2 bedroom homes for sale in Winter Park, FL

2 days on RocketTour

$1,188 Closing Credit¹

$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

5 days on RocketTour

$1,425 Closing Credit¹

$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

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5 days on RocketTour

$2,791 Closing Credit¹

$235,000

2 beds • 2 baths • 913 sqft

1250 S Denning Dr Unit 230, Winter Park, FL 32789

#O6302829, Jenny Lake, Listing Office: FANNIE HILLMAN & ASSOCIATES

6 days on RocketTour

$3,206 Closing Credit¹

$270,000

2 beds • 1.5 baths • 1,036 sqft

3310 Royal St, Winter Park, FL 32792

#G5096126, Kevin Schudel, Listing Office: BUY IT INC

7 days on RocketTour

$5,926 Closing Credit¹

$499,000

2 beds • 1 bath • 954 sqft

3601 Midiron Dr, Winter Park, FL 32789

#O6302210, Juliana Usquiano, Listing Office: EMPIRE NETWORK REALTY

7 days on RocketTour

$2,968 Closing Credit¹

$249,900

2 beds • 2 baths • 1,015 sqft

200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792

#O6301808, Lucy Gonzalez Zabala, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

Tour

$1,602 Closing Credit¹

$134,900

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

Room to negotiate?

Median Sold Price

$467.8K

Avg. Sale Time

53 Days

Based on our March 2025 Market Report.

Tour

$7,707 Closing Credit¹

$649,000

2 beds • 2 baths • 1,057 sqft

225 E Canton Ave Unit 225, Winter Park, FL 32789

#O6301796, Richard Palmano, Listing Office: PALMANO GROUP RE BROKERAGE LLC

Tour

$2,611 Closing Credit¹

$219,900

2 beds • 2 baths • 1,173 sqft

2348 Sun Valley Cir, Winter Park, FL 32792

#O6299701, Freddie Crespo, Listing Office: INVESTOR'S REAL ESTATE LLC

Tour

$8,608 Closing Credit¹

$724,900

2 beds • 2.5 baths • 1,718 sqft

640 Killarney Bay Ct Unit 4, Winter Park, FL 32789

#O6300075, Brandon Geers, Listing Office: COMPASS FLORIDA LLC

$3,159 Closing Credit¹

$265,995

2 beds • 2 baths • 1,092 sqft

5518 Cretan Way, Winter Park, FL 32792

#O6300087, Liam Pool, Listing Office: HOMEVEST REALTY

Tour

$1,673 Closing Credit¹

$140,900

2 beds • 1 bath • 881 sqft

1695 Lee Rd Unit E214, Winter Park, FL 32789

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

Tour

$6,234 Closing Credit¹

$525,000

2 beds • 1 bath • 943 sqft

2507 Lafayette Ave, Winter Park, FL 32789

#O6297775, William Grim, III, Listing Office: RE/MAX ASSURED

Tour

$6,828 Closing Credit¹

$575,000

2 beds • 1 bath • 1,000 sqft

1821 Goodrich Ave, Winter Park, FL 32789

#O6299740, Mick Night, Listing Office: PREMIER SOTHEBY'S INTL. REALTY

Tour

$7,588 Closing Credit¹

$639,000

2 beds • 1 bath • 901 sqft

100 S Interlachen Ave Unit 107F, Winter Park, FL 32789

#O6295321, Beth Hobart, Listing Office: MAINFRAME REAL ESTATE

Tour

$2,731 Closing Credit¹

$230,000

2 beds • 2 baths • 956 sqft

2500 Lee Rd Unit 208, Winter Park, FL 32789

#O6297570, Debbie Jones, Listing Office: KELLER WILLIAMS REALTY AT THE PARKS

Tour

$3,384 Closing Credit¹

$285,000

2 beds • 1 bath • 710 sqft

151 N Orlando Ave Unit 115, Winter Park, FL 32789

#O6299179, Jackie O'Leary, Listing Office: FANNIE HILLMAN & ASSOCIATES

Tour

$2,968 Closing Credit¹

$249,900

2 beds • 2.5 baths • 1,031 sqft

3254 Oak Lake Pl Unit 137, Winter Park, FL 32792

#O6298927, Darryl Henderson, Jr, Listing Office: GLOBAL ENTERPRISE REALTY GROUP

$3,324 Closing Credit¹

$279,900

2 beds • 2 baths • 939 sqft

2404 Gallery View Dr Unit 1, Winter Park, FL 32792

#O6298040, Lolita Clay, Listing Office: CHARLES RUTENBERG REALTY ORLANDO

Tour

$3,324 Closing Credit¹

$279,900

2 beds • 2 baths • 1,669 sqft

2309 Sun Valley Cir Unit 2309, Winter Park, FL 32792

#O6298238, Kristin Vogt, Listing Office: CENTURY 21 INTEGRA

Tour

$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

$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

Tour

$2,968 Closing Credit¹

$249,900

2 beds • 2.5 baths • 960 sqft

255 Sandlewood Trl, Winter Park, FL 32789

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

$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

Tour

$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

Tour

$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.

Tour

$2,255 Closing Credit¹

$189,900

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

Tour

$6,531 Closing Credit¹

$550,000

2 beds • 2 baths • 1,947 sqft

1430 Hyde Park Dr, Winter Park, FL 32792

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

Tour

$830 Closing Credit¹

$69,900

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

$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

$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

$2,136 Closing Credit¹

$179,900

2 beds • 2 baths • 802 sqft

7352 Swallow Run Unit 7352, Winter Park, FL 32792

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

$8,847 Closing Credit¹

$745,000

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

$1,294 Closing Credit¹

$109,000

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

$2,601 Closing Credit¹

$219,000

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

$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

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. The number of listings in Winter Park, FL increased by 10.4% between February 2025 and March 2025. In March 2025, listings were on the market for 53 days. During the same period, the median list price in this real estate market was $467,846. Winter Park, FL housing market in March 2025 saw over 7 listings sold above listed price, more than 28 sold at listed price and over 58 sold below.

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

What is it like to live in Winter Park, FL

Overview

Winter Park is located in Orange County, Florida. There are roughly 30,427 residents, living in 13,373 households. The average temperature for Winter Park this time of the year is low of 66F and high of 88F. On average, Winter Park gets about 3.79 inches of precipitation in May. Most residents are home owners (62%), have a post secondary degree (63%) and are single, no kids (51%).

Data provided by Home Junction

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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Schools near Winter Park, FL

Housing market reports in Orange County

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