$1,049,861Average Value$639Average Price per Sq Ft8Homes For Sale
North Fork Long Island village with wineries and bay beaches
Situated at the foot of Long Island’s North Fork, Jamesport is a semi-rural, semi-suburban area with acres of fields dedicated to winemaking and a quaint downtown with popular owner-operated businesses. “While there are plenty of farms and vineyards, infrastructure is starting to grow because of sales,” says Carol Szynaka, a broker with Daniel Gale Sotheby’s, member of the prestigious Gold Circle of Excellence and a longtime resident of neighboring Cutchogue. “New residents want more restaurants, groceries—everything.” The area has grown significantly since the Covid-19 pandemic and yet Jamesport maintains its small-town charm with generationally rooted year-rounders welcoming in newcomers and seasonal residents.
Main Road in Jamesport has its historic district with its cute shops and restaurants.
Love Lane Kitchen in nearby Mattituck is wildly popular even on the sometimes sleepy North Fork.
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Pristine waterfronts on two sides
Peconic Bay and Long Island Sound coastlines are more subdued yet equally idyllic compared to the Atlantic Ocean beaches in the far pricier Hamptons, just to the south. Homes here are also much more modestly priced. Situated along the Sound, Iron Pier Beach has up-to-date facilities and a boat launch. Miles of pristine and sparsely built-up waterfront extend in either direction. Much of this land is in the Hallock State Park Preserve. On the other side of town, South Jamesport Beach and Park juts out into the bay and includes amenities like tennis courts and a marina. The distance between both waterbodies is only four miles. Great Peconic Bay Marina is another option for residents to dock their seacraft. Indian Island County Park in nearby Aquebogue is a 275-acre nature preserve with wetland trails, campsites, a playground and dog run. Indian Island Golf Course is also close by.
This Marina in Jamesport is a relaxing place to Dock your boat and cruise around town.
Hallock State Park Preserve, beside a vineyard in Jamesport, has extensive hiking to the sound.
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Main Road shopping and North Fork wine country
Jamesport’s Main Road is a segment of New York State Route 25 with a number of historic sites, independent stores and eateries including steak house Cliff’s Elbow Room, bakery The Treatery Long Island and brunch spot Main Road Biscuit Co. Homestead Farm was built in 1760 and operates a popular farmstand that sells eggs, produce and honey, among other goods. Long Island’s North Fork is famous for its thriving wine industry. Jamesport Vineyards is one of the area’s oldest wineries, but Jason’s Vineyard is arguably the most renowned. CUDDY'S is a locally beloved watering hole close to the bay. Jamesport Farm Brewery is situated near the Sound. The closest grocery stores are in Riverhead where there’s a Fine Fare and Gala Fresh Farms. There are also several big box stores located along Riverhead’s Old Country Road.
Creative combinations involving biscuits is the forte of Main Road Biscuit Co. in Jamesport.
The many rows of Vineyards Vines in Jamesport is a wonderful vineyard to visit.
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Postwar ranches and coastal colonials
Homes are mainly near the center of the village on Peconic Bay and in a cluster in the middle of the peninsula while a few grand estates can be found on the Long Island Sound or bayside. While ranch-style homes on quarter and third acre lots range from $500,000 to $650,000, midsized Brookfield colonial and Expanded Cape Cod homes sell for $700,000 to $900,000. Larger waterfront houses with pools and/or private beaches fetch between $900,000 and $2.5 million, depending on size and condition. Because the area is only a few feet above sea level, homes closest to the water might require flood insurance.
The most affordable style of home in Jamesport would most likely be the ranch or the cottage.
Waterfront homes in Jamesport are desired due to their views of the Peconic Bay or Sound.
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Riverhead Central School District
Young Jamesport residents get their education in the Riverhead Central School District. They can begin at Aquebogue Elementary School, which has a B rating from Niche and a favorable 10 to 1 student-teacher ratio. Riverhead Middle has a C-plus, while Riverhead Senior High has a B-plus. Both are situated in the same complex which is a 15-minute drive from downtown Jamesport.
Riverhead High School serves part of the North Fork of Long Island.
Aquebogue Elementary School in Riverhead offers a great curriculum for grades K-5 in Jamesport.
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Route 25 and the Long Island Rail Road
Jamesport is bisected by New York State Route 25, which gets residents to points further east and west, where it eventually connects to the Long Island Expressway, providing a straight shot to New York City. The 90-mile drive takes two and a half to three hours, depending on traffic, which tends to be heavier in the summer. The Long Island Rail Road has a station in Riverhead with a ride to Midtown Manhattan’s Penn Station taking two hours.
The Riverhead LIRR is the closest LIRR stop west of Jamesport.
Just a 10-15 minute drive from Jamesport is the LIE, the main artery to New York City.
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Written By
Adrian Madlener
Photography Contributed By
Joseph Popovich
Video By
Alex Jacobsen
Interested in learning more about homes in this area?
Reach out to
Mia Kaiser,
an experienced agent in this area.
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On average, homes in Jamesport, NY sell after 115 days on the market compared to the national average of 55 days. The median sale price for homes in Jamesport, NY over the last 12 months is $989,000, up 8% from the median home sale price over the previous 12 months.
Experience spectacular sunrise-to-sunset views of the Great Peconic Bay from this charming North Fork beach house, ideally situated on a quiet, pristine lane in the desirable hamlet of Laurel. Just moments from a private sandy beach, this inviting retreat offers the ultimate coastal lifestyle.The home features 3 bedrooms and 1 bath, along with a bright enclosed porch showcasing stunning water
Welcome to Sea Crest Estates, a new 13-home luxury community located around the corner from Jamesport’s Iron Pier Beach. This exceptional new-construction residence blends timeless architecture, designer finishes, and modern energy efficiency with a spacious open-concept floor plan. The first level features soaring ceilings, oversized Andersen 400 Series windows, and six-inch wide-plank white oak
Looking for the ultimate North Fork retreat near the beach? Look no further. This exceptional Colonial-style residence offers a spacious, sun-drenched floor plan designed for comfortable everyday living and effortless entertaining.Step inside to a bright, inviting interior with generous room sizes, abundant natural light, and an easy, flowing layout. The main level features an updated
This custom-built, modern home in Jamesport is close to Riverhead’s wineries, the Great Peconic Marina, and beaches. Ideal for year-round living or vacationing, it features five bedrooms, three full baths, two half baths, and four spacious decks. Inside, enjoy a dramatic double-height living room with 20-foot ceilings, a wood-burning fireplace, a gas-burning fireplace, and large European
Move-In Ready and Furnished, Ultra-Luxury, Brand-New Construction! Featuring an Exclusive Imported Woodtone Hardie Plank Exterior with an Unmatched, Gorgeous Two-tone Finish that Requires No Maintenance. Complete with a $150,000 Landscaping Package and Set Back 1,000 Feet from the Road, this 1.2-Acre Estate Lot Seamlessly Blends Natural Beauty and Privacy, Epitomizing the North Fork Aesthetic at
There are properties that offer more space, and then there are places that offer an entirely different way of living. Positioned in the heart of the North Fork, Starry Night Farms invites you to embrace a way of life that has become increasingly sought after yet is rarely found. Set on 6.3 exquisite acres, this remarkable equestrian estate is ideal for horse enthusiasts, hobby farmers, and those
Set just a block from the beach in the heart of charming South Jamesport, this circa 1837 Captain's house offers a rare combination of authentic history and modern comfort. Wide plank floors and period details remain intact and define the home's shared living spaces and four bedrooms. A tasteful 2007 renovation and addition brought the space up to date without disturbing its historical integrity.
Located in the hamlet of Jamesport on nearly an acre at the end of a quiet cul-de-sac, this 3-bedroom, 2-bath ranch offers a rare combination of privacy, usable outdoor space, and a desirable North Fork location. Being sold by its original owner, the oversized property provides plenty of room to enjoy the outdoors and is surrounded by the natural beauty the area is known for. A haven for
Nestled between green farm fields and the lapping waves of Flanders Bay, 56 Lagoon Court West is near to the best of everything the North Fork has to offer. Upon entering the home, you are greeted by double height ceilings hinting at the spaciousness of the rest of the home. Flowing through the formal dining room to the rear of the home, the brand new eat in kitchen and living room with gas
A rare chance to own a renowned 40-acre vineyard estate bordering pristine state parkland. This meticulously maintained farm features 16.3 acres of fully irrigated vinifera vines, including highly desirable varietals such as Cabernet Franc, Syrah, and Sauvignon Blanc. With 15-year-old vines at peak production, the property has a proven track record as a trusted fruit source for leading winemakers
Nestled atop a private, secluded Lane in the heart of Jamesport, this stunning contemporary home offers the perfect blend of space, privacy, and endless potential. Set on 1.57 beautifully landscaped and wooded acres, this 3-bedroom, 3.5-bath residence boasts approximately 3,100 square feet of thoughtfully designed living space. The home features an inviting eat-in kitchen, formal dining room, and
Experience spectacular sunrise-to-sunset views of the Great Peconic Bay from this charming North Fork beach house, ideally situated on a quiet, pristine lane in the desirable hamlet of Laurel. Just moments from a private sandy beach, this inviting retreat offers the ultimate coastal lifestyle.The home features 3 bedrooms and 1 bath, along with a bright enclosed porch showcasing stunning water
Welcome to this Oversized Gorgeous 6 bedroom, 4 full bathroom estate nestled on a private cul-de-sac Located in the exclusive SEA COVE ESTATES community of South Jamesport. Situated on nearly half an acre, this impressive 3,847 square foot home offers the perfect blend of luxury, comfort, and resort-style living. Designed for both everyday living and unforgettable entertaining, the backyard is a
Welcome to Sea Crest Estates, a new 13-home luxury community located around the corner from Jamesport’s Iron Pier Beach. This exceptional new-construction residence blends timeless architecture, designer finishes, and modern energy efficiency with a spacious open-concept floor plan. The first level features soaring ceilings, oversized Andersen 400 Series windows, and six-inch wide-plank white oak
The advertised rate of $14,761/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
The advertised rate of $14,761/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 24, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can
Off season winter rental from September 2026 to May 2027 $3500 a month plus utilities- Charming get away- bay beach at the end of the road private residential community- house has large and airy open floor plan. Fully furnished, kitchen / pots,pans and dishes. Great retreat ,four bedrooms, one and half baths, living room with fireplace, open floor plan with kitchen and dining area, laundry, fully
Bay Front Bargain, $5000 a month, five bedrooms, sugar sand beach, private yard with garden, on site parking- large eat in kitchen, living room with fireplace, fully equipped kitchen, laundry ( washing machine and clothes dryer) wood burning fireplace and great bay views ! Call for apppointment. No pets, no smoking- ideal winter get away or short term rental while you remodel or are between
Escape to your own piece of paradise in this stunning bayfront home in Jamesport, NY, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or
Brand New Modern Zen Bayfront, IG Pool, Right On The Beach!Like No Other. Stunner brand new construction Modern Beauty sited right on an open bay sandy Beach. One of the finest and extraordinary new build waterfront homes on the entire North Fork. The location will amaze you, your own sugar sand beach right at your door step to enjoy your favorite water sports, sunrise and sunsets. The deep
BAY BEACH BEAUTY! NOW FOR RENT YEAR ROUND OR SUMMER MONTHS!BAY BEACH RENTAL! 6 BR/3B. Now "Year Round" Rental or Summer Months, Fully Furnished - $6900 per month year round. Also June 2027 - at $25,000 and August to LD Tuesday 2027 - at $35.000. True North Fork Beauty and the Beach. Wow All Day and Night Open Views, sand in your toes right at your doorstep. Location in the private and
Welcome to this delightful retreat nestled in the heart of Jamesport. This charming home features three spacious bedrooms and two full bathrooms, offering comfort, flexibility, and the perfect setting for North Fork living.Available as a winter rental, the property offers a warm and inviting place to call home during the quieter months on the North Fork. The outdoor area is a true
Perfect summer rental on Great Peconic Bay, fully renovated with direct access to a sandy, protected cove with warm, calm waters. Just minutes from North Fork beaches, wineries, and top destinations, 23 Scallop Lane offers the ideal blend of waterfront luxury and easy summer living. Bring your boat — monthly marina slip availability may be available, with pricing dependent on vessel
Patricia Pascullo SalegnaDouglas Elliman Real Estate
Pristine and private post-modern home in Jamesport Now Available for the Off-Season from Now through April 30, 2026 for $9,000 Per Month. Summer 2026 Now Available for Booking! July for $35,000 or August for $40,000. Nestled away on a pin-drop quiet cul-de-sac and situated on a shy acre of meticulously landscaped property. All just around the corner from the coveted Iron Pier Beach and Park. This
July only $21,000! North Fork. Bay Front Charmer On The Beach at 15 Downs Boulevard in Jamesport. In coveted Fairhaven Private Community. Vintage cottage right on sandy bay beachfront. Summer 2026 June $14,000, July $21,000, Spring and Fall/Winter Rates Available. Lovely and well kept getaway full of olde time appeal. Spacious open plan with water views, new central air, new waterside patio and
A Great Beach House Now Available for Seasonal Rental from August 1 through May 31. October - May 31st Monthly for $4375 Per Month. August through Labor Day for $9500. Remainder of September for $7500. Enjoy the Large Galley Kitchen with All Stainless Appliances with Dining Area has Rear Deck Access and View. The L-Shaped Living Room with Vaulted Ceilings and Fireplace Boasts a Wall of Sliding
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