Affordable homes for sale in Winter Park, FL

Tour

$59,900

2 beds • 1.5 baths • 1,085 sqft

194 Scottsdale Sq Unit 194, Winter Park, FL 32792

#O6294859, Katie Nguyen, Listing office: THE NAVY HOUSE

Tour

$85,000

1 bed • 1 bath • 785 sqft

167 Scottsdale Sq Unit 167, Winter Park, FL 32792

#S5129326, Nevelle Chambers, Listing office: LA ROSA REALTY ORLANDO LLC

Room to negotiate?

Median Sold Price

$460K

Avg. Sale Time

41 Days

Based on our June 2025 Market Report.

Tour

$89,900

Studio • 1 bath • 549 sqft

3071 George Mason Ave Unit 5, Winter Park, FL 32792

#O6289736, Katherine Bordelon, Listing office: CASTLE & COTTAGE REALTY LLC

Tour

$90,000

1 bed • 1 bath • 785 sqft

337 Scottsdale Sq Unit 337, Winter Park, FL 32792

#TB8373292, Michel Pineda Monsalve, Listing office: HOMERIVER GROUP

Tour

$95,000

2 beds • 2 baths • 1,066 sqft

3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

#O6318835, Ali Khaku, MBA, Listing office: DALTON WADE INC

$100,000

2 beds • 2 baths • 1,020 sqft

101 Scottsdale Sq Unit 101, Winter Park, FL 32792

#O6285553, Kevin Kendrick, Listing office: EXP REALTY LLC

Tour

$100,000

2 beds • 2 baths • 1,020 sqft

166 Scottsdale Sq Unit 166, Winter Park, FL 32792

#O6281523, Lawrence Shao, Listing office: KYLIN REALTY LLC

Tour

$110,000

2 beds • 2 baths • 1,020 sqft

330 Scottsdale Sq Unit 330, Winter Park, FL 32792

#O6297922, Emad Terkawi, Listing office: CENTURY 21 CARIOTI

Tour

$112,000

2 beds • 2 baths • 1,020 sqft

318 Scottsdale Sq Unit 318, Winter Park, FL 32792

#O6275119, Brittneyann Cover, Listing office: RE/MAX ASSURED

Tour

$115,000

1 bed • 1 bath • 785 sqft

293 Scottsdale Sq Unit 293, Winter Park, FL 32792

#O6269553, Cassandra Kelly Flores, Listing office: COLDWELL BANKER REALTY

Tour

$120,000

2 beds • 1.5 baths • 1,085 sqft

316 Scottsdale Sq Unit 316, Winter Park, FL 32792

#O6303221, Tyann Huynh, Listing office: JADE KEY REALTY LLC

Tour

$127,000

2 beds • 2 baths • 1,066 sqft

3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792

#O6314262, Claudia Villarroel, Listing office: ROBERT SLACK LLC

Tour

$129,000

1 bed • 1 bath • 803 sqft

3045 Aaron Burr Ave Unit 10, Winter Park, FL 32792

#S5114398, TATA Rojas, Listing office: TBO REAL ESTATE PARTNERS INC

Tour

$129,900

2 beds • 2.5 baths • 1,090 sqft

7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792

#O6302214, Nicole Rader, Listing office: MAINFRAME REAL ESTATE

Tour

$130,000

3 beds • 2 baths • 1,250 sqft

334 Scottsdale Sq Unit 334, Winter Park, FL 32792

#V4940331, John Sheynkman, Listing office: CHARLES RUTENBERG REALTY ORLANDO

Tour

$130,000

1 bed • 1 bath • 735 sqft

1000 S Semoran Blvd Unit 415, Winter Park, FL 32792

#O6316826, Jhoana Loyo Urrutia, Listing office: LA ROSA REALTY LLC

$134,900

2 beds • 2 baths • 1,267 sqft

7340 Daniel Webster Dr Unit 6-C, Winter Park, FL 32792

#TB8327713, Frank Smith, Listing office: KELLER WILLIAMS SUBURBAN TAMPA

Tour

$135,000

2 beds • 1.5 baths • 1,085 sqft

126 Scottsdale Sq Unit 126, Winter Park, FL 32792

#O6261570, Thomas Hicks, Sr, Listing office: LPT REALTY

Tour

$137,500

2 beds • 1 bath • 881 sqft

1695 Lee Rd Unit E214, Winter Park, FL 32789

#O6300348, Martha Grasty, Listing office: RE/MAX ASSURED

$139,900

2 beds • 2.5 baths • 1,085 sqft

7449 Daniel Webster Dr Unit 3, Winter Park, FL 32792

#O6314250, Chris Creegan, Listing office: CREEGAN GROUP

$139,900

2 beds • 2 baths • 1,030 sqft

3053 George Mason Ave Unit 8, Winter Park, FL 32792

#O6256375, Dan Graves, Listing office: GRAVES REALTY

Tour

$139,900

1 bed • 1 bath • 803 sqft

3060 George Mason Ave Unit 10C, Winter Park, FL 32792

#O6299685, John Silva, Listing office: JOHN SILVA REALTY & ASSOCIATES

Tour

$144,900

1 bed • 1 bath • 638 sqft

1695 Lee Rd Unit A209, Winter Park, FL 32789

#O6271289, Zep Bholai-Lawrence, Listing office: FUSILIER REALTY GROUP

Tour

$149,000

1 bed • 1 bath • 776 sqft

1000 S Semoran Blvd Unit 408, Winter Park, FL 32792

#R4909221, Scott Butts, Listing office: KIMBRIDGE REALTY, LLC

Tour

$149,000

1 bed • 1 bath • 776 sqft

1000 S Semoran Blvd Unit 404, Winter Park, FL 32792

#R4909220, Scott Butts, Listing office: KIMBRIDGE REALTY, LLC

Tour

$149,000

1 bed • 1 bath • 796 sqft

1000 S Semoran Blvd Unit 306, Winter Park, FL 32792

#R4909222, Scott Butts, Listing office: KIMBRIDGE REALTY, LLC

Tour

$149,900

2 beds • 1.5 baths • 1,085 sqft

110 Scottsdale Sq Unit 110, Winter Park, FL 32792

#O6285115, Ana Semmel, Listing office: KARDOSH REALTY

Tour

$150,000

1 bed • 1 bath • 793 sqft

200 St Andrews Blvd Unit 911, Winter Park, FL 32792

#O6320474, Jonathan Lacko, Listing office: WINTER PARK REAL ESTATE CO LLC

Tour

$154,000

2 beds • 2 baths • 1,020 sqft

285 Scottsdale Sq Unit 285, Winter Park, FL 32792

#O6278117, David Sanchez, Listing office: RE/MAX TOWN & COUNTRY REALTY

Tour

$154,000

2 beds • 2 baths • 1,020 sqft

116 Scottsdale Sq Unit 2, Winter Park, FL 32792

#O6278124, David Sanchez, Listing office: RE/MAX TOWN & COUNTRY REALTY

Tour

$154,000

2 beds • 2 baths • 1,020 sqft

243 Scottsdale Sq Unit 243, Winter Park, FL 32792

#O6278106, David Sanchez, Listing office: RE/MAX TOWN & COUNTRY REALTY

Tour

$154,900

2 beds • 1 bath • 881 sqft

1695 Lee Rd Unit E103, Winter Park, FL 32789

#S5121244, Jason Price, Listing office: ROBERT SLACK LLC

$155,000

1 bed • 1 bath • 678 sqft

302 Lewfield Cir Unit 302, Winter Park, FL 32792

#O6294146, Heather Spirazza, Listing office: REGENCY REAL ESTATE LLC

Tour

$155,000

3 beds • 2 baths • 1,250 sqft

228 Scottsdale Sq Unit 228, Winter Park, FL 32792

#S5125620, Amanda Lindsey, Listing office: VYLLA HOME

Tour

$155,000

1 bed • 1 bath • 678 sqft

130 Lewfield Cir Unit 130, Winter Park, FL 32792

#O6303927, Renee Kumar, Listing office: LA ROSA REALTY LLC

Tour

$159,000

1 bed • 1 bath • 638 sqft

1695 Lee Rd Unit B109, Winter Park, FL 32789

#O6280513, Jalinette Ortiz, Listing office: EXP REALTY LLC

Tour

$159,900

2 beds • 2 baths • 1,049 sqft

1000 S Semoran Blvd Unit 608, Winter Park, FL 32792

#O6315008, Maria Peralta, Listing office: CHARLES RUTENBERG REALTY ORLANDO

$160,000

1 bed • 1 bath • 678 sqft

296 Lewfield Cir, Winter Park, FL 32792

#TB8384159, Jonathan Minerick, Listing office: HOMECOIN.COM

Tour

$163,000

1 bed • 1 bath • 678 sqft

141 Lewfield Cir Unit 141, Winter Park, FL 32792

#O6312660, Jo Ann Lamar, Listing office: PREMIER SOTHEBY'S INTL. REALTY

Tour

$165,000

1 bed • 1 bath • 753 sqft

4936 Tangerine Ave Unit 4936, Winter Park, FL 32792

#O6309448, Israel Vinas, Listing office: VINAS DEL MAR REALTY, INC.

Winter Park, FL Real Estate Market Overview

There are 387 affordable homes for sale in Winter Park, FL. The following market insights reflect all property types in the Winter Park, FL real estate market. The inventory of homes for sale in Winter Park, FL between May 2025 and June 2025 decreased by 5%. The median list price of listings available in June 2025 was $460,000, while the average time on the real estate market was 41 days. In June 2025 more than 7 listings in Winter Park, FL were sold above the asking price. During the same period more than 19 listings were sold at asking price, while more than 58 were sold below.