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Winter Park

Luxury listings for sale in Winter Park

18 of 18 Homes
COMPARE

US$6,995,000

901 GOLFVIEW, Winter Park, FL

5 br5 BA, 1 HALF BA5,479 sf
Virtual tour

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY., MICK NIGHT - 407-629-4446

Open house

US$6,900,000

1260 ALABAMA, Winter Park, FL

6 br5 BA, 2 HALF BA6,396 sf
Virtual tour

Listing Courtesy of KELLY PRICE & COMPANY LLC., KELLY PRICE - 407-645-4321

US$6,888,888

2661 Via Tuscany, Winter Park, FL

4 br4 BA, 1 HALF BA4,636 sf
Virtual tour

Listing Courtesy of THE KEYES COMPANY., BELINDA TERESITA MORENO - 954-529-4915

Coming soon

US$6,200,000

698 N NEW YORK, Winter Park, FL

5 br5 BA, 1 HALF BA5,096 sf
Virtual tour

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY., MICK NIGHT - 407-629-4446

US$6,000,000

1571 WOODLAND Ave, Winter Park, FL

5 br6 BA, 2 HALF BA7,397 sf
Virtual tour

Listing Courtesy of CHARLES RUTENBERG REALTY ORLANDO., VONDA FIELDS - 321-438-6906

US$5,999,990

2661 VIA TUSCANY, Winter Park, FL

4 br4 BA, 1 HALF BA3,880 sf
Virtual tour

Listing Courtesy of COLDWELL BANKER REALTY., NOHORA GOMEZ - 407-748-1242

US$5,600,000

2228 AZALEA, Winter Park, FL

5 br5 BA, 1 HALF BA5,152 sf
Virtual tour

Listing Courtesy of COMPASS FLORIDA LLC., QUENTIN GREEN, II - 773-418-5359

US$5,500,000

313 SYLVAN Dr, Winter Park, FL

4 br4 BA, 1 HALF BA4,775 sf
Virtual tour

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY., MICK NIGHT - 407-629-4446

NEW

US$5,500,000

1166 PALMER, Winter Park, FL

5 br5 BA, 2 HALF BA5,181 sf

Listing Courtesy of KELLER WILLIAMS ADVANTAGE REALTY., PRENTICE WILLIAMS - 321-438-8955

US$5,195,900

825 PALMER, Winter Park, FL

5 br5 BA, 2 HALF BA5,122 sf

Listing Courtesy of CORCORAN PREMIER REALTY., LAURA EARL - 443-994-9441

US$4,950,000

231 CHELTON Cir, Winter Park, FL

4 br5 BA, 2 HALF BA5,550 sf
Virtual tour

Listing Courtesy of BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY., JOSEPH DOHER - 407-203-0007

Contract signed

US$4,750,000

2525 TEMPLE, Winter Park, FL

5 br4 BA, 1 HALF BA4,542 sf
Virtual tour

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES., MARYSTUART DAY - 407-620-8683

US$4,650,000

857 BROCK, Winter Park, FL

5 br5 BA, 1 HALF BA4,827 sf
Virtual tour

Listing Courtesy of ONE LUXURY INTERNATIONAL LLC., JULIE CHRISTENSEN - 407-592-2055

Open house

US$4,595,000

1525 GRANVILLE, Winter Park, FL

5 br5 BA, 1 HALF BA5,211 sf
Virtual tour

Listing Courtesy of ONE LUXURY INTERNATIONAL LLC., JULIE CHRISTENSEN - 407-592-2055

PRICE REDUCED

US$4,500,000

503 N INTERLACHEN Ave, Winter Park, FL

Virtual tour

Listing Courtesy of KELLY PRICE & COMPANY LLC., KELLY PRICE - 407-645-4321

US$4,400,000

702 VIA BELLA, Winter Park, FL

4 br5 BA, 1 HALF BA3,720 sf
Virtual tour

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY., MICK NIGHT - 407-629-4446

NEW

US$4,325,000

250 W READING, Winter Park, FL

5 br4 BA, 1 HALF BA4,853 sf

Listing Courtesy of RE/MAX 200 REALTY., BRIAN MITNIK - 407-421-2832

US$4,299,000

2403 EUSTON, Winter Park, FL

Virtual tour

Listing Courtesy of COLDWELL BANKER REALTY., MARIE HELEN LEDBETTER - 407-286-4363

Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed.

Copyright © 2026 MLS GRID. All Rights Reserved.

LAST UPDATE DATE On SEP 18 2026 AT 11:58 PM COORDINATED UNIVERSAL TIME (UTC).

All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright 2026 Beaches Multiple Listing Service, Inc. 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. The listing broker's offer of compensation is made to participants of BeachesMLS, where the listing is filed, as well as participants of MLSs participating in MLSAdvantage or a data share with BeachesMLS.

LAST UPDATE DATE On SEP 18 2026 AT 11:58 PM COORDINATED UNIVERSAL TIME (UTC).