Homes for sale in Winter Park.

330 active listings in Winter Park, FL — live Stellar MLS inventory.

Communities in Winter Park

60 subdivisions with active listings

The Enclave Winter Park11 Lawndale7 Winter Park Pines7 Cedarwood Village 16 Colonies6 Glencoe Sub5 Lake Forest Park5 Orwin Manor Westminster Sec5 Stratford A Winter Park Condo5 Comstock Park4 Karolina On Killarney4 Killarney Estates4 Lakeside Manor Apts Condo4 Parkview Village4 Whisperwood Condo4 Winter Park Estates4 Winter Park Village4 Aloma3 Charmont3 Chateaux Du Lac3 Cloisters Condo3 Goldenrod Villas Condo3 Grayson Square3 Killarney Bay Condo3 Killarney Circle3 Lakeview Terrace3 Meadows At Hawks Crest3 Phillips Circle Rep3 South Lakemont Shores3 Sylvan Heights3 Sylvan Lake Shores3 Waterfall Cove3 Winter Park3 Winter Park Woods Condo3 Albert Lee Ridge Add 022 Aloma Trails2 Casa Aloma2 Cloister Grove Sub2 Eastgate Sub2 Ellno Willo2 Forest Hills2 Four Seasons Condo2 Fremar2 Georgetown Estates2 Green Oaks Rep 022 Hidden Oaks Condo Ph 122 Howell Branch Woods2 Howell Heights2 J Kronenberger Sub2 Kenilworth Shores Sec 072 Lake Killarney Condo2 Lake Knowles Terrace2 Lake Knowles Terrace Add 022 Landings At Hawks Crest2 Laurel Springs2 Lost Creek2 Maitland Shores2 Na2 Preserve At Hawks Crest2 Sylvan Park2

Listings in Winter Park

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ActiveSingle Family Residence360°

$8,950,000

1120 Preserve Point Dr

Winter Park, FL 32789

7 bd · 11 ba · 11,255 sqft

Windsong-Preserve Point

MLS# O6350054

ActiveSingle Family Residence

$6,950,000

40 Palmer Ave

Winter Park, FL 32789

5 bd · 6 ba · 5,905 sqft

Robert Dhu Macdonald Park

MLS# O6380444

ActiveSingle Family Residence

$6,900,000

1260 Alabama Dr

Winter Park, FL 32789

6 bd · 7 ba · 6,396 sqft

J Kronenberger Sub

MLS# O6387200

ActiveSingle Family Residence360°

$6,495,000

550 Palmer Ave

Winter Park, FL 32789

5 bd · 7 ba · 5,939 sqft

Osceola Place

MLS# O6349188

ActiveSingle Family Residence360°

$6,000,000

Winter Park, FL 32789

5 bd · 8 ba · 7,397 sqft

Comstock Park

MLS# O6411706

ActiveSingle Family Residence360°

$5,995,000

1200 Via Salerno

Winter Park, FL 32789

5 bd · 6 ba · 5,476 sqft

Cloister Grove Sub

MLS# O6381761

ActiveSingle Family Residence360°

$5,250,000

2211 Azalea Pl

Winter Park, FL 32789

5 bd · 7 ba · 7,278 sqft

Maitland Shores

MLS# O6319674

Active360°

$4,500,000

503 N Interlachen Ave

Winter Park, FL 32789

0.48 acres

Winter Park

MLS# O6331207

ActiveTownhouse360°

$4,295,000

643 N Park Ave

Winter Park, FL 32789

3 bd · 5 ba · 4,231 sqft

Park Hill

MLS# O6403591

ActiveSingle Family Residence360°

$4,285,000

1441 Cardinal Ct

Winter Park, FL 32789

4 bd · 6 ba · 4,066 sqft

Winflor Court Pt Rep

MLS# O6399395

ActiveSingle Family Residence360°

$4,200,000

141 W Lake Sue Ave

Winter Park, FL 32789

5 bd · 7 ba · 5,500 sqft

Virginia Heights

MLS# O6406437

Active360°

$4,200,000

1298 Beachview Ave

Winter Park, FL 32789

0.34 acres

Killarney Estates

MLS# O6405064

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 29, 2026 at 12:35 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA