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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

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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?
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Pricing your home
What's worth fixing first
Find a seller's agent

3 beds With a pool

119 listings

Homes Under $2.5M in Southold, NY

Homes Under $2.5M in Southold, NY

24 of 119 Listings

Homes Under $2.5M in Southold, NY

24 of 119 Listings

Open house Sat, Oct 3 · 12:30 PM18

Active

$795,000

3 bd · 2 ba · 2,000 sqft

29400 County Road 48, Southold, NY

Sheri Winter Parker · Corcoran

Open house Sat, Oct 3 · 11:45 AM27Active

$1,349,000

3 bd · 3 ba · 2,925 sqft

1600 Westview Drive, Southold, NY

Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

$2,350,000

3 bd · 4 ba · 2,700 sqft

860 Hillcrest Drive, Southold, NY

Bridget Elkin · Compass Greater NY LLC

Open house Sat, Oct 3 · 12:00 PM35Active

$1,150,000

3 bd · 2 ba · 1,204 sqft

13700 Oregon Road, Southold, NY

Thomas J. Uhlinger · Douglas Elliman Real Estate

Open house Sat, Oct 3 · 11:00 AM43Active

$1,149,999

3 bd · 2 ba · 1,775 sqft

2000 Westphalia Road, Southold, NY

Stephen Zappalla · Keller Williams Realty Elite

Open house Sat, Oct 3 · 11:30 AM10Active

$699,000

2 bd · 1 ba · 1,200 sqft

216 Broad Street, Southold, NY

Jennifer A. Benton · Compass Greater NY LLC

Open house Sun, Oct 4 · 1:00 PM50Active

$1,850,000

3 bd · 4 ba · 3,457 sqft

225 Marion Lane, Southold, NY

Laura Wanamaker · Howard Hanna Coach

Open house Sat, Oct 3 · 10:30 AM23Active

$1,565,000

4 bd · 3 ba · 2,577 sqft

5750 Aldrich Lane, Southold, NY

Bryce Levy CBR · Daniel Gale Sothebys Intl Rlty

Open house Sat, Oct 3 · 11:00 AM36Active

$1,189,000

4 bd · 4 ba · 3,000 sqft

25105 Main Road N, Southold, NY

Suzette Reiss CBR · Douglas Elliman Real Estate

Open house Sat, Oct 3 · 1:00 PM22Active

$835,000

1 bd · 2 ba · 886 sqft

2820 Shipyard Lane 2C1, Southold, NY

Denice L. Lara SFR CBR · Daniel Gale Sothebys Intl Rlty

$1,595,000

4 bd · 2 ba · 1,885 sqft

1000 Haywaters Road, Southold, NY

Nicholas J. Planamento · William Raveis New York LLC

Open house Sat, Oct 3 · 11:00 AM49Active

$2,395,000

4 bd · 5 ba · 3,000 sqft

795 Bayview Avenue, Southold, NY

Donielle Cardinale McKinnon CBR · Daniel Gale Sothebys Intl Rlty

$649,000

2 bd · 1 ba · 1,100 sqft

995 Schoolhouse Road, Southold, NY

Rachael York · Coldwell Banker Reliable R E

Open house Sat, Oct 3 · 11:00 AM43Active

$1,750,000

4 bd · 4 ba · 2,930 sqft

775 Mulford Court, Southold, NY

Kristy B. Naddell · Douglas Elliman Real Estate

$1,200,000

2 bd · 2 ba · 886 sqft

1405 Village Lane, Southold, NY

Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

Price Reduced27Active

$1,325,000

3 bd · 3 ba · 3,200 sqft

750 Reeve Avenue, Southold, NY

Scott Bortzner CBR · Compass Greater NY LLC

$925,000

2 bd · 1 ba · 925 sqft

738 Conklin Road, Southold, NY

Gerald J. Cibulski CBR E-PRO CRS G · Century 21 Albertson Realty

Open house Sat, Oct 10 · 12:00 PM36Active

$1,100,000

4 bd · 3 ba · 2,000 sqft

61341 Route 25, Southold, NY

Nancy J. Cervelli · Daniel Gale Sothebys Intl Rlty

$605,000

2 bd · 2 ba · 1,200 sqft

2555 Youngs Avenue 11a, Southold, NY

Timothy O'Keefe · Signature Premier Properties

$950,000

3 bd · 2 ba · 1,321 sqft

985 Silver Colt Road, Southold, NY

Deborah A. Dooley CBR · Signature Premier Properties

$1,495,000

4 bd · 4 ba · 4,300 sqft

3995 Wells Avenue, Southold, NY

James Bissett · Hedgestone Commercial Rlty LLC

Open house Sat, Oct 3 · 1:00 PM28Active

$999,000

3 bd · 2 ba · 2,000 sqft

280 Marina Lane, Southold, NY

Gayle Marriner Smith CBR · Daniel Gale Sothebys Intl Rlty

$1,100,000

4 bd · 3 ba · 2,050 sqft

185 Maiden Lane, Southold, NY

Bridget Elkin · Compass Greater NY LLC

$925,000

3 bd · 2 ba · 1,727 sqft

1035 Theresa Drive, Southold, NY

Marco L. Maida · Compass Greater NY LLC

1 2…5

About Homes Under $2.5M in Southold, NY

Homes Under $2.5M in Southold, NY: 119 active listings as of October 3, 2026, 10:26 UTC.

Homes Under $2.5M in nearby cities

Homes Under $2.5M in Southampton
Homes Under $2.5M in East Hampton

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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.

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Thomas O'Leary

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Lic. #10311208632

Listing data & MLS disclosures

OneKey MLS: The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX 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. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

Southold, NY community profile

Area: 15.2 sq. mi.

Source: HJN community data

Southold housing market

August 2026 · This period is still settling

Homes on the market · MLS, as of Aug 24, 2026

Median list price: $1,599,000
Homes for sale: 55

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

Median home size: 1,634 sq. ft.

Homes Under $2.5M in Southold, NY