Winter Park Homes for Sale

$11,900,000

Virtual Tour

1120 Preserve Point Dr, Winter Park, FL 32789

11,255 SqFt

7 Beds | 11 Baths

ACTIVE

$10,999,999

Virtual Tour

2660 Via Tuscany, Winter Park, FL 32789

4,564 SqFt

4 Beds | 5 Baths

ACTIVE

$6,950,000

1400 Alabama Dr, Winter Park, FL 32789

7,916 SqFt

5 Beds | 9 Baths

PENDING

$6,100,000

Virtual Tour

541 Virginia Dr, Winter Park, FL 32789

4,725 SqFt

4 Beds | 4 Baths

ACTIVE

$5,700,000

Virtual Tour

1660 Palmer Ave, Winter Park, FL 32789

6,406 SqFt

5 Beds | 7 Baths

ACTIVE

$5,695,000

Virtual Tour

210 Chelton Cir, Winter Park, FL 32789

5,264 SqFt

5 Beds | 6 Baths

PENDING

$5,400,000

Virtual Tour

2228 Azalea Pl, Winter Park, FL 32789

5,072 SqFt

5 Beds | 6 Baths

ACTIVE

$4,985,000

2161 Sharon Rd, Winter Park, FL 32789

6,338 SqFt

5 Beds | 7 Baths

ACTIVE

$4,875,000

Virtual Tour

229 Alexander Pl, Winter Park, FL 32789

4,431 SqFt

4 Beds | 6 Baths

ACTIVE

$4,799,900

Virtual Tour

1691 Chestnut Ave, Winter Park, FL 32789

4,582 SqFt

5 Beds | 5 Baths

PENDING

$4,600,000

Virtual Tour

2118 Lake Dr, Winter Park, FL 32789

6,000 SqFt

6 Beds | 6 Baths

PENDING

$4,500,000

1336 College Pt, Winter Park, FL 32789

3,181 SqFt

4 Beds | 5 Baths

ACTIVE

$4,500,000

Virtual Tour

702 Via Bella, Winter Park, FL 32789

3,720 SqFt

5 Beds | 6 Baths

ACTIVE

$4,500,000

Virtual Tour

421 Lakewood Dr, Winter Park, FL 32789

5,847 SqFt

5 Beds | 9 Baths

PENDING

$4,395,000

1840 W Fawsett Rd, Winter Park, FL 32789

4,129 SqFt

5 Beds | 5 Baths

ACTIVE

$4,200,000

Virtual Tour

571 Lake Front Blvd, Winter Park, FL 32789

5,500 SqFt

7 Beds | 5 Baths

ACTIVE

$4,100,000

Virtual Tour

1751 Glencoe Rd, Winter Park, FL 32789

4,520 SqFt

5 Beds | 6 Baths

ACTIVE

$3,892,000

Virtual Tour

1391 Richmond Rd, Winter Park, FL 32789

4,635 SqFt

4 Beds | 6 Baths

ACTIVE

$3,295,000

Virtual Tour

1730 Winchester Dr, Winter Park, FL 32789

4,080 SqFt

5 Beds | 6 Baths

ACTIVE

$3,250,000

Virtual Tour

1900 W Fawsett Rd, Winter Park, FL 32789

4,600 SqFt

4 Beds | 5 Baths

PENDING

$3,250,000

Virtual Tour

1833 Loch Berry Rd, Winter Park, FL 32789

4,770 SqFt

5 Beds | 5 Baths

ACTIVE

$3,130,000

Virtual Tour

210 E Lake Sue Ave, Winter Park, FL 32789

4,188 SqFt

5 Beds | 6 Baths

PENDING

$2,999,900

Virtual Tour

2550 Venetian Way, Winter Park, FL 32789

4,875 SqFt

4 Beds | 5 Baths

ACTIVE

$2,995,000

Virtual Tour

884 Audubon Ln, Winter Park, FL 32789

2,995 SqFt

4 Beds | 4 Baths

PENDING

$2,995,000

Virtual Tour

1400 Place Picardy, Winter Park, FL 32789

4,411 SqFt

5 Beds | 6 Baths

ACTIVE

$2,990,000

Virtual Tour

1860 Via Contessa, Winter Park, FL 32789

7,000 SqFt

8 Beds | 6 Baths

ACTIVE

$2,949,999

2652 Lake Howell Ln, Winter Park, FL 32792

3,898 SqFt

5 Beds | 4 Baths

ACTIVE

$2,895,000

Virtual Tour

1630 Lasbury Ave, Winter Park, FL 32789

4,912 SqFt

5 Beds | 5 Baths

ACTIVE

$2,650,000

Virtual Tour

1010 N Pennsylvania Ave, Winter Park, FL 32789

4,074 SqFt

4 Beds | 5 Baths

PENDING

$2,500,000

Virtual Tour

450 Lakewood Dr, Winter Park, FL 32789

4,676 SqFt

5 Beds | 6 Baths

ACTIVE

$2,495,000

Virtual Tour

140 Cortland Ave, Winter Park, FL 32789

4,168 SqFt

5 Beds | 4 Baths

PENDING

$2,495,000

Virtual Tour

147 S Interlachen Ave Unit 400, Winter Park, FL 32789

5,159 SqFt

4 Beds | 5 Baths

ACTIVE

$2,399,900

Virtual Tour

301 Rippling Ln, Winter Park, FL 32789

3,694 SqFt

4 Beds | 6 Baths

ACTIVE

$2,395,000

Virtual Tour

2412 Chantilly Ave, Winter Park, FL 32789

4,506 SqFt

5 Beds | 7 Baths

ACTIVE

$2,374,000

Virtual Tour

2522 Lafayette Ave, Winter Park, FL 32789

3,399 SqFt

4 Beds | 4 Baths

ACTIVE

$2,300,000

Virtual Tour

1032 Early Ave, Winter Park, FL 32789

2,894 SqFt

4 Beds | 3 Baths

PENDING

$2,279,000

Virtual Tour

141 Oakwood Way, Winter Park, FL 32789

3,909 SqFt

5 Beds | 4 Baths

ACTIVE

$2,200,000

Virtual Tour

1446 Berkshire Ave, Winter Park, FL 32789

4,612 SqFt

5 Beds | 6 Baths

PENDING

$2,160,000

Virtual Tour

2234 Via Luna, Winter Park, FL 32789

3,554 SqFt

6 Beds | 4 Baths

ACTIVE

$2,119,000

Virtual Tour

785 N Phelps Ave, Winter Park, FL 32789

2,964 SqFt

5 Beds | 5 Baths

ACTIVE

$2,000,000

2260 Mulbry Dr, Winter Park, FL 32789

3,246 SqFt

5 Beds | 4 Baths

ACTIVE

$1,999,993

Virtual Tour

1451 Lyndale Blvd, Winter Park, FL 32789

3,853 SqFt

6 Beds | 4 Baths

ACTIVE

$1,895,000

Virtual Tour

817 Antonette Ave, Winter Park, FL 32789

3,971 SqFt

4 Beds | 3 Baths

ACTIVE

$1,890,000

Virtual Tour

2248 Middleton Ave, Winter Park, FL 32792

3,505 SqFt

4 Beds | 5 Baths

PENDING

$1,850,000

Virtual Tour

1470 Place Picardy, Winter Park, FL 32789

4,227 SqFt

5 Beds | 6 Baths

ACTIVE

$1,799,000

Virtual Tour

1731 Windsor Dr, Winter Park, FL 32789

3,669 SqFt

4 Beds | 4 Baths

ACTIVE

$1,795,000

Virtual Tour

279 Rippling Ln, Winter Park, FL 32789

3,472 SqFt

4 Beds | 3 Baths

ACTIVE

$1,775,000

1682 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

ACTIVE

$1,775,000

1702 Arbor Park Dr, Winter Park, FL 32789

2,950 SqFt

4 Beds | 4 Baths

ACTIVE

$1,759,000

1660 Walnut Ave, Winter Park, FL 32789

2,172 SqFt

4 Beds | 4 Baths

ACTIVE

$1,750,000

Virtual Tour

1350 Lyndale Blvd, Winter Park, FL 32789

3,478 SqFt

4 Beds | 5 Baths

ACTIVE

$1,675,000

607 Ellen Dr, Winter Park, FL 32789

2,812 SqFt

4 Beds | 5 Baths

ACTIVE

$1,649,000

Virtual Tour

1429 Chapman Cir, Winter Park, FL 32789

3,116 SqFt

4 Beds | 4 Baths

ACTIVE

$1,625,000

Virtual Tour

1650 Lakehurst Ave, Winter Park, FL 32789

3,777 SqFt

4 Beds | 4 Baths

ACTIVE

$1,600,000

Virtual Tour

281 Brewer Ave, Winter Park, FL 32789

4,029 SqFt

5 Beds | 5 Baths

PENDING

$1,599,900

1417 Miller Ave, Winter Park, FL 32789

3,312 SqFt

5 Beds | 4 Baths

ACTIVE

$1,580,000

Virtual Tour

1750 Winchester Dr, Winter Park, FL 32789

2,637 SqFt

4 Beds | 4 Baths

ACTIVE

$1,575,000

Virtual Tour

627 Country Club Dr, Winter Park, FL 32789

2,858 SqFt

4 Beds | 4 Baths

PENDING

$1,550,000

Virtual Tour

1871 Taylor Ave, Winter Park, FL 32789

3,401 SqFt

4 Beds | 5 Baths

PENDING

$1,500,000

Virtual Tour

1741 Pine Ave, Winter Park, FL 32789

3,297 SqFt

4 Beds | 3 Baths

ACTIVE

$1,500,000

Virtual Tour

2015 Summerfield Rd, Winter Park, FL 32792

2,958 SqFt

4 Beds | 4 Baths

ACTIVE

$1,475,000

1600 Barcelona Way, Winter Park, FL 32789

3,014 SqFt

4 Beds | 4 Baths

ACTIVE

$1,445,000

Virtual Tour

1371 Lyndale Blvd, Winter Park, FL 32789

2,739 SqFt

4 Beds | 3 Baths

ACTIVE

$1,420,000

Virtual Tour

840 W Comstock Ave, Winter Park, FL 32789

2,350 SqFt

4 Beds | 4 Baths

PENDING

$1,395,000

1771 Winchester Dr, Winter Park, FL 32789

2,516 SqFt

4 Beds | 4 Baths

PENDING

$1,395,000

Virtual Tour

2536 Brookshire Ave, Winter Park, FL 32792

3,140 SqFt

4 Beds | 4 Baths

ACTIVE

$1,395,000

Virtual Tour

777 Halifax Ave, Winter Park, FL 32792

3,161 SqFt

5 Beds | 5 Baths

ACTIVE

$1,380,000

Virtual Tour

1400 S Pennsylvania Ave, Winter Park, FL 32789

2,060 SqFt

4 Beds | 3 Baths

ACTIVE

$1,375,000

1213 Richmond Rd, Winter Park, FL 32789

3,204 SqFt

4 Beds | 3 Baths

ACTIVE

$1,350,000

Virtual Tour

858 Douglas Ave, Winter Park, FL 32789

2,334 SqFt

4 Beds | 4 Baths

PENDING

$1,350,000

Virtual Tour

181 N Phelps Ave, Winter Park, FL 32789

3,000 SqFt

4 Beds | 4 Baths

ACTIVE

$1,299,990

Virtual Tour

2258 E Howard Dr, Winter Park, FL 32789

2,747 SqFt

4 Beds | 3 Baths

PENDING

$1,299,000

Virtual Tour

7440 Aloma Ave, Winter Park, FL 32792

4,435 SqFt

5 Beds | 5 Baths

ACTIVE

$1,295,000

Virtual Tour

1611 Chestnut Ave, Winter Park, FL 32789

2,916 SqFt

4 Beds | 4 Baths

ACTIVE

$1,295,000

Virtual Tour

433 Carolina Ave, Winter Park, FL 32789

2,700 SqFt

5 Beds | 4 Baths

ACTIVE

$1,275,000

Virtual Tour

1681 Blue Ridge Rd, Winter Park, FL 32789

2,762 SqFt

4 Beds | 4 Baths

PENDING

$1,275,000

Virtual Tour

1611 Walnut Ave, Winter Park, FL 32789

2,635 SqFt

4 Beds | 3 Baths

ACTIVE

$1,275,000

Virtual Tour

N 726/720 Pennsylvania Ave, Winter Park, FL 32789

2,284 SqFt

6 Beds | 4 Baths

ACTIVE

$1,275,000

Virtual Tour

N 726 And 720 Pennsylvania Ave, Winter Park, FL 32789

2,284 SqFt

6 Beds | 4 Baths

ACTIVE

$1,250,000

Virtual Tour

1585 Chestnut Ave, Winter Park, FL 32789

2,220 SqFt

4 Beds | 3 Baths

ACTIVE

$1,195,000

Virtual Tour

1690 Oneco Ave, Winter Park, FL 32789

2,703 SqFt

4 Beds | 3 Baths

ACTIVE

$1,190,000

Virtual Tour

567 Osceola Ave, Winter Park, FL 32789

2,651 SqFt

4 Beds | 4 Baths

PENDING

$1,150,000

Virtual Tour

708 Balmoral Rd, Winter Park, FL 32789

2,786 SqFt

4 Beds | 3 Baths

ACTIVE

$1,099,900

Virtual Tour

1840 Biscayne Dr, Winter Park, FL 32789

2,641 SqFt

5 Beds | 3 Baths

ACTIVE

$1,095,000

Virtual Tour

1444 Pelican Bay Trl, Winter Park, FL 32792

3,121 SqFt

4 Beds | 5 Baths

ACTIVE

$1,090,000

Virtual Tour

1975 Biscayne Dr, Winter Park, FL 32789

3,270 SqFt

5 Beds | 4 Baths

ACTIVE

$1,070,000

2330 Westminster Ct, Winter Park, FL 32789

3,296 SqFt

5 Beds | 3 Baths

ACTIVE

$995,000

Virtual Tour

210 Laurel Park Ct, Winter Park, FL 32792

2,838 SqFt

4 Beds | 3 Baths

ACTIVE

$950,000

Virtual Tour

5325 Cypress Reserve Pl, Winter Park, FL 32792

3,598 SqFt

5 Beds | 4 Baths

ACTIVE

$925,000

Virtual Tour

625 Worthington Dr, Winter Park, FL 32789

2,133 SqFt

4 Beds | 2 Baths

ACTIVE

$900,000

Virtual Tour

675 Overspin Dr, Winter Park, FL 32789

2,962 SqFt

4 Beds | 4 Baths

ACTIVE

$895,000

Virtual Tour

1263 Verdant Glade Pl, Winter Park, FL 32792

2,589 SqFt

4 Beds | 4 Baths

ACTIVE

$869,000

1795 Walker Ave, Winter Park, FL 32789

1,813 SqFt

5 Beds | 3 Baths

ACTIVE

$850,000

1310 Aloma Ave, Winter Park, FL 32789

2,533 SqFt

4 Beds | 3 Baths

PENDING

$849,000

705 Baffie Ave, Winter Park, FL 32789

2,563 SqFt

4 Beds | 3 Baths

ACTIVE

$849,000

Virtual Tour

2955 Lolissa Ln, Winter Park, FL 32789

3,902 SqFt

4 Beds | 3 Baths

ACTIVE

$820,000

Virtual Tour

5618 Winterbrook Way, Winter Park, FL 32792

2,866 SqFt

5 Beds | 4 Baths

ACTIVE

$815,000

Virtual Tour

1316 Fountain Hills Ct, Winter Park, FL 32792

2,823 SqFt

4 Beds | 4 Baths

ACTIVE

$799,900

Virtual Tour

2804 Dike Rd, Winter Park, FL 32792

2,503 SqFt

4 Beds | 3 Baths

ACTIVE

$799,000

Virtual Tour

744 London Rd, Winter Park, FL 32792

2,804 SqFt

5 Beds | 3 Baths

ACTIVE

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