Open house Sun, Oct 4 · 11:00 AM31$265,000
2 bd · 2 ba · 908 sqft
1250 S Denning Dr #119, Winter Park, FL
Justin McCarthy · FANNIE HILLMAN & ASSOCIATES
Open Houses in Winter Park, FL
Hide MapOpen Houses in Winter Park, FL
24 of 27 Listings
Open house Sun, Oct 4 · 11:00 AM31$265,000
2 bd · 2 ba · 908 sqft
1250 S Denning Dr #119, Winter Park, FL
Justin McCarthy · FANNIE HILLMAN & ASSOCIATES
Open house Sun, Oct 4 · 1:00 PM73$2,089,000
4 bd · 4 ba · 3,479 sqft
1951 Winter Park Rd, Winter Park, FL
Holly Wilton · KELLER WILLIAMS WINTER PARK
Open house Sun, Oct 4 · 1:00 PM31$1,599,000
4 bd · 4 ba · 2,942 sqft
533 Country Club Dr, Winter Park, FL
Jill Healey · KELLER WILLIAMS WINTER PARK
Open house Sat, Oct 10 · 12:00 PM50$925,000
4 bd · 3 ba · 2,578 sqft
2572 Fifeshire Dr, Winter Park, FL
MaryAnne Branner · PREMIER SOTHEBY'S INTL. REALTY
Open house Sun, Oct 4 · 2:00 PM41$675,000
4 bd · 2 ba · 1,688 sqft
2215 Woodcrest Dr, Winter Park, FL
Shari Klafter · KELLER WILLIAMS WINTER PARK
Open house Sun, Oct 4 · 11:00 AM64$895,000
4 bd · 3 ba · 1,876 sqft
618 Blairshire Cir, Winter Park, FL
Ken Pozek · REAL BROKER, LLC
Open house Sun, Oct 4 · 12:00 PM33$380,000
3 bd · 2 ba · 1,277 sqft
4870 Seminole Ave, Winter Park, FL
Tamara Mazo Ferro · COLDWELL BANKER REALTY
Open house Sun, Oct 4 · 12:00 PM61$2,195,000
4 bd · 5 ba · 2,850 sqft
1271 Palmer Ave, Winter Park, FL
JR Keelin · KELLY PRICE & COMPANY LLC
Price ReducedOpen house Sun, Oct 4 · 12:00 PM73$769,000
4 bd · 3 ba · 2,141 sqft
2410 Sherbrooke Rd, Winter Park, FL
Li Ju Huang · AMERICA REAL ESTATE COMPANY LL
Price ReducedOpen house Sun, Oct 4 · 12:00 AM38$659,900
3 bd · 2 ba · 1,420 sqft
274 N Ranger Blvd, Winter Park, FL
Shannon Lee · EXPLORE FLORIDA REALTY SERVICES LLC
Open house Sun, Oct 4 · 2:00 PM31$725,000
3 bd · 2 ba · 1,563 sqft
1850 Bryan Ave, Winter Park, FL
Jennifer King · CORCORAN PREMIER REALTY
Open house Sun, Oct 4 · 1:00 PM67$575,000
2 bd · 3 ba · 1,648 sqft
1259 Indiana Ave, Winter Park, FL
Karan Wienker · COLDWELL BANKER REALTY
Price ReducedOpen house Sun, Oct 4 · 12:00 PM31$664,000
3 bd · 3 ba · 1,794 sqft
900 Carver St, Winter Park, FL
Farhad Haniff · EXP REALTY LLC
Price ReducedOpen house Sun, Oct 4 · 11:00 AM38$575,000
4 bd · 2 ba · 1,936 sqft
7525 Lodge Pole Trl, Winter Park, FL
Amy Turner · KELLER WILLIAMS WINTER PARK
Open house Sun, Oct 4 · 2:00 PM35$899,000
3 bd · 3 ba · 2,022 sqft
1621 Chestnut Ave, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC
Price ReducedOpen house Sun, Oct 4 · 10:00 AM38$825,000
2 bd · 2 ba · 1,540 sqft
1431 Palm Ave, Winter Park, FL
Kelsey Payton · ALL REAL ESTATE & INVESTMENTS
Price ReducedOpen house Sun, Oct 4 · 12:00 PM48$915,000
3 bd · 4 ba · 2,093 sqft
1927 S Lakemont Ave, Winter Park, FL
Abby Green · IAD REAL ESTATE
Price ReducedOpen house Sun, Oct 4 · 1:00 PM35$430,000
3 bd · 2 ba · 1,645 sqft
3740 Hawthorne Ln, Winter Park, FL
John Crea · FLORIDA REALTY INVESTMENTS
Price ReducedOpen house Sun, Oct 4 · 11:00 AM54$464,000
3 bd · 2 ba · 1,737 sqft
2703 Tierra Cir, Winter Park, FL
Tony Ubaldini · EXP REALTY LLC
Price ReducedOpen house Sun, Oct 4 · 2:00 PM57$1,525,000
4 bd · 4 ba · 3,723 sqft
341 E Reading Way, Winter Park, FL
Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES
Price ReducedOpen house Sun, Oct 4 · 12:00 AM31$1,262,500
4 bd · 4 ba · 3,024 sqft
2015 Summerfield Rd, Winter Park, FL
Courtney Lindsay · UNITED REAL ESTATE PREFERRED
Price ReducedOpen house Sun, Oct 4 · 2:00 PM44$2,050,000
5 bd · 5 ba · 2,889 sqft
240 N Phelps Ave, Winter Park, FL
Nick McKee · KELLER WILLIAMS WINTER PARK
Price ReducedOpen house Sun, Oct 4 · 12:00 AM38$1,369,000
5 bd · 4 ba · 2,446 sqft
1473 Berkshire Ave, Winter Park, FL
Gilson Rodrigues · KARDOSH REALTY
Price ReducedOpen house Sun, Oct 4 · 12:00 PM37$1,499,000
3 bd · 5 ba · 2,756 sqft
641 Northwood Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
Open Houses in Winter Park, FL: 27 active listings as of .
Stellar MLSAn open house is a scheduled time to view a home. Some open houses are held in person and some as a livestream. The times shown here come from the listing’s MLS and can change or be cancelled, so check the listing before you plan to attend.
Source: HJN community data
September 2026 · This period is still settling
Selling at 97.9% of asking price
Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026