17

Southold, NY Homes for Sale with Acreage

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  • /35

    $1,695,000

    • 6 Beds
    • 3 Baths
    • 2,911 Sq Ft

    56861 Private Rd B (Main), Southold, NY 11971

    Dream big, live LARGE! This newly renovated home is ready for it's close-up! The new Chef's Kitchen is designed with easy summer hosting in mind, with new appliances, gorgeous counter-tops and a Hamptons vibe. Large open plan living room with a wood-burning fire-place, and large dining area are ready for your whole tribe! All of the upstairs bedrooms (including the primary suite) have a shared

    Agent Photo

    Regan Battuello

    The Agency Northshore NY

    (934) 200-4963

    56861 Private Rd B (Main), Southold, NY 11971
  • /21

    $989,000

    • 2 Beds
    • 1 Bath
    • 1,200 Sq Ft

    2070 Cedar Dr, Southold, NY 11971

    2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find — a welcoming home in a peaceful setting. There’s a sandy neighborhood beach right across the street and it’s positioned near other beaches, marinas, and North Fork vineyards. Located in a highly desirable Southold waterfront enclave, the property presents a compelling opportunity for both lifestyle buyers

    Agent Photo

    Dawn Watson

    Serhant East End LLC

    (631) 840-6859

    2070 Cedar Dr, Southold, NY 11971
  • /19

    $239,000

    • 1 Bath
    • 250 Sq Ft

    52325 County Road 48 Unit 31, Southold, NY 11971

    Seasonal Condo Near a Memorable Long Island Sound Beach (Town Beach). Studio Apartment with Efficiency Kitchen and is Located on the 2nd Floor. The Condo Offers a Community Room, Lawn with BBQ Area, Laundry, Off Street Parking, Boat Storage, Beach Storage. Electric, Water, Cable and Sewer/Cesspool included in Common Charge of $253 Monthly. SEASONAL CONDO OPEN APRIL TO NOVEMBER. NOT YEAR ROUND.

    Paul Loeb Douglas Elliman Real Estate

    52325 County Road 48 Unit 31, Southold, NY 11971
  • /4

    $1,600,000

    • Land
    • 2 Acres
    • $800,000 per Acre

    55975 Route 25, Southold, NY 11971

    2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. 4 Buildings Possible As Of Right. Great Route 25 Exposure & Great Location In Center Of Hamlet! Commercial Listing MLS# 3530579

    Colin McCarthy Thomas J McCarthy Real Estate

    55975 Route 25, Southold, NY 11971
  • /46

    $3,799,999

    • 5 Beds
    • 6 Baths
    • 5,285 Sq Ft

    150 Deer Run, Southold, NY 11971

    Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed by the renowned firm of Nelson and Pope utilizing steel beam construction throughout and Benjamin Obdyke Hydrogap house wrap, the home features solid white oak hardwood floors, as well as many custom details including maple cabinetry and vanities, Marvin Elevate windows, sliding and French doors, mahogany

    Jeffrey Mead Corcoran

    150 Deer Run, Southold, NY 11971
  • /5

    $799,000

    • Land
    • 2.29 Acres
    • $348,908 per Acre

    1350 Hortons Ln, Southold, NY 11971

    Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot, Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Just Moments Away From The Vibrant Town Life, You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom

    Thomas McCarthy Thomas J McCarthy Real Estate

    1350 Hortons Ln, Southold, NY 11971
  • /5

    $1,499,000

    • Land
    • 4.24 Acres
    • $353,538 per Acre

    18365 County Road 48, Southold, NY 11935

    Motivated Seller! Opportunity to own 4+ acres of buildable vacant land in the heart of Cutchogue on Long Island’s scenic North Fork. Water, electric, and natural gas connections are available at the street, making this an ideal site to build your dream home, private retreat, or investment property. Enjoy a peaceful setting surrounded by vineyards, farm stands, and open farmland, while being just

    Michael Graziose Redfin Real Estate

    18365 County Road 48, Southold, NY 11935
  • /50

    $1,299,000

    • 3 Beds
    • 1.5 Baths
    • 2,000 Sq Ft

    2055 Boisseau Ave, Southold, NY 11971

    Southold, North Fork: The historic Boisseau farmhouse, built around 1890, is situated on 1.75 acres (76,230 square feet) with R40 residential zoning, in a picturesque setting featuring mature trees and a sprawling lawn. The property is adjacent to fallow, and partially wooded acreage owned by the Town of Southold. The traditional home boasts a charming covered front porch, an entry foyer, and a

    Nicholas Planamento William Raveis New York LLC

    2055 Boisseau Ave, Southold, NY 11971
  • /29

    $3,295,000

    • 4 Beds
    • 5.5 Baths
    • 7,341 Sq Ft

    80 Deer Run, Southold, NY 11971

    Southold Stunner- New ConstructionThis one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was built to check every box. Inside you're met with all-day sunshine, four legit bedrooms, 4.5 spa-like baths (sanitary system in place for 7 bedrooms), and a true chef's kitchen-with a 48" Sub Zero, Wolf double range + wall oven,

    Sheri Winter Parker Corcoran

    80 Deer Run, Southold, NY 11971
  • /7

    $150,000

    • 1 Bath
    • 230 Sq Ft

    52325 County Road 48 Unit 8, Southold, NY 11971

    Waterfront Studio Condo in Southold property features living room / kitchen combo with 1 Queen Size bed and 2 pull out trundle beds which can become 1 full size bed. outdoor area includes boat storage for small fee BBQ area on grounds free laundry room. Rentals are permitted can be rented seasonally if desired.Low property taxes and low common charges which include all utilities.Seasonal

    Peter Vekiarellis ERealty Advisors Inc

    52325 County Road 48 Unit 8, Southold, NY 11971
  • /36

    $4,900,000

    • Land
    • 51 Acres
    • $96,078 per Acre

    44075 Route 25, Peconic, NY 11958

    Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres,

    Susan Orioli Engel & Volkers North Fork

    44075 Route 25, Peconic, NY 11958
  • /6

    $1,799,000

    • Land
    • 8.65 Acres
    • $207,977 per Acre

    420 Leon Rd, Southold, NY 11971

    Calling all builders and investors! Beautiful 8.65 acres of cleared, leveled land in Southold Town. This parcel is zoned R-80, (2 Acre zoning) and has 250' of frontage on Sound Avenue (North Road) and access from adjacent Leon Road. Sellers will not consider offers "subject to" any permits or approvals.

    Melissa Principi Douglas Elliman Real Estate

    420 Leon Rd, Southold, NY 11971
  • /3

    $850,000 Pre-Foreclosure

    • 3 Beds
    • 4 Baths
    • 2,100 Sq Ft

    150 Baywater Ave, Southold, NY 11971

    Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of Southold’s oldest and most significant properties. Ideally positioned, it is just moments from one of the East End’s finest sandy bay beaches and Croteaux Vineyards, as well as a short drive to renowned wineries, farm stands, and

    Marco Maida Compass Greater NY LLC

    150 Baywater Ave, Southold, NY 11971
  • /42

    $3,850,000 Open Sun 12PM - 2PM

    • 6 Beds
    • 4 Baths
    • 4,663 Sq Ft

    105 Waterview Dr, Southold, NY 11971

    Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6-bedroom, 4-bath colonial offers a den/office, bonus room, and sweeping water views from nearly every room. Thoughtfully designed for both comfort and future flexibility, the residence provides substantial expansion potential.

    Roric Tobin Compass Greater NY LLC

    105 Waterview Dr, Southold, NY 11971
  • /7

    $1,499,000

    • Land
    • 5.25 Acres
    • $285,524 per Acre

    11200 N Bayview Rd, Southold, NY 11971

    Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards,

    Kathleen Travers Douglas Elliman Real Estate

    11200 N Bayview Rd, Southold, NY 11971
  • /23

    $4,300,000

    • Land
    • 45.77 Acres
    • $93,948 per Acre

    46975 Main Rd, Southold, NY 11971

    Some estates are acquired. The exceptional are entrusted to the next chapter. Set within the North Fork’s most storied agricultural landscape, this extraordinary lifestyle farm unfolds across protected vineyard acreage and open sky - a private world defined by refinement, scale, and possibility. Being offered together are two parcels: 43.7 preserved acres, where development rights have been sold

    Andrea Parks Douglas Elliman Real Estate

    46975 Main Rd, Southold, NY 11971
  • /46

    $1,499,000

    • 4 Beds
    • 1.5 Baths
    • 1,880 Sq Ft

    1760 Albertson Ln, Greenport, NY 11944

    Scenic and bucolic, this 3+ acre country farm is steeped in classic North Fork charm. The property features an authentic 1800s four-bedroom, one and a half bath, farmhouse, a 2+ car garage (1976) with a workshop, office and mechanics pit, and a 1985 barn equipped with three horse stalls and ample space for tractors. Additional structures include a cinderblock chicken coop and a pig sty, offering

    Paul Loeb Douglas Elliman Real Estate

    1760 Albertson Ln, Greenport, NY 11944

Home Trends in Southold, NY

Housing Trends

Median Sale Price
$899,000
Median Single Family Sale Price
$1,150,000
Median Townhouse Sale Price
$733,750
Median 2 Bedroom Sale Price
$512,500
Average Price Per Sq Ft
$670
Number of Homes for Sale
41
Last 12 months Home Sales
96
Months of Supply
5.10
Median List Price
$1,162,500
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-10%
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