Open house Sat, Oct 31 · 1:00 PM39$450,000
5 bd · 3 ba · 1,636 sqft
1825 Chilean Ln, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
Homes with a Pool in Winter Park, FL
Hide MapHomes with a Pool in Winter Park, FL
24 of 120 Listings
Open house Sat, Oct 31 · 1:00 PM39$450,000
5 bd · 3 ba · 1,636 sqft
1825 Chilean Ln, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
NewOpen house Sat, Oct 31 · 12:00 PM44$1,650,000
4 bd · 4 ba · 2,754 sqft
1900 Sunset Dr, Winter Park, FL
Andrea Parra Chopite, PA · FANNIE HILLMAN & ASSOCIATES
NewOpen house Fri, Oct 30 · 4:00 PM100$5,695,000
4 bd · 4 ba · 4,725 sqft
541 Virginia Dr, Winter Park, FL
Scott Brazdo · EXP REALTY LLC
Open house Sat, Oct 31 · 12:00 PM69$2,100,000
5 bd · 6 ba · 4,155 sqft
1355 Hibiscus Ave, Winter Park, FL
Nadia Moayeri · PALMANO GROUP RE BROKERAGE LLC
Open house Fri, Oct 30 · 5:00 PM29$410,000
3 bd · 2 ba · 1,318 sqft
1021 Princess Gate Blvd, Winter Park, FL
Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
41$1,050,000
4 bd · 3 ba · 2,787 sqft
1735 Demetree Dr, Winter Park, FL
Melissa Johnson · EXP REALTY LLC
56$5,995,000
5 bd · 6 ba · 5,476 sqft
1200 Via Salerno, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC
12$419,900
4 bd · 2 ba · 1,427 sqft
603 Carnation Dr, Winter Park, FL
William Ward · A-WARD WINNING REALTY LLC
56$4,500,000
5 bd · 6 ba · 4,754 sqft
1631 Hillcrest Ave, Winter Park, FL
Chris Quarles · CHRIS QUARLES PROPERTIES LLC
32$699,900
3 bd · 2 ba · 1,666 sqft
1884 Jessica Ct, Winter Park, FL
Abby Nelson · RE/MAX 200 REALTY
Open house Sat, Oct 31 · 11:00 AM26$509,999
3 bd · 2 ba · 1,460 sqft
808 Densmore Dr, Winter Park, FL
Karly Campbell · NOVA REAL ESTATE SERVICES INC
Open house Sat, Oct 31 · 11:00 AM98$3,195,000
4 bd · 6 ba · 4,311 sqft
1825 Whitehall Dr, Winter Park, FL
Ahmad Hassan, PA · COMPASS FLORIDA LLC
Price Reduced33$515,000
3 bd · 3 ba · 1,602 sqft
7641 Village Green Drive, Winter Park, FL
Jannett Jhasmin Marten · Compass Florida, LLC
76$3,495,000
5 bd · 6 ba · 4,483 sqft
1600 Legion Dr, Winter Park, FL
Brian Teach · COLDWELL BANKER REALTY
16$2,629,000
5 bd · 5 ba · 3,682 sqft
1681 Woodland Ave, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
Open house Sun, Nov 1 · 9:00 AM58$1,349,000
4 bd · 4 ba · 2,575 sqft
1939 Woodcrest Dr, Winter Park, FL
Jose Martinez Rivera LLC · LA ROSA REALTY PREMIER LLC
Price Reduced16$314,000
3 bd · 2 ba · 1,229 sqft
1740 Puritan Ave, Winter Park, FL
Brenda Brooks · KELLER WILLIAMS REALTY SMART 1
44$1,249,000
6 bd · 6 ba · 5,021 sqft
1445 Via Sangro Pl, Winter Park, FL
Kevin Asenjo · COLDWELL BANKER REALTY
70$6,000,000
5 bd · 7 ba · 4,806 sqft
1011 McKean Cir, Winter Park, FL
Clay Wooten · UNITED REAL ESTATE PREFERRED
Open house Sat, Oct 31 · 2:00 PM47$950,000
2 bd · 2 ba · 1,947 sqft
1411 Devon Rd, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
Open house Sat, Oct 31 · 12:00 PM67$3,390,000
5 bd · 7 ba · 4,520 sqft
1751 Glencoe Rd, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
38$1,399,900
4 bd · 4 ba · 2,984 sqft
1737 Indiana Ave, Winter Park, FL
Tori Nguyen · LOKATION
51$519,900
4 bd · 3 ba · 1,842 sqft
731 Bongart Rd, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
25$255,000
2 bd · 2 ba · 1,026 sqft
1500 Gay Rd #26-C, Winter Park, FL
Lianna Dangelo · SOTERA LIVING
Homes with a Pool in Winter Park, FL: 120 active listings as of .
BeachesMLSStellar MLSSource: HJN community data
September 2026
Selling at 97.9% of asking price
Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026