Southold Land for Sale

**Discover Southold: A Charming Community with Exceptional Schools**

Nestled in the heart of Suffolk County, New York, Southold is a picturesque town that offers a perfect blend of serene landscapes, rich history, and a welcoming community spirit. Known for its stunning waterfront views and charming vineyards, Southold is not just a beautiful place to live; it’s also home to an outstanding school district that prioritizes educational excellence.

The Southold School District is renowned for its commitment to providing a high-quality education to students from kindergarten through high school. With a focus on academic achievement, personalized learning, and community involvement, the district fosters an environment where students can thrive. Small class sizes allow for individualized attention, ensuring that every child receives the support they need to excel. The dedicated faculty and staff are passionate about nurturing young minds, making Southold schools a top choice for families seeking a nurturing educational atmosphere.

For those looking to plant roots in this idyllic town, there is an array of land for sale that offers the perfect opportunity to build your dream home. Imagine waking up to the gentle sounds of nature, with the beauty of Southold’s landscapes just outside your door. Whether you’re envisioning a cozy cottage or a modern family abode, the available parcels of land provide the canvas for your vision.

With its exceptional schools, vibrant community, and stunning surroundings, Southold is an ideal place to call home. Explore the possibilities today and make your dream of living in this charming town a reality!

Newest Southold Land for Sale

$799,000

1031247 MLS

Build your North Fork dream in the heart of Southold. This exceptional 0.96-acre parcel is nestled among mature trees and surrounded by the scenic beauty of farmland and nature. This peaceful setting with easy access to Long Island Sound beaches, with breathtaking sunsets, acclaimed wineries, farm stands, marinas, and charming village amenities. Buyer is responsible for verifying all zoning, permits, and permitted uses with the Town of Southold. Artist Rendering- For Illustrative Purposes Only. Images are artistic interpretations and should not be relied upon as representations of existing conditions, future improvements, or development potential. All land use, zoning, and building approvals are subject to review by the Town of Southold and applicable agencies.

13260 Soundview Avenue, Southold

$650,000

1017614 MLS

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 capture it and create your safe haven, your wellness retreat. This is what the doctor ordered! Steps from Little Fish and Kenney's and McCabe Beaches. Hurry up, this one is going to go fast!

420 Lake Drive, Southold

$3,899,000

992332 MLS

Some estates are acquired. The exceptional are entrusted to the next chapter. Set within the North Fork’s most storied agricultural landscape, this extraordinary lifestyle farm unfolds across protected vineyard acreage and open sky - a private world defined by refinement, scale, and possibility. Being offered together are two parcels: 43.7 preserved acres, where development rights have been sold to safeguard the integrity of the land, and a separate 1.84-acre parcel with development rights intact. The result is both permanence and potential -protected beauty paired with the opportunity to create something entirely your own. Twenty-five acres of mature vines - Merlot, Cabernet Franc, Chardonnay, Sauvignon Blanc, and Pinot Blanc - stretch in disciplined rows across the landscape. Three acres of Dwarf Tall Spindle apples flourish alongside more than 200 peach and nectarine trees, complemented by berries and cultivated vegetables. The plantings are established. The soil is proven. The setting is timeless. A 3,600-square-foot Morton building with refrigeration anchors the farm’s operations, housing equipment that is included in the offering. The infrastructure is in place for continued vineyard production, expanded agricultural pursuits, or a refined farm-to-table vision executed at the highest level. The cleared and level 1.84-acre residential parcel invites the creation of a bespoke estate residence - perhaps with pool and terraces overlooking the vines - designed with intention, privacy, and architectural distinction. Here, mornings begin with light rising over the vineyard rows. Evenings settle into quiet horizon views. The landscape itself becomes both backdrop and legacy. Positioned within the North Fork’s celebrated wine and agricultural corridor - yet moments from acclaimed dining, marinas, beaches, and charming villages - this is a rare convergence of pastoral serenity and cultivated lifestyle. Impeccably maintained and deeply rooted, this offering is not merely land. It is a long-view investment in beauty, heritage, and possibility - awaiting its next discerning custodian.

46975 Main Road, Southold

$1,799,000

992553 MLS

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 Sound Avenue (North Road) and access from adjacent Leon Road. Sellers will not consider offers "subject to" any permits or approvals.

420 Leon Road, Southold

$499,000

931612 MLS

.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. This is a triangle shape lot with 258ft of frontage on N Bayview Rd and 178ft/182ft deep on each side. A rare opportunity to create your own coastal retreat in one of the North Fork’s most desirable neighborhoods. No preliminary work has been done with the DOH, Planning Board, or building dept at this time. Please don't walk property without your agent present.

11195 N Bayview Road, Southold

$2,250,000

914178 MLS

Build your dream home on this exceptional waterfront lot offering unobstructed, forever views and breathtaking sunsets over the pristine waters of the sound. With plans already in place, you can break ground on your custom home without delay. Nestled in one of the most sought-after locations on the North Fork, this property offers the perfect blend of privacy and convenience—just minutes from local vineyards, farm stands, dining, beaches, and marinas. Set in a serene and scenic location, this property offers direct access to miles of beach for peaceful walks along the shore, and is just moments from the tranquil Goldsmith Inlet, perfect for kayaking, paddleboarding, or simply enjoying nature at its finest. Whether you’re looking for a peaceful weekend retreat or a full-time coastal haven, this rare opportunity delivers it all. A one-of-a-kind acre-and-a-half property situated on a 40-foot-high bluff above the Long Island Sound, with clear views of the Connecticut shoreline and gorgeous northwest sunsets! Hidden off North Road (County Road 48) in Peconic, access is via a mile-long private road. This is the final piece of a six-lot subdivision. Delivering a powerful feeling of privacy, in a totally natural, very wooded setting! Truly a MUST SEE for the individual searching for solitude, privacy, and relaxation! Board of Health Permit is issued. Building Permit is issued...all are included!

4760 Blue Horizon Bluffs, Peconic

$4,900,000

896328 MLS

Step into the heart of North Fork wine country with the rare opportunity to own Osprey’s Dominion, an award-winning, fully operational winery and vineyard with a celebrated brand and loyal following. Perfectly positioned along the highly visible Main Road (Route 25) in Peconic, this landmark estate combines prime location, modern facilities, and limitless growth potential. Spanning over 50 acres, the property includes a 4.46-acre winery parcel with development rights intact and an additional 46.36 acres of vineyard with 34.5 acres under vine. The estate features approximately 19,500 square feet across three primary buildings, including a beautifully appointed tasting room with seating for more than sixty guests, cocktail capacity exceeding one hundred, and an expansive outdoor patio overlooking the vines. The winery itself houses a temperature-controlled production facility with fermentation cellar, bottling line, and laboratory, while the barrel and storage building provides over 8,000 square feet of climate-controlled space for aging and inventory. The setting is as breathtaking as it is functional, with panoramic vineyard views, manicured lawns, and a blend of rustic charm and refined elegance that makes the property a sought-after destination for wine enthusiasts, weddings, corporate events, and private celebrations. Outdoor features include a pergola-covered patio bar, gazebo, and multiple gathering spaces designed to enhance the guest experience. The sale includes the Osprey’s Dominion brand, extensive winemaking and agricultural equipment, and existing inventory, ensuring a seamless transition for a new owner. With a loyal customer base, a wine club of hundreds of members, and a certified sustainable harvest underway, the vineyard is positioned for continued success. This is a rare chance to acquire a turnkey winery in one of New York’s most vibrant wine regions. Whether you are an experienced vintner or an investor seeking a marquee North Fork asset, Osprey’s Dominion offers unmatched prestige, proven operations, and boundless potential.

44075 Route 25, Peconic

$1,499,000

827387 MLS

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 equestrian grazing meadow to an adjoining 33 acre estate, this land offers a tranquil, secluded location close to gorgeous Bay beaches. Borders preserved land. Just a few scenic miles to fine dining and cafes, tasting rooms & vineyards, marinas, golfing, boutique shopping, galleries, and more. A once in a lifetime opportunity to build your dream estate - perfect for an all inclusive equestrian facility. All with the utmost privacy in this amazing piece of paradise. Potential for 2 acre subdivision.

11200 N Bayview Road, Southold

$799,000

817145 MLS

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 Just Moments Away From The Vibrant Town Life; You’ll Be Close To Fine Dining, Shopping, And Everything The North Fork Has To Offer. This Unique Parcel Comes With Suffolk County Health Department Approval For An 8-Bedroom Conventional Septic System, (I/A NOT REQD.) Making It Ready For Your Grand Vision. Whether You're Looking To Build A Sprawling Family Estate, A Charming Vineyard Retreat, Or Anything In Between, The Possibilities Are Endless. Truly "Shovel Ready" Embrace The Tranquility Of Country Living With All The Benefits Of Being Near The Heart Of The North Fork’s Sought-After Attractions. Don’t Miss This Rare Opportunity To Create Your Own Slice Of Paradise!

1350 Hortons Lane, Southold

$1,600,000

L3530714 MLS

2 Acres Of Highly Desirable Hamlet Business Zoning. Subdividable Into Half Acre Lots Or Build Multiple Structures. Multiple Residential Units Possible Or Residential/Commercial Mix. Four Buildings Possible As Of Right. Excellent Route 25 Exposure & Great Location In Center Of The Hamlet! Commercial Listing MLS# 3530579

55975 Route 25, Southold

Start Your Search

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.