New Suffolk charming 2-bedroom cottage invites you to spend the summer immersed in one of the North Fork's most sought-after and picturesque hamlets. Thoughtfully reimagined, this 2-bedroom, 2-bath home has been fully refreshed to blend timeless coastal charm with modern comfort--creating the perfect retreat to relax, unwind, and truly enjoy the season. Inside, you'll find a light-filled interior with an easy, flowing layout designed for summer living. The updated kitchen and living spaces feel both elevated and inviting, ideal for quiet mornings or hosting friends after a day by the water. Step outside and enjoy the peaceful setting--whether it's morning coffee or afternoons in the sun, or evenings under the stars. The home captures that effortless North Fork lifestyle where everything feels just a little slower, a little quieter, and a lot more enjoyable.Perfectly positioned just moments from New Suffolk's beloved Sound-front sandy beach--arguably one of the most serene and swimmable stretches on the North Fork--you're also a short distance to two of Long Island's finest dining and waterfront destinations: Legends Restaurant and Minnows. Spend your days at the beach, your afternoons exploring nearby vineyards and farm stands, and your evenings enjoying unforgettable sunset dining. This is summer on the North Fork at its best--effortless, elevated.Remaining Availability for the season JAugust 24th - September 14th still available Off Season Rate $3,500. Rental Permit # 0879
Listing by Kieran Collings• Douglas Elliman Real Estate
•Source:OneKey® MLS as Distributed by MLS Grid #980096
Contact 250 Oak Rd
Policies
ParkingOther
Type
Other
Features:Driveway
Amenities
In-unitAir Conditioning
Air Conditioning
Around 250 Oak Rd
Schools
Places
Transit
Choice and nearby schools may not serve this home. Please check the school district website to see all schools serving this home.
7/10
Mattituck Cutchogue Elementary School
Public, K-6 • Nearby • 1.9mi
6/10
Mattituck Junior Senior High School
Public, 7-12 • Nearby • 2.6mi
6/10
Southold Junior Senior High School
Public, 7-12 • Nearby • 4.8mi
Provided by GreatSchools
About North
Fork
North Fork, located between Riverhead and Greenport, is a coastal and agricultural Calverton neighborhood with working vineyards and wide-open bayfront views. The mood concentrates around the Sound Avenue corridor near the Calverton hamlet center, where farm stands, tasting rooms, and low-key eateries set a weekend rhythm. Architectural character leans to shingled cottages, ranch homes, and barn-like outbuildings tied to the area’s farming roots. Macari Vineyards, Jamesport Farm Brewery, and Harbes Family Farm act as local pillars for tastings, seasonal events, and market-style shopping. Peconic Bay and the Long Island Sound frame the landscape with beaches, marinas, and long, flat roads made for cycling. The pace stays rural, with small clusters of storefronts separated by fields and rows of vines.
Provided by Walk Score and Local Logic
Historical weather
New Suffolk, NY • 11956
Average low and high temperatures (°F)
35
25
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25
49
35
58
43
66
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78
62
83
69
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62
73
59
64
50
54
41
41
29
Jan
Feb
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Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 91° expected this year, 19 days in 30 years
8/10 Wind Factor
80% chance of strong winds in next 30 years
3/10 Air Factor
2 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Sun exposure
In this area, properties receive around 9 hours in
June and 4.6 hours in December, which is comparable to the
U.S. average for solar exposure.
This property is priced $12,292 above the rental estimate.
Asking rent
$14,500
Rental estimate
$2,208
Nearby comparable rentals
The Rental Estimate uses 0 recent nearby rental.
Sale and tax history for 250 Oak Rd
Sale History
Tax History
Date
Event
Price
ONEKEY #980096
Apr 4, 2026
Listed for Rent
$14,500
Public Records
Apr 21, 2025
Sold
$1,080,000
OneKey® MLS as Distributed by MLS Grid #810766
Mar 11, 2025
Sold
$1,080,000
Jan 22, 2025
Pending
—
Jan 7, 2025
Listed
$1,075,000
Experience the charm of this completely remodeled country cottage in New Suffolk, where comfort meets elegance. Boasting breathtaking year-round views of West Creek, this home features an inviting open Great Room with high ceilings, exposed rustic beams, and a cozy wood-burning fireplace, making it the perfect spot for relaxation and entertainment. The gourmet kitchen is fully remodeled and equipped with ample counter space, a spacious peninsula, a farmhouse sink, and a high-end gas range/oven. The adjacent dining area provides an ideal setting for gatherings and celebrations. On the main level, you will find two generously sized bedrooms adorned with beautiful hardwood floors throughout. The fully finished basement enhances the living space with a large media room, a second fireplace, a home office, and an additional full bathroom. Set on a generous 1/3 acre, this property features a stone patio off the rear of the house, offering a peaceful outdoor retreat with potential space for an in-ground pool. As a bonus, the new owner will enjoy convenient creek access to West Creek, as well as access to the stunning sugar sand beach within the New Suffolk community and other Park's District Beaches. Don’t miss your chance to own this exceptional home that perfectly blends modern living with the tranquility of country life!
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Listing provided courtesy of: Douglas Elliman Real Estate
Listing agent: Kieran Collings (9179725383)
Based on information submitted to the MLS GRID as of Sun Sep 13 2026. 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.
Last Updated: 2026-06-09T12:27:45.504Z
250 Oak Rd is a 1550 square foot property with 2 bedrooms and 2 bathrooms. We estimate that 250 Oak Rd would rent between $2,208 / mo.