Homes Under $2.75M in Winter Park, FL

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24 of 299 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

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New28Active
$450,000
3 bd · 2 ba · 1,346 sqft
506 Lander Rd, Winter Park, FL
Mike Derenthal · DERENTHAL REALTY
Open house Sun, Oct 25 · 11:00 AM24Active
$620,000
3 bd · 2 ba · 1,762 sqft
624 Dunraven Dr, Winter Park, FL
Beth Logullo · KELLER WILLIAMS WINTER PARK
New55Active
$985,000
5 bd · 3 ba · 3,296 sqft
2330 Westminster Ct., Winter Park, FL
Lisa Fleming · FANNIE HILLMAN & ASSOCIATES

Listing data & MLS disclosures

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-10-23 14:55:39 UTC
realMLS (Northeast Florida Multiple Listing Service): 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. Data is deemed reliable but is not guaranteed accurate by NEFMLS.
Listing information ©2026 Northeast Florida Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-19 15:30:33 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.

About Homes Under $2.75M in Winter Park, FL

Homes Under $2.75M in Winter Park, FL: 299 active listings as of October 25, 2026, 11:11 UTC.

Property types among these 299 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property type	Listings	Share
Single Family Residence	187	62.5%
Condominium	79	26.4%
Townhouse	29	9.7%

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 30, 2026

Median sale price: $566,750$404,625–$1,046,250 typical range
Price per sq. ft.: $342
Sales: 108
Paid in cash: 43.5%

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: 27.8%

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.

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

Homes Under $2.75M in Winter Park, FL

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Listing data & MLS disclosures

About Homes Under $2.75M in Winter Park, FL

Winter Park housing market

Homes that sold · County records, as of Sep 30, 2026

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

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Winter Park, FL community profile

Explore Winter Park homes

Listing data & MLS disclosures

Winter Park, FL community profile

Winter Park housing market

Homes that sold · County records, as of Sep 30, 2026

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

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

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Your local brokerage

Your local brokerage