355 South Street

Windham NY 12496

1438 sq. ft.

56628 sq. ft.

Single-Family

Last sold for $635,000

Patricia Charbonneau, last sold this property on 20 April 2026 after 865 days on market.

Overview

Excellent location with ease of access to Windham Mountain Club and town of Windham! Tucked up amongst the tress at the foot of Windham Mountain you will find this truly picturesque and enchanting home featuring 2 bedrooms and 2 full bath, plus extra sleeping loft and a 2 car garage with a cozy 1 bedroom apt! This home is brimming with character; the gable roof lines and classic detailing add visual interest and charm. The unique floor plan makes for an ideal mountain get away. Relax in the cozy sitting area, the sun filled, well-appointed kitchen offers plenty of counter space to create memorable meals to enjoy around the banquet styled table, with sliding doors out to the beautiful, private patio. The timber frame vaulted ceilings in the living area create an open airy feeling, while the warm woodstove adds to the rustic charm. The main floor also offers an elegant, full bath with a tastefully tiled walk in shower. The second floor offers a comfortable, bright primary bedroom, a cheerful bunkroom, an additional loft sleeping area and a large full bath with jetted tub, large walk-in closet and reading nook adding to the charm and functionality of this offering. The spacious 2 car garage offers a lovely 1 bedroom apt. with kitchenette, full bath and cozy living area with extra sleeping to use for guests or rental opportunity. The property will delight you with its striking circular stone fire pit with wood and stone seating, prominent attractive gazebo, stone walkways, flowering trees and evergreen shrubs. This offering may be the closet you'll come to stepping inside a storybook setting. A nature lovers paradise where you will enjoy skiing, snowboarding, hiking, biking, golf, yoga, day saps, indie bookstore, walking the Windham Path, fine restaurants, seasonal farmers markets and so much more.

Features

2 bedrooms

2 bathrooms

2 carspaces

2 garage spaces

1438 sq. ft. floor area

56628 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 2 bedroom single-family properties sold in Windham over the last 12 months, the estimated median property value of 355 South Street is $519k.

Median value

$519k

Estimated value range

$220k - $635k

Median days on market

136

Estimated value trend

65%

increase over the last 12 months

Average days on market is based on recent, comparable sales in Windham. 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 355 South Street

2026

Sold

$635,000

20 Apr 2026 by Patricia Charbonneau, of Brainard Ridge Management

Happy sellers in Windham

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