New28$450,000
3 bd · 2 ba · 1,346 sqft
506 Lander Rd, Winter Park, FL
Mike Derenthal · DERENTHAL REALTY
Single-Family Homes in Winter Park, FL
Hide MapSingle-Family Homes in Winter Park, FL
24 of 219 Listings
New28$450,000
3 bd · 2 ba · 1,346 sqft
506 Lander Rd, Winter Park, FL
Mike Derenthal · DERENTHAL REALTY
Open house Sun, Oct 25 · 11:00 AM24$620,000
3 bd · 2 ba · 1,762 sqft
624 Dunraven Dr, Winter Park, FL
Beth Logullo · KELLER WILLIAMS WINTER PARK
New55$985,000
5 bd · 3 ba · 3,296 sqft
2330 Westminster Ct., Winter Park, FL
Lisa Fleming · FANNIE HILLMAN & ASSOCIATES
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 Sun, Oct 25 · 12:00 PM26$509,999
3 bd · 2 ba · 1,460 sqft
808 Densmore Dr, Winter Park, FL
Karly Campbell · NOVA REAL ESTATE SERVICES INC
Open house Sun, Oct 25 · 12:00 PM99$3,195,000
4 bd · 6 ba · 4,311 sqft
1825 Whitehall Dr, Winter Park, FL
Ahmad Hassan, PA · COMPASS FLORIDA LLC
39$650,000
4 bd · 3 ba · 1,770 sqft
1458 Lone Feather Trl, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
29$450,000
4 bd · 3 ba · 1,866 sqft
239 Orange Terrace Dr, Winter Park, FL
Chris Creegan · CREEGAN GROUP
Price Reduced33$515,000
3 bd · 3 ba · 1,602 sqft
7641 Village Green Drive, Winter Park, FL
Jannett Jhasmin Marten · Compass Florida, LLC
8$425,000
3 bd · 3 ba · 1,907 sqft
2913 Clever Lane, Winter Park, FL
HELEN WELLS · MAXREV, LLC
Open house Sun, Oct 25 · 2:00 PM76$3,495,000
5 bd · 6 ba · 4,483 sqft
1600 Legion Dr, Winter Park, FL
Brian Teach · COLDWELL BANKER REALTY
7$4,695,000
11 bd · 8 ba · 3,615 sqft
617 N Interlachen Ave, Winter Park, FL
Greg Owen · EASY REALTY
35$479,900
3 bd · 2 ba · 1,647 sqft
7536 Village Green Dr, Winter Park, FL
Karen Bagwell · RE/MAX TOWN & COUNTRY REALTY
16$2,629,000
5 bd · 5 ba · 3,682 sqft
1681 Woodland Ave, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
58$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
29$305,000
3 bd · 1 ba · 1,216 sqft
2640 Beverly Ave, Winter Park, FL
Celeste Martinez · REAL BROKER, LLC
30$415,900
3 bd · 2 ba · 1,412 sqft
3409 Ferndell Dr, Winter Park, FL
Veronica Lewis · LPT REALTY, 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
43$750,000
5 bd · 4 ba · 3,496 sqft
8061 Pleasant Pine Cir, Winter Park, FL
Mark Humphreys · RE/MAX ASSURED
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
41$320,000
3 bd · 2 ba · 1,156 sqft
148 Oak Grove Rd, Winter Park, FL
Kelly Althof · CENTRAL FLORIDA REALTY EXPERTS
Open house Sun, Oct 25 · 11:00 AM47$950,000
2 bd · 2 ba · 1,947 sqft
1411 Devon Rd, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
Single-Family Homes in Winter Park, FL: 219 active listings as of .
BeachesMLSrealMLS (Northeast Florida Multiple Listing Service)Stellar 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