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3 beds New construction With a pool

Homes Under $2M in Winter Park, FL

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24 of 283 Listings

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24 of 283 Listings

Price Reduced26

Homes Under $2M in Winter Park, FL — Page 11

283 listings

Homes Under $2M in Winter Park, FL

Hide Map

24 of 283 Listings

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Homes Under $2M in Winter Park, FL

24 of 283 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced26

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$399,000

3 bd · 3 ba · 1,907 sqft

1995 Canny CV, Winter Park, FL

Rosemary Siegler · KELLER WILLIAMS ELITE PARTNERS III REALTY

Price Reduced24Active

$175,000

2 bd · 3 ba · 1,031 sqft

7327 Forest Hill Ct #223, Winter Park, FL

Leda Vaz · M L VAZ REALTY INC

43Active

$1,599,000

5 bd · 4 ba · 3,028 sqft

1864 Grinnell Ter, Winter Park, FL

Robyn Brehne-Glass · COLDWELL BANKER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced40Active

$490,900

3 bd · 3 ba · 1,786 sqft

525 Ololu Dr, Winter Park, FL

Gisela Rojas · CAISSA REALTY INVESTMENT INC

Price Reduced39Active

$1,495,000

4 bd · 2 ba · 2,640 sqft

446 Melrose Ave, Winter Park, FL

Audra Wilks · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced24Active

$524,900

3 bd · 2 ba · 1,434 sqft

1741 Westchester Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced9Active

$320,000

2 bd · 1 ba · 749 sqft

811 Overspin Dr, Winter Park, FL

Rick Singh · RICK SINGH REAL ESTATE

29Active

$229,000

3 bd · 3 ba · 1,151 sqft

7454 Wynnewood Sq #188, Winter Park, FL

Manoj Patel · APPLE REALTY

Price Reduced39Active

$1,299,000

4 bd · 4 ba · 2,459 sqft

102 Bell Pl, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

21Active

$140,000

2 bd · 3 ba · 1,090 sqft

3021 Aaron Burr Ave #3, Winter Park, FL

Daiana Garcia Medrano · NAIM REAL ESTATE LLC

36Active

$630,000

6 bd · 3 ba · 3,145 sqft

2600 Euston Rd, Winter Park, FL

Suheil Flores · AROD PARTNERS REALTY

Price Reduced28Active

$99,900

2 bd · 1 ba · 881 sqft

1695 Lee Rd #D211, Winter Park, FL

Brandy Ray · LOKATION

10Active

$325,000

3 bd · 2 ba · 1,518 sqft

7393 Grand Ave, Winter Park, FL

Latisha Smith · DREAM HOME REALTY GROUP AND ASSOCIATES LLC

28Active

$825,000

4 bd · 4 ba · 2,589 sqft

1131 Wildmeadow Run, Winter Park, FL

Joann Beck · BECK REALTY LLC

Price ReducedOpen house Sat, Oct 24 · 12:00 PM36Active

$1,485,000

4 bd · 4 ba · 3,048 sqft

1570 Palmer Ave, Winter Park, FL

David Auerbach · PARK TOWN REAL ESTATE LLC

10Active

$1,550,000

4 bd · 4 ba · 2,756 sqft

905 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

11Active

$1,550,000

4 bd · 4 ba · 2,738 sqft

901 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

Price Reduced20Active

$419,000

4 bd · 2 ba · 1,376 sqft

501 Heritage Blvd, Winter Park, FL

Bernardo Carrasquel · EXP REALTY LLC

21Active

$189,000

2 bd · 2 ba · 1,018 sqft

2918 Antique Oaks Cir #25, Winter Park, FL

Ken Warren · PREMIER MANAGEMENT GROUP INC

Price Reduced68Active

$799,000

5 bd · 3 ba · 2,242 sqft

1927 Eland Ave, Winter Park, FL

Ryan Leitter · CHARLES RUTENBERG REALTY ORLANDO

9Active

$1,595,000

3 bd · 2 ba · 2,012 sqft

1113 Via Del Mar, Winter Park, FL

David Barany · BAY HILL REALTY LLC

Price Reduced74Active

$829,500

4 bd · 2 ba · 3,950 sqft

1521 Heron Wood Pl, Winter Park, FL

Ronald Trotter · RE/MAX INNOVATION

Price Reduced55Active

$459,900

2 bd · 3 ba · 1,428 sqft

630 Killarney Bay Ct #3, Winter Park, FL

Anthony Consalvo · FLORIDA ONE REAL ESTATE LLC

Price Reduced50Active

$1,380,000

4 bd · 4 ba · 2,170 sqft

1751 Goodrich Ave, Winter Park, FL

Stephanie Baldner · EXP REALTY LLC

1…10 11 12

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

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 30, 2026

Median sale price: $566,750$404,625–$1,046,250 typical range
Price per sq. ft.: $342
Sales: 108
Paid in cash: 43.5%

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

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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

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 30, 2026

Median sale price: $566,750$404,625–$1,046,250 typical range
Price per sq. ft.: $342
Sales: 108
Paid in cash: 43.5%

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: 27.8%

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.