WELCOME TO PARADISE. Commanding 2.38 private acres on the bay in Southold’s coveted Paradise Point, this remarkable waterfront estate possesses the cinematic North Fork p...
Listing courtesy of Listing Agent: Nicholas J. Planamento (Nicholas.Planamento@Raveis.com) from Listing Office: William Raveis New York LLC.
Welcome to 230 Jennings Road, a charming four-bedroom, 3 bath retreat ideally located on a cul-de-sac a few moments from downtown Southold. This inviting home features a ...
Listing courtesy of Listing Agent: Scott V. Bennett CBR (scott.bennett@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Private Southold Retreat on 2.18 Acres- Tucked away at the end of a private lane in desirable North Fork location, this special property offers the perfect balance of pri...
Listing courtesy of Listing Agent: Nancy J. Cervelli (nancycervelli@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Welcome to this corner residence at Founders Village, where easy, low-maintenance living meets the North Fork lifestyle. This 1,200-square-foot home offers 2 bedrooms, 2...
Listing courtesy of Listing Agent: Timothy O'Keefe (tokeefe@signaturepremier.com) from Listing Office: Signature Premier Properties.
Bring your vision to the waterfront in Southold. Set along a peaceful creek with direct water access, this fully gutted home offers a rare opportunity to create a custom ...
Listing courtesy of Listing Agent: James Bissett (absolutepropertycareli@gmail.com) from Listing Office: Hedgestone Commercial Rlty LLC.
A rare opportunity to create a custom North Fork residence in desirable Wildberry Fields. This .61-acre level, wooded parcel is situated on a private 9-lot country road a...
Listing courtesy of Listing Agent: Kim Pirreca (kpirreca@bhhslaffey.com) from Listing Office: BERKSHIRE HATHAWAY.
Welcome to 650 Greenfields Lane, an inviting ranch-style home on just shy an acre of property, nestled in the heart of Southold, NY. This charming residence offers three ...
Listing courtesy of Listing Agent: Barbara J. Poliwoda (barbara.poliwoda@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Wake up to the salt air at your new coastal compound, a rare waterfront opportunity for those seeking something truly different. Unapologetically distinctive, this mid-ce...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
Ideally Located Vacant Land. A Rare Opportunity to Create Your Own North Fork Retreat or Year-Round Home on Desirable Hyatt Road, a Quiet Setting Just Off Soundview Aven...
Listing courtesy of Listing Agent: Paul Loeb CBR (Paul.Loeb@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Welcome to 2600 Boisseau Avenue, the best deal in all of Southold. This well-maintained 3-bedroom, 1-bath ranch situated on a spacious .39-acre property in the heart of t...
Listing courtesy of Listing Agent: Zachary Scher CBR (zachscher@gmail.com) from Listing Office: Signature Premier Properties.
Unit 3C offers a rare opportunity to create something truly your own. This 2-bedroom, 2-bath condo is ready for a new vision and offers the perfect blank canvas for buyer...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
New Construction Luxury Southold Home underway set to be complete September 2026. Nestled in the prestigious Wildberry Fields, this new home blends coastal elegance with ...
Listing courtesy of Listing Agent: Shaun McQuilkin (quilks308@gmail.com) from Listing Office: Migrate Realty LLC.
Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an...
Listing courtesy of Listing Agent: Mariah J. Mills (mariahmills@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Welcome to 1025 Seawood Drive, where space, comfort, and the North Fork lifestyle come together beautifully! Experience the relaxed sophistication of North Fork living in...
Listing courtesy of Listing Agent: Clorinda F. Tagios (clorinda.tagios@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Set on five bucolic acres, this property perfectly captures the pastoral character that defines the region at its best. Mature trees frame the entrance, and split-rail fe...
Listing courtesy of Listing Agent: Bridget Elkin (bridget.elkin@compass.com) from Listing Office: Compass Greater NY LLC.
Location!Location!Location! Some homes are beautiful, others are truly one of a kind. 595 Greenfields Lane is both! Set on nearly 1 acre of meticulously landscaped prop...
Listing courtesy of Listing Agent: Giuseppe Pinello (giuseppepinello922@gmail.com) from Listing Office: Exit Realty Achieve.
The Laurel Collection by MarrCon is an exclusive enclave of eight newly constructed luxury homes ideally located in the heart of Southold. With only 3 residences remainin...
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
High-Visibility Commercial Land in Southold. Rare opportunity to acquire a highly visible vacant parcel along main road in Southold Town. Zoned "General Business", the pr...
Listing courtesy of Listing Agent: Melissa Principi (Melissa.Principi@elliman.com) from Listing Office: Douglas Elliman Real Estate.
North Fork living, refined. Welcome to Wildberry. Your newly constructed dream home, where design, light, and landscape converge - set against sweeping, vineyard views an...
Listing courtesy of Listing Agent: Melissa Principi (Melissa.Principi@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Welcome to North Fork living! Nestled in the desirable, private beach community of Laughing Water, this charming 3-bedroom, 2-bath Ranch sits on a 0.38-acre lot. Inside,...
Listing courtesy of Listing Agent: Patricia Shackel (patricia.shackel@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Life on the North Fork doesn't get better than this! Set along the Long Island Sound in one of Southold's most desirable locations, this chic waterfront escape offers swe...
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Gorgeous estate-like Nantucket shingle home to be completed early August with time to enjoy summer of 2026 and the Fall Harvest Season on the North Fork! Seller will con...
Listing courtesy of Listing Agent: Jeffrey R. Mead (Jeff.mead@corcoran.com) from Listing Office: Corcoran.
This charming cedar shingle Cape has been expanded and completely renovated, resulting in a home that exudes a timeless sense of place across three full floors of living ...
Listing courtesy of Listing Agent: Bridget Elkin (bridget.elkin@compass.com) from Listing Office: Compass Greater NY LLC.
The Dune Road of the North Fork. Do you love the beach? You know that feeling, tranquility and the sound of the waves off in the distance. Well, this is your chance to ca...
Listing courtesy of Listing Agent: Sheri Winter Parker (swp@corcoran.com) from Listing Office: Corcoran.
This breezy, open-concept home was made for hosting, with seamless flow and water views at every turn. Set on 101 feet of Corey Creek frontage, you get a brand-new bulkhe...
Listing courtesy of Listing Agent: Sheri Winter Parker (swp@corcoran.com) from Listing Office: Corcoran.
Rarely does a Southold waterfront property offer such a compelling combination of privacy, direct bay access, and expansive water views. Set on a protected inlet with a p...
Listing courtesy of Listing Agent: Andrea Parks (andrea.parks@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Located in one of the most sought-after locations on the North Fork sits this quintessential cedar shake farmhouse situated on 2 private acres! This home combines timeles...
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Classic Americana meets the North Fork lifestyle on Southold's Bayview Peninsula. Set on a level half acre backing to protected town owned land, this four bedroom, three ...
Listing courtesy of Listing Agent: Joshua Whalley (Joshua.Whalley@elliman.com) from Listing Office: Douglas Elliman Real Estate.
The Summer has never been sweeter in this coastal cottage right on the water. Peaceful breezes blow while you sit on the covered deck and watch the paddle boarders go by....
Listing courtesy of Listing Agent: Joseph Nina (joseph.nina@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Experience the best of North Fork living in this stunning new construction home offering beautiful water views and deeded beach access. Thoughtfully designed with modern ...
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
This turnkey opportunity in Southold, bordering beautiful Goose Creek, offers a private dock and is perfect for those seeking a North Fork beach house with a boater's lif...
Listing courtesy of Listing Agent: Alexis Meadows (Alexis.meadows@compass.com) from Listing Office: Compass Greater NY LLC.
Scandinavian Chic Waterfront Masterpiece with Panoramic Water Views | Southold Built in 2022 with exceptional craftsmanship and professionally curated interiors, this br...
Listing courtesy of Listing Agent: Laura M. Cochran (laura@lauracochran.com) from Listing Office: BERKSHIRE HATHAWAY.
Enter the Season and enjoy North Fork Serenity with the creek across the street to launch into what Southold has to offer. Discover the perfect blend of coastal charm ...
Listing courtesy of Listing Agent: Karyn Flores GRI SFR (karyn.flores@compass.com) from Listing Office: Compass Greater NY LLC.
It's time to put your money in Real Estate! Here's a property that is in prime condition and generates an income plus appreciation! Hamlet Business (HB) zoned property, i...
Listing courtesy of Listing Agent: Lee Beninati CBR (lee@beninatiassociates.com) from Listing Office: Beninati Associates.
Welcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beautiful beaches of Southold. Blending comfort, charm, and endless backyard potentia...
Listing courtesy of Listing Agent: Susan M. Orioli (susan.orioli@evrealestate.com) from Listing Office: Engel & Volkers North Fork.
Explore a prime location in Southold, perfect for a beach getaway, featuring the highly sought-after Kenneys Beach—one of the most picturesque beaches on the North Fork. ...
Listing courtesy of Listing Agent: Alexis Meadows (Alexis.meadows@compass.com) from Listing Office: Compass Greater NY LLC.
Welcome to 920 Cedar Point E in Southold, a spectacular 1.4-acre waterfront estate overlooking one of the most breathtaking stretches of the Peconic Bay, complete with a ...
Listing courtesy of Listing Agent: William C. McIntosh (williammcintosh@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Designer Modern Farm 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 qua...
Listing courtesy of Listing Agent: Arelis Olivieri (aolivieri@rininfo.com) from Listing Office: RIN.
Set on nearly four acres along one of the North Fork’s most coveted stretches of sandy bay beach, this is a rare opportunity to secure an exceptional waterfront property ...
Listing courtesy of Listing Agent: Bridget Elkin (bridget.elkin@compass.com) from Listing Office: Compass Greater NY LLC.
Quintessential North Fork Beach House!! Perched high above with breathtaking views of the Long Island Sound, this stunning custom-built home offers the perfect blend of ...
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Newly built and beautifully enhanced with many expensive upgrades since purchase, 1665 Glenn Road offers a turnkey North Fork retreat with thoughtful upgrades, elevated ...
Listing courtesy of Listing Agent: Kristy B. Naddell (kristy.naddell@elliman.com) from Listing Office: Douglas Elliman Real Estate.
A rare opportunity to create a truly bespoke North Fork lifestyle or equestrian estate in the heart of Southold’s celebrated agricultural landscape. Privately set across ...
Listing courtesy of Listing Agent: Andrea Parks (andrea.parks@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Calling all builders and investors! Beautiful 8.65 acres of cleared, leveled land in Southold Town. This parcel is zoned R-80, (2 Acre zoning) and has 250' of frontage on...
Listing courtesy of Listing Agent: Melissa Principi (Melissa.Principi@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Four-decade Southold institution for sale --- North Road Deli! Route 48 visibility, 12,000+ cars per day, fully equipped and ready to go. Deli, bagels, breakfast, lunch, ...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highpoint Meadows community of Southold. Set on a corner lot, this property offers a ...
Listing courtesy of Listing Agent: Scott V. Bennett CBR (scott.bennett@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Steeped in history and set on a 1.05-acre parcel in the heart of the North Fork, this circa-1663 residence presents a rare opportunity to preserve and reimagine one of So...
Listing courtesy of Listing Agent: Marco L. Maida (marco.maida@compass.com) from Listing Office: Compass Greater NY LLC.
The classic North Fork lifestyle you have been waiting for has finally arrived. Nestled in a quiet Southold neighborhood, 500 Summer Lane offers the rare opportunity to c...
Listing courtesy of Listing Agent: Catherine Flood (catherine.flood@compass.com) from Listing Office: Compass Greater NY LLC.
Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold—an extraordinary historic residence originally built in circa 1720 and impeccably m...
Listing courtesy of Listing Agent: Trish Bergin (tbergin@signaturepremier.com) from Listing Office: Signature Premier Properties.
Waterfront living designed for effortless coastal comfort. Ideally located just moments from one of Southold’s premier beaches, this updated 3-bedroom, 2-bath contemporar...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
.38-acre wooded level lot in a private and natural setting. Ideally located near Paradise Point, Cedar Beach, Southold shops, vineyards, farmstands and Greenport Brewery....
Listing courtesy of Listing Agent: Mariah J. Mills (mariahmills@danielgale.com) from Listing Office: Daniel Gale Sothebys Intl Rlty.
Discover a rare waterfront property where privacy, space, and breathtaking views come together on 6.5 gated acres. Spanning two single-and-separate lots, this refreshed 6...
Listing courtesy of Listing Agent: Roric Tobin (roric.tobin@compass.com) from Listing Office: Compass Greater NY LLC.
Waterfront Opportunity on Bay Home Road. Welcome to 535 Bay Home Road, a rare and flexible offering on one of the North Fork’s most coveted canal-front streets, located ...
Listing courtesy of Listing Agent: Kim Pirreca (kpirreca@bhhslaffey.com) from Listing Office: BERKSHIRE HATHAWAY.
For Sale - Zoned Hamlet Business Turnkey Commercial Property with Apartment - Prime Beach Route Location! Incredible opportunity to own a fully equipped commercial prope...
Listing courtesy of Listing Agent: Sheri Winter Parker (swp@corcoran.com) from Listing Office: Corcoran.
Southold Stunner- New Construction This one's a North Fork knockout. Set at the end of a quiet cul de sac on over 2 private acres, minutes from the sand, the house was bu...
Listing courtesy of Listing Agent: Sheri Winter Parker (swp@corcoran.com) from Listing Office: Corcoran.
2-Acre Private Oasis with Custom "To Be Built" Luxury Home - Excellent Location Near Town, Beaches & Vineyards! Discover the perfect blend of privacy, luxury and conveni...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
Extremely rare offering of 5.25 acres of undeveloped, wooded land in bucolic Paradise Point - the crown jewel of the charming hamlet of Southold. Once an scenic equestri...
Listing courtesy of Listing Agent: Kathleen M. Travers (Kathleen.Travers@elliman.com) from Listing Office: Douglas Elliman Real Estate.
Discover The Perfect Canvas For Your Dream Estate On This Expansive 2+ Acre Lot Offering The Ideal Balance Of Privacy And Convenience. Nestled In A Serene Setting, Yet Ju...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
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 set...
Listing courtesy of Listing Agent: Nicholas J. Planamento (Nicholas.Planamento@Raveis.com) from Listing Office: William Raveis New York LLC.
2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Comm...
Listing courtesy of Listing Agent: Colin McCarthy C2EX (colin.mccarthy@thomasjmccarthy.com) from Listing Office: Thomas J McCarthy Real Estate.
2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Com...
Listing courtesy of Listing Agent: Thomas J. McCarthy C2EX (tmccarthy.tmccarthy@gmail.com) from Listing Office: Thomas J McCarthy Real Estate.
Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . 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.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. This information is not verified for authenticity or accuracy and is not guaranteed and may not reflect all real estate activity in the market. ©2026 The Real Estate Board of New York, Inc. All rights reserved.
Southold homes for sale offer an unparalleled blend of maritime heritage, agricultural beauty, and sophisticated coastal living on Long Island's renowned North Fork. This historic town, established in 1640, combines centuries-old charm with modern amenities, creating an ideal destination for discerning homebuyers seeking waterfront tranquility just 90 minutes from Manhattan. Southold Long Island real estate encompasses everything from grand waterfront estates overlooking Peconic Bay to charming historic homes nestled among world-class vineyards.
See Southold ListingsSouthold homes for sale offer an unparalleled blend of maritime heritage, agricultural beauty, and sophisticated coastal living on Long Island's renowned North Fork. This historic town, established in 1640, combines centuries-old charm with modern amenities, creating an ideal destination for discerning homebuyers seeking waterfront tranquility just 90 minutes from Manhattan. Southold Long Island real estate encompasses everything from grand waterfront estates overlooking Peconic Bay to charming historic homes nestled among world-class vineyards.
The Southold real estate market features an impressive variety of properties to suit different lifestyles and budgets:
Whether you're seeking a primary residence, vacation retreat, or investment opportunity, Southold's diverse housing stock provides exceptional options in one of Long Island's most desirable locations.
The Southold Long Island real estate market benefits from the area's unique position as both a year-round community and a premier seasonal destination. Properties here command premium prices due to the town's limited inventory, strict zoning laws that preserve its rural character, and proximity to some of the East Coast's finest wineries. Waterfront properties, particularly those with deep-water access, represent some of the most sought-after real estate on Long Island, while historic properties in the village center offer charm and walkability that's increasingly rare in today's market.
When searching for Southold homes for sale, working with a local expert is crucial due to the area's unique considerations. Properties near the water require thorough inspections for flood zones and environmental regulations, while historic homes may have preservation restrictions that affect renovations. The seasonal nature of the North Fork means timing your purchase strategically can provide advantages, and understanding local zoning laws is essential, particularly for properties with agricultural or commercial potential.
Buyers should also consider the area's year-round vs. seasonal amenities, proximity to ferry services for travel to Connecticut, and the growing agritourism industry that continues to enhance property values. Many successful Southold property owners appreciate the town's commitment to preserving its agricultural heritage while embracing sustainable development.
When you choose Edify Real Estate for your Southold property search, you gain access to exclusive market insights and personalized service tailored to this unique North Fork community. Our team understands the nuances of Southold's diverse neighborhoods, from the waterfront enclaves of Pine Neck and Arshamomaque to the village center's historic district. We provide comprehensive guidance on everything from maritime rights and vineyard regulations to school districts and seasonal rental potential, ensuring you make informed decisions in this sophisticated market.
Stay ahead of the latest trends in Southold's real estate market in Long Island. Edify Real Estate provides the insight, data, and local expertise you need to navigate buying or selling in Southold with confidence. Contact us today for a personalized market report.
Please contact us for a personalized market report.
Explore exceptional real estate opportunities in Southold, Long Island and beyond with Edify Real Estate. Whether you're searching for your dream home, a modern condo, or preparing to sell your current property, our team brings sharp market insight, accurate valuations, and a refined negotiation strategy tailored to today's market.
Edify Real Estate brings unmatched expertise to the Southold Long Island real estate market, combining deep local knowledge with innovative marketing strategies to serve our North Fork clients. Our team understands that buying or selling property in Southold requires specialized insight into waterfront regulations, agricultural zoning, historic preservation guidelines, and the unique seasonal rhythms that define this prestigious community. We've built lasting relationships with local inspectors, attorneys, and contractors who understand the specific requirements of Southold properties, from antique farmhouses to modern waterfront estates.
Whether you're drawn to Southold for its world-class wineries, pristine beaches, or rich maritime history, Edify Real Estate provides the personalized attention and market expertise necessary to navigate this exclusive market successfully. Our comprehensive approach includes detailed neighborhood analyses, connection to trusted local professionals, and ongoing support that extends well beyond closing day. We're committed to helping you discover why Southold represents one of Long Island's most coveted addresses, where agricultural heritage meets coastal sophistication in perfect harmony.