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

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

Save search Advertise Sign In

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

Registered offenders on the map

Show registered offenders

Registered offenders on the map

Show registered offenders

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

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

Registered offenders on the map

Show registered offenders

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

3 beds New construction With a pool

Homes Under $200K in Winter Park, FL

40 listings

Homes Under $200K in Winter Park, FL

Homes Under $200K in Winter Park, FL

24 of 40 Listings

Homes Under $200K in Winter Park, FL

24 of 40 Listings

New11

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$170,000

1 bd · 1 ba · 793 sqft

200 Saint Andrews Blvd #3408, Winter Park, FL

Natalia Moege · PARK 26 REALTY LLC

$169,900

1 bd · 1 ba · 645 sqft

2500 Lee Rd #123, Winter Park, FL

Scott Sheldon · HOME WISE REALTY GROUP, INC.

$159,000

1 bd · 1 ba · 793 sqft

200 Saint Andrews Blvd #704, Winter Park, FL

Alexis Jacobsen · EXP REALTY LLC

$5,000

3 bd · 2 ba · 1,229 sqft

1187 Sawmill Court, Winter Park, FL

Jaime L Boone · Jaime L Boone LLC

$140,000

2 bd · 1 ba · 881 sqft

1695 Lee Rd #C206, Winter Park, FL

Ingrid Garcia Rodriguez · INVESTMENT REALTY

$100,000

1 bd · 1 ba · 785 sqft

173 Scottsdale Sq #173, Winter Park, FL

Paola Jimenez · AXEN REALTY, LLC

$150,000

2 bd · 2 ba · 1,063 sqft

7453 Daniel Webster Dr #a5, Winter Park, FL

Laila Dkhissi · LA ROSA REALTY PREMIER LLC

$134,900

2 bd · 2 ba · 756 sqft

7302 Swallow Run #7302, Winter Park, FL

Katie Nguyen · THE NAVY HOUSE

$170,000

2 bd · 3 ba · 1,031 sqft

7476 Woodburn Ct #38, Winter Park, FL

Habib Fahs · COLDWELL BANKER REALTY

$165,000

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C109, Winter Park, FL

Valerie Wanzer · REAL ESTATE PROFESSIONALS SE

$130,000

1 bd · 1 ba · 645 sqft

2500 Lee Rd #143, Winter Park, FL

Carol Wittman · PALMANO GROUP RE BROKERAGE LLC

Price Reduced11Active

$159,900

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C205, Winter Park, FL

Hitesh Khatri · CFRP REALTY LLC

$189,900

2 bd · 2 ba · 953 sqft

222 Lewfield Cir, Winter Park, FL

Joshua Neudigate · MARKET CONNECT REALTY LLC

Price Reduced36Active

$194,900

2 bd · 2 ba · 1,037 sqft

623 Grenadine Ct #623, Winter Park, FL

Carolyn Kickhofel · COLDWELL BANKER REALTY

$147,000

1 bd · 1 ba · 678 sqft

285 Lewfield Cir #285, Winter Park, FL

Millie Soto · COLDWELL BANKER REALTY

Price Reduced16Active

$143,500

1 bd · 1 ba · 749 sqft

3019 Antique Oaks Cir #127, Winter Park, FL

Steven Koleno · BEYCOME OF FLORIDA LLC

$180,000

1 bd · 1 ba · 638 sqft

1695 Lee Rd #D107, Winter Park, FL

Hoover Yap · PRIMESTATE REALTY, INC.

Price Reduced15Active

$105,000

1 bd · 1 ba · 796 sqft

1000 S Semoran Blvd #302, Winter Park, FL

Amaal Barakat · KELLER WILLIAMS ADVANTAGE III

Price Reduced22Active

$115,000

1 bd · 1 ba · 735 sqft

1000 S Semoran Blvd #305, Winter Park, FL

Melissa Vance · MAINFRAME REAL ESTATE

Price Reduced15Active

$164,500

1 bd · 1 ba · 732 sqft

1500 Gay Rd #4D, Winter Park, FL

Janice Erickson · REALCOM REAL ESTATE SERVICES INC

Price Reduced45Active

$170,000

2 bd · 3 ba · 1,031 sqft

7450 Wynnewood Sq #189, Winter Park, FL

Kim King · REAL ESTATE PROFESSIONALS SE

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

1 2

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
Waterfront Homes

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.

© 2026 Realty.com. All rights reserved.PrivacyTermsCalifornia Privacy RightsAccessibilityLicensing

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Listing data & MLS disclosures

Space Coast MLS (Space Coast Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-09-29 11:01:04 UTC
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 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 40.9%

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.