$961,839Average Value$812Average Price per Sq Ft2Homes 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 is a relaxing place To Dock your boat and cruise around town.
NID537928 Hallock State Park Preserve, beside a vineyard 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
Video By
Alex Jacobsen
Interested in learning more about homes in this area?
Reach out to
Gene Gilyutin,
an experienced agent in this area.
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On average, homes in Jamesport, NY sell after 78 days on the market compared to the national average of 50 days. The median sale price for homes in Jamesport, NY over the last 12 months is $1,442,000, up 68% from the median home sale price over the previous 12 months.
Welcome to 264 Washington Avenue in the Heart of the Village of Jamesport on the North Fork of Long Island. Originally Built in 1883. Lovingly Inhabited and Maintained Over the Years. A Very Special Home and Property. All Updated Throughout While Keeping the Old-World Charm and Detailing. Custom Built-Ins, Moldings and Wood Flooring are Mostly Original. Stained Glass Accents. The Eat-In Kitchen
Modern Farmhouse with Private Beach Access & Heated Saltwater PoolNestled in the heart of South Jamesport, this exceptional new construction Modern Farmhouse offers the perfect North Fork lifestyle—where luxury meets laid-back coastal charm. This home provides exclusive access to pristine bay beaches, while being moments from the region’s top wineries, farm stands, and restaurants.This
Introducing a captivating waterfront property on the Peconic Bay in Jamesport boasting a large lot with over 100 feet of waterfront and direct beach access. This stunning waterfront property is a blank canvas waiting for your vision to transform it into an extraordinary masterpiece. Nestled in a prime location, the property boasts expansive views of the water, providing an ever-changing backdrop
This charming 2-bedroom, 2-bathroom ranch-style home has been tastefully renovated including a new roof, siding, and gutters. The interior is equally impressive with its modern, open floorplan.Step outside to find a private oasis complete with an inground pool, newly lined and with new energy efficient pump for your enjoyment. A gazebo provides a shaded retreat, while the expansive Trex deck and
Rare opportunity for year-round living in the coveted beach community of Aquebogue! This beautifully renovated single-story ranch features 3 bedrooms and 2 full baths, including a main-level primary suite with its own private bath. The open-concept great room offers soaring vaulted ceilings, perfect for relaxing or entertaining. Enjoy the comfort of central air conditioning and effortless
Experience South Jamesport Like Never Before with Bayfront living literally on your backyard doorstep. Step out into your garden and straight onto your own private beach — where the bay greets you from sunrise to sunset as boats drift by Like clockwork. This charming 3-bedroom, 2-bath cottage offers a front-row seat to waterfront living at its finest, nestled in one of the North Fork’s most
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 four bedrooms, two full baths, two half baths, and four spacious decks. Inside, enjoy a dramatic double-height living room with 20-foot ceilings, a gas-burning fireplace, and large European tilt-and-turn windows. The custom
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