$1,020,340Average Value$639Average Price per Sq Ft6Homes 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
Amy Satchell,
an experienced agent in this area.
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On average, homes in Jamesport, NY sell after 110 days on the market compared to the national average of 54 days. The median sale price for homes in Jamesport, NY over the last 12 months is $989,000, up 21% from the median home sale price over the previous 12 months.
Spacious Mattituck Colonial In the Heart of the North Fork, Featuring 4 Bedrooms and 2.5 Bathrooms, built in 1999, Full basement-725 sq.ft. with separate entrance, large property, shy 1 acre lot(.91)., room for pool and tennis/recreation area. Close to local beaches, schools, local farm produce/products, transportation bus & LIRR.
Welcome to this secluded and bright home nestled next to a beautiful apple orchard in the heart of Jamesport Hamlet. This elegant home boasts 3 bedrooms and 2 bathrooms with an open floor plan. Forced air climate control throughout the home with vaulted ceilings and skylights for natural light, large parking garage for many cars and an electric car charging station! This property features beach
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
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
Right where you want to be! Enjoy living within a short walk to the Jamesport sugar sand beach! Boat ramp & tennis courts. Just minutes away. 4 Bedrooms, 2.5 baths, hardwood floors. Spacious family room, living room, Eat in Kitchen with center island and dining area, and upstairs balcony. Full basement and attached 2 car garage. Wine country calling! Experience the beautiful North Fork!
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
Welcome to 8 Railroad Avenue, a haven of comfort and convenience nestled in the heart of Jamesport. This 2-bedroom, 2-bathroom residence boasts a new roof, siding, and gutters, promising a worry-free living experience. The secluded backyard is a personal oasis, complete with a pool featuring a new lining and energy-efficient pump. A gazebo and Trex deck offer the perfect spots for relaxation,
Discover 32.4 acres of prime land, perfect for agricultural pursuits and equestrian enthusiasts. This property features a 10,000 square foot indoor riding arena and is fully fenced for horses. Zoned RLC and APZ, it offers versatile opportunities for development. Ideally situated in the heart of the North Fork of Long Island, it is conveniently close to beautiful beaches and renowned vineyards.
Brand new and just completed, this ultra-custom turnkey masterpiece represents the quintessential North Fork lifestyle. A masterfully crafted estate home uniting rustic authenticity with modern ultra-luxury on an exceptionally secluded, oversized mega lot. Tucked back 800 ft. from the road and immersed in nature with a canopy of mature trees and native plants, you will feel world’s away – yet you
Beautiful flat usable farmland with southern exposure and deer fencing. Currently used as a nursery. Temporary greenhouses on property. This parcel includes 2 deeds. One is a 2 plus acre building lot adjacent to the 8.9-acre farm. Grow your own food, live the dream! Also good for boutique vineyard, field crops, or nursery. Perfect for the Equestrian who wants their own barn and facility. Privacy
Welcome to this luxurious new construction in the heart of South Jamesport, just half a mile from the beach and 200 yards from deep-water marina. Located in an exceptional neighborhood, this beautifully crafted home features 3 spacious bedrooms and 2.5 elegant bathrooms, including a stunning primary ensuite with a marble bathroom, double vanity, and large custom closets. Designed with an
VINEYARD VIEWS!Strategically positioned at the end of a picturesque vineyard and surrounded by preserved land to the North and East, this vacant residential land is an exceptional opportunity to build your dream home. This expansive 1.6-acre parcel, offers a rare combination of tranquility and beauty. The property boasts a generous 160-foot lot frontage, providing ample space for your
If you want to be directly on a sandy Peconic Bay beach, this is the one you’ve been waiting for. Step out to the waterfront deck overlooking the sandy beach and let the day do its thing, coffee at sunrise, grilling at sunset, and sweeping bay views in between. After a beach day, rinse off in the outdoor shower and head right back outside (because it’s summer). You’re also adjacent to South
Welcome to 335 Herricks Lane, Unit B, a beautifully renovated gem nestled in the heart of Jamesport, NY. This property is a testament to high-quality living, offering two spacious bedrooms and two well-appointed bathrooms, with radiant heat flooring in the living room, ensuring ample space for all residents.The property's key feature is the expansive farmland views from every room, providing
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
Discover the rare opportunity to live year-round in the heart of South Jamesport, on one of the largest lots in the area—an expansive 1.1 acres of open yard space. Enjoy waterviews right from your front yard, with the bay beach just five houses away and multiple access points to the shoreline only a stone’s throw from your door. Perfectly positioned for convenience and lifestyle, this home is
Idyllic One Bedroom Furnished Cottage In Historic Jamesport Campground Circle. Nature lover's or artist's retreat. Enclosed Porch, Kitchen, Dining Area, Living Room, Bedroom, Bathroom . Fully insulated. All good appliances including stackable washer/ dryer. A quiet space less than 1/2 half mile from town and/or beach. Enjoy all the North Fork has to offer: Beaches, Wineries, Restaurants, Marinas,
A Great Beach House Now Available for Seasonal Rental from August 1 through May 31. October - May 31st Monthly for $4500 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
Escape to this serene 3-bedroom cottage in Historic South Jamesport beach community. The beautiful interior features 2 full beds, 1 twin bed, and a cozy living room, perfect for unwinding after a day of exploring. Cottage amenities include WiFi, Cable TV, a washer and dryer, AC or heat, all your needs are covered. Relax on the comfortable porch or outdoor patio with propane barbeque. Steps to
North Fork. Beauty and the Beach at 11 Beach Road, Jamesport. Open Bayfront Right On The Bay Beach! Private "Fairhaven" Community, stunner mid century modern. Available Winter Months at $6,900 per, August thru Labor Day Tues the 8th $35,000. 5 weeks this year! Sand in your toes right out your door, full walls of glass, gorgeous open bay views from every room. Sparkling hot tub spa for 6 added to
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 only July offered $29,500, September $12,000, Fall/Winter months at only $6900 per (with 2 month minimum). Lovely and well kept getaway full of olde time appeal. Spacious open plan with water views, new central air, new
Relax and unwind at this open-concept waterfront home. Situated in a private neighborhood with views of Peconic Bay from most of the rooms. The home boasts 2 new decks, and an updated new master bath. Getaway by yourself, or with friends and family. First-floor bedroom and bath. Four beds, 3 baths, in total. Updated master bath with spa-like -Jacuzzi bathtub, rainfall shower head to relax the
Bay Front Bargain, $3500 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
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