Luxury Homes in Winter Park, FL

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24 of 69 Listings

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24 of 69 Listings

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69 listings

Luxury Homes in Winter Park, FL

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24 of 69 Listings

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Luxury Homes in Winter Park, FL

24 of 69 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

New29

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$1,399,900

4 bd · 4 ba · 2,984 sqft

1737 Indiana Ave, Winter Park, FL

Tori Nguyen · LOKATION

Open house Sat, Oct 10 · 1:00 PM33Active

$3,250,000

5 bd · 6 ba · 4,459 sqft

2823 Parkland Circle, Winter Park, FL

Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY

12Active

$1,699,900

4 bd · 4 ba · 2,661 sqft

2613 Lafayette Ave, Winter Park, FL

Matt Tomaszewski · CORCORAN PREMIER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Open house Sat, Oct 10 · 12:00 AM8Active

$2,125,000

5 bd · 5 ba · 3,713 sqft

918 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

11Active

$3,195,000

5 bd · 6 ba · 4,139 sqft

2119 Howard Dr, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

4Active

$1,995,000

4 bd · 4 ba · 3,314 sqft

2007 Edwin Blvd, Winter Park, FL

Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP

21Active

$1,950,000

5 bd · 5 ba · 3,560 sqft

513 Dunraven Dr, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

Open house Sat, Oct 10 · 2:00 PM96Active

$2,095,000

4 bd · 4 ba · 3,776 sqft

555 E Lake Sue Ave, Winter Park, FL

Claudia Davidson · KELLER WILLIAMS WINTER PARK

52Active

$6,195,000

5 bd · 6 ba · 5,096 sqft

698 N New York Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

55Active

$1,890,000

4 bd · 4 ba · 3,307 sqft

2614 Parkland Dr, Winter Park, FL

Ryan Gaston · JW GASTON LLC

18Active

$2,990,000

5 bd · 5 ba · 4,050 sqft

532 Langholm Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

Open house Sat, Oct 10 · 12:00 PM73Active

$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 Sat, Oct 10 · 12:00 PM31Active

$1,599,000

4 bd · 4 ba · 2,942 sqft

533 Country Club Dr, Winter Park, FL

Jill Healey · KELLER WILLIAMS WINTER PARK

41Active

$3,695,999

4 bd · 5 ba · 3,658 sqft

1742 Temple Dr, Winter Park, FL

Mark Anthony Buot · ROI AVE LLC

78Active

$3,495,000

5 bd · 6 ba · 4,478 sqft

662 Granville Drive, Winter Park, FL

Nathalie Bates · PREMIER SOTHEBY'S INTL. REALTY

49Active

$6,995,000

5 bd · 6 ba · 5,479 sqft

901 Golfview Ter, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

13Active

$5,500,000

5 bd · 7 ba · 5,181 sqft

1166 Palmer Ave, Winter Park, FL

Prentice Williams · KELLER WILLIAMS ADVANTAGE REALTY

Open house Sun, Oct 11 · 2:00 PM61Active

$2,195,000

4 bd · 5 ba · 2,850 sqft

1271 Palmer Ave, Winter Park, FL

JR Keelin · KELLY PRICE & COMPANY LLC

41Active

$4,400,000

4 bd · 6 ba · 3,720 sqft

702 Via Bella, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

3Active

$4,325,000

5 bd · 5 ba · 4,853 sqft

250 W Reading Way, Winter Park, FL

Brian Mitnik · RE/MAX 200 REALTY

7Active

$5,195,900

5 bd · 7 ba · 5,122 sqft

825 Palmer Ave, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

18Active

$2,725,000

5 bd · 5 ba · 3,784 sqft

1773 Walnut Ave, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced89Active

$1,550,000

6 bd · 5 ba · 5,239 sqft

1257 Wading Waters Cir, Winter Park, FL

Rob Breese, III · RE/MAX TOWN & COUNTRY REALTY

72Active

$3,395,000

5 bd · 6 ba · 4,015 sqft

160 W Rockwood Way, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

Listing data & MLS disclosures

Stellar MLS: 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.

Winter Park housing market

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $602,500$441,750–$1,016,350 typical range
Price per sq. ft.: $358
Sales: 78
Paid in cash: 46.2%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Listing data & MLS disclosures

Stellar MLS: 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.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Winter Park housing market

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $602,500$441,750–$1,016,350 typical range
Price per sq. ft.: $358
Sales: 78
Paid in cash: 46.2%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000

Homes for sale

383

Median days on market

18 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 38.1%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,731 sq. ft.

Luxury Homes in Winter Park, FL

Luxury Homes in Winter Park, FL

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Park housing market

Homes that sold · County records, as of Sep 23, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Winter Park, FL community profile

Explore Winter Park homes

Your local brokerage

Listing data & MLS disclosures

Winter Park, FL community profile

Winter Park housing market

Homes that sold · County records, as of Sep 23, 2026

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Price trend · Assessor repeat sales, as of Sep 30, 2026

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026