185 Roxbury Street

The home

About this home

Once home to a former Mayor of Keene, this classic New Englander blends timeless character with thoughtful updates just a five-minute walk to Central Square. Situated on a spacious corner lot of over a quarter acre, this versatile property is ideal as a single-family home, multigenerational residence, or investment opportunity. You'll love the classic charm with two welcoming porches, two entrances, two staircases, a two-car attached garage, and an impressive attached barn. The fenced backyard is perfect for children and pets, while the generous side yard offers space for gardening, entertaining, or relaxing. The custom eat-in kitchen features beautiful blue cabinetry, large subway tile, a deep Ruvati stainless sink, French door refrigerator, and abundant workspace. It flows into a formal dining room, spacious living room, and flexible bonus room ideal as a home office, den, or first-floor bedroom. Refinished original hardwood floors add warmth throughout. Upstairs are three generously sized bedrooms with oversized closets, abundant natural light, fresh neutral paint, and beautiful wide-plank wood floors. Recent improvements include vinyl siding, replacement windows, updated 200-amp electrical service, waterproof flooring in the kitchen and baths, and efficient two-zone heating. The attached barn offers incredible potential for a workshop, studio, home business, gym, or future accessory dwelling unit with applicable approvals. Ample parking accommodates multiple vehicles, recreational equipment, or even a camper. Enjoy the convenience of walking or biking to downtown Keene's restaurants, shopping, parks, entertainment, and the Monadnock Food Co-op while enjoying the privacy and space of a generous in-town lot. A rare opportunity to own a home filled with history, charm, flexibility, and endless possibilities.

Property information

Details at a glance

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Estimated monthly cost

Explore costs at the $389,900 asking price. Adjust the assumptions to your situation.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

Listing history

Price and status timeline

No additional listing history is available for public display.

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Price & market context

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Active city listing statistics from PrimeMLS as of September 12, 2026. Asking prices are not completed-sale values.

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Common questions

About 185 Roxbury Street