886 Keene Rd
Winchester, NH 03470
For Sale
Historic Charm Meets Comfort, Privacy & Convenience in Winchester, NH
Welcome to a truly special home where history, warmth, and location come together beautifully. Originally built in 1875 as a schoolhouse, this charming 2-bedroom, 1-bath home has been thoughtfully expanded over the years while preserving its timeless character. Offering 1,424 square feet of living space, this property is solid, well cared for, and full of soul — the kind of home you can feel the moment you walk in.
Set on a generous 0.47-acre lot, the home offers rare privacy with no homes behind it, as the rear of the property directly abuts a scenic rail trail walking path . Whether you enjoy peaceful morning walks, evening strolls, or simply the serenity of nature, this setting is hard to find and easy to love.
Warm, Cozy & Well-Maintained
The “bones” of this home are strong — it has been well maintained, cared for, and thoughtfully updated. The current owner recently remodeled the bathroom, featuring a beautiful tiled shower that adds modern comfort while blending seamlessly with the home’s historic charm.
Expanded Living with Practical Space
An addition added valuable living space, including a large kitchen, laundry room, extra storage, and a one-car garage — features that enhance everyday convenience while keeping the home cozy and functional. The layout flows comfortably, making the space ideal for year-round living or a relaxing weekend retreat.
Outdoor Privacy & Peace
The fenced-in front yard offers a welcoming outdoor space, while the backyard feels like your own private escape. With no neighbors behind you, the home enjoys a peaceful, secluded feel that’s perfect for unwinding, gardening, or simply enjoying the quiet.
Ideal Location with Easy Access
Conveniently located near shopping, dining, and everyday essentials, this home is just a short hop to:
Keene, New Hampshire
Brattleboro, Vermont
North Central Massachusetts
This makes it an excellent option for commuters, remote workers, or anyone seeking a quiet home base with easy regional access.
A Place to Settle In
Whether you’re searching for a full-time residence, a weekend getaway, or a peaceful sanctuary, this Winchester home offers charm, history, privacy, and convenience in one inviting package. Homes with this kind of story, setting, and care don’t come along often.
Sale is contingent upon the seller securing suitable housing.
Winchester, New Hampshire — A Charming Rural Town with Big Lifestyle Appeal
Nestled in the southwestern corner of New Hampshire, the historic town of Winchester offers small-town living with abundant outdoor recreation, community events, and proximity to nearby cities like Keene and Brattleboro. Originally settled in the early 1730s and incorporated in 1753, Winchester blends rich history with rural New England charm.
Winchester is home to roughly 4,100–4,300 residents — a community that’s grown steadily and draws homebuyers seeking affordability and space.
Population: ~4,150 (2020 U.S. Census)
Density: ~75 people per square mile
Character: Rural, family-oriented, and close-knit
Compared to urban hubs, Winchester offers a slower pace of life with a strong connection to nature, community traditions, and local events like the annual Pickle Festival on Main Street every September.
If outdoor activities matter to your buyers, Winchester checks all the boxes:
One of New Hampshire’s largest state parks — more than 13,000+ acres of hiking, biking, snowmobiling and trails interwoven through forests and ponds.
Swim, kayak, fish, paddleboard, or relax along the Ashuelot River corridor and scenic lakes.
Iconic local landmarks like the Coombs Covered Bridge and Ashuelot Covered Bridge draw history buffs and photographers alike.
Conant Public Library — a beautiful Romanesque building built in 1891.
Winchester Memorial Church — rich Colonial Revival history.
Ellen Lambert Murphy Community Center — family-friendly recreation year-round.
With Routes 10, 78, and 119 running through town, Winchester provides straightforward access to Keene, NH, and Brattleboro, VT — perfect for commuters who want rural peace but regional connectivity.
The community spirit thrives through seasonal markets, music in the park, and family-oriented festivals that residents look forward to year after year.
While Winchester’s small size means a tight-knit school community, check local performance and ratings before you buy:
Winchester School (PK-8) — public grade school serving younger students.
Keene High School — a public high school option in nearby Keene.
(Note: GreatSchools and niche ratings vary — buyers often pair this with personal visits and town reports.)
One of New Hampshire’s strongest long-term draws is its unique tax structure:
No personal income tax on wages — residents keep more of what they earn.
No statewide sales tax — attractive for shoppers and consumers.
These policies set New Hampshire apart from most states and make it especially appealing for retirees, remote workers, and people relocating from high-tax states.
Without income or general sales taxes, New Hampshire depends heavily on property taxes to fund public services, including schools and municipal operations. That means property taxes here are among the highest in the U.S., but are balanced against no income and no sales taxation.
Buyers looking in Winchester see a mix of historic homes, rural acreage, and seasonal properties — each offering space, privacy, and natural surroundings. Recent market data suggests:
Median home prices cluster in the mid-range for Cheshire County
Strong demand for comfortable, affordable homes with acreage and outdoor access.
Winchester’s real estate is ideal for first-time buyers, outdoor enthusiasts, retirees, and anyone who appreciates quieter community living with New England character.
Affordable homes relative to urban New England markets
Access to premier hiking, fishing, and nature spaces
No income or sales tax — strong fiscal appeal
Classic New England lifestyle with local community events
Close-knit, historic town with scenic beauty
If buyers want nearby alternatives or additions:
Hinsdale, NH — a small town with scenic river access.
Jaffrey, NH — a larger community with more amenities.
Chesterfield, NH — known for covered bridges and river activities
This property is located at 886 Keene Rd, Winchester, NH 03470
