1111 Main St

Greenport West NY 11944

2363 sq. ft.

42253 sq. ft.

Single-Family

Last sold for $1,200,000

Jon Tomlinson, last sold this property on 05 December 2025 after 135 days on market.

Overview

A Creative Sanctuary in the Heart of Greenport. Tucked away on a tree-lined street in one of the “prettiest towns in America” (Forbes), this Cape Cod-style, wood-shingled home offers a rare blend of charm, privacy, and proximity to everything that makes Greenport so desirable. Perfectly situated on a full acre of land, the backyard abuts 8 acres of preserved open space owned by the Town of Southold — a rare buffer that offers both tranquility and an enduring sense of privacy. It’s less than a 15-minute stroll to 67 Steps Beach on the Long Island Sound and the vibrant heart of the village — including shops, galleries, restaurants, the North Fork Arts Center / movie theater, and the Greenport LIRR. Just a short bike ride away are Norman Klipp Park/Gull Pond Beach, 5th Street Beach, and the waterfront Kontokosta Winery. You’ll also find several nearby noteworthy wineries and farm stands that define the North Fork lifestyle. Inside, the home features three spacious bedrooms and two recently-updated full bathrooms, along with a wood-burning fireplace and original 1956 details that exude character. A separate 400 sq ft studio/office with vaulted ceilings, skylight, and radiant heated floors offers the ideal space for creative work, yoga, or lounging. Out back, the private garden and gravel patio were designed by Manscapers NY and feel like an outdoor room — complete with lounge chairs, shaded dining under mature trees, string lights, and layers of thoughtfully placed perennials, ferns, and herbs. It’s the perfect spot to gather with friends, grill, or unwind and watch the sunset. Whether year-round or as a weekend retreat, this is a home that invites creativity, connection, and calm — all just minutes from Greenport Village and the sea.

Features

3 bedrooms

2 bathrooms

3 carspaces

2363 sq. ft. floor area

42253 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 3 bedroom single-family properties sold in Greenport West over the last 12 months, the estimated median property value of 1111 Main St is $999k.

Median value

$999k

Estimated value range

$450k - $1.65m

Median days on market

107

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Greenport West. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1111 Main St

2025

Sold

$1,200,000

05 Dec 2025 by Jon Tomlinson, of Daniel Gale Sothebys Intl Rlty

2017

Sold

$605,225

18 Jan 2017 by Carole Marcus, of Douglas Elliman Real Estate

Happy sellers in Greenport West

We have insufficient information to provide an overview of customer satisfaction for Greenport West. Viewing the agent profiles, reviews and sales for Greenport West can provide insights for this location.