Realty.com
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
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 searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

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
Realty.com
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 searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Registered offenders on the map

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
Homes with a Pool in Southold, NY
60 listings

Homes with a Pool in Southold, NY

Homes with a Pool in Southold, NY

Show Map
24 of 60 Listings
Map

Homes with a Pool in Southold, NY

24 of 60 Listings

  1. 860 Hillcrest Drive — photoNew24

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas
Active

$2,350,000

3 bd · 4 ba · 2,700 sqft

860 Hillcrest Drive, Southold, NY

Bridget Elkin · Compass Greater NY LLC

  • 225 Marion Lane — photoOpen house Fri, Oct 2 · 4:00 PM50Active

    $1,850,000

    3 bd · 4 ba · 3,457 sqft

    225 Marion Lane, Southold, NY

    Laura Wanamaker · Howard Hanna Coach

  • 5750 Aldrich Lane — photoOpen 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

  • 775 Mulford Court — photoOpen 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

  • 2555 Youngs Avenue 11a — photo11Active

    $605,000

    2 bd · 2 ba · 1,200 sqft

    2555 Youngs Avenue 11a, Southold, NY

    Timothy O'Keefe · Signature Premier Properties

  • 3360 Wunneweta Road — photo27Active

    $4,750,000

    6 bd · 9 ba · 8,500 sqft

    3360 Wunneweta Road, Southold, NY

    Marco L. Maida · Compass Greater NY LLC

  • 3995 Wells Avenue — photo3Active

    $1,495,000

    4 bd · 4 ba · 4,300 sqft

    3995 Wells Avenue, Southold, NY

    James Bissett · Hedgestone Commercial Rlty LLC

  • 2737 Rocky Point Road — photo35Active

    $1,675,000

    4 bd · 3 ba · 2,117 sqft

    2737 Rocky Point Road, Southold, NY

    Amy L. Kirincic · The Agency Northshore NY

  • 405 Birch Lane — photo27Active

    $1,425,000

    3 bd · 3 ba · 2,679 sqft

    405 Birch Lane, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  • 2105 Pequash Avenue — photo22Active

    $3,300,000

    5 bd · 6 ba · 4,195 sqft

    2105 Pequash Avenue, Southold, NY

    Christine L. Peddy · Engel & Volkers North Fork

  • 2080 Elijahs Lane — photo26Active

    $1,249,000

    4 bd · 3 ba · 2,578 sqft

    2080 Elijahs Lane, Southold, NY

    Kristy B. Naddell · Douglas Elliman Real Estate

  • 1200 Indian Neck Lane — photo43Active

    $3,250,000

    5 bd · 5 ba · 4,460 sqft

    1200 Indian Neck Lane, Southold, NY

    Esteban Gomez · Compass Greater NY LLC

  • 9305 Soundview Avenue — photo24Active

    $2,950,000

    4 bd · 4 ba · 4,241 sqft

    9305 Soundview Avenue, Southold, NY

    Thomas J. McCarthy C2EX · Thomas J McCarthy Real Estate

  • 390 Wildberry Lane — photoPrice ReducedOpen house Sat, Oct 3 · 11:00 AM11Active

    $3,095,000

    4 bd · 5 ba · 5,100 sqft

    390 Wildberry Lane, Southold, NY

    Shaun McQuilkin · Migrate Realty LLC

  • 225 Lakeside Drive S — photo28Active

    $2,200,000

    3 bd · 3 ba · 2,600 sqft

    225 Lakeside Drive S, Southold, NY

    Mariah J. Mills · Daniel Gale Sothebys Intl Rlty

  • 130 Tasker Lane — photo25Active

    $1,175,000

    4 bd · 3 ba · 2,400 sqft

    130 Tasker Lane, Southold, NY

    Kristen E. Rishe CBR · Signature Premier Properties

  • 2850 Main Bayview Road — photo44Active

    $2,695,000

    3 bd · 2 ba · 1,650 sqft

    2850 Main Bayview Road, Southold, NY

    Bridget Elkin · Compass Greater NY LLC

  • 2820 Shipyard Lane 1B2 — photoPrice ReducedOpen house Sun, Oct 4 · 1:00 PM35Active

    $779,000

    2 bd · 2 ba · 1,100 sqft

    2820 Shipyard Lane 1B2, Southold, NY

    Paul Loeb CBR · Douglas Elliman Real Estate

  • 1140 Park Avenue — photo50Active

    $11,500,000

    5 bd · 5 ba · 5,000 sqft

    1140 Park Avenue, Southold, NY

    Alexis Meadows · Compass Greater NY LLC

  • 1135 Wildberry Lane — photo43Active

    $2,895,000

    5 bd · 6 ba · 3,240 sqft

    1135 Wildberry Lane, Southold, NY

    Melissa Principi · Douglas Elliman Real Estate

  • 1600 King Street — photo34Active

    $8,400,000

    6 bd · 7 ba · 5,700 sqft

    1600 King Street, Southold, NY

    Janet J. Markarian · Daniel Gale Sothebys Intl Rlty

  • 1850 Highland Road — photoPrice Reduced33Active

    $1,375,000

    4 bd · 3 ba · 2,096 sqft

    1850 Highland Road, Southold, NY

    Phyllis L. Caldwell ABR SFR · Daniel Gale Sothebys Intl Rlty

  • 705 Gus Drive — photo27Active

    $2,249,000

    4 bd · 4 ba · 3,800 sqft

    705 Gus Drive, Southold, NY

    Donna J. Fakiris · Modern Age Realty Group LLC

  • 150 Deer Run — photoOpen house Sat, Oct 3 · 10:30 AM45Active

    $3,675,000

    5 bd · 6 ba · 5,285 sqft

    150 Deer Run, Southold, NY

    Jeffrey R. Mead · Corcoran

  • 123
    Realty.com

    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

    Equal Housing OpportunityEqual Housing Lender

    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.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    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.