Welcome to The Waverly at Fleet’s Neckone of Cutchogue’s most coveted coastal enclaveswhere 275 Pinewood Road offers an exceptional opportunity to own in a high-value North Fork location with private beach rights to one of the finest stretches of shoreline on the North Fork. This captivating 6-bedroom, 4-bath residence, featuring new town water and a National Grid gas hookup, is ideally positioned on a beautiful property with a building permit already secured for a 16x32" heated saltwater pool. A highly desirable layout includes a private ground-floor primary bedroom suite complete with a full bathroom and a spacious den. An additional 5 bedrooms provide ample space for entertaining. The open floor plan features a spacious living room with a wood-burning fireplace, hardwood floors, and a formal dining room. Modern kitchen features new white shaker cabinets, quartz countertops and stainless steel appliances. A sun porch sitting room has sliding glass doors leading to the deck. A separate laundry room includes a new washer and dryer. An Attached garage and large basement offer room for expansion. Set in a premier neighborhood known for its coastal lifestyle, this home is just moments from pristine beaches, vineyards, farm stands, and everything that makes the North Fork special. Whether you’re seeking a year-round residence, weekend retreat, or investment in a sought-after beach community, this property delivers. A rare opportunity to secure your place in Fleet’s Neckwhere lifestyle, location, and long-term value converge. Swim, kayak, and keep a motor boat at the Shagwong Marina all walking distance from your home. A brand new playground at Pequash Beach. Just 80 miles from New York City, and the Hampton Jitney stops right in Cutchogue. Mint condition home, photos and furniture in rooms are real - a great home to tour and make your own.
Single-familyProperty Type
1961Year Built
0.33 acresLot Size
$717Price/Sq.Ft.
$8/moHOA Dues
1 garage spacesParking
Listing by Christine Peddy• Engel & Volkers 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
Offer insights
275 Pinewood Rd · $1,799,000
$1.81M and above
75% chance or better to win
Why $1.81M+ is a strong offer
DAYS ON MARKET
37 days
The average home goes pending in 26 days.
SALE-TO-LIST
103.1%
Most homes are selling 3% above list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
First-floor bedroom
First-floor full bathroom
Eat-in kitchen
Formal dining room
Kitchen island
Open floor plan
Primary bathroom
Master suite on main level
Washer/dryer hookup
Storm door(s)
Deck
Bedrooms
Two-level home (bedroom count not provided)
Bathrooms
2 full bathrooms
2 half bathrooms
Kitchen
Dishwasher
Gas range
Oven
Refrigerator
Stainless steel appliances
Laundry & utility
Washer
Dryer
Washer/dryer hookup
Heating & cooling
Central air conditioning
Forced air heating
Oil heating
Exterior features
Boat slip
Mailbox
Rain gutters
Back yard fencing
Deck
Home design
Single family residence
Updated/remodeled
Two levels
Parking
Driveway
Garage (1 garage space)
Total parking for 4 vehicles
No carport
Construction
Frame construction
Concrete perimeter foundation
Utilities
PSEG electric
Cesspool or septic tank
Cable available
Electricity available
Natural gas connected
Water available
HOA & community
Has association (Fleet's Neck Property Owners Association)
Association amenities include park and powered boats allowed
Association fee $95 annually (fee includes: Other)
Discover this inviting five-bedroom colonial located in the highly desirable Fleets Neck beach community of Cutchogue. Designed with comfort and space in mind, this home is ideal for hosting extended family and guests. The first floor offers a warm and welcoming layout, featuring a living room with a cozy wood-burning fireplace that opens to a bright family room with sliders leading to the rear deck. The spacious first-floor primary suite includes its own sitting area or office, providing a private retreat. An open-concept kitchen with a charming breakfast nook, a formal dining room, and a powder room complete the main level. Upstairs, you’ll find four generous guest bedrooms—one with its own half bath—along with a hall bath. Perfect for year-round or seasonal living, this home is just moments from two sandy bay beaches, a marina, and a local park. For those seeking an authentic North Fork lifestyle, this property truly delivers. Restaurants, shops, farm stands, wineries, breweries, boating—everything that makes the area special is right at your fingertips.
Year
Property tax
Land + Additions
Assessment*
2026
$13,677
$800 + $7,100
$7,900
2025
$13,677 (+15.6%)
$800 + $7,100
$7,900
2024
$11,830 (+7.8%)
$800 + $7,100
$7,900
2023
$10,975 (+3.1%)
$800 + $7,100
$7,900
2022
$10,643
$800 + $7,100
$7,900
2021
$10,643 (+3.7%)
$800 + $7,100
$7,900
2020
$10,262 (+1.6%)
$800 + $7,100
$7,900
2019
$10,102 (+1.8%)
$800 + $7,100
$7,900
2018
$9,926 (+1.9%)
$800 + $7,100
$7,900
2017
$9,736 (−0.2%)
$800 + $7,100
$7,900
2016
$9,752 (+3.8%)
$800 + $7,100
$7,900
2015
$9,391 (+2.2%)
$800 + $7,100
$7,900
2014
$9,188 (+3.3%)
$800 + $7,100
$7,900
2013
$8,897 (+2.4%)
$800 + $7,100
$7,900
2012
$8,691 (+3.2%)
$800 + $7,100
$7,900
2011
$8,421 (−2.1%)
$800 + $7,100
$7,900
2010
$8,604 (+2.9%)
$800 + $7,100
$7,900
2009
$8,362
$800 + $7,100
$7,900
Public record
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
0.33 Acres
Year renovated
—
Finished Sq. Ft.
—
Unfinished Sq. Ft.
—
Total Sq. Ft.
—
Year built
—
Style
Single Family Residential
County
Suffolk County
APN
1000110000300003000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Sep 15, 2026.
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
4/10 Heat Factor
7 days above 90° expected this year, 18 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
Historical weather
Cutchogue, NY • 11935
Average low and high temperatures (°F)
35
25
37
25
50
35
59
43
68
53
80
62
83
68
79
62
74
60
65
51
54
41
42
29
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
81/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Cutchogue. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.7 hrs
4.6 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 275 Pinewood Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $964,000 and $1,785,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $964K to $1.8M.