Southold, NY Homes

/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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/12
$4,850 per month
- 2 Beds
- 2 Baths
- 1,100 Sq Ft
- House for Rent
775 Hickory Rd, Southold, NY 11971

Delightful North Fork Year-Round Rental located at 775 Hickory Road, Southold. Completely furnished, high end appliances, radiant heat, updated electric, and more. The large eat in kitchen is open to the dining & living area with a fireplace and sliding doors that lead you out to the expansive patios, where you will relax and enjoy the sea breeze. There is a master suite with full bath, guest

Jeanmarie Bay William Raveis New York LLC

775 Hickory Rd, Southold, NY 11971
$365,000 Sold Jun 17, 2025
- 805 Sq Ft
- $453/SF
- 72 Days On Market
- 2 Beds
- 1 Bath
- Built 1968
55075 Main Rd Unit 1, Southold, NY 11971

One-level living is at its finest in this meticulously maintained two-bedroom end unit co-op located in the heart of Southold with shopping and transportation at your fingertips. Eat-in kitchen, large living & dining area, full bath, hardwood flooring, washer & dryer, and covered front porch with seating area facing the pond. Common charges include heat, water, ground care, management, etc.

Scott Bennett Douglas Elliman Real Estate

55075 Main Rd Unit 1, Southold, NY 11971

Est $2,750,630 Not Listed For Sale
- 4 Beds
- 2.5 Baths
750 Cedar Point Dr E, Southold, NY 11971

750 Cedar Point Dr E, Southold, NY 11971

/50
$1,425,000 Open Sun 11AM - 1PM
- 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
/13
$12,000 per month
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- House for Rent
425 Lake Dr, Southold, NY 11971

Welcome to Paradise!! 425 Lake Drive is a magical lake-front beach home located in Southold on the North Fork. Adventure abounds on beautiful fresh-water Great Pond. Explore the lake on two kayaks, two canoes, take a swim, or just relax in the hammock and then enjoy the refreshing outdoor shower. This 3-bedroom, 1-bathroom home comes fully equipped and comfortably furnished. Dine al fresco on the

Robert Wilner Douglas Elliman Real Estate

425 Lake Dr, Southold, NY 11971
$1,375,000 Sold Jun 16, 2025
- 1,547 Sq Ft
- $889/SF
- 107 Days On Market
- 3 Beds
- 2 Baths
- Built 2016
5950 N Bayview Rd, Southold, NY 11971

Stunningly Renovated Home with Exceptional Design and Outdoor LivingEvery detail of this impeccable home has been thoughtfully curated by a published interior designer to create a space of unparalleled elegance and comfort. Recently renovated from top to bottom, this residence is a seamless blend of sophisticated design and modern luxury, offering the ultimate in style and functionality.

Lisa Gillooly Compass Greater NY LLC

5950 N Bayview Rd, Southold, NY 11971

Est $1,974,431 Not Listed For Sale
- 4 Beds
- 2 Baths
250 Midway Rd, Southold, NY 11971

250 Midway Rd, Southold, NY 11971

/25
$1,299,999
- 3 Beds
- 2 Baths
- 1,300 Sq Ft
58425 Route 48, Greenport, NY 11944

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

William Walters Daniel Gale Sothebys Intl Rlty

58425 Route 48, Greenport, NY 11944
/16
$4,000 per month
- 2 Beds
- 1 Bath
- 750 Sq Ft
- House for Rent
8515 Soundview Ave, Southold, NY 11971

Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quiet mornings with water views and spend your days kayaking, paddle boarding, or fishing right from your backyard. Barbecue and dine on the spacious deck with a sunset view of the lake. Ideally situated just moments from Kenny's

Nicole Fitzgerald Signature Premier Properties

8515 Soundview Ave, Southold, NY 11971
$650,000 Sold Jun 09, 2025
- 1,575 Sq Ft
- $413/SF
- 18 Days On Market
- 3 Beds
- 2 Baths
- Built 1957
1720 Carroll Ave, Peconic, NY 11958

Lovingly maintained ranch in the heart of the North Fork. Total three beds, two full baths with a full finished basement. The home is light and airy with plenty of natural light; the generous .65 acre lot has mature trees and perenial plantings. The property has plenty of room for future expansion and a pool. Around the block from Peconic Park and a short drive to beaches, farm stands, and

Bridget Elkin Compass Greater NY LLC

1720 Carroll Ave, Peconic, NY 11958

Est $1,421,853 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,600 Sq Ft
60 Water Terrace, Southold, NY 11971

60 Water Terrace, Southold, NY 11971

/36
$1,349,000
- 3 Beds
- 1.5 Baths
- 1,068 Sq Ft
633 Pine Neck Rd, Southold, NY 11971

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

Tom Uhlinger Douglas Elliman Real Estate

633 Pine Neck Rd, Southold, NY 11971
/13
$5,000 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- House for Rent
8415 Soundview Ave, Southold, NY 11971

Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and is just around the corner from Kenny's Beach and the popular Little Fish restaurant. Enjoy kayaking, paddle boarding, and fishing right from your backyard. Centrally located in the heart of the North Fork, you're perfectly

Nicole Fitzgerald Signature Premier Properties

8415 Soundview Ave, Southold, NY 11971
$525,000 Sold May 28, 2025
- 900 Sq Ft
- $583/SF
- 35 Days On Market
- 3 Beds
- 1 Bath
- Built 1961
900 Pine Ave, Southold, NY 11971

Charming Cottage with Water Views in Goose Bay Estates being sold AS IS.Discover the perfect blend of tranquility and opportunity with this quaint 3 bedroom, 1 bath cottage nestled in the serene Goose Bay Estates. Boasting peaceful water views and direct access to the beach, this property offers the ideal setting for launching kayaks, paddleboards, or simply enjoying the soothing

Diana Mellone Daniel Gale Sothebys Intl Rlty

900 Pine Ave, Southold, NY 11971

Est $1,034,770 Not Listed For Sale
- 3 Beds
- 2 Baths
505 Longview Ln, Southold, NY 11971

505 Longview Ln, Southold, NY 11971

/32
$1,400,000 Pending
- 3 Beds
- 2 Baths
- 2,000 Sq Ft
8095 Soundview Ave, Southold, NY 11971

Escape to serenity in this exceptional Southold retreat, perfectly perched on the shores of Great Pond. Offering breathtaking water views, this waterfront home is a nature lover’s dream. In mint condition and move-in ready, it has been designed with intention and built with uncompromising quality. Every detail—inside and out—has been thoughtfully crafted to maximize the peaceful, panoramic

Nicole Fitzgerald Signature Premier Properties

8095 Soundview Ave, Southold, NY 11971
/20
$3,500 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
475 Youngs Ave Unit c, Southold, NY 11971

Southold, North Fork: Discover the epitome of easy living at Unit C "Baldwin T. Payne" in Southold, North Fork. This condo-like residence, part of the North Fork Resident's Inn, offers a one-of-a-kind opportunity to embrace a modern lifestyle in a historic setting. The unit boasts a spacious layout with direct garden access, abundant natural light, and contemporary furnishings. With upscale

Nicholas Planamento William Raveis New York LLC

475 Youngs Ave Unit c, Southold, NY 11971
$599,000 Sold May 21, 2025
- 900 Sq Ft
- $666/SF
- 11 Days On Market
- 2 Beds
- 1 Bath
- Built 1959
45 Smith Dr N, Southold, NY 11971

This cute two-bedroom house in Goose Bay Estates has deeded beach rights and marina access. Bring vision and creativity to this investment opportunity or starter home. It will need renovations to reach its true potential! It has a sunroom with a wood-burning stove, a one-car garage, and a great corner property. Interior pics coming soon!

Kristy Naddell Douglas Elliman Real Estate

45 Smith Dr N, Southold, NY 11971

Est $915,291 Not Listed For Sale
- 4 Beds
- 2 Baths
1100 Rambler Rd, Southold, NY 11971

1100 Rambler Rd, Southold, NY 11971

/22
$949,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
6815 Soundview Ave, Southold, NY 11971

Embrace waterfront living in this delightful two-bedroom cottage, complete with a two-car garage. This is an outdoor enthusiast's dream, offering endless opportunities for kayaking, paddle boarding, and fishing right from your backyard. Enjoy serene water views of Great Pond from your spacious deck. As one of the earliest homes built on the pond, and bordering preserved land, this property

Donielle Cardinale Daniel Gale Sothebys Intl Rlty

6815 Soundview Ave, Southold, NY 11971
/39
$42,000 per month
- 6 Beds
- 5.5 Baths
- 6,600 Sq Ft
- House for Rent
57305 Route 48, Greenport, NY 11944

Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full

Zepur Diktas Compass Greater NY LLC

57305 Route 48, Greenport, NY 11944
$2,350,000 Sold May 12, 2025
- 288 Days On Market
- 3 Beds
- 3 Baths
- Built 1890
800 Lighthouse Rd, Southold, NY 11971

This quintessential vintage farmhouse is the epitome of old-world charm meets modern sophistication! Sited on 1.5 acres of park-like property and lovingly renovated with thoughtful additions including a heated saltwater gunite pool, electric pool cover, pool house with an outdoor fireplace, outdoor kitchen with a Gaucho grill and sink, a separate office studio, 3 bedrooms and 3 bathrooms. Plenty

Sheri Winter Parker Corcoran

800 Lighthouse Rd, Southold, NY 11971

Est $1,241,965 Not Listed For Sale
- 4 Beds
- 2 Baths
65 Pleasant Place, Southold, NY 11971

65 Pleasant Place, Southold, NY 11971

/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
/42
$7,500 per month
- 4 Beds
- 2 Baths
- 2,000 Sq Ft
- House for Rent
6710 Soundview Ave, Southold, NY 11971

Enjoy Southold this Summer at a Scandinavian Farm Ranch. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout. Incredible Natural Light in the Home. The Kitchen is Simple and Sleek Overlooking All. The Large

Rene Giacobbe Douglas Elliman Real Estate

6710 Soundview Ave, Southold, NY 11971
$1,720,000 Sold Apr 25, 2025
- 3,700 Sq Ft
- $465/SF
- 155 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2002
9390 N Bayview Rd, Southold, NY 11971

Spanning 3.82 acres, this generous home seamlessly blends luxury with comfort. The formal entry opens to an oversized great room, where a soaring ceiling and a striking stone fireplace are complemented by a wet bar-perfect for entertaining. The kitchen, updated in 2023 with sleek stainless-steel appliances, counters, and backsplash, is a chef's dream. Two well-sized bedrooms share a large full

Mariah Mills Daniel Gale Sothebys Intl Rlty

9390 N Bayview Rd, Southold, NY 11971

/2
Est $727,529 Not Listed For Sale
- 3 Beds
- 2 Baths
1430 Bay Haven Ln, Southold, NY 11971

1430 Bay Haven Ln, Southold, NY 11971

/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
/30
$10,000 per month
- 3 Beds
- 1.5 Baths
- 1,578 Sq Ft
- House for Rent
425 Old Shipyard Ln, Southold, NY 11971

Southold-Enjoy the North Fork in this adorable cottage. Located in Founder's Landing Southold beach community. Three bedrooms, living room, kitchen with dining area and sunroom overlooking yard and pool. This charming home has everything you need for a great summer getaway. Close to community beach and Park. Close to town, restaurants, shopping, The giving room yoga and juice bar, Southold fish

Amy Kirincic The Agency Northshore NY

425 Old Shipyard Ln, Southold, NY 11971
$520,000 Sold Apr 14, 2025
- 1,100 Sq Ft
- $473/SF
- 22 Days On Market
- 2 Beds
- 2 Baths
- Built 1985
2555 Youngs Ave Unit 4B, Southold, NY 11971

Welcome to Founders Village, a charming 55+ senior community that offers the perfect blend of comfort and convenience. This delightful space offers oak floors throughout, an expansive living room with soaring ceilings, and a cozy wood-burning fireplace that invites relaxed evenings at home. Step outside to your own landscaped patio- a serene retreat designed for peaceful seclusion with

Jerry Cibulski Century 21 Albertson Realty

2555 Youngs Ave Unit 4B, Southold, NY 11971

Est $792,955 Not Listed For Sale
- 2 Beds
- 1 Bath
580 Jacobs Ln, Southold, NY 11971

580 Jacobs Ln, Southold, NY 11971

/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
/26
$22,000 per month
- 5 Beds
- 2 Baths
- 3,000 Sq Ft
- House for Rent
45 Budds Pond Rd, Southold, NY 11971

Available for two week rentals! Escape to your dream Southold summer in this spacious 5-bedroom, 2-bathroom home boasting an in-ground heated pool and convenient dock space. Bathed in natural light and surrounded by lush gardens, this home offers ample space for entertaining and ensuring guests feel right at home. Spend sunny afternoons basking by the pool under the awning or take a leisurely

Mackenzie Needham Daniel Gale Sothebys Intl Rlty

45 Budds Pond Rd, Southold, NY 11971
$660,000 Sold Apr 07, 2025
- 1,600 Sq Ft
- $412/SF
- 286 Days On Market
- 3 Beds
- 2 Baths
- Built 1960
700 Bayview Ave, Southold, NY 11971

Welcome to 700 Bayview Ave, in Southold. This charming retreat is across the street from Hashamomuck Marine Waterway, inlet to Peconic Bay. Featuring a bright and airy layout with tons of potential and charm. 3 bedrooms, 2 bathrooms. Newer hardwood floors on 2nd floor. Full finished tiled basement. Large yard with newer PVC fence and shed. Side and front trex steps recently installed. Centrally

Cynthia Dgheim Century 21 Albertson Realty

700 Bayview Ave, Southold, NY 11971

Est $1,175,578 Not Listed For Sale
- 3 Beds
- 2.5 Baths
1715 Minnehaha Blvd, Southold, NY 11971

1715 Minnehaha Blvd, Southold, NY 11971

/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
/23
$25,000 per month
- 5 Beds
- 7 Baths
- 3,500 Sq Ft
- House for Rent
495 N Parish Dr, Southold, NY 11971

Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just moments

Nicholas Planamento William Raveis New York LLC

495 N Parish Dr, Southold, NY 11971
$760,000 Sold Apr 03, 2025
- 1,000 Sq Ft
- $760/SF
- 16 Days On Market
- 2 Beds
- 1 Bath
- Built 1938
805 Oak Ave, Southold, NY 11971

A delightful coastal cottage nestled in the heart of Southold, this year-round residence offers a unique blend of comfort, charm, and potential, all wrapped up in an inviting package.Step inside to discover two cozy bedrooms, beamed ceilings, hardwood floors, dining area with a charming window seat and a warm and inviting fireplace all add to the home's cozy ambiance.But the allure of

Rita Rooney Douglas Elliman Real Estate

805 Oak Ave, Southold, NY 11971

Est $3,122,727 Not Listed For Sale
- 3 Beds
- 4 Baths
- 3,300 Sq Ft
1480 Old Wood Path, Southold, NY 11971

1480 Old Wood Path, Southold, NY 11971

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