Southold, NY Houses for Sale

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  /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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  /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
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  /38

  $2,630,000

  • 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
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  /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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  /12

  $2,450,000

  • 4 Beds
  • 5.5 Baths
  • 4,671 Sq Ft

  20210 Soundview Ave, Southold, NY 11971

  Located just a few feet from the beach, 20210 Soundview Avenue offers a modern farmhouse-style home, meticulously renovated with the finest materials and upgrades including all new heating/cooling. Set on an acre of land, this 4-bedroom, 5.5-bathroom residence boasts an open-concept living and dining area that seamlessly flows into a chef's kitchen, ideal for entertaining. The home features two

  Marco Maida Compass Greater NY LLC

  20210 Soundview Ave, Southold, NY 11971
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  /38

  $1,895,000

  • 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
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  /33

  $1,674,999

  • 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
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  /35

  $1,450,000 Open Sat 12PM - 2PM

  • 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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  /12

  $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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  /16

  $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 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
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  /43

  $3,995,000

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

  1750 Mount Beulah Ave, Southold, NY 11971

  Welcome to one of the North Fork's most iconic and impeccably restored estates, where timeless grandeur blends seamlessly with refined modern living. Originally built circa 1915, this Georgian estate, formally known as the Cosden Estate, has been lovingly restored for today's modern luxuries while maintaining its historic vibe. Set on a professionally landscaped acre in one of Southold's most

  Kristy Naddell Douglas Elliman Real Estate

  1750 Mount Beulah Ave, Southold, NY 11971
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  /39

  $1,249,999

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  4710 Old Rd N, Southold, NY 11971

  Welcome to 4710 Old North Rd, a private Southold retreat. This beautifully maintained 2,400 sqft Expanded Cape offers the perfect blend of comfort, space, and privacy in the heart of Southold. Situated on over 3 scenic acres, with potential for subdivision, this home is a rare North Fork find featuring 4 spacious bedrooms, 2.5 bathrooms, a full basement, a 2-car garage and a heated in-ground

  Zachary Scher Signature Premier Properties

  4710 Old Rd N, Southold, NY 11971
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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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  /50

  $3,649,999

  • 4 Beds
  • 5.5 Baths
  • 6,366 Sq Ft

  465 Ripple Water Ln, Southold, NY 11971

  Welcome to your bespoke farmhouse retreat nestled in the serene beauty of the North Fork of Long Island. This custom-crafted home offers an unparalleled blend of luxury, comfort, and tranquility, enveloped by a meticulously designed landscape that creates a secluded oasis. Approaching the property, you're greeted by a custom landscape package featuring Belgian block pathways, crushed pea gravel,

  Jerry Cibulski Century 21 Albertson Realty

  465 Ripple Water Ln, Southold, NY 11971
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  /35

  $2,750,000

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  2335 Minnehaha Blvd, Southold, NY 11971

  Step into a world of endless summer at this quintessential Nantucket-style cedar shake home, perfectly sited with expansive views of the Peconic bay and Corey creek. With its charming Dutch doors and expansive upper and lower decks, you’ll be invited to soak in the refreshing sea breezes and panoramic waterside vistas along with views of your private dock across the street, deep enough for a 66’

  Mariah Mills Daniel Gale Sothebys Intl Rlty

  2335 Minnehaha Blvd, Southold, NY 11971
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  /44

  $2,649,000

  • 4 Beds
  • 4.5 Baths
  • 2,842 Sq Ft

  285 Blue Marlin Dr, Southold, NY 11971

  Interior Completed! The pool and landscaping are slated for completion the end of August. With incredible water views and access to a picturesque private beach, 285 Blue Marlin exemplifies luxury coastal living at its finest. Constructed by the North Fork’s most revered builders, no expense has been spared and the utmost attention to detail is evident with attributes such as designer fixtures,

  Connie Liappas Compass Greater NY LLC

  285 Blue Marlin Dr, Southold, NY 11971
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  /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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  /38

  $1,899,000

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

  480 Ackerly Pond Ln, Southold, NY 11971

  Welcome to 480 Ackerly Pond Ln on the charming North Fork! Experience the pinnacle of North Fork living in this bespoke custom-built residence, thoughtfully designed to blend modern elegance with timeless craftsmanship. Nestled on a quiet property and offering seamless access to Southold Town beaches, vineyards, breweries, marinas, and North Fork restaurants, this exceptional property delivers

  Catherine Flood Compass Greater NY LLC

  480 Ackerly Pond Ln, Southold, NY 11971
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  /33

  $2,295,000

  • 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

  $679,999

  • 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

  $1,350,000

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

  1145 Bay Haven Ln, Southold, NY 11971

  Gracious and stylish in a coveted beach community, this beautifully renovated home offers a spacious open floor plan complemented by an office, den, and bonus room. The second floor features an expansive primary suite, separated from two additional bedrooms by a charming landing and nook. Additional full baths on the first and second floors. The large backyard has plenty of room for future

  Bridget Elkin Compass Greater NY LLC

  1145 Bay Haven Ln, 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 Open Sat 11AM - 1PM

  • 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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  /17

  $875,000

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  265 Custer Ave, Southold, NY 11971

  Beautiful solid built ranch home located on a quiet street with a park like half acre of property. This home has three nice size bedrooms, an open floor plan from the kitchen through the dining area, into the living room with a wood burning fireplace. There is a laundry room on the first floor with half bath, and a den. The brick patio offers a very nice private setting overlooking the back

  Kenneth Poliwoda Douglas Elliman Real Estate

  265 Custer Ave, Southold, NY 11971
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  /26

  $899,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  2575 Oaklawn Ave, Southold, NY 11971

  Beautiful , Comfortable home .Vacation, Retirement, Starter or even an investment.Close to town, School, public transportation, Banking and Shopping.Beach within biking or walking distance.Outdoor rurniture included.Sunsetter awning over patio,perfect dining area overlooking the pool.Beautiful Bridge over Jockey Creek, to make your moonlight strolls a Joy. Sunsets,sunrise, fishing

  Carol Bohn Carol A Bohn

  2575 Oaklawn Ave, Southold, NY 11971
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  /29

  $999,000

  • 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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  /12

  $2,295,000

  • 3 Beds
  • 3.5 Baths
  • 3,210 Sq Ft

  2215 Laurel Ave, Southold, NY 11971

  Welcome to the Laurel Collection by Marrcon, a showcase of modern luxury in the heart of Southold. Set on .80 acres, this newly built 3,200 SF one story home with soaring ceilings offers 3 bedrooms and 3.5 baths, blending timeless coastal design with top-tier craftsmanship. Large basement with egress and walkout can be finished to suit and extra bedrooms can be added if needed.The home’s

  Kristy Naddell Douglas Elliman Real Estate

  2215 Laurel Ave, 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
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  /47

  $2,850,000

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft

  54985 Middle Rd, Southold, NY 11971

  Southold, North Fork. This exceptional waterfront estate features a private beach on Long Island Sound and offers stunning sunsets that enhance its luxurious, resort-like atmosphere. Conveniently located between the vibrant maritime village of Greenport and the charming hamlet of Southold, .71 acres of level land designated as a FEMA safe zone (Zone X). With approximately 78 feet of bulkheaded

  Nicholas Planamento William Raveis New York LLC

  54985 Middle Rd, Southold, NY 11971
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  /36

  $2,850,000

  • 4 Beds
  • 5 Baths
  • 3,500 Sq Ft

  54985 County Road 48, Southold, NY 11971

  Southold, North Fork. This exceptional waterfront estate features a private beach on Long Island Sound and offers stunning sunsets that enhance its luxurious, resort-like atmosphere. Conveniently located between the vibrant maritime village of Greenport and the charming hamlet of Southold, .71 acres of level land designated as a FEMA safe zone (Zone X). With approximately 78 feet of bulkheaded

  Nicholas Planamento William Raveis (Mattituck)

  54985 County Road 48, Southold, NY 11971
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  /22

  $2,495,000

  • 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
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  /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
• 

  

  /17

  $779,000

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  570 N Bayview Rd, Southold, NY 11971

  Perfect opportunity for 1st time buyers, downsizers, or investors! This original-style 3-bedroom, 1-bath ranch, perfectly situated just steps from a beautiful Goose Creek beach in a highly desirable Southold location. With a spacious backyard and room for a pool, this home offers a fantastic opportunity to make it your own. Enjoy the convenience of single-level living, featuring a primary bedroom

  Ryan Springer Corcoran

  570 N Bayview Rd, Southold, NY 11971
• 

  

  /10

  $1,999,000

  • 4 Beds
  • 2.5 Baths
  • 3,800 Sq Ft

  25 Lighthouse Rd, Southold, NY 11971

  Every so often a truly exceptional home comes available – and this is one of those homes. On a quiet, historic Southold lane, the home sits at the end of a long driveway providing plenty of privacy. A short distance to both Long Island Sound and Peconic Bay beaches, restaurants, wineries, and shopping in both Southold and Greenport, this exquisitely designed custom-built Nantucket style home

  Janet Bidwell Douglas Elliman Real Estate

  25 Lighthouse Rd, Southold, NY 11971
• 

  

  /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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