Homes for Sale near Southold Junior/Senior High School

• 

  

  

  /22

  $529,000

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

  2555 Youngs Ave Unit 7D, Southold, NY 11971

  2BR 2Bath condo in Founders Village, Southolds premier 55+ active community. Unit features high ceilings, large primary suite, back patio and full basement. $435 monthly maintenance includes snow removal, beautiful landscaping, access to clubhouse and pool, maintenance of the roof and siding. Located about one half mile from local stores and shops as well as public transportation.

  

  Timothy O'Keefe

  Signature Premier Properties

  (631) 430-5573

  2555 Youngs Ave Unit 7D, Southold, NY 11971
• 

  Explore Southold Junior/Senior High School

• 

  

  

  /27

  $888,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  625 Glenn Rd, Southold, NY 11971

  Situated in an area rich in the founding history of Southold Town, what likely began as wooded trails connecting water, homesteads and farmland eventually evolved into today’s quiet tree and creek lined Glenn Road. Stake your Southold claim in this lovingly updated 3-bedroom, 2-bath home.The tastefully renovated kitchen is a standout feature, offering stainless steel appliances, a

  

  Timothy O'Keefe

  Signature Premier Properties

  (631) 856-2225

  625 Glenn Rd, Southold, NY 11971
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  /47

  $2,795,000

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

  430 Salt Marsh Ln, Peconic, NY 11958

  This stunning Peconic sound front property, perched elegantly on a hill with breathtaking views of the sound, has been recently updated with a new roof and siding. Featuring 5 spacious bedrooms and 3 modern baths, the home offers expansive open living and recreation areas, perfect for relaxation and entertaining. Outside, the beautifully landscaped grounds boast an all-weather tennis court, a

  

  Geoff Gifkins

  Nest Seekers International LLC

  (631) 250-6738

  430 Salt Marsh Ln, Peconic, NY 11958
• 

  

  

  /7

  $2,095,000

  • 4 Beds
  • 3.5 Baths
  • 3,245 Sq Ft

  265 Arshamomaque Ave, Southold, NY 11971

  This beautiful Newly Constructed Modern Craftsman/Cottage style home, tucked away down a private lane, boasting 3245 sq' interior living space, black onyx saltwater pool and serene wooded property while providing access to two exclusive bayside beach areas located in desirable Beixedon Estates. This beautiful newly constructed home is ideally situated between quaint Southold Town and the vibrant

  Cathleen Dolson Corcoran

  265 Arshamomaque Ave, Southold, NY 11971
• 

  

  

  /50

  $2,998,000

  • 4 Beds
  • 3 Baths
  • 3,253 Sq Ft

  5805 Main Bayview Rd, Southold, NY 11971

  Stunning Waterfront Retreat w/ Modern Luxury on 4+ Private Acres. Experience serene luxury in this completely renovated home offering year-round views of Goose Creek and 250 feet of direct waterfront. Nestled on nearly 4.5 acres of pristine landscape, this private oasis is located in a highly desirable community with amenities including beach access, kayak storage, and docking. Designed for both

  Kristy Naddell Douglas Elliman Real Estate

  5805 Main Bayview Rd, Southold, NY 11971
• 

  

  /29

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 2,627 Sq Ft

  700 Gin Ln, Southold, NY 11971

  Step inside and wow—this home lives much larger than it looks from the outside! With a floorplan that truly fits today’s lifestyle, you’ll love how the open living room, dining area, and kitchen all flow together to create the perfect space for everyday living or effortless entertaining. And yes, there’s a main-floor bedroom suite with laundry nearby, making one-level living totally doable if

  Jerry Cibulski Century 21 Albertson Realty

  700 Gin Ln, Southold, NY 11971
• 

  

  /50

  $2,430,000

  • 4 Beds
  • 6 Baths
  • 5,500 Sq Ft

  4745 N Bayview Rd, Southold, NY 11971

  Discover unparalleled luxury and space in this magnificent 5,500 sqft residence, perfectly situated on a double lot. Recently refreshed with a full interior and exterior paint, this home exudes a pristine and inviting atmosphere.Step into your private oasis, where lush, meticulously maintained gardens envelop the entire property, with full landscape lighting, offering a serene and

  Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  4745 N Bayview Rd, Southold, NY 11971
• 

  

  /38

  $2,650,000

  • 4 Beds
  • 4.5 Baths
  • 3,238 Sq Ft

  1665 Glenn Rd, Southold, NY 11971

  Southold-West Creek Estates - Just completed, beautiful, light-filled home. Attention to detail and a gracious lifestyle begins at the front entry with a wood and glass front door and natural wood architectural accents. The large great room features a living area with a two sided gas fireplace, dining area, and a generous chef's eat-in kitchen. The second side of the fireplace faces the covered

  Barry Novick Daniel Gale Sothebys Intl Rlty

  1665 Glenn Rd, Southold, NY 11971
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  /38

  $1,795,000

  • 4 Beds
  • 2.5 Baths
  • 3,110 Sq Ft

  1260 Water Terrace, Southold, NY 11971

  Welcome to your own slice of paradise in the coveted Angel Shores beach community. This beautifully crafted home offers deeded bay beach access at the end of the road, and a spectacular backyard retreat—complete with vibrant gardens, an inviting inground pool, hot tub, and tranquil waterfall. Whether you're entertaining guests or enjoying a quiet evening at home, this outdoor space delivers the

  Katie Schimpf Daniel Gale Sothebys Intl Rlty

  1260 Water Terrace, 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
• 

  

  /35

  $1,450,000

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  1025 Long Creek Dr, Southold, NY 11971

  In the last month there have been lots of updates made to this exquisite waterfront home with wrap around porches and breathtaking views. Don’t miss this opportunity to own a waterfront property on the North Fork. Perfectly situated on the protected and tranquil water way of Arshomomaque, where you can enjoy fishing, crabbing, clamming, boating, or just relax and listen to the birds. The first

  Barbara Poliwoda Douglas Elliman Real Estate

  1025 Long Creek Dr, Southold, NY 11971
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  /50

  $1,425,000

  • 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
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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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  /40

  $1,150,000

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  3700 Minnehaha Blvd, Southold, NY 11971

  3700 Minnehaha Blvd., Southold, a darling waterfront home nestled in Laughing Waters private beach community. This home has something for everyone! For boaters, this home is so convenient, with its very own bulkhead and easy access to the Great Peconic Bay, just untie your boat and go! For nature lovers, the views and wildlife sightings are amazing and all from the comfort of your waterside

  Rita Rooney Douglas Elliman Real Estate

  3700 Minnehaha Blvd, Southold, NY 11971
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  /27

  $998,000

  • 4 Beds
  • 2 Baths
  • 2,200 Sq Ft

  730 Pine Neck Rd, Southold, NY 11971

  ****Open House cancelled***Completely renovated raised ranch just moments away from the quaint Southold village, Goose Creek and Founders Beach, local farms, and wineries. All the work has been done for you, just unpack and start living your best life! Great room with gas fireplace, 2-year-old chef's Kitchen with quartz counters and stainless appliances, lower-level guest suite complete with

  Cindy Succoso Douglas Elliman Real Estate

  730 Pine Neck Rd, Southold, NY 11971
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  /18

  $13,000,000

  • 6 Beds
  • 4 Baths
  • 6,000 Sq Ft

  59600 Main Rd, Southold, NY 11971

  A singular opportunity to acquire 22.20 contiguous acres on the Peconic Bay, offering 470 feet of premier bayfront and a private sandy beach. More than 10 acres are planted with mature vines producing an impressive range of grape varietals, including Pinot Noir, Merlot, Cabernet Franc, Malbec, Petit Verdot, Sauvignon Blanc, Chardonnay, and Gruner Veltliner. Development rights are intact, allowing

  Bridget Elkin Compass Greater NY LLC

  59600 Main Rd, Southold, NY 11971
• 

  

  /21

  $645,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  335 Dogwood Ln, Southold, NY 11971

  Just 950 feet from the beloved Kenney's Beach this charming 3 bed room, one bath beach cottage offers a rare opportunity to create your dream retreat in one of the most desirable locations on the North Fork. This property is brimming with potential both inside and out.Enjoy sun filled days by the beach and stop by Little Fish for sunset cocktails at night. Inside, you’ll find a cozy

  Natalie Hough Daniel Gale Sothebys Intl Rlty

  335 Dogwood Ln, Southold, NY 11971
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  /14

  $1,175,000

  • 3 Beds
  • 3 Baths
  • 2,936 Sq Ft

  480 N Bayview Road Extension, Southold, NY 11971

  Embrace refined living in this charming residence nestled in the heart of Southold. Enjoy the expansive .75-acre grounds that provide a sanctuary of tranquility. Situated on a meandering hill, this home offers a serene and private retreat. The modern, chic interior is beautifully designed for comfort and style. The welcoming foyer unfolds into a spacious living room, flowing effortlessly into a

  Alexis Meadows Douglas Elliman Real Estate

  480 N Bayview Road Extension, Southold, NY 11971
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  /28

  $4,795,000

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

  19620 Soundview Ave, Southold, NY 11971

  Experience the epitome of luxury living in this modern new construction estate, a truly unique offering on the East End framed by breathtaking vineyard views. This newly constructed estate, spanning 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 a generous foyer leading to four

  Alexis Meadows Douglas Elliman Real Estate

  19620 Soundview Ave, Southold, NY 11971
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  /9

  $775,000

  • 1 Bed
  • 4 Baths
  • 2,890 Sq Ft

  Unlisted Address

  Great office space with apartment! The office has 5+ exam rooms, large waiting area and 2 half baths. The 1 bedroom, 1 bath apartment has a large kitchen, loft area and large deck. The property sits on one acre and has ample parking. The office and apartment must be owner occupied, or the entire structure could be converted to all living space as well as keeping the apartment. Many uses for this

  Andrew Stype Andrew Stype Realty Inc

  Unlisted Address
• 

  

  /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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  /47

  $1,399,000

  • 4 Beds
  • 2.5 Baths
  • 3,226 Sq Ft

  1465 Ackerly Pond Ln, Southold, NY 11971

  Nestled in the heart of Southold’s coveted North Fork, 1465 Ackerly Pond Lane offers a rare opportunity to own a custom home on over 2.5 acres of serene, private land. This single-family property is surrounded by natural beauty and tucked away on a quiet lane, making it ideal for those seeking peace and space just minutes from the village, vineyards, and beaches. Home features a large gourmet

  Scott Bennett Douglas Elliman Real Estate

  1465 Ackerly Pond Ln, Southold, NY 11971
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  /9

  $699,000

  • Land
  • 7 Acres
  • $98,036 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, which could average about 600 cases of

  Melissa Principi Douglas Elliman Real Estate

  1135 Boisseau Ave, Southold, NY 11971
• 

  

  /20

  $3,900,000

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  5615 Soundview Ave, Southold, NY 11971

  Includes TWO lots totaling one residential waterfront lot with a preexisting two story house on 7 acres. The other is an additional vacant buildable lot available with nearly 2 acres. With 250 feet of private sandy beach, you'll have endless opportunities. Explore a rich natural landscape with a dedicated nature trail, home to wild blueberries, cranberries, and beach plums, plus an osprey

  Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  5615 Soundview Ave, Southold, NY 11971
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  /20

  $3,200,000

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft

  5615 Soundview Ave, Southold, NY 11971

  Residential waterfront lot with a preexisting two story house. Imagine owning over 7 acres of pristine woodland in Peconic Dunes, your very own waterfront haven on the Long Island Sound. With 250 feet of private sandy beach, you'll have endless opportunities for swimming, fishing, and soaking in incredible sunsets. Explore a rich natural landscape with a dedicated nature trail, home to wild

  Donielle Cardinale Daniel Gale Sothebys Intl Rlty

  5615 Soundview Ave, Southold, NY 11971
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  /23

  $850,000

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft

  2955 Hyatt Rd, Southold, NY 11971

  This bright and airy 3-bedroom, 2-bathroom home on Southold's charming Hyatt Road offers a perfect blend of open and closed living spaces. With numerous windows and skylights, the home seamlessly integrates with the surrounding mature landscaping. Each bedroom boasts vaulted ceilings and picturesque views of the park-like setting. The Primary has a large ensuite bath. Conveniently located just

  Bridget Elkin Compass Greater NY LLC

  2955 Hyatt Rd, Southold, NY 11971
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  /37

  $1,899,000

  • 5 Beds
  • 5.5 Baths
  • 3,350 Sq Ft

  480 Ackerly Pond Ln, Southold, NY 11971

  Step into this custom home where luxury craftsmanship provides everyday tranquility. Experience the pinnacle of North Fork living in this bespoke custom-built residence, thoughtfully constructed with modern elegance and a timeless design. Nestled on a quiet property and offering seamless access to Southold Town beaches, vineyards, breweries, marinas, and North Fork restaurants, this exceptional

  Catherine Flood Compass Greater NY LLC

  480 Ackerly Pond Ln, Southold, NY 11971
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  /29

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 3,735 Sq Ft

  500 Meadow Ct Unit 28, Southold, NY 11971

  Lovely light-filled 3-bedroom 3 bath inland end-unit in The Cove – a small hidden gem of a waterfront community nestled in the heart of the North Fork. There are boat slips for your boat with easy access to the beautiful Peconic Bay, boat racks for your paddleboard/kayak, a gunite in-ground pool, and combination tennis/pickleball court – both of which were just resurfaced this year! The airy open

  Gayle Marriner Smith Daniel Gale Sothebys Intl Rlty

  500 Meadow Ct Unit 28, Southold, NY 11971
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  /33

  $2,180,000

  • 3 Beds
  • 3 Baths
  • 2,500 Sq Ft

  2300 Glenn Rd, Southold, NY 11971

  Located in one of Southold’s most coveted locations, this waterfront oasis offers peace, privacy, and stunning views of Goose Creek. Surrounded by professionally designed and meticulously maintained landscaping, this property exudes tranquility and natural beauty.The home features a spacious and thoughtfully designed layout with wood floors throughout. The updated kitchen is a chef’s

  Kristy Naddell Douglas Elliman Real Estate

  2300 Glenn Rd, Southold, NY 11971
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  /35

  $649,999

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  900 Cedar Dr, Southold, NY 11971

  Welcome to the North Fork. This pristine Ranch home features 3 Bedrooms 1 bath Updated Kitchen with dining area and access to large deck and cozy fire pit, full semi finished basement with laundry room and storage plus 1 1/2 car garage. Imagine your days wine tasting, strolling the hamlet of Southold, a short drive to Greenport with top notch Restaurants and Shops or just relaxing on the beaches

  Lisa Cerreta BERKSHIRE HATHAWAY

  900 Cedar Dr, Southold, NY 11971
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  /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
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  /15

  $895,000

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

  57020 Route 25, Southold, NY 11971

  Residential/Hamlet Business OpportunityBeautifully restored and updated Colonial Path House located in the heart of wine country. The front facade of the house has been restored to clapboard siding and cedar shake. The original rooms on the first floor include a parlor with wood burning fireplace, an adjacent dining room, farm kitchen and full bath/laundry room. Antique wide plank floors

  Eugene Rindfuss Coldwell Banker Reliable R E

  57020 Route 25, Southold, NY 11971
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  /29

  $999,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,550 Sq Ft

  515 Corey Creek Ln, Southold, NY 11971

  Welcome to this beautifully maintained 3-bedroom, 2-bath ranch set on a pristine half-acre. Enjoy the best of indoor and outdoor living with a spacious living room w/FP, bright den and primary BR ensuite. Step outside to your own private oasis - an expansive 16'x32' inground pool surrounded by manicured landscaping and plenty of room for entertaining. Private cul de sac and association with its

  Thomas McCarthy Thomas J McCarthy Real Estate

  515 Corey Creek Ln, Southold, NY 11971
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  /42

  $699,900

  • 2 Beds
  • 1 Bath
  • 796 Sq Ft

  560 Clark Rd, Southold, NY 11971

  Discover this beautifully maintained 2-bedroom, 1-bathroom cottage nestled on a tranquil road just moments from the beach. Perfectly blending modern comforts with coastal charm, this home offers a serene retreat for beach lovers and those seeking a peaceful lifestyle. Enjoy the convenience of being close to the beach, allowing for easy access to sun, sand, and sea. Relax in your own

  Kristen Rishe Signature Premier Properties

  560 Clark Rd, Southold, NY 11971
• 

  

  /22

  $2,395,000

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

  600 Glenn Rd, Southold, NY 11971

  Welcome to 600 Glenn Rd, Southold, NY, a contemporary masterpiece built in 2025, situated in the coveted bayside enclave of Southold. This exceptional property features clean lines and light-filled living areas, offering a modern and luxurious lifestyle. The home boasts a walnut-clad entry, 4” select white-washed white oak flooring, 4 bedrooms, and 5.5 baths. Enjoy the expansive upper and lower

  Cathleen Dolson Corcoran

  600 Glenn Rd, Southold, NY 11971
• 

  

  /33

  $899,000

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

  4100 Youngs Ave, Southold, NY 11971

  ***PRICE REDUCTION***Nestled on the North Fork in picturesque Southold, this charming and sophisticated farmhouse offers the perfect blend of modern luxury and timeless elegance. Featuring 5 spacious bedrooms and 3 beautifully appointed bathrooms on 2 floors, the home underwent a comprehensive renovation less than 5 years ago. No detail was overlooked- ensuring a truly elevated living experience.

  Jeannine Kowaleski William Raveis (Westhampton Beach)

  4100 Youngs Ave, Southold, NY 11971
• 

  

  /33

  $775,000

  • 3 Beds
  • 2 Baths
  • 1,600 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
• 

  

  /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 scenic miles to fine dining and cafes, tasting rooms &

  Kathleen Travers Douglas Elliman Real Estate

  11200 N Bayview Rd, Southold, NY 11971
• 

  

  /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
• 

  

  /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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