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Homes Under $2M in Winter Park, FL — Page 10

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3 beds New construction With a pool

Homes Under $2M in Winter Park, FL

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23 of 289 Listings

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23 of 289 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

35Active
$470,000
4 bd · 2 ba · 2,250 sqft
2008 Houndslake Drive, Winter Park, FL
Kevin McCulty · Mark Spain Real Estate
Price Reduced20Active
$374,900
3 bd · 2 ba · 1,666 sqft
1840 Aster Dr, Winter Park, FL
Brendon Spalding · KONA REALTY SERVICES LLC
42Active
$725,000
4 bd · 3 ba · 2,196 sqft
1316 Blue Stem Ln, Winter Park, FL
Matthew Fong · AFFINITY REALTY LLC

Price Reduced59Active
$455,000
4 bd · 3 ba · 1,903 sqft
8433 Commander CV, Winter Park, FL
Brandi Cepeda · CEPEDA REAL ESTATE LLC
Price Reduced38Active
$774,900
3 bd · 4 ba · 2,030 sqft
1265 Arlington Pl, Winter Park, FL
Erika Beerbower · FANNIE HILLMAN & ASSOCIATES
Price Reduced15Active
$420,000
3 bd · 2 ba · 1,676 sqft
1535 Lawndale Cir, Winter Park, FL
Raul Pino · SOVEREIGN REAL ESTATE GROUP
28Active
$199,900
2 bd · 1 ba · 851 sqft
2500 Lee Rd #220, Winter Park, FL
Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS
Price Reduced38Active
$1,369,000
5 bd · 4 ba · 2,446 sqft
1473 Berkshire Ave, Winter Park, FL
Gilson Rodrigues · KARDOSH REALTY
Price Reduced37Active
$1,499,000
3 bd · 5 ba · 2,756 sqft
641 Northwood Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced28Active
$695,000
4 bd · 3 ba · 1,647 sqft
2831 Mulford Ave, Winter Park, FL
Patrick Arenson · UNITED REAL ESTATE PREFERRED
Price Reduced57Active
$399,900
3 bd · 2 ba · 1,366 sqft
5503 Albert Dr, Winter Park, FL
Fernando Perez de Armas · AXEN REALTY, LLC
Price Reduced63Active
$649,900
3 bd · 2 ba · 1,370 sqft
840 W Canton Ave, Winter Park, FL
Ken Pozek · REAL BROKER, LLC
Price Reduced37Active
$535,000
3 bd · 4 ba · 1,937 sqft
1250 Formosa Ave, Winter Park, FL
Jeanine Louis, LLC · EXP REALTY LLC
5Active
$500,000
4 bd · 3 ba · 2,031 sqft
2054 Eastbrook Blvd, Winter Park, FL
Melissa Stalzer · LPT REALTY, LLC
48Active
$695,000
4 bd · 3 ba · 2,312 sqft
715 S Ranger Blvd, Winter Park, FL
Chuck Tolfa · DAHLIA REALTY GROUP
Price Reduced42Active
$836,000
3 bd · 3 ba · 2,017 sqft
338 Blue Heron Dr, Winter Park, FL
Samuel Kingsford · STOCKWORTH REALTY GROUP
Price Reduced55Active
$459,900
4 bd · 2 ba · 1,624 sqft
1320 Gladiolas Dr, Winter Park, FL
Deborah Morgan · OPTIMA REAL ESTATE
Price Reduced38Active
$998,000
4 bd · 4 ba · 2,469 sqft
1404 Border Dr, Winter Park, FL
Brian Hyser · THE AGENCY FL
Price Reduced50Active
$1,600,000
4 bd · 4 ba · 3,065 sqft
723 Symonds Ave, Winter Park, FL
Nick McKee · KELLER WILLIAMS WINTER PARK
Price Reduced37Active
$599,000
4 bd · 3 ba · 2,102 sqft
1946 Strathaven Rd, Winter Park, FL
Youbel Montesino · LPT REALTY, LLC
Price Reduced49Active
$1,049,900
5 bd · 5 ba · 3,652 sqft
1448 Lake Florence Way, Winter Park, FL
Abby Nelson · RE/MAX 200 REALTY
Price Reduced33Active
$1,498,000
3 bd · 4 ba · 2,467 sqft
1841 Lake Spier Drive, Winter Park, FL
Nicole Seybold · FANNIE HILLMAN & ASSOCIATES
41Active
$248,900
2 bd · 3 ba · 1,300 sqft
193 Lewfield Cir, Winter Park, FL
Efrain Reyes · COLDWELL BANKER REALTY

1…9 10 11…13

Listing data & MLS disclosures

Daytona Beach Area Association of REALTORS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Daytona Beach Area Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-21 01:34:03 UTC
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
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.

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.

Listing data & MLS disclosures

Daytona Beach Area Association of REALTORS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Daytona Beach Area Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-21 01:34:03 UTC
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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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.