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Southold NY Real Estate & Homes for Sale

57 Properties Found

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$5,750,000

4105 Soundview Ave Southold, NY 11952

MLS: 887298 Photos
Beds:
3
Baths:
5.00
Sq.Ft.:
3,557
Status:
NEW LISTING
MLS#:
887298
Type:
Single Family
Lot size:
2.45 Acres
Year built:
1986
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Corcoran 631-765-1300
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ADDITIONAL INFORMATION

Perched on a 100-foot-high bluff with commanding views of Long Island Sound, this exceptional 3 + bedroom, 5 bath contemporary home is a rare fusion of design, privacy, and natural beauty. Originally designed and built in 1986 by architect Sanford Hanuer for his own use, the 3,348 sq ft residence was completely reimagined in 2011, preserving its architectural integrity while introducing luxurious modern updates. Set on 2.45 acres with 190 feet of private beachfront, the home is sited at an angle to capture uninterrupted water views from every room. Floor-to-ceiling windows, bluestone and wide ash plank flooring, and three fireplaces create a warm yet sophisticated interior. The Eggersmann-designed kitchen with butler’s pantry is a chef’s dream, and the home’s layout includes a loft and multiple decks and patios ideal for seamless indoor-outdoor living. The white-stained cedar exterior blends harmoniously with the surroundings. Below the home, a 50-foot pool with lanai and expansive deck is tucked 10 feet down the bluff, preserving both privacy and unobstructed views. Two + bedrooms are sectioned off to serve as a separate guest cottage. Every inch of this property has been thoughtfully designed to elevate the art of waterfront living — from floor to ceiling windows, white Italian marble bathrooms to golden-hour dinners on the patio overlooking the Sound. This is not to be missed!

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$888,000

625 Glenn Rd Southold, NY 11971

MLS: 886341 Photos

Open House:

Saturday, 7/12 11:00-1:00PM

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,610
Status:
NEW LISTING
MLS#:
886341
Type:
Single Family
Lot size:
0.46 Acres
Year built:
1967
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Signature Premier Properties 631-765-6000
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ADDITIONAL INFORMATION

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 spacious well lit center island, and modern finishes ideal for both everyday living and entertaining. Both bathrooms have been updated with a clean, pleasant aesthetic and the primary suite offers comfort, privacy, and ease for daily living. In 2023, a massive influx of cool arrived in the form of central air throughout the home. This was just in time to enjoy the sun-filled family room overlooking the yard. Step outside to relax under the custom pergola or beside the flowing water rock feature, perfect for entertaining or peaceful moments alone. This is a wonderful opportunity to enjoy modern living surrounded by the classic Southold charm. Living on Glenn Road offers places you in close proximity to all Southold has to offer.

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$1,249,999

4710 Old North Rd Southold, NY 11971

MLS: 885894 Photos

Open House:

Saturday, 7/12 11:00-1:00PM

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,400
Status:
NEW LISTING
MLS#:
885894
Type:
Single Family
Lot size:
3.04 Acres
Year built:
1978
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Signature Premier Properties 631-751-2111
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ADDITIONAL INFORMATION

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 saltwater pool. Step inside and feel the warmth of the charming interior—highlighted by gleaming hardwood floors, a cozy brick fireplace in the dining area, and abundant natural light throughout. The updated eat-in kitchen boasts granite countertops, stainless steel appliances, custom cabinetry, and plenty of space for entertaining or everyday cooking. The updated bathrooms feature modern tilework, stylish vanities, and sleek fixtures—offering a spa-like feel with practical function, including a beautifully renovated main bath with a glass-enclosed tub and marble-style finishes. Enjoy multiple living and gathering spaces, including a large sunroom with vaulted ceilings and exposed beams—ideal for relaxing with friends or curling up with a book. The generously sized bedrooms offer peaceful views and flexible layouts for family, guests, or a home office. Step outside to your own private oasis with a resort-style in-ground pool, expansive patio area for dining and lounging, and wide-open lawns perfect for games, gardening, or simply enjoying the tranquility of nature. Recent updates include Central Air, new heating system & hot water tank, 8 year old roof/siding/windows, water filter with reverse osmosis, and Mahogany porch. Whether you're seeking a year-round residence, the ultimate weekend escape, or potential multi-lot subdivision, this Southold gem delivers peace, privacy, and proximity to all the North Fork has to offer—beaches, vineyards, farm stands, and charming local shops just minutes away. Don't miss this unique opportunity to own a slice of paradise in Southold. Taxes only $9,216.84 before the STAR credit!

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$699,999

15 Youngs Ave Southold, NY 11952

MLS: 883793 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
800
Status:
Active
MLS#:
883793
Type:
Single Family
Lot size:
0.42 Acres
Year built:
1960
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Keller Williams Realty Elite 516-795-6900
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ADDITIONAL INFORMATION

Welcome to 15 Youngs Avenue, a charming 3-bedroom, 1-bathroom bungalow set on a spacious .42-acre lot in the picturesque North Fork town of Mattituck. This home features an inviting open concept layout that seamlessly connects the living, dining, and kitchen areas—perfect for both everyday living and effortless entertaining. Natural light pours through the windows, enhancing the home's bright, airy feel. The single-level design offers both comfort and flexibility, making it ideal for a variety of lifestyles. Step outside and enjoy a deep backyard with mature landscaping and a private inground pool—a great setting for relaxing weekends, summer gatherings, or quiet outdoor moments. Located close to beaches, farm stands, and renowned local vineyards, this property offers the best of North Fork living—whether as a full-time residence, weekend escape, or investment opportunity.

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$1,399,000

1465 Akerly Pond Ln Southold, NY 11971

MLS: 856096 Photos

Open House:

Saturday, 7/12 11:30-1:30PM

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Beds:
4
Baths:
3.00
Sq.Ft.:
3,226
Status:
Active
MLS#:
856096
Type:
Single Family
Year built:
2005
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

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 kitchen, 4 bedrooms, 2.5 baths, hardwood floors, mudroom, oversized 3 car garage, large, 11 foot deep basement with 3 egress windows ready to be finished. The lot is zoned for residential use and offers ample room for a custom pool, small vineyard, gardens, tennis, pickleball, etc. or garden retreat. Whether you're envisioning a weekend escape or a full-time residence, this substantial property provides the canvas to bring your dream home to life in one of Long Island’s most charming coastal communities. Brand New Boiler/Heating system.

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$2,650,000

1665 Glenn Rd Southold, NY 11971

MLS: 877793 Photos

Open House:

Monday, 7/14 12:00-1:30PM

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Beds:
4
Baths:
5.00
Sq.Ft.:
3,238
Status:
Active
MLS#:
877793
Type:
Single Family
Lot size:
0.52 Acres
Year built:
2024
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
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ADDITIONAL INFORMATION

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 rear porch. All spaces share a wall of windows and doors opening to the rear porch, enhancing the indoor/outdoor ease that is perfect for entertaining. The expansive kitchen features plentiful quartz countertops, custom tile backsplash, a huge island, and stainless Bosch and XO appliances. A dream for cooking and hosting. A first-floor primary bedroom with a stunning marble bathroom has doors and windows that open to the rear porch and face the lovely pool and yard. A large state-of-the art media room with a 98-inch screen and sound system. A laundry room and powder room complete the first floor. Spacious rooms bathed in natural light throughout the house. 4 zone Sonos built-in sound system. Wood floors throughout. and full basement with 9' ceilings and 3 egress windows. Upstairs are three ensuite bedrooms, an office nook, and a sitting room that opens to a spacious roof deck with water views. The half-acre property is beautifully landscaped with specimen plantings. New stone walkways. The covered rear porch offers shade and access to the heated, black onyx, 18' by 36' heated salt water swimming pool. New limestone hardscape surrounds the pool. Attached two car garage with electric vehicle car charger. Access to Southold Park District beaches. If you are looking for an extraordinary, new, move-in ready home perfectly situated for you to enjoy the North Fork experience, this house checks off all the boxes. Restaurants, golf, beaches, shopping, farm stands, wineries, breweries, boating... you name it. It's all right here.

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$1,195,000

205 Pine Ave Southold, NY 11971

MLS: 880690 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,280
Status:
Active
MLS#:
880690
Type:
Single Family
Lot size:
0.57 Acres
Year built:
1930
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-477-2220
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ADDITIONAL INFORMATION

Spectacular Goose Bay Estates home! This North Fork home is the sanctuary you have been looking for. Situated on a beautifully landscaped half acre with inground pool, outdoor dining area with an exquisite patio, perfect for grand entertaining or to enjoy complete solitude. The home offers an open floor plan complete with four bedrooms (one being a primary en suite), three full bathrooms, an updated kitchen, living room with stone wood burning fireplace, den, and a sunroom/office which overlooks the picturesque park like property. There is plenty of storage space in the attached two car garage and full basement. Additional amenities include central air conditioning, in ground sprinklers, a shed, new swing set, outdoor shower, a gazebo and generator hook up. A special bonus for the right buyer, the home can be sold fully furnished so you can enjoy your summer immediately. Amazing location with private beaches, near wineries, restaurants, shops and public transportation.

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$1,525,000

130 Sunset Ln Southold, NY 11944

MLS: 880117 Photos

Open House:

Sunday, 7/13 11:00-12:30PM

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Beds:
4
Baths:
5.00
Sq.Ft.:
3,200
Status:
Active
MLS#:
880117
Type:
Single Family
Lot size:
0.17 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

Timeless Charm Meets Modern Luxury – Stunning New Construction Colonial. Step into a seamless blend of turn-of-the-century elegance and contemporary comfort in this exquisite new construction Colonial. Designed with classic architectural details and high-end finishes throughout, this 4-bedroom, 4.5-bathroom residence offers over 2,700 square feet of thoughtfully crafted living space. From the moment you arrive, the crushed stone driveway and detached 1-car garage set the tone for the timeless appeal of this home. Inside, you’ll find gleaming hardwood floors throughout, complemented by custom millwork that adds warmth and character to every room. The open floor plan is anchored by a spacious Great Room with a stately fireplace, creating a cozy yet sophisticated gathering space. The gourmet kitchen opens effortlessly to the dining and living areas, ideal for entertaining. The main-level primary suite is a serene retreat, featuring a spa-like en-suite bathroom and ample closet space. A charming laundry/mudroom with custom red brick flooring offers both function and style. Downstairs, the fully finished basement expands the living space with a second fireplace, a wet bar, a full bathroom, and a dedicated media room—perfect for movie nights or game-day entertaining. Enjoy outdoor living on the private patio, ideal for morning coffee or summer barbecues. Every inch of this home reflects a perfect balance of traditional craftsmanship and modern convenience. A rare opportunity to own a new home with historic character in every detail that is in close proximity to Greenport Village, walk to 67 Steps Beach along the LI Sound and direct access to all that the North Fork has to offer! (Room for pool w/ ZBA approval)

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$2,450,000

20210 Soundview Ave Southold, NY 11971

MLS: 876405 Photos
Beds:
4
Baths:
6.00
Sq.Ft.:
4,671
Status:
Active
MLS#:
876405
Type:
Single Family
Year built:
1984
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
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ADDITIONAL INFORMATION

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 luxurious primary suites- one on the first floor and another on the second- along with a sprawling finished basement with plenty of natural light. Outside, enjoy a 25x50ft heated pool, IPE wood deck, and serene water views. There is also the option for a tennis court upon request, as well as the ability to customize finishes, including paint colors, bathroom materials, and appliances. Additional information: Exterior Features:Tennis Green ; Features: Insulated Doors; Interior Features: Guest Quarters

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$2,425,000

435 Maple Ln Southold, NY 11944

MLS: 872722 Photos

Open House:

Saturday, 7/12 1:00-3:00PM

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Beds:
4
Baths:
5.00
Sq.Ft.:
4,500
Status:
Active
MLS#:
872722
Type:
Single Family
Subdivision:
Cleaves Point
Lot size:
1.19 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: LI Probate Realty Inc 631-765-3000
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ADDITIONAL INFORMATION

Brand-New Coastal Retreat with Pool, Pool House & Deeded Bay Beach Rights. Introducing a stunning new construction that redefines North Fork luxury- offering 4,500 square feet of beautiful living space across three levels, including a full walkout basement. With 4 bedrooms, 5 bathrooms, and an effortless indoor-outdoor flow, this exceptional home is designed for both upscale entertaining and relaxed everyday living. Step outside into your own private resort, where a 20 x 40 inground pool takes center sage, surrounded by an expansive patio, a cozy fire pit, and lush landscaping. The 500 square-foot pool house adds an elevated touch, complete with a wet bar, half bath, covered patio, and an outdoor shower - perfect for rinsing off after a sun-soaked day at your Deeded Peconic Bay beach just moments away. Inside, high ceilings, wide-open living spaces, and elegant finishes create a warm and inviting atmosphere. A gourmet kitchen, spa-inspired bathrooms and generous bedrooms offer comfort and style at every turn. The walkout lower level provides even more flexibility - ideal for a home theater, gym, or guest suite. An attached two-car garage ensures convenience with plenty of storage for beach or golf gear. Located one minute from the beautiful Islands End golf course and 3 minutes to historic Greenport Village, this home blends coastal serenity with village convenience. Whether you're seeking a full-time residence or a luxe weekend escape, this property is a rare North Fork find that truly has it all.

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$2,630,000

4745 N Bayview Rd Southold, NY 11971

MLS: 869007 Photos
Beds:
4
Baths:
6.00
Sq.Ft.:
5,500
Status:
Active
MLS#:
869007
Type:
Single Family
Lot size:
1.03 Acres
Year built:
1965
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-298-0300
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ADDITIONAL INFORMATION

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 beautiful backdrop. The expansive grounds provide ample space for relaxation, recreation, and entertaining, ensuring everyone can find their favorite spot to unwind. This impressive home boasts four generously sized bedrooms and an abundance of bathrooms, including three full baths and three convenient half baths. The heart of the home, the kitchen, is a true architectural marvel featuring a dramatic two-story open ceiling that creates an airy and grand ambiance. A unique catwalk leads to an inspiring office space, perfect for remote work or creative pursuits. Beyond the main house, a spectacular in-ground heated pool awaits, promising endless enjoyment. Complementing the pool is a fully equipped pool house, complete with a stylish bar and beverage cooler – ideal for hosting unforgettable gatherings and making every day feel like a vacation. This exceptional property offers a rare combination of grandeur, comfort, and resort-style living, all within the privacy of your own expansive estate.

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$3,649,999

465 Ripplewater Ln Southold, NY 11971

MLS: 872443 Photos
Beds:
4
Baths:
6.00
Sq.Ft.:
6,366
Status:
Active
MLS#:
872443
Type:
Single Family
Subdivision:
Estates On West Creek
Lot size:
0.7 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Century 21 Albertson Realty 631-765-3800
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ADDITIONAL INFORMATION

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, and towering 20-ft established trees and shrubs, evoking a sense of timeless elegance and privacy. Exterior lighting gracefully illuminates the walkways and architectural details, while wall wash cove lighting on the masonry-covered porch casts a gentle glow over the pool area, inviting you to unwind in its serene ambiance. Step into the enclosed backyard to discover a sanctuary of relaxation and entertainment, complete with elegant blue stone paths, a spacious entertaining patio, and an in-pool lounge deck with dual umbrella stands. A mesmerizing masonry water feature adds a touch of sophistication, while the in-pool beverage bench ensures refreshments are always close at hand. The rear of the house has been thoughtfully designed with architectural elements that tell a captivating story from every angle, creating a visual masterpiece that complements the surrounding landscape. Approach the double entry wood doors to find an oversized masonry sitting porch, perfect for indulging in weekend morning coffee conversations or simply soaking in the tranquil surroundings. Inside, the home boasts luxurious amenities at every turn. Off the foyer, a large den with custom cabinetry provides a peaceful retreat, while the two-story living room serves as the heart of the home, anchored by a granite fireplace and bathed in natural light. The professional kitchen is a chef's dream, featuring a Kohler pre-rinse faucet, a 45 inch workstation sink with sound deadening technology, and custom lighting that highlights the island and cabinet details. The open floor plan seamlessly flows into the dining space, offering stunning views of the yard, pool, and covered porch. A mudroom with slate plank floors and shoe lockers in the custom designed cabinetry leads to the laundry room, complete with a deep stainless steel sink, slide out laundry baskets for each of the four bedrooms and a pet washing station. The main floor suite boasts an elegant walk-in closet and a luxury bath fitted with a Toto washlet toilet, a freestanding soaking tub, and a roll-in shower. Upstairs, each bedroom offers ceiling details and attached bathrooms, while the custom open staircase leads to a finished basement featuring a movie theater, a home office space, and a beverage center. The walk-out basement opens to a covered cocktail patio and bluestone path leading to the pool deck. Located in a waterfront community with direct access to Goose Creek sandy beach, this home offers the ultimate retreat for those seeking luxury and tranquility on the North Fork. Don't miss your chance to experience the epitome of North Fork living.

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$1,895,000

1260 Water Ter Southold, NY 11971

MLS: 868556 Photos

Open House:

Saturday, 7/12 10:30-12:30PM

More Open House Info >

Beds:
4
Baths:
3.00
Sq.Ft.:
3,110
Status:
Active
MLS#:
868556
Type:
Single Family
Lot size:
0.83 Acres
Year built:
2004
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-298-4130
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ADDITIONAL INFORMATION

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 ultimate in North Fork living. Inside, the heart of the home is a spacious eat-in kitchen with center island that opens to a formal dining area, ideal for gatherings of any size. The main level also features an adjacent family room with a gas fireplace, a dedicated home office, and a living room—each thoughtfully designed with soaring ceilings and detailed crown moldings for a touch of elegance throughout. The home features four spacious bedrooms and two and a half baths, including a generously sized primary en-suite that serves as a peaceful retreat. Three additional large bedrooms provide comfortable accommodations for family or guests. Enjoy effortless indoor-outdoor living with a classic wrap-around front porch to relax and sip lemonade and a large back deck that flows into the lush, private backyard oasis. Whether you're seeking a year-round residence or a seasonal escape, this exceptional property invites you to unpack and start enjoying all that the North Fork lifestyle has to offer.

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$2,750,000

2335 Minnehaha Blvd Southold, NY 11971

MLS: 868314 Photos
Beds:
4
Baths:
3.00
Sq.Ft.:
2,800
Status:
Active
MLS#:
868314
Type:
Single Family
Subdivision:
Laughing Waters
Lot size:
0.47 Acres
Year built:
2002
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

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’ boat. A waterside storage shed keeps all of your water toys, from paddle boards to kayaks, within easy reach and protected. Inside, the open floor plan connects a gourmet kitchen to a cozy living room with a built-in wet bar, all overlooking the water. Originally designed as a main floor Mastersuite, the home’s addition now serves as a golf simulator room, adding a playful twist to luxury living. Upstairs offers another Mastersuite option as well as 2 additional bedrooms, laundry, plenty of storage, and a full bath. For those moments when you seek tranquility, multiple decks, patios, and a private man-made beach on Corey Creek offer serene spots to unwind. Alternatively, the natural beach of the Laughing Waters homeowners association on the bay provides an idyllic setting for relaxation, where the sounds of the residents laughing epitomize the joyous community spirit. This property is not just a home; it's a lifestyle, where every day feels like summer camp. Perfect for those who cherish waterfront living, active recreation, and the simple joys of nature, 2335 & 2480 Minnehaha Blvd is a dream come true. Don't miss the chance to make this enchanting retreat your own and create memories that will last a lifetime.

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$799,000

50605 Route 25 Southold, NY 11971

MLS: 865793 Photos
Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
865793
Type:
Single Family
Lot size:
0.25 Acres
Year built:
1701
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-477-0013
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ADDITIONAL INFORMATION

A Hidden Gem of Serenity and Style. Tucked away in a private, storybook setting, this stunningly charming and meticulously crafted 1600s home is a true sanctuary. Surrounded by mature specimen trees and lush, professionally landscaped gardens, every inch of this light-filled retreat exudes warmth and character. Rich wood floors flow throughout the thoughtfully designed interior, which offers an eat-in kitchen ideal for culinary creativity, a cozy yet elegant living room, and a gracious dining area perfect for entertaining. Step outside to your own private haven, a spacious rear deck ideal for quiet mornings or evening gatherings, a flagstone patio, and a whimsical meditation tower offering peaceful seclusion. A separate studio/office cottage with its own bathroom adds the perfect touch of flexibility for guests, creative pursuits, or working from home in total privacy. This one-of-a-kind property is more than a home, it’s a lifestyle retreat waiting to be cherished.

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$890,000

2955 Hyatt Rd Southold, NY 11971

MLS: 843099 Photos
Beds:
3
Baths:
2.00
Sq.Ft.:
1,425
Status:
Active
MLS#:
843099
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1961
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
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ADDITIONAL INFORMATION

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 0.3 miles from McCabes Beach and a short drive to both downtown Southold and Greenport, this property provides both tranquility and easy access to local amenities. Full basement and attached 1 car garage.

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$1,950,000

480 Akerly Pond Ln Southold, NY 11971

MLS: 863916 Photos
Beds:
5
Baths:
6.00
Sq.Ft.:
3,350
Status:
Active
MLS#:
863916
Type:
Single Family
Lot size:
0.7 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY LLC 516-970-5133
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ADDITIONAL INFORMATION

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 luxury, privacy, and convenience for your best North Fork life! From the moment you step inside, the home makes a lasting impression. A covered front porch invites you into a light-filled foyer accented with shiplap details and 9-foot ceilings that continue throughout the home. Warm hardwood floors and refined finishes create an atmosphere of understated elegance. The main level features a spacious open-concept layout anchored by a gas fireplace and custom built-ins in the living room, seamlessly flowing into the chef’s kitchen—complete with a large center island, high-end appliances, and thoughtful design details perfect for entertaining. The first-floor primary suite offers a peaceful retreat with a walk-in closet and a luxurious en-suite bath featuring a freestanding soaking tub, heated flooring, and a built-in towel warmer. A mudroom with heated tile provides access to laundry, a half bath, and the attached two-car garage. Upstairs, you'll find a second primary suite with a walk-in closet and dual vanity bath, a junior suite, two additional bedrooms served by a beautiful full bath, and a second laundry room—ensuring convenience and flexibility for family and guests. The fully finished basement leaves no detail overlooked, featuring 9-foot ceilings, an egress window for natural light, a dedicated home office, a wine cellar, wet bar, and a full bathroom—ideal for both relaxation and entertaining. This basement provides a blank slate full of potential for its first owner. Step outside to the private backyard oasis, where a fiberglass 14' x 35' in-ground pool and bluestone patio offer the perfect setting for outdoor gatherings or quiet moments of reflection. With no neighbors to the rear, you’ll enjoy unmatched peace and privacy. A separate well-pump for the irrigation system supports the home’s thoughtful energy efficiency, inside and out. Whether you’re looking for luxury space, a peaceful retreat, or easy North Fork living, this property delivers it all with access to Town of Southold Beaches, vineyards, Greenport Harbor Brewery, marinas, and amazing restaurants a short distance away!

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$3,900,000

5615 Soundview Ave Southold, NY 11971

MLS: 863319 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
863319
Type:
Single Family
Lot size:
9.05 Acres
Year built:
1983
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-298-0300
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ADDITIONAL INFORMATION

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 platform. The existing structure provides an exceptional site to build the custom home you've always envisioned.

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$3,200,000

5615A Soundview Ave Southold, NY 11971

MLS: 863292 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
1,500
Status:
Active
MLS#:
863292
Type:
Single Family
Lot size:
7.22 Acres
Year built:
1983
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-298-0300
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ADDITIONAL INFORMATION

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 blueberries, cranberries, and beach plums, plus an osprey platform. The existing structure provides an exceptional site to build the custom home you've always envisioned. Need more acreage? The lot behind this is also available for purchase (1.84 Acres). Tax Map #: 1000-058.00-01.00-002.002

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$995,000

500 Meadow Ct Unit 28 Southold, NY 11971

MLS: 862942 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
3,735
Status:
Active
MLS#:
862942
Type:
Condo
Subdivision:
The Cove
Lot size:
0.25 Acres
Year built:
1994
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Daniel Gale Sothebys Intl Rlty 631-734-5439
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ADDITIONAL INFORMATION

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 concept living room and dining room share a wood burning fireplace and there is a balcony off the living room. The kitchen has granite counters and sliding glass doors to the deck and the backyard. Also on the first floor is a spacious primary bedroom suite with sliders to the deck and a large ensuite bathroom. The 2nd level has two more generous bedrooms, a library/media room, and full bath. There is storage galore in the finished basement with a separate laundry area, and a one-car garage. The entire community is presently in the process of being re-shingled with handsome grey Hardi-shingles and white trim. Beaches, wineries, farms, breweries, golf, & hamlet shopping, dining, and transportation just moments away! A perfect, maintenance-free Retreat!

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$2,295,000

2300 Glenn Rd Southold, NY 11971

MLS: 861882 Photos
Beds:
3
Baths:
3.00
Sq.Ft.:
2,500
Status:
Active
MLS#:
861882
Type:
Single Family
Lot size:
0.58 Acres
Year built:
1968
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Douglas Elliman Real Estate 631-354-8100
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ADDITIONAL INFORMATION

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 dream—complete with cherry cabinets, quartz countertops, high-end appliances, and limestone flooring. The large living room, anchored by a charming wood-burning fireplace, is perfect for relaxing or entertaining. Enjoy serene water views from multiple rooms and take full advantage of the private dock with floater—ideal for kayaking, boating, or simply soaking in the setting. A large waterfront patio provides plenty of room for entertaining. The primary suite includes an ensuite bath for added comfort. A full basement offers generous storage and expansion potential, and a whole-house generator ensures peace of mind. This rare Southold gem blends luxury, functionality, and waterfront living—ideal as a year-round residence or weekend escape.

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$2,100,000

655 N Sea Dr Southold, NY 11957

MLS: 828111 Photos
Beds:
4
Baths:
5.00
Sq.Ft.:
4,028
Status:
Active
MLS#:
828111
Type:
Single Family
Subdivision:
Orient By The Sea
Lot size:
0.57 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Century 21 Albertson Realty 631-765-3800
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ADDITIONAL INFORMATION

Here's a stunning new construction home, part of a thoughtfully designed series that blends quality craftsmanship with modern convenience. Wide oak floors set the stage for an open floor plan, where a professional kitchen with oversized island flows into a spacious dining area and beverage bar - perfect for beach house gatherings. The living room in anchored by a cozy fireplace with built in bookcases, creating an inviting space to gather after a day biking and experiencing the hiking trails. Designed for comfort, the main level features a primary suite, along with a mudroom, laundry room, and a covered back porch overlooking a beautifully contoured yard. Upstairs, an open sitting/office room adds another cozy retreat, accompanied by a secondary primary suite, two additional bedrooms and a full bath. Need even more space? The finished basement with an outside entrance offers a full bath, ideal for media room, gym or home office. Located in the private Orient By The Sea beach community, this home offers access to miles of beach, scenic picnic spot with grilling and tables and some of the best sunsets over the water on the North Fork. Adjacent to Orient Beach State Park , you'll have easy access to a playground, nature trails, a popular summer concession stand, even kayak rentals. Plus, the charter fishing boats, Orient Point Ferry with access to Foxwoods Casino and entertainment 20 minutes off the New London Ferry, entertainment options abound.

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$679,999

900 Cedar Dr Southold, NY 11971

MLS: 856542 Photos
Beds:
3
Baths:
1.00
Sq.Ft.:
1,100
Status:
Active
MLS#:
856542
Type:
Single Family
Lot size:
0.27 Acres
Year built:
1967
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: BERKSHIRE HATHAWAY 516-200-5700
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ADDITIONAL INFORMATION

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 close proximity to the Peconic Bay and the Long Island Sound. Year round living awaits.

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$2,699,000

285 Blue Marlin Dr Southold, NY 11971

MLS: 862752 Photos

Open House:

Saturday, 7/12 10:30-12:30PM

More Open House Info >

Beds:
4
Baths:
5.00
Sq.Ft.:
2,842
Status:
Active
MLS#:
862752
Type:
Single Family
Lot size:
0.46 Acres
Year built:
2025
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY LLC 516-517-4751
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ADDITIONAL INFORMATION

Incredible water views and part of a private beach association with mooring, 285 Blue Marlin is a 4 bedroom, 4.5 bath new construction colonial-style home that is nearly complete! With details epitomizing North Fork coastal living, this home is being constructed with high end finishes including Maibec treated cedar siding where the utmost in attention to detail is evident. A welcoming covered front porch is perfect for enjoying those sea breezes and water views. The first floor features 9' ceilings, an eat-in chef's kitchen with Thermadore appliances and an open layout that seamlessly connects the living room and dining room. There is also a family room with gas fireplace, mudroom, laundry room and powder room. The second floor includes 4 generously sized ensuite bedrooms and a deck with water views. A shy half-acre property with beautiful in-ground pool and attached two-car garage, complete this special home.

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$1,350,000

1145 Bay Haven Ln Southold, NY 11971

MLS: 858803 Photos

Open House:

Saturday, 7/12 12:00-1:30PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
3,000
Status:
Active
MLS#:
858803
Type:
Single Family
Lot size:
0.35 Acres
Year built:
1964
Contact:
Inquire About This Property, [email protected], 877-559-9633
A broker reciprocity listing Courtesy: Compass Greater NY LLC 631-251-8644
Request Info Save Property
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ADDITIONAL INFORMATION

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 development. Ideally situated just a few hundred yards from your association sandy bay beach and less than 3 miles to the shops and restaurants of Southold Hamlet. Don't miss the opportunity to visit this fantastic North Fork opportunity!

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Andrea D. Conner, License 10311208085, Xome Inc., License 10991227159, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

Listings courtesy of One Key MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 11/13/2024. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. Per New York legal requirement, click here for the Standard Operating Procedures. Copyright 2025, OneKey MLS, Inc. All Rights Reserved.


Southold Real Estate

Southold is located in New York. Southold, New York has a population of 23,571. Southold is less family-centric than the surrounding county with 21.26% of the households containing married families with children. The county average for households married with children is 32.94%.

The median household income in Southold, New York is $92,229. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Southold is 56.1 years.

Southold Weather

The average high temperature in July is 80.9 degrees, with an average low temperature in January of 23.6 degrees. The average rainfall is approximately 48 inches per year, with 27.3 inches of snow per year.

Southold Map

Southold Real Estate Market Conditions

  • Median sales price

    $805,000
    16.1%
    change since last quarter

  • # Active listings

    71
    30-day change

Southold Schools and Demographics

Education near Southold, NY

City County
High School Graduates 92.84 90.39
College Degree - 2 year 9.44 9.66
College Degree - 4 year 48.04 38.31
Graduate Degree 15.03 12.89
Expenditures per Student 30,219 30,219
Students per Teacher 12.3 12.3

Elementary Schools near Southold, NY

Grades Students P/T Ratio ZIP
Greenport Elementary School PK - 06 330 15 11944
Mattituck-Cutchogue Elementary School KG - 06 580 10.4 11935
New Suffolk School PK - 06 17 6.8 11956
Southold Elementary School KG - 06 403 11 11971

High Schools near Southold, NY

Grades Students P/T Ratio ZIP
Greenport High School 07 - 12 353 15.3 11944
Southold Junior-Senior High School 07 - 12 423 11.2 11971

Ungraded Schools near Southold, NY

Grades Students P/T Ratio ZIP
Shelter Island School PK - 12 221 6.8 11964

Demographics near Southold, NY

City County
Neighborhood Type Suburban
Population 23,571 1,522,998
Population Density 438 1,670
Median Age 56.1 41.7
People per Household 2.3 3
Median Household Income 92,229 111,660
Average Income per Capita 60,908 49,404

Real estate near Southold

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