18

Southold, NY Homes for Sale with Acreage

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  • /20

    $989,000

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

    2070 Cedar Dr, Southold, NY 11971

    Spanning over an acre in desirable Goose Bay Estates, this exceptional property offers serene water views from on high and is a mere tenth of a mile from the sandy shores of Goose Creek private beach. Beautifully updated and maintained, the two-bedroom, one-bath cottage features a cozy fireplace and gleaming hardwood floors, complemented by a recently renovated kitchen, glassed-in Florida room,

    Agent Photo

    Dawn Watson

    Serhant East End LLC

    (631) 840-6859

    2070 Cedar Dr, 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
  • /25

    $2,999,000

    • 8 Beds
    • 7 Baths
    • 5,600 Sq Ft

    1350 Hortons Ln, Southold, NY 11971

    2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Prime Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and convenience with this exceptional 2-acre vacant lot, tucked away in a serene, secluded setting --- Yet just minutes from downtown, pristine beaches, and world-class vineyards, shopping and dining. Plans are in-place for a "To Be Built"

    Thomas McCarthy Thomas J McCarthy Real Estate

    1350 Hortons Ln, Southold, NY 11971
  • /46

    $3,825,000

    • 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, this lovely home follows an entertainer's dream layout: open Great Room concept with fireplace, Chef's gourmet kitchen with custom cabinetry and Bertazzoni appliances, large island and breakfast nook, formal dining room with Butler's pantry, a first floor junior

    Jeffrey Mead Corcoran

    150 Deer Run, Southold, NY 11971
  • /4

    $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
  • /50

    $1,350,000 Open Sat 11AM - 12:30PM

    • 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
  • /28

    $4,495,000

    • 7 Beds
    • 7.5 Baths
    • 7,300 Sq Ft

    19620 Soundview Ave, Southold, NY 11971

    Experience the epitome of luxury living in this modern newly construction estate, a truly unique offering on the East End framed by breathtaking vineyard views. This newly constructed estate is move in ready with C/O in hand and spans an impressive 7,300 square feet, is a testament to meticulous craftsmanship and thoughtful design, where simplicity meets elegance. Upon arrival, you are greeted by

    Alexis Meadows Douglas Elliman Real Estate

    19620 Soundview Ave, Southold, NY 11971
  • /36

    $6,299,000

    • Land
    • 51 Acres
    • $123,510 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
  • /42

    $3,850,000

    • 4 Beds
    • 3 Baths
    • 4,103 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 4-bedroom, 3-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
  • /6

    $4,495,000

    • Land
    • 36 Acres
    • $124,861 per Acre

    50100 County Road 48, Southold, NY 11971

    Attention Developers and Discerning Investors! Opportunity knocks with this 36-acre parcel, Development Rights in Tact, nestled in the heart of the North Fork. Ideally positioned along Arshamomack Creek with access to both County and Municipal roadways, this property offers a perfect setting for the development of either workforce housing, an exclusive residential enclave or a private estate. A

    Lisa Gillooly Compass Greater NY LLC

    50100 County Road 48, 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
  • /44

    $1,695,000

    • 3 Beds
    • 3 Baths
    • 1,850 Sq Ft

    3630 Soundview Ave, Peconic, NY 11958

    3630 Soundview Avenue in Peconic offers the perfect balance of modern living and coastal charm- a nature lovers paradise Tucked along Southold’s Sound-front corridor, this newly renovated contemporary is just across the street from a dune trail leading directly to a sandy beach. Goldsmith's Inlet, Kenney's Beach and McCabe's Beach are also close by, giving you endless opportunities to enjoy the

    Scott Bennett Douglas Elliman Real Estate

    3630 Soundview Ave, Peconic, NY 11958
  • /43

    $2,995,000

    • 4 Beds
    • 3 Baths
    • 2,600 Sq Ft

    10947 N Bayview Rd, Southold, NY 11971

    Set on over two secluded acres within the coveted Shellfisher Preserve association near Paradise Point, this extraordinary estate offers sweeping water views from the backyard, kitchen, and upstairs rooms. A private deeded beach and your own deep-water dock is just a short pathway away. The property is graced by a pristine tidal lagoon, preserved and maintained by the Peconic Land Trust. The

    Melissa Principi Douglas Elliman Real Estate

    10947 N Bayview Rd, Southold, NY 11971
  • /10

    $925,000

    • Land
    • 2 Acres
    • $462,500 per Acre

    195 Mount Beulah Ave, Southold, NY 11971

    Build Your Dream Estate in Southold. Prime 2 Acre Corner Lot Near the BeachAn exceptional opportunity awaits in one of Southold’s most desirable neighborhoods. This premium 2-acre corner parcel provides the ideal setting to design and build a custom luxury residence with plenty of room for a pool, pool house, guest cottage, tennis or pickleball courts, lush gardens, and expansive outdoor

    Kristy Naddell Douglas Elliman Real Estate

    195 Mount Beulah Ave, Southold, NY 11971
  • /33

    $1,649,999

    • 4 Beds
    • 4 Baths
    • 3,000 Sq Ft

    3715 Hortons Ln, Southold, NY 11971

    Designer Modern Farmhouse ranch set on over 3.35 Acres with farm and scenic views. Renovated 2023. Open concept Living room, Dining room and Kitchen, Gorgeous kitchen with quartz countertops, Stainless Steel Appliances, built in wine cooler, new windows throughout, new interior doors, new exterior doors, new flooring, updated designer baths, new boiler, new well pump, new hot water heater.

    Arelis Olivieri RIN

    3715 Hortons Ln, Southold, NY 11971
  • /10

    $399,000

    • Land
    • 7.13 Acres
    • $55,961 per Acre

    1135 Boisseau Ave, Southold, NY 11971

    Turn-key 7-acre vineyard that you've been dreaming of in Southold! Perfectly situated near the village and shops. The vines are in their prime and have been meticulously maintained. Planted in 2006 is 2.2 Acres of Chardonnay and 2.5 Acres of Merlot and 1/2 acre Muscat Ottonel was planted in 2019. Producing approximately 2-3 tons per acre of grapes annually. Fully deer fenced, irrigated by well

    Melissa Principi Douglas Elliman Real Estate

    1135 Boisseau Ave, Southold, NY 11971
  • /40

    $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
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