2 Bedroom Homes in Winter Park, FL

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3 beds New construction With a pool

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24 of 48 Listings

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2 Bedroom Homes in Winter Park, FL

24 of 48 Listings

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48 listings

2 Bedroom Homes in Winter Park, FL

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24 of 48 Listings

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2 Bedroom Homes in Winter Park, FL

24 of 48 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

24Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$140,000

2 bd · 1 ba · 881 sqft

1695 Lee Rd #C206, Winter Park, FL

Ingrid Garcia Rodriguez · INVESTMENT REALTY

31Active

$265,000

2 bd · 2 ba · 908 sqft

1250 S Denning Dr #119, Winter Park, FL

Justin McCarthy · FANNIE HILLMAN & ASSOCIATES

52Active

$319,000

2 bd · 2 ba · 1,287 sqft

192 Balfour Dr #2, Winter Park, FL

Tricia Ramsby · BHHS FLORIDA REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

31Active

$227,000

2 bd · 2 ba · 1,120 sqft

602 Trinidad Ct #602, Winter Park, FL

Clara Herrera · CLARA HERRERA REALTY

20Active

$150,000

2 bd · 2 ba · 1,063 sqft

7453 Daniel Webster Dr #a5, Winter Park, FL

Laila Dkhissi · LA ROSA REALTY PREMIER LLC

33Active

$359,000

2 bd · 1 ba · 830 sqft

1306 S Pennsylvania Ave #5, Winter Park, FL

Lisa Gould · KELLER WILLIAMS WINTER PARK

24Active

$134,900

2 bd · 2 ba · 756 sqft

7302 Swallow Run #7302, Winter Park, FL

Katie Nguyen · THE NAVY HOUSE

33Active

$234,900

2 bd · 2 ba · 1,295 sqft

2383 Sun Valley Cir #2383, Winter Park, FL

Carmen Aridas · RE/MAX PRIME PROPERTIES

28Active

$170,000

2 bd · 3 ba · 1,031 sqft

7476 Woodburn Ct #38, Winter Park, FL

Habib Fahs · COLDWELL BANKER REALTY

18Active

$165,000

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C109, Winter Park, FL

Valerie Wanzer · REAL ESTATE PROFESSIONALS SE

28Active

$245,000

2 bd · 2 ba · 908 sqft

1250 S Denning Dr #127, Winter Park, FL

Drew Henner · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced11Active

$159,900

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C205, Winter Park, FL

Hitesh Khatri · CFRP REALTY LLC

30Active

$269,000

2 bd · 2 ba · 1,008 sqft

5108 Lazy Oaks Dr #5108, Winter Park, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

25Active

$269,000

2 bd · 1 ba · 710 sqft

151 N Orlando Ave #242, Winter Park, FL

Alexander Scures · COLONIALTOWN REALTY

31Active

$245,000

2 bd · 2 ba · 913 sqft

1250 S Denning Dr #Unit 233, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

47Active

$189,900

2 bd · 2 ba · 953 sqft

222 Lewfield Cir, Winter Park, FL

Joshua Neudigate · MARKET CONNECT REALTY LLC

41Active

$285,000

2 bd · 3 ba · 960 sqft

283 Sandlewood Trl #3, Winter Park, FL

Crystal Adams · RE/MAX INNOVATION

Price Reduced39Active

$975,000

2 bd · 2 ba · 1,763 sqft

311 E Morse Blvd #4-5, Winter Park, FL

Kim Garcia · KELLER WILLIAMS ADVANTAGE REALTY

Price Reduced36Active

$194,900

2 bd · 2 ba · 1,037 sqft

623 Grenadine Ct #623, Winter Park, FL

Carolyn Kickhofel · COLDWELL BANKER REALTY

86Active

$739,000

2 bd · 2 ba · 1,311 sqft

250 Carolina Ave #205, Winter Park, FL

Troy Hensley · BHHS FLORIDA REALTY

Price Reduced32Active

$184,900

2 bd · 2 ba · 1,365 sqft

7468 Canford Ct #24, Winter Park, FL

Javier Albelo Rivera · EMPIRE NETWORK REALTY

24Active

$254,000

2 bd · 2 ba · 1,316 sqft

2477 Tahoe Cir #2477, Winter Park, FL

Kyle Clark · RE/MAX TOWN & COUNTRY REALTY

Price Reduced37Active

$279,900

2 bd · 3 ba · 1,236 sqft

5210 Lazy Oaks Dr, Winter Park, FL

Karen Sweat · IHOME REALTY FL LLC

Price Reduced29Active

$268,000

2 bd · 2 ba · 1,295 sqft

2475 Tahoe Cir, Winter Park, FL

Sarah Doyer · COLDWELL BANKER 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

August 2026

Selling at 97.6% of asking price

Buyers here are paying below asking. MLS · 90 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $548,000$350,000–$1,187,500 typical range
Price per sq. ft.: $319
Sales: 110
Paid in cash: 40.9%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 11.6%

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

Explore Winter Park homes

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

August 2026

Selling at 97.6% of asking price

Buyers here are paying below asking. MLS · 90 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $548,000$350,000–$1,187,500 typical range
Price per sq. ft.: $319
Sales: 110
Paid in cash: 40.9%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 11.6%

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Park housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 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 Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026