still settling
Selling at 97.6% of asking price
Buyers here are paying below asking. MLS · 42 sales · as of Sep 30, 2026