$1,026,146Average Value$650Average 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
Deborah Pirro,
an experienced agent in this area.
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On average, homes in Jamesport, NY sell after 108 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 $965,000, up 14% from the median home sale price over the previous 12 months.
Welcome to 108 Vista Court, tucked away on a quiet cul-de-sac off Peconic Bay Boulevard, in Jamesport. This classic, move-in ready 3-bedroom, 2.5-bath center hall Colonial places you in the heart of North Fork living. You'll enjoy a sandy beach, tennis and pickleball courts, launching ramp and marina, and boating on Peconic Bay just a half mile down the road. Start your day with coffee on the
Bayfront haven in the heart of Jamesport, NY with stunning views and sandy bay beach. This home blends comfort and charm, with a stunning 50ft bulkhead complete with water and electric connectivity. Enjoy an open floor plan including living room with a wood-burning fireplace, dining area, and kitchen with ceramic flooring, new refrigerator, stove and washer/dryer. The home boasts a new,
This is the one you’ve been waiting for! Beautiful expanded 3-bedroom, 2 full bath ranch located on a private road with beach access just steps away to the PECONIC BAY. This light and bright home features wood floors, gas cooking/heat, and a wood-burning fireplace that adds warmth and charm. The expanded layout offers a spacious living room, dining room, and an eat-in kitchen, along with a
Move right in and start your North Fork dream today—this home is truly turn-key. Impeccably renovated and expanded in 2022 by a highly regarded architect in collaboration with Gabrielsen Builders, this contemporary Jamesport retreat offers effortless living in the heart of the North Fork. Set back over 130 feet on a lush, tree-filled .70-acre lot, the home combines modern comfort, thoughtful
New Construction,Modern Farmhouse with Private Beach Access And Heated Saltwater Pool. Nestled in the heart of South Jamesport, this exceptional New Construction 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
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
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. King size Colonial fit for a queen! 4 Bedrooms, 2.5 baths, hardwood floors. Spacious family room with potential for a first-floor en suite primary bedroom, living room, Eat in Kitchen with center island and dining area, and upstairs balcony. Full basement
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
Calling all investors! An opportunity to purchase one of the historic homes in Campground Circle, Jamesport, NY. These unique homes rarely come on the market. This property also has a cottage on the premises. Note* Sellers to stay in the house as tenants after the sale. Cottage is for owner's use. Historic and charming In the Storybook Setting known as Campground Circle. House has wraparound
Privacy Personified. Tucked nearly 1,000 feet from the road and enveloped by soaring trees and open farmland, this brand-new construction is finished, furnished, and ready for its first chapter. The CO is expected in May, meaning you could be sipping the first North Fork wines of spring while the summer crowd is still scrambling. Priced at $1,750,000 on an oversized estate lot, this is a
Modern, Sleek & Sophisticated, This Stunning One Of A Kind Custom Built Post Modern/Contemporary Is Perfectly Situated Tucked Away At The End Of A Beautiful Cul De Sac Community & Is A Perfect Second Home/Summer Getaway Or Year Round Residence With It's Close Proximity To Long Island Sound Iron Pier Beach & Bayfront South Jamesport Beach, Farmstands, Wineries, Championship Golf Courses, Quaint
Step into the timeless grandeur of Wisteria Court, one of South Jamesport's most admired historic estates. Wisteria Court stands proudly as an iconic 1913 Queen Anne Colonial set on a .75-acre double corner property in the heart of South Jamesport, just two blocks from the beautiful Great Peconic Bay. This grand residence offers rare legal two-family status and expansive living space, surrounded
Welcome to this delightful ranch nestled in the heart of Riverhead, NY. This charming residence, built in 1909, combines historical elegance with modern comforts, offering a unique living experience for all. Picture residing in this cozy home, brimming with character. It features two spacious bedrooms and a full bathroom, providing ample space for relaxation and rejuvenation. The home is set on a
Book your summer vacation on the North Fork! This beautifully updated ranch home is available as a seasonal rental and located in the heart of Jamesport Village. A great getaway for the summer months. Close to Bay & Sound Beaches and all the North Fork has to offer. Home features open floor plan for Living Room, Dining Room & Kitchen, has a Primary Bedroom with en-suite; 3 additional guest
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
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 size. June
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
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
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
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 $28,000, 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
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