Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Sell

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Home Loans

Find an Agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Save search

Map layers

Safety

Sex offendersRegistered offenders, from official state registriesCamerasLicense-plate readers, CCTV and more, as mapped on OpenStreetMap

Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

Buy

Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Rentals
Commercial

82 listings

Sell

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Home Loans

Find an Agent

Save search

3 beds New construction With a pool

Condos in Winter Park, FL

Hide Map

24 of 82 Listings

Map

24 of 82 Listings

Price Reduced31

Condos in Winter Park, FL — Page 3

82 listings

Condos in Winter Park, FL

Hide Map

24 of 82 Listings

Map

Condos in Winter Park, FL

24 of 82 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced31

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Active

$275,000

2 bd · 2 ba · 1,008 sqft

5184 Lazy Oaks Dr, Winter Park, FL

Joyce Gary · PAINE-ANDERSON PROPERTIES, INC

42Active

$279,900

2 bd · 2 ba · 1,295 sqft

2305 Sun Valley Cir, Winter Park, FL

Ryan Barnett · MARKET CONNECT REALTY LLC

42Active

$285,000

2 bd · 2 ba · 1,495 sqft

2372 Sun Valley Cir #2372, Winter Park, FL

Sheila Mathews · COLDWELL BANKER REALTY

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced11Active

$138,000

1 bd · 1 ba · 776 sqft

1000 S Semoran Blvd #408, Winter Park, FL

Scott Butts · KIMBRIDGE REALTY, LLC

Price Reduced13Active

$138,000

1 bd · 1 ba · 796 sqft

1000 S Semoran Blvd #306, Winter Park, FL

Scott Butts · KIMBRIDGE REALTY, LLC

Price Reduced5Active

$138,000

1 bd · 1 ba · 776 sqft

1000 S Semoran Blvd #404, Winter Park, FL

Scott Butts · KIMBRIDGE REALTY, LLC

Price Reduced32Active

$210,000

2 bd · 3 ba · 1,578 sqft

7488 Whisperwood Dr #28, Winter Park, FL

Miranda Azer · PARKVIEW REAL ESTATE

Price Reduced26Active

$235,000

2 bd · 2 ba · 1,026 sqft

1500 Gay Rd #3C, Winter Park, FL

Heather Frazee · FANNIE HILLMAN & ASSOCIATES

30Active

$199,900

1 bd · 1 ba · 582 sqft

151 North Orlando Avenue #142, Winter Park, FL

Chris Creegan · CREEGAN GROUP

Price Reduced39Active

$1,775,000

3 bd · 4 ba · 3,112 sqft

101 S New York Ave #311, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

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

41Active

$248,900

2 bd · 3 ba · 1,300 sqft

193 Lewfield Cir, Winter Park, FL

Efrain Reyes · COLDWELL BANKER REALTY

Price Reduced28Active

$350,000

1 bd · 1 ba · 987 sqft

700 Melrose Ave #J24, Winter Park, FL

Scott Butts · KIMBRIDGE REALTY, LLC

Price Reduced37Active

$650,000

3 bd · 2 ba · 1,350 sqft

300 Carolina Ave #402C, Winter Park, FL

Erin Baker · FANNIE HILLMAN & ASSOCIATES

Price Reduced44Active

$899,000

1 bd · 2 ba · 1,109 sqft

269 E Canton Ave #269, Winter Park, FL

Cathy Sawruk Williams · COLDWELL BANKER REALTY

Price Reduced24Active

$175,000

2 bd · 3 ba · 1,031 sqft

7327 Forest Hill Ct #223, Winter Park, FL

Leda Vaz · M L VAZ REALTY INC

29Active

$229,000

3 bd · 3 ba · 1,151 sqft

7454 Wynnewood Sq #188, Winter Park, FL

Manoj Patel · APPLE REALTY

Price Reduced41Active

$275,000

2 bd · 2 ba · 1,008 sqft

5143 Lazy Oaks Dr #5143, Winter Park, FL

Mindy Machock · KELLER WILLIAMS REALTY AT THE PARKS

21Active

$140,000

2 bd · 3 ba · 1,090 sqft

3021 Aaron Burr Ave #3, Winter Park, FL

Daiana Garcia Medrano · NAIM REAL ESTATE LLC

Price Reduced34Active

$159,000

2 bd · 3 ba · 1,108 sqft

7300 Daniel Webster Dr #M7, Winter Park, FL

Rosa Rodriguez · STIRLING INTERNATIONAL REAL ES

Price Reduced35Active

$159,000

2 bd · 3 ba · 1,090 sqft

3027 Aaron Burr Ave #L1, Winter Park, FL

Rosa Rodriguez · STIRLING INTERNATIONAL REAL ES

21Active

$189,000

2 bd · 2 ba · 1,018 sqft

2918 Antique Oaks Cir #25, Winter Park, FL

Ken Warren · PREMIER MANAGEMENT GROUP INC

Price Reduced55Active

$459,900

2 bd · 3 ba · 1,428 sqft

630 Killarney Bay Ct #3, Winter Park, FL

Anthony Consalvo · FLORIDA ONE REAL ESTATE LLC

20Active

$299,999

2 bd · 1 ba · 710 sqft

151 N Orlando Ave #118, Winter Park, FL

Adriana Montes · FLORIDA DREAMS REALTY GRP INC

1 2 3 4

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

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 28, 2026

Median sale price: $565,000$410,000–$952,600 typical range
Price per sq. ft.: $342
Sales: 92
Paid in cash: 44.6%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000

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

By price

Homes Under $200K
Homes Under $300K
Homes Under $400K
Homes Under $500K
Homes Under $600K
Homes Under $700K
Homes Under $800K
Homes Under $900K
Homes Under $1M
Homes Under $1.25M
Homes Under $1.5M
Homes Under $1.75M
Homes Under $2M
Homes Under $2.25M
Homes Under $2.5M
Homes Over $3M
Luxury Homes

By bedrooms

2 Bedroom Homes
3 Bedroom Homes
4 Bedroom Homes
5 Bedroom Homes

By type

Single-Family Homes
Townhomes
Condos

By feature

New Construction Homes
Homes with a Pool

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.

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

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 28, 2026

Median sale price: $565,000$410,000–$952,600 typical range
Price per sq. ft.: $342
Sales: 92
Paid in cash: 44.6%

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: 28.1%

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.