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21 Kapper Dr, Winchester
$299,000
3 Beds ⋅ 1 Baths ⋅ 5077847 MLS
Makeover Magic! This beautifully renovated 3-bedroom, 1-bath ranch has been completely gutted to the studs and thoughtfully rebuilt by a local builder. Upgraded electrical panel and lines, and here’s what’s NEW - an energy-efficient furnace, all plumbing, drywall, windows, doors, flooring, kitchen, bathroom, and appliances!The upgrades continue outside with a brand-new roof and vinyl siding for added peace of mind! Situated on a level, cleared one-acre lot in a neighborhood with open fields behind the property, this home offers both privacy and charm. New front steps, a, 12x12 deck off the kitchen and granite countertops will be completed prior to closing, making this home truly move-in ready. Currently being finished and ready just in time for you - don’t miss this stunning transformation!

21 Kapper Dr, Winchester

20 Bilo Ave, Winchester
$295,000
3 Beds ⋅ 1 Baths ⋅ 5074463 MLS
Updated and ready to love, this bright and sunny 3-bedroom, 1-bath home offers 1,145 square feet of comfortable living space in a convenient Winchester location near schools. Fresh paint throughout and new vinyl plank flooring create a clean, modern feel, while new stainless steel appliances shine in the spacious kitchen, complete with a breakfast bar open to the living room—perfect for everyday living and entertaining. Enjoy peace of mind with a durable metal roof and plenty of storage and hobby space in the oversized one-car garage, featuring room for a workshop and separate 100-amp electric service. Outside, a lovely backyard provides space to relax, garden, or play. A move-in-ready home that combines updates, functionality, and charm—Just 5 minutes from the Mass border it's an easy commute to VT or Mass. Winchester is home to Pisgah State Park for hiking, the Ashuelot River & Forest Lake for summer water sports and the famous Pickle Festival. Don’t miss this one!

20 Bilo Ave, Winchester

19 Toofs Dr, Winchester
$295,000
3 Beds ⋅ 2 Baths ⋅ 5072273 MLS
An Abundance of amenities in the 3 bdr/2bath ranch house..Spacious open yard fully fenced in for children playground or family dogs. Large garage with built in workspace and ample storage. Newer laminate floors throughout complementing freshly painted walls. Eat in Kitchen with open view to living room.. enjoy front porch for summer days relaxation. Recent METAL ROOF and Vinyl SIDING award low maintenance and curb appeal. A full basement housing newer Buderus furnace, a pellet stove and sheetrock walls ready for new owner to build out to your specs (2 small rooms already completed) good size laundry room set up in place. Family friendly neighborhood and kids can walk or bike to elementary/middle schools. OPENHOUSE JAN 3,2026 FROM 11:00 am UNTIL 3:00 PM..

19 Toofs Dr, Winchester

12 Rabbit Hollow Rd, Winchester
$289,900
3 Beds ⋅ 1 Baths ⋅ 5105294 MLS
Your own little piece of New Hampshire, just moments from Forest Lake! Set on 3.1 peaceful acres, this three-bedroom, one-bath ranch offers the privacy of a country setting with swimming, fishing, kayaking and days by the water close to home. The interior has been thoughtfully opened up to create a spacious, open-concept main living area, giving the home a much larger and more inviting feel. Recent improvements include new flooring, mini-split heating and cooling, a new well head, new appliances with much of the major work already completed. There is still an opportunity for the next owner to add their own cosmetic finishing touches and truly make the space their own. Single-level living keeps things comfortable and convenient, while the full basement provides plenty of additional storage and utility space. Outside, more than three acres, which are cleared to the boundary line, provide the breathing room people come to New Hampshire looking for. Garden, entertain, enjoy a fire under the stars, or simply appreciate having your own private piece of land. Close to Forest Lake and surrounded by the quiet of the countryside, 12 Rabbit Hollow Road is ready for its next chapter. Showings start at the open house, Saturday 8/22 *11AM-1PM* & Sunday 8/23 *11AM-1PM*

12 Rabbit Hollow Rd, Winchester

290 Scotland Rd, Winchester
$283,000
3 Beds ⋅ 2 Baths ⋅ 5081709 MLS
(The septic report should be under show docs later today).Drive up the driveway to a private homesite with old garden beds, privacy, perhaps a place for a horse. This one level home will work for almost anyone! Enter this 2 bath home through an enclosed porch which could be part mudroom and partially an area to relax on in good weather. The kitchen has a good working area with a double sink, refrigerator, electric stove and the washer and dryer behind closed doors. The livingoom has a large picture window and there are 3 bedrooms and 2 baths. One bath is in a bedroom. The full concrete basement has been dry and houses the fairly new gas furnace and circuit breakers. The price includes Tony Poanessa's 10k estimate for new roof shingles. Some cosmetics and interior and exterior work is needed. This could be a happy place to live.

290 Scotland Rd, Winchester

71 Parker St, Winchester
$277,000
3 Beds ⋅ 1 Baths ⋅ 5073384 MLS
New Year, New Home! Come see this charming 3 bedroom, 1 bathroom home with a spacious yard on a quiet street just steps from the elementary school. Situated on one of the prettiest streets in Winchester, this home provides the benefit of being close to downtown, but with the solitude and beauty of green fields behind you. With your vision, this 1950's ranch could become your dream home. It has the space you need, a convenient layout, plus a large, dry basement with laundry, and a good sized garage beneath the house. While it could use some cosmetic updating to really bring it to life, this home has everything you need. A sunny family room, cozy woodstove, and convenient walkout kitchen to the backyard are some of my favorite features. Start the new year right--come make this house your home! This sale is subject to seller finding suitable housing.

71 Parker St, Winchester

12 Miner Ct, Winchester
$259,000
3 Beds ⋅ 1 Baths ⋅ 5056219 MLS
Welcome to 12 Miner Court – a delightful 3-bedroom, 1-bath home set on a .47-acre lot with a semi-private backyard at the end of a quiet dead-end street, just minutes from downtown Winchester. Inside, you’ll find freshly painted rooms that feel bright and inviting, complemented by a newer forced hot air heating system and water heater for comfort and efficiency. The home’s metal roof and vinyl siding offer durability and low maintenance, giving you more time to enjoy life. Winchester is a friendly New Hampshire town known for its community spirit, seasonal festivals, and easy access to outdoor recreation. Located close to the Massachusetts border, Winchester offers quick access to Keene, Brattleboro, and beyond—making it ideal for both commuters and those who appreciate a quieter pace. This move-in-ready home is a wonderful opportunity to put down roots in a welcoming community. New oil tank and updated electric.

12 Miner Ct, Winchester

415 Richmond Rd, Winchester
$249,500
2 Beds ⋅ 2 Baths ⋅ 5063358 MLS
Open concept, 2 bdrm, 1.5 bath home in a convenient tri-state location with access to major routes heading North/South and East/West! Cathedraled first floor has a spacious kitchen/living area with tiled breakfast bar, generous counter & storage space, and a slider opening to a quaint rear deck overlooking the forested surroundings. In addition, there is a large, first floor bedroom w/hardwood floors, a walk in closet, and an exterior balcony in addition to a full bath. An open loft w/hardwood floors overlooks the main level on the second floor and is versatile in use, leading to a comfortable and cozy guest bedroom with hardwood floors and a half bath. As a bonus, there is a part-finished walkout basement offering additional living area. Current owner has made numerous improvements over their ownership, and this property provides opportunity for a new owner to continue to customize to reflect their taste! Relax on the decks and enjoy the sights and sounds of nature in this sloping wooded setting without having the maintenance of a large yard. Light & airy throughout! Showings begin Friday, October 3rd, by appointment only.

415 Richmond Rd, Winchester

886 Keene Rd, Winchester
$220,000
2 Beds ⋅ 1 Baths ⋅ 5075827 MLS
Buyers financing fell through so this awsome home is on the market again! New price! From the moment you arrive, the home makes a warm first impression with classic appeal. A fenced-in front yard creates a welcoming buffer from the road, perfect for pets, gardening, or simply enjoying your own outdoor space. The seller added new gutters to the home. Inside, the home feels cozy and comfortable, offering two well-proportioned bedrooms and a recently remodeled bathroom that adds modern convenience without sacrificing character. The layout is efficient and inviting, ideal for year-round living, a weekend retreat, or a low-maintenance lifestyle. A one-car garage provides both vehicle protection and valuable storage—something you’ll appreciate in every season. Out back, the setting truly shines. The private backyard abuts a Rail Trail and wooded land, with no neighbors behind you, creating a peaceful, natural backdrop. Despite the home’s convenient location on a main road, the interior remains surprisingly quiet—once inside, it feels like a hidden sanctuary tucked away from the world. Location is another standout feature. Just a short distance away from Keene, New Hampshire, and close to shopping, dining, southern Vermont, and northern Massachusetts, this home offers the best of both worlds: accessibility when you want it and privacy when you need it. Whether you’re seeking a primary residence, a getaway, or a smart rental investment, this property offers flexibility and long-term appeal. Septic has failed. CASH OR CONVENTIONAL FINANCING ONLY. HOME IS SOLD AS IS. The sale is contingent upon the seller finding suitable housing, already identified and under contract.

886 Keene Rd, Winchester

49 Scotland Rd, Winchester
$199,000
3 Beds ⋅ 2 Baths ⋅ 5063001 MLS
Set back from the road offering your own good size front yard with a front deck, new stairs and a back landing with updated stairs. Why rent? Offering an open lr/kitchen, a master with afull bath is across from the other 2 bedrooms and the 2nd bath. The laundry space is very practical and is  located near a back door. The pantry closet offers more Kitchen storage.  The 2 car garage is a plus for workshop, storage, and vehicle space. (Siding the exterior may result in a tax increase.) The mail box across the street is on your own small lot. Above ground pool can stay or not. Disclosure change.. furnace serviced Jan. 17, 2025 Seller has been making recent improvements to the property.. A list is available.

49 Scotland Rd, Winchester

16 Harbourt Dr, Winchester
$108,500
2 Beds ⋅ 2 Baths ⋅ 5081339 MLS
Welcome to a unique opportunity —one of the only homes in the park with this kind of open, pastoral backdrop. Set along neighboring farmland, this 2 beds, 2 bath open concept living space home offers a sense of space and relaxed atmosphere that’s hard to come by. Instead of looking out at other homes, you’ll enjoy open land views out your back door and a vacant lot across the road. Step inside to a bright, comfortable layout that makes everyday living easy, a well maintained and cared for home. And just beyond the empty lot a gentle brook adds to the charm. If you’ve been looking for something a little different—something inviting, and connected to the outdoors—this home is truly special. Central air for those hot days/nights and forced air heat. Living room/kitchen floors replaced 2023, driveway repaved 2024, generator, kitchen bar stools included, appliances included in as-is working order. Come experience the charm for yourself. The lot has many lovely perennial plants including Rose of Sharon, Red Maples, Burning Bush and Lilac.

16 Harbourt Dr, Winchester

4 Earl Ave, Winchester
$100,000
3 Beds ⋅ 2 Baths ⋅ 5068491 MLS
Welcome to 4 Earl Ave in the desirable South Parrish Co-op! This lovely and well-maintained 3-bedroom, 1.5-bath mobile home offers comfortable living on a beautiful lot surrounded by mature trees. The home features a bright, inviting kitchen with abundant storage and workspace, perfect for everyday cooking or entertaining. The open living area flows seamlessly into the back enclosed porch addition, creating a warm and versatile space to relax or gather. Enjoy morning coffee or evening barbecues on the private back deck, while the treed setting provides both shade and privacy. The primary bedroom includes a full bath just steps away and the additional bedrooms are conveniently serviced by a Jack-and-Jill bath. With 995 sq. ft. of thoughtfully designed space, this home combines comfort and charm in a peaceful community setting. Located just minutes from downtown Winchester and Keene, and an easy location for commuting to VT and Mass. This property offers easy access to shopping, dining, and outdoor recreation. Come see why 4 Earl Ave is the perfect place to call home!

4 Earl Ave, Winchester

28 Staddle Hill Rd, Winchester
$100,000
2 Beds ⋅ 1 Baths ⋅ 5064700 MLS
Escape to your own private woodland retreat! A seasonal charming cabin retreat tucked away among the trees offering the perfect getaway for those seeking peace, quiet, and a connection with nature. The property is ideal for seasonal use, whether you’re enjoying long summer days, crisp autumn evenings, or relaxing weekend getaways. The cabin features a cozy open concept living area, and a deck great for morning coffee or watching wildlife wander by - a good location to explore Pisgah State Park, for hiking biking and fishing. Walk the Ashuelot Recreation trail and visit historic covered bridges like Coombs Covered Bridge or swim at Forest Lake. Whether you’re looking for a writer’s hideaway, a weekend escape, or a base for outdoor adventures, this cabin delivers a rare blend of seclusion and natural beauty. Sold "as is" with furnishings included. Easy access to multiple states. It is less than 30 minutes to Keene NH, Brattleboro, VT and Greenfield, MA. Note: Seasonal property – not suitable for year-round occupancy.

28 Staddle Hill Rd, Winchester

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