Southold, NY Homes for Sale

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  /21

  $735,000

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  860 N Bayview Rd, Southold, NY 11971

  Location, Location, Location !!!This beautiful ranch home is located just around the bend from the Goose Creek Beach. There are three large bedrooms, an eat in kitchen, formal dining room, living room, full basement, garage, and an enclosed breezeway in between the home and garage. The property has a nice grass lawn with mature plantings, and the rear yard is fenced with room for a pool.

  Kenneth Poliwoda Douglas Elliman Real Estate

  860 N Bayview Rd, Southold, NY 11971
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  /38

  $1,077,000

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

  380 Hickory Rd, Southold, NY 11971

  Head inside this custom-built, one-owner home nestled in a serene mid-block location, just moments from Southold's finest beaches including Kenney’s and McCabe’s Beach and a few blocks from Little Fish restaurant. This move-in-ready post-modern home boasts an open-to-above entry with gleaming hardwood floors, well-appointed rooms, and a professionally designed kitchen featuring high-end stainless

  William Ortiz Redfin Real Estate

  380 Hickory Rd, Southold, NY 11971
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  /33

  $850,000

  • 3 Beds
  • 2 Baths
  • 2,306 Sq Ft

  155 Shepard Dr, Southold, NY 11971

  This charming brick house offers ample space and with a few updates it would be a perfect forever home. Its nestled in a serene neighborhood with an eat in kitchen , formal dining room, spacious living room with wood burning fireplace, 3 spacious bedrooms and 2 full bathrooms with convenience of laundry room on first floor. 2 car garage with potential loft area. It is surrounded with mature

  Isaac Israel Richmond Realty Corp

  155 Shepard Dr, Southold, NY 11971
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  /26

  $527,500

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  2555 Youngs Ave Unit 11D, Southold, NY 11971

  Welcome to Founders Village in Southold. This quiet and quaint 55+ community is located in the heart of Southold Town. This 2 bed 2 bath condo is ready for you to make it home. Just minutes away to Jitney, train station, shopping, groceries, retail, dining, post office, gym and so much more. Either enjoy the beautiful common grounds with the community pool & club house in a quaint setting, or

  Patrick Carpenter Signature Premier Properties

  2555 Youngs Ave Unit 11D, Southold, NY 11971
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  /7

  $1,700,000

  • Land
  • 5 Acres
  • $323,810 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 equestrian grazing meadow to an adjoining 33 acre estate, this land offers a scenic, tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land.Just a few miles to fine dining and cafes, tasting rooms & vineyards,

  Kathleen Travers Douglas Elliman Real Estate

  11200 N Bayview Rd, Southold, NY 11971
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  /29

  $999,000

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

  9875 Main Bayview Rd, Southold, NY 11971

  Amazing opportunity to own a charming 1830s home with a detached accessory apartment built in 2016. Renovated in 2003, this home sits on an acre of land surrounded by unbuildable land, offering privacy and a peaceful setting. With great bones and timeless appeal, the main house features a well-designed floor plan, a cozy living room with a wood-burning fireplace, and plenty of character

  Kristy Naddell Douglas Elliman Real Estate

  9875 Main Bayview Rd, Southold, NY 11971
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  /26

  $849,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  150 Hobart Rd, Southold, NY 11971

  Experience the ultimate North Fork retreat in Southold—this stunning, turnkey cottage is a true embodiment of coastal living! Ideally situated near Founder’s Landing Park with effortless beach access and close to the Wharf House, this charming cedar-shake farmhouse is designed for entertaining and showcases an unrivaled in-town location where a car is simply unnecessary. Take advantage of

  Nicholas Planamento William Raveis New York LLC

  150 Hobart Rd, Southold, NY 11971
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  /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
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  /6

  $4,495,000

  • Land

  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

  50100 County Road 48, Southold, NY 11971
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  /16

  $999,999 Open Sat 11AM - 1PM

  • 5 Beds
  • 2 Baths
  • 1,500 Sq Ft

  65 Lake Dr, Southold, NY 11971

  The Perfect Beach Bungalow Getaway! An Idyllic Location, With Kenney's Beach Practically At Your Doorstep, This Charming Bungalow Offers Ample Space For Everyone With Five Bedrooms And Two Bathrooms. Relax And Unwind On The Outside Decks Enjoying Morning Coffee, Fresh Sea Breezes And Evening Sunsets Or Warm-up Indoors by the Fireplace. With Its Wonderful Location, Numerous Amenities And

  Thomas McCarthy Thomas J McCarthy Real Estate

  65 Lake Dr, Southold, NY 11971
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  /8

  $690,000

  • 3 Baths
  • 1,860 Sq Ft

  Unlisted Address

  1-1/2 story medical office, with reception area, offices, exam rooms, 1 full bathroom, 2 half bathrooms, supply room, attic storage, 80% full, unfinished basement w/6-1/2 ft ceiling and outside entrance, 20 crawl space. Detached garage. Great location. Area is mixed use with single family residential homes, offices and light business. Zoned Residential/Office - Currently used as a medical

  Andrew Stype Andrew Stype Realty Inc

  Unlisted Address
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  /35

  $2,399,000

  • 6 Beds
  • 5.5 Baths
  • 3,630 Sq Ft

  47100 Route 25, Southold, NY 11971

  The Beautiful Gunite Pool with Spa Features and Beach Rights to the lovely South Harbor Beach, add to the allure of this stunning, North Fork Farmhouse, cleverly Re-imagined and Restored in 2023! Start your tour as you step across the expansive covered Front Porch and enter the Elegant Entry Hall featuring wonderfully Preserved, Decorative Wood Floors. As you pass through the hall, you'll

  Deborah Kusa Douglas Elliman Real Estate

  47100 Route 25, Southold, NY 11971
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  /25

  $1,299,999

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  58425 Route 48, Greenport, NY 11944

  Views that never end! Welcome to your picturesque beachfront retreat along the Long Island Sound, where breathtaking water views and private beach access create a serene escape. Enjoy year-round sunsets that will take your breath away. This charming home features a fantastic layout with sun-soaked, high ceilings in the great room, seamlessly connecting the eat-in kitchen, living room, and dining

  William Walters Daniel Gale Sothebys Intl Rlty

  58425 Route 48, Greenport, NY 11944
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  /27

  $9,275,000

  • 5 Beds
  • 4.5 Baths
  • 4,627 Sq Ft

  1750 Hobart Rd, Southold, NY 11971

  Welcome to a stunning, one-of-a-kind waterfront home in the highly sought-after hamlet of Southold. This custom, new construction, modern residence is perfectly situated on Town Creek, featuring 160 feet of waterfront and expansive views of Peconic Bay. It includes a private 6' x 20' floating dock connected by an 82' Trex catwalk. Constructed with meticulous attention to detail, this home is

  Alexis Meadows Douglas Elliman Real Estate

  1750 Hobart Rd, Southold, NY 11971
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  /33

  $6,900,000

  • Land
  • 51 Acres
  • $135,294 per Acre

  44075 Route 25, Peconic, NY 11958

  Welcome to a rare opportunity to own a legacy in the heart of Long Island's famed wine country. Nestled on 51 acres in the coveted North Fork, this stunning winery and vineyard is more than a property; it's a chance to cultivate your dreams and continue a tradition of excellence. 46 total DRS acres of which 35 acres have mature vines. 4.46 acres of development rights in tact. Spanning 46 acres of

  Kristy Naddell Douglas Elliman Real Estate

  44075 Route 25, Peconic, NY 11958
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  /21

  $1,199,000

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  1500 Hortons Ln, Southold, NY 11971

  Welcome Home to this sunny 3-bedroom, 2.5-bath Equestrian home built in 2001set on a sprawling 1.94-acre lot with 2-stall horse barn! Full basement with 8ft ceilings & OSE to yard, 2-car attached garage & fenced horse pasture. Formal Living Room with Vaulted ceilings, Formal dining room, large EIK with sliders to rear deck & patio. Large Primary bedroom suite with bathroom, large WIC and views

  Stephen Abruzzo Gateway to The Hamptons R E

  1500 Hortons Ln, Southold, NY 11971
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  /30

  $3,275,000

  • 4 Beds
  • 3 Baths

  10947 N Bayview Rd, Southold, NY 11971

  Compound with House, Barn and 70' Deep Water Dock in Private Marina. Water views from the backyard, kitchen and second floor bedrooms. Nestled on secluded 2+ acres in the coveted "Shellfisher Preserve" association near Paradise Point. Private deeded beach located down a short pathway. Bonus Space with views: 1,800 sqft detached post-and-beam barn has 3 car garage and studio space above. The

  Melissa Principi Douglas Elliman Real Estate

  10947 N Bayview Rd, Southold, NY 11971
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  /2

  $599,000

  • Land
  • 3.03 Acres
  • $197,690 per Acre

  Unlisted Address

  Calling all privacy seekers! Located in the heart of Long Island's North Fork, this 3 acre flag lot is close to all that this area has to offer. Goldsmiths Inlet Park is just .5 mile down the road while Kennys sandy LI Sound beach is just 1.3 miles away. Close to vineyards, award winning dining, golf and so much more!

  Erica McKenzie Andrew Stype Realty Inc

  Unlisted Address
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  /4

  $1,600,000

  • Land
  • 2.00 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
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  /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
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  /32

  $1,100,000

  • 6 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  1755 Yennecott Dr, Southold, NY 11971

  Nestled on a wooded lot, this location feels private while only short distance to downtown Southold and 10 Minutes East to the Village of Greenport. With spacious, airy rooms and hardwood floors, this inviting residence promises a cozy and warm ambiance from the moment you step inside, hand painted wall mosaic, 2 fire places, Spacious Eat In Kitchen, Formal Dining room, Family room and when its

  Isaac Israel Richmond Realty Corp

  1755 Yennecott Dr, Southold, NY 11971
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  /36

  $1,349,000

  • 3 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  633 Pine Neck Rd, Southold, NY 11971

  A must see secluded water front Compound. Rarely do you find two houses on a one acre lot. Main cottage is 3 BR, Eik, FDR,, LR with fireplace, hardwood floors, basement and inviting water side covered porch, second cottage has Primary ensuite and guest Br with second bath, Eik, LR w/Fireplace hardwood floors full basement. Small out building, Additional information: Appearance:Very good

  Tom Uhlinger Douglas Elliman Real Estate

  633 Pine Neck Rd, Southold, NY 11971
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  /36

  $1,345,000

  • 3 Beds
  • 1.5 Baths
  • 2,350 Sq Ft

  155 2nd Ave, Peconic, NY 11958

  Steps from the Sound and tucked away on a quiet private road, this lovingly owner-built reverse beach house offers the perfect blend of privacy, charm, and North Fork living. With 3 bedrooms and 1.5 baths, the home was thoughtfully designed with an open-concept kitchen and living area upstairs to maximize stunning water views from the back deck. A cozy gas fireplace adds warmth and comfort,

  Derek Greene Greene Realty Group

  155 2nd Ave, Peconic, NY 11958

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