2 bedroom homes for sale in Winter Park, FL

11 hours on Rocket

$1,306 Closing Credit¹

$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

16 hours on Rocket

$10,000 Closing Credit¹

$915,000

2 beds • 2 baths • 1,143 sqft

100 S Interlachen Ave Unit 503, Winter Park, FL 32789

#O6292044, Drew Henner, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

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1 day on RocketTour

$3,205 Closing Credit¹

$269,900

2 beds • 2.5 baths • 960 sqft

255 Sandlewood Trl, Winter Park, FL 32789

#O6296680, Freddie Crespo, Listing Office: INVESTOR'S REAL ESTATE LLC

1 day on Rocket

$3,088 Closing Credit¹

$260,000

2 beds • 2 baths • 908 sqft

1250 S Denning Dr Unit 111, Winter Park, FL 32789

#O6297033, Alayna Phillips, Listing Office: EXP REALTY LLC

4 days on RocketTour

$6,709 Closing Credit¹

$565,000

2 beds • 2 baths • 1,400 sqft

690 Osceola Ave Unit 502, Winter Park, FL 32789

#O6296168, Ashley Jacobs, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

4 days on RocketTour

$4,144 Closing Credit¹

$349,000

2 beds • 1.5 baths • 1,056 sqft

3204 Netherwood, Winter Park, FL 32792

#O6296588, Renee Anthony, Listing Office: WATSON REALTY CORP.

4 days on RocketTour

$7,066 Closing Credit¹

$595,000

2 beds • 1 bath • 972 sqft

1230 N Denning Dr, Winter Park, FL 32789

#O6295433, Ed Klein, Listing Office: FANNIE HILLMAN & ASSOCIATES

Room to negotiate?

Median Sold Price

$467.8K

Avg. Sale Time

53 Days

Based on our March 2025 Market Report.

6 days on RocketTour

$2,375 Closing Credit¹

$200,000

2 beds • 2 baths • 1,127 sqft

200 Saint Andrews Blvd Unit 1603, Winter Park, FL 32792

#O6295572, Catherine D'Amico, Listing Office: FANNIE HILLMAN & ASSOCIATES

6 days on RocketTour

$6,828 Closing Credit¹

$575,000

2 beds • 2 baths • 1,947 sqft

1430 Hyde Park Dr, Winter Park, FL 32792

#O6291312, Heather Pryor, Listing Office: KELLER WILLIAMS ADVANTAGE REALTY

6 days on RocketTour

$949 Closing Credit¹

$79,900

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

$2,838 Closing Credit¹

$239,000

2 beds • 2 baths • 916 sqft

3106 Patel Dr, Winter Park, FL 32792

#O6294321, Karen Jacobs, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

Tour

$2,197 Closing Credit¹

$185,000

2 beds • 2.5 baths • 1,031 sqft

3208 Oak Lawn Pl Unit 218, Winter Park, FL 32792

#O6277045, Ali Khaku, MBA, Listing Office: REALTY HUB

Tour

$2,886 Closing Credit¹

$243,000

2 beds • 2.5 baths • 1,578 sqft

7461 Swallow Run Unit 46, Winter Park, FL 32792

#O6294302, Phil Bellmany, Listing Office: CALVARY REAL ESTATE GROUP LLC

Tour

$4,274 Closing Credit¹

$359,900

2 beds • 2.5 baths • 1,550 sqft

1517 Florentino Ln, Winter Park, FL 32792

#O6293141, Lou DiBerardino, Listing Office: KELLER WILLIAMS WINTER PARK

$2,255 Closing Credit¹

$189,900

2 beds • 2 baths • 802 sqft

7352 Swallow Run Unit 7352, Winter Park, FL 32792

#O6293447, Ashley Quandt, Listing Office: LEERDAM PROPERTIES INC.

Tour

$1,680 Closing Credit¹

$141,500

2 beds • 1 bath • 881 sqft

1695 Lee Rd Unit D211, Winter Park, FL 32789

#O6293611, Brandy Ray, Listing Office: LOKATION

$9,441 Closing Credit¹

$795,000

2 beds • 2 baths • 949 sqft

101 S Interlachen Ave Unit 104, Winter Park, FL 32789

#O6290188, Kelly Price, Listing Office: KELLY PRICE & COMPANY LLC

Tour

$3,088 Closing Credit¹

$260,000

2 beds • 2 baths • 1,295 sqft

2471 Tahoe Cir Unit 00, Winter Park, FL 32792

#O6291369, Kevin Wilhelm, Listing Office: MLSB THE BUREAU POWERED BY CAROM REALTY

Tour

$1,413 Closing Credit¹

$119,000

2 beds • 2 baths • 1,066 sqft

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

#O6286150, Ali Khaku, MBA, Listing Office: REALTY HUB

Tour

$2,850 Closing Credit¹

$240,000

2 beds • 2.5 baths • 1,578 sqft

7468 Swallow Run Unit 38, Winter Park, FL 32792

#O6290118, Chris Creegan, Listing Office: CREEGAN GROUP

Tour

$1,425 Closing Credit¹

$120,000

2 beds • 2 baths • 1,020 sqft

245 Scottsdale Sq Unit 245, Winter Park, FL 32792

#O6277055, LoAn Schoeman, Listing Office: COMPASS FLORIDA LLC

Tour

$2,244 Closing Credit¹

$189,000

2 beds • 2 baths • 1,060 sqft

200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

#1040232, Larissa Arraiza-Pattison, Listing Office: Better Homes & Gardens RE Star

Tour

$1,188 Closing Credit¹

$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

$2,244 Closing Credit¹

$189,000

2 beds • 2 baths • 1,067 sqft

200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

#V4941401, Patricia Wojewoda, Listing Office: BETTER HOMES & GARDENS RE STAR

Tour

$5,818 Closing Credit¹

$489,900

2 beds • 2 baths • 1,088 sqft

535 N Interlachen Ave Unit 107, Winter Park, FL 32789

#O6287695, Mary Colton, Listing Office: FANNIE HILLMAN & ASSOCIATES

Tour

$2,434 Closing Credit¹

$205,000

2 beds • 2 baths • 1,018 sqft

2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792

#O6288546, Dean Nikolic, Listing Office: PMI PROPERTY ALLIANCE

Tour

$2,375 Closing Credit¹

$200,000

2 beds • 2 baths • 1,020 sqft

145 Scottsdale Sq Unit 145, Winter Park, FL 32792

#S5122349, Julio Cesar Perez, Listing Office: GLOVEN REALTY

$2,671 Closing Credit¹

$224,888

2 beds • 1.5 baths • 1,393 sqft

7466 Canford Ct Unit 25, Winter Park, FL 32792

#O6287253, Hillary Alvarez, Listing Office: KELLER WILLIAMS ADVANTAGE III

Tour

$2,007 Closing Credit¹

$169,000

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

$4,382 Closing Credit¹

$369,000

2 beds • 1 bath • 1,000 sqft

151 N Orlando Ave Unit 229, Winter Park, FL 32789

#O6283364, Justin Adams, Listing Office: EXP REALTY LLC

Tour

$2,019 Closing Credit¹

$170,000

2 beds • 2 baths • 756 sqft

7266 Swallow Run Unit 7266, Winter Park, FL 32792

#G5093483, Jessica Riccardo, Listing Office: TRINITY REAL ESTATE SALES LLC

Tour

$1,603 Closing Credit¹

$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

$1,330 Closing Credit¹

$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

$2,197 Closing Credit¹

$185,000

2 beds • 2 baths • 1,062 sqft

3060 George Mason Ave Unit 12D, Winter Park, FL 32792

#S5121342, Adriana Sanchez, Listing Office: AGENT TRUST REALTY CORPORATION

Tour

$2,136 Closing Credit¹

$179,900

2 beds • 2 baths • 1,056 sqft

3011 George Mason Ave Unit 3, Winter Park, FL 32792

#G5093322, Kayla Long, Listing Office: WHEATLEY REALTY GROUP

Tour

$2,136 Closing Credit¹

$179,900

2 beds • 1 bath • 881 sqft

1695 Lee Rd Unit E103, Winter Park, FL 32789

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

Tour

$1,829 Closing Credit¹

$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

$1,829 Closing Credit¹

$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

$1,829 Closing Credit¹

$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

$2,730 Closing Credit¹

$229,900

2 beds • 2 baths • 1,105 sqft

2923 Antique Oaks Cir Unit 39, Winter Park, FL 32792

#OM695642, Michell Carrasquero, Listing Office: GLOBALWIDE REALTY LLC

Winter Park, FL Real Estate Market Overview

Find your perfect 2 bedroom home in Winter Park, FL. Browse 2 in Winter Park, FL and connect with a Rocket Homes agent to get your dream home. In March 2025 in Winter Park, FL there were 10.4% more homes for sale than in February 2025. In March 2025 median list price was $467,846 and the average listing age was 53 days. While more than 7 listings in Winter Park, FL in March 2025 were sold above asking price, there were more than 28 listings sold at asking price, and more than 58 were sold below.

From Rocket Homes Real Estate and based on county public records data

Schools near Winter Park, FL

Elementary Schools

Brookshire Elementary School
2500 Cady Way
Public District PK-5
Aloma Elementary School
2949 Scarlet Rd
Public District KG-5
Hungerford Elementary School
230 S College Ave
Public District PK-5

Middle Schools

Glenridge Middle School
2900 Upper Park Rd
Public District 6-8

High Schools

Winter Park High School
2100 Summerfield Rd
Public Magnet 9-12

Data provided by Great Schools

2 bedroom homes for sale in Winter Park, FL

Winter Park, FL Real Estate Market Overview

What is it like to live in Winter Park, FL

Overview

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