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666 Main Street Unit 211, Winchester
$664,000
2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.
Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER (2026) for improved energy efficiency and beauty, now with a fabulous price improvement. The kitchen features UPDATED APPLIANCES, GRANITE COUNTERS with an eating bar and PANTRY CLOSET, open to the living room with a fireplace and the dining room with a NEW CHANDELIER. The spacious primary bedroom has a LARGE WALK-IN CLOSET, a sink area before the entry to the water closet where you’ll find a large tub. The second bedroom/office offers DOUBLE CLOSET and is across the hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR, NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (2026), NEW WASHER AND DRYER (2025) and NEW HOT WATER HEATER (2024). Benefit from COVERED PARKING in the garage below the building, the association POOL, TWO ELEVATORS, and the convenience of being only one flight of stairs up from street level. The location near town center, TRAIN, shopping, restaurants, schools and library is superb. Great layout, garage parking, ideal location, and numerous recent improvements make this a wonderful opportunity. New budget conforms to lending guidelines. Make your appointment to see this today!

666 Main Street Unit 211, Winchester
60 Lake St Unit E, Winchester
$660,000
2 Beds ⋅ 2 Baths ⋅ 73572854 MLS
Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all off, you have a private outdoor patio with water views! One deeded parking space included with an additional second space available for $40 per month. Prime location - walk to downtown restaurants, commuter rail, schools, supermarket, beach, and much more. Updates include kitchen (2020) downstairs bathroom (2023) new windows (2026) heating (2020)

60 Lake St Unit E, Winchester
60 Forest Lake Rd, Winchester
$650,000
2 Beds ⋅ 2 Baths ⋅ 5106346 MLS
Bring your dreams to life on this sprawling 17.8-acre Winchester property, offering endless opportunities to create the homestead you’ve been waiting for! The 1.75-story log cabin features two bedrooms, two full baths, and a bonus room that could serve as a third bedroom. Vaulted ceilings and a stone fireplace create a warm and inviting living space, while multiple porches spanning three sides of the home provide plenty of room to relax and enjoy the peaceful surroundings. The updated kitchen and first-floor bathroom, first-floor laundry, and full basement are additional features of this well-maintained home. This property offers so much more than just a home. A three-car garage (24x28) with a rear lean-to provides additional storage, while the six-bay shop (22x36) offers plenty of room for vehicles, equipment, and projects, complete with workbench areas and more rear lean-to storage. The two-story barn (30x52) features water and electricity, stalls, and a tack room. Outside, fruit trees are scattered on the front lawn and gardens can be found across landscaped grounds. Up on a knoll behind the house, you’ll find a self-proclaimed “campground,” complete with an RV pole barn (20x36), water access, and multiple electrical hookups. A screen house, wood shed, and fire pit create a perfect gathering space overlooking the field and pond. Whether you’re looking for space for your hobbies, animals, equipment, family, or a private place to make your own, this property offers the space and flexibility to do so. Conveniently located in Winchester, NH, just 20 minutes from Keene, 30 minutes from Brattleboro, VT, and 10 minutes from the Massachusetts border. Realtor is a relative of the seller. Seller has never occupied the property. Buyers to do their own due diligence. Please do not access the property without being accompanied by a licensed agent.

60 Forest Lake Rd, Winchester
247 Washington St Unit 11, Winchester
$600,000
3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ['Winchester Green'] BLDG.
Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

247 Washington St Unit 11, Winchester
484 Scofield Mountain Rd, Winchester
$599,000
3 Beds ⋅ 2 Baths ⋅ 5101558 MLS
Rustic charm, warm wood accents and lovely beam ceilings make this true log house feel like HOME. The outdoor space is a dream; situated on 6.32 acres, this property features a charming front porch, large back deck to relax on warm summer nights, spacious yard with fire pit for cold winter nights & smores, walking and ATV trails and your very own Christmas trees growing! Well landscaped with many perennials to enjoy throughout all of the seasons. Inside timeless log home charm meets all of the modern updates and amenities throughout. This 3 bedroom home has so much to offer; the main floor living boasts a spacious living room featuring a stunning fireplace, wide plank pine floors and wood beam ceilings; fully applianced kitchen with brand new appliances, woodburning Crawford cookstove as well as gas stove, plenty of cabinets and a breakfast bar. A first floor office or bedroom, lovely tiled full bathroom and a large sunroom displaying tiled floors and woodstove offer access to the expansive yard through the sliding glass doors. Enjoy access to the attached two car garage complete with a large bonus room; perfect for guests, a game or movie room and so much more! On the second story of the home you will find the primary bedroom presenting a walk in closet and tiled bathroom with walk in shower. Additionally there are 2 more bedrooms that complete the upstairs. Fine quality throughout and attention to detail make this home a true retreat!! Private yet minutes to amenities!

484 Scofield Mountain Rd, Winchester
49 Keene Rd, Winchester
$589,000
6 Beds ⋅ 4 Baths ⋅ 5114832 MLS
Welcome to this brand new, turn-key two-family home, offering the perfect opportunity for investors or owner-occupants looking to offset their mortgage! Each side of this modern duplex features an identical, spacious layout boasting 3 bedrooms and 1.5 bathrooms. Built from the ground up with contemporary living in mind, both units come with fully applianced kitchens equipped with brand-new refrigerators, stoves, microwaves, and dishwashers. Side-by-side design means no neighbors above or below you, maximizing peace and privacy. Enjoy complete independence and low maintenance with fully separate utilities for each unit, including individual meters for electricity, gas, and water. Each unit has a full basement with plenty of space for all of your needs. Whether you are an investor looking to add a premium, low-maintenance asset to your portfolio, or a homeowner looking to live in one side and let the tenant pay your mortgage, this property is a rare find.

49 Keene Rd, Winchester
49 Keene Rd, Winchester
$589,000
5114050 MLS
Welcome to this brand new, turn-key two-family home, offering the perfect opportunity for investors or owner-occupants looking to offset their mortgage! Each side of this modern duplex features an identical, spacious layout boasting 3 bedrooms and 1.5 bathrooms. Built from the ground up with contemporary living in mind, both units come with fully applianced kitchens equipped with brand-new refrigerators, stoves, microwaves, and dishwashers. Side-by-side design means no neighbors above or below you, maximizing peace and privacy. Enjoy complete independence and low maintenance with fully separate utilities for each unit, including individual meters for electricity, gas, and water. Each unit has a full basement with plenty of space for all of your needs. Whether you are an investor looking to add a premium, low-maintenance asset to your portfolio, or a homeowner looking to live in one side and let the tenant pay your mortgage, this property is a rare find.

49 Keene Rd, Winchester
418 Forest Lake Rd, Winchester
$499,900
2 Beds ⋅ 2 Baths ⋅ 5101659 MLS
Set back from the road at the end of a well-maintained driveway sits this adorable waterfront home with gorgeous views over Forest Lake! The property features an open concept kitchen/dining/living area overlooking the water, a large deck, screened in porch, 2 ample sized bedrooms plus a full bath to complete the first level. Downstairs offers a bonus bunk room, sitting area, plus bath and laundry. Add in the handy storage shed, plenty of available parking spaces, large .40 acre lot, private dock and beach area on your 103 feet of lake frontage, and you have the total package!

418 Forest Lake Rd, Winchester
200 Swanton St Unit 303, Winchester
$495,000
2 Beds ⋅ 1 Baths ⋅ 73578112 MLS ⋅ ['Parkview'] BLDG.
Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both generously sized bedrooms offer excellent closet space and flexible living options. The living area overlooks a scenic duck pond and professionally maintained grounds, creating a peaceful setting year-round. The secure card-entry building offers ample resident parking, guest parking off Swanton Street, and access to an in-ground pool. HOA includes heat, hot water, electricity, and AC for exceptional convenience and value. One basement storage unit is included.

200 Swanton St Unit 303, Winchester
305 Richmond Rd, Winchester
$475,000
5093431 MLS
ATTENTION INVESTORS! Through no fault of the Seller, this property is back on the market. The next Buyer will benefit from the July general and septic inspections. The bank ordered appraisal in excess of asking price is also available for review. This well-maintained multi-family property is located near the Massachusetts border, offering convenient access for commuters and tenants from both states. The property includes four residential units that are currently 100% occupied with reliable long-term tenants. It also features two separate income-producing workshop/garage spaces that provide additional revenue streams and enhance overall cash flow. Recent major capital improvements include a brand new roof, newly replaced rear stairs and decking, a fully replaced leach field, and septic connections to the two 1,000-gallon tanks that were serviced and replaced where needed. These updates ensure the property is in excellent condition and reduce future maintenance costs for the new owner. Tenants pay their own heat, hot water, and electricity, which keeps operating expenses low. This property has consistently delivered positive cash flow to the current owner, and keeping it occupied has never been an issue thanks to strong local demand. Current rents are below market rate and the leases are expiring, creating an immediate upside opportunity for a new owner to implement market-rate increases and boost net operating income right away. Whether you are an experienced investor looking to add a turnkey, low-maintenance asset to your portfolio or a buyer seeking a solid, cash-flowing property with built-in equity through recent upgrades, 305 Richmond Road is worth serious consideration. Priced to attract serious investors schedule your showing today and see the value for yourself. This property is not going to last long!

305 Richmond Rd, Winchester
200 Swanton Street Unit T35, Winchester
$450,000
2 Beds ⋅ 1 Baths ⋅ 73496844 MLS
BACK ON MARKET DUE TO FINANCING ! PARKVIEW WINCHESTER CONDOMINIUMS! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. Off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more. HEAT , HOT WATER AND ELECTRICITY ARE INCLUDED IN THE CONDOMINIUM FEE. EASY TO SHOW! OPEN HOUSE ON SATURDAY 11: 00 -- 1:00 PM AND SUNDAY 12:00--2:00 PM

200 Swanton Street Unit T35, Winchester
71 Headlands Rd, Winchester
$445,000
3 Beds ⋅ 2 Baths ⋅ 5096976 MLS
This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living.

71 Headlands Rd, Winchester
42 Parker St, Winchester
$425,000
5110811 MLS
Large two family home!!! In town location. Close to schools, shopping and amenities. Many original features; staircase and lovely banister in entrance hall, moldings, fireplace surround as well as turret and alcove windows. Large units; one 2 bedroom and one 3 bedroom. All separate utilities. Well maintained property ready for you to take ownership!

42 Parker St, Winchester
253 Back Ashuelot Rd, Winchester
$425,000
1 Beds ⋅ 1 Baths ⋅ 5095024 MLS
Are you a company boss, family or a fun loving person or one who just wants to relax and enjoy your own RIVERFRONT? These 2 buildings & the open yard can provide room for MANY to stay overnight & enjoy dinners & indoor & outdoor fun. You have been putting in key words as you search for a special property. "log home, my own river waterfront, kayaking, fishing, privacy, guest house or art studio, garage, garden areas, nearby hiking and snowmobiling,year round fun" ...Well here you are! This delightful log home has an open concept first floor with many windows to the yard , beautiful pine floors, a spacious bathroom with a large shower a large bedroom on the second floor. the water view side of the first floor could be enclosed for a bedroom. It has BBHW oil heat. NH Fish and Game stocks the river with fish. Close by are hiking and snowmobile trails (Ashuelot) bridge . Pisgah Park is nearby. You can kayak to Town from your yard along the Ashuelot River.. Enjoy the pavilion picnic place overlooking the river. Across the lawn is the guest house (cabin or art studio) built in 2012. The first floor is open concept and the second floor has a bathroom, the walls have been insulated, there is electric heat but one might add a mini-split for winter use. You can sit on the deck and relish the river view. The river side front yard gets lots of afternoon sun on a good day. The paved driveway leads to the 2 car garage for vehicles and boat storage, a newer roof and just a few steps to the 8x6 mudroom into the kitchen/living area. If you want privacy but still want a few friendly area neighbors the Back Ashuelot Rd. area is for you! Just off Rte.10 it is a short drive to Rte. 91 and picturesque routes to Eastern Massachusetts, and sbout 30 minutes to Keene,NH or Brattleboro,Vt. Recent work done to the ext. logs.. There has been a property flood evaluation done here & these homes are NOT in a flood zone less than a half hour to Keene and to Brattleboro.

253 Back Ashuelot Rd, Winchester
166 Keene Rd, Winchester
$419,900
3 Beds ⋅ 2 Baths ⋅ 5092617 MLS
Seller contribution of $10,000 towards interest rate buydown. Welcome to 166 Keene Road in Winchester, a charming 3-bedroom, 1.5-bath New Englander that combines classic character with thoughtful modern updates. This inviting home offers comfortable living spaces, abundant natural light, and a warm atmosphere that immediately feels like home. Recent improvements include an updated roof, solar panels for enhanced energy efficiency, a spacious back deck ideal for entertaining and outdoor enjoyment, fresh paint throughout the interior, updated light fixtures, and a new dishwasher, allowing the next owner to move in with confidence. The functional floor plan provides flexibility for everyday living, whether you're gathering with family, working from home, or hosting friends. Outside, enjoy the benefits of outdoor living from the rear deck or wrap around front porch, perfect for summer barbecues, morning coffee, or simply relaxing while taking in the surroundings. The solar system helps reduce energy costs while adding long-term value and sustainability. 465' of frontage on Ashuelot River. Conveniently located with easy access to local amenities, schools, shopping, dining, and recreational opportunities, this property offers the perfect balance of small-town New Hampshire living and modern convenience. Easy commute to Keene, Mass, Brattleboro and Interstate 91.

166 Keene Rd, Winchester
63 Shore Road Unit 14, Winchester
$400,000
1 Baths ⋅ 73471078 MLS
Rarely available and completely renovated commercial condo at Judkin Green is turnkey and awaits its new owner. All the work has been done for you! Perfectly located in Downtown Winchester and close to shopping, restaurants, the Lowell Line and the nearby Winchester Center Commuter Rail station. Featuring three offices and a terrific boardroom with glass doors as well as an in-unit private half bath, kitchenette with sink, microwave and dedicated water line for your auto-fill coffee maker. Just recently the home of a local accounting firm, Unit 14 offers a stylish & modern center for your burgeoning business. Includes one off street parking space for your convenience. Judkin Green is well managed which will serve both you and your clients very well. Schedule your private showing today.

63 Shore Road Unit 14, Winchester
366 Keene Rd, Winchester
$399,900
3 Beds ⋅ 2 Baths ⋅ 5108720 MLS
Sellers are motivated and ready to make a move! Quick and flexible closing available!!! Welcome home to this stunning, three-year-old Colonial featuring 3 bedrooms and 2 bathrooms. Perfectly blending classic architectural charm with modern design, this home offers bright, spacious rooms and an open floor plan designed for effortless everyday living and entertaining. At the heart of the home is a chef-inspired kitchen equipped with a large center island, premium granite countertops, sleek cabinetry, and stainless steel appliances. The main level flows seamlessly from the kitchen into the inviting living and dining areas, creating a warm and connected atmosphere. Upstairs, you will find a generous primary suite with an en-suite bath, alongside two additional well-proportioned bedrooms and laundry area for your convenience. Step outside through the dining area to your private back deck, perfect for morning coffee or weekend barbecues. The deck overlooks a beautiful, level yard that offers plenty of space for outdoor activities, gardening, or relaxing in your own peaceful retreat. With all the benefits of recent construction, this home is entirely move-in ready.

366 Keene Rd, Winchester
200 Swanton St Unit 727, Winchester
$399,000
1 Beds ⋅ 1 Baths ⋅ 73579389 MLS ⋅ ['Parkview Condominiums'] BLDG.
Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and electricity, as well as access to the in-ground swimming pool. A private basement storage unit is also included for added convenience. With its comfortable layout, private balcony, pond and garden views, included utilities, and convenient location, this move-in-ready condo is a great opportunity you won’t want to miss!

200 Swanton St Unit 727, Winchester
63 Shore Rd Unit 32, Winchester
$399,000
2 Baths ⋅ 73565929 MLS
Exceptional location downtown at Judkin Green, directly outside the heart of Winchester Center. This bright, modern, and impeccably clean professional office offers the convenience of being right at the center of town while providing the accessibility and ease of a professional office building. Unit #32 features a welcoming reception area and waiting room, plus four individual private office spaces, creating a functional and polished environment for a variety of professional uses. Two covered parking spaces are welcomed amenity, providing convenient on-site parking for owners, employees, or clients. In addition, there is ample additional parking nearby for clients and visitors. The building also features an elevator for easy access. New heat pump in 2024. With Winchester Center's shops, restaurants, services, and commuter rail right nearby, this is a rare opportunity to own a well-appointed professional office in one of Winchester's most convenient and desirable locations.

63 Shore Rd Unit 32, Winchester
35 Old Spofford Rd, Winchester
$389,900
2 Beds ⋅ 2 Baths ⋅ 5112269 MLS
Nestled on 5 private acres in Winchester, you’ll find this charming ranch style home offering the perfect combination of one-level living, privacy, and outdoor recreation! Upon entering, you’ll be greeted by a large and inviting living room/kitchen with plenty of space to relax and entertain. This home offers a primary bedroom with a 1/2 bath, another generously sized bedroom, a laundry room, and a full bath on the main level. The finished basement provides even more livable space and features a pellet stove, making it a great spot for a recreation room, hobby area, or additional entertaining space. Step outside and enjoy the expansive wrap-around deck, where you can take in the peaceful views and beautiful private surroundings. The property directly abuts the Ashuelot Rail Trail, offering easy access to walking, biking, and other outdoor activities right from your own backyard! There is also plenty of room for all your toys, tools, and equipment with 2 sheds, a detached 1 car garage, and a metal carport. A detached ground-mounted solar panel system and generator hook up add to the functionality of this property. Located just 20 minutes from Keene, this home offers the privacy and tranquility of country living while still being conveniently close to shopping, restaurants, schools, medical facilities, and other amenities. Whether you’re looking for a full-time residence, weekend getaway, or simply a place to enjoy the peace and beauty of southwestern New Hampshire, this property has so much to offer! Schedule your private showing today!

35 Old Spofford Rd, Winchester
156 Forest Lake Rd, Winchester
$377,000
4 Beds ⋅ 1 Baths ⋅ 5113915 MLS
Discover the possibilities at this inviting property set on 1.23 private acres in Winchester, New Hampshire! Offering 4 bedrooms, 1 full bath, and a versatile bonus room, this home provides plenty of space to make it your own. Whether you're looking for room to spread out, space for hobbies, or an opportunity to create a home that reflects your personal style, there's plenty of potential here. The bonus room offers flexibility for a home office, hobby space, playroom, or additional living area, depending on your needs. A 2-car garage provides valuable space for vehicles, storage, tools, or recreational equipment. Enjoy the privacy and breathing room of a generous lot while taking advantage of all that southwestern New Hampshire has to offer. If you've been searching for a property with four bedrooms, a garage, and room to make your vision a reality, 156 Forest Lake Road is worth a closer look. Bring your ideas and explore the possibilities!

156 Forest Lake Rd, Winchester
10 Burt Hill Rd, Winchester
$350,000
3 Beds ⋅ 2 Baths ⋅ 5105670 MLS
Price improvement!! Step inside this comfortable updated ranch. With 3 bedrooms, including the primary with en suite, this home is designed for easy, enjoyable living with space for all. Enjoy the outdoors from the huge screened-in porch, perfect for relaxing, entertaining, or simply taking in the peaceful surroundings. An additional enclosed porch provides even more flexible living space. The home has been modified for added accessibility, features newer flooring throughout, and central A/C for year-round comfort. Peace of mind comes easy with an automatic standby generator, while the vinyl siding and metal roof provide durable, low-maintenance exterior protection. The fenced-in backyard offers a great space for pets, gardening, recreation, or simply enjoying the outdoors. For those who like to tinker or tackle projects, the basement workshop provides a dedicated workspace as well as storage. This home offers low-maintenance living at its best. A home where you can spend less time on upkeep and more time enjoying life. Interior paint needs refreshing. Price reflects condition of the property, being sold "As Is".

10 Burt Hill Rd, Winchester
44 Gunn Mountain Rd, Winchester
$349,900
4 Beds ⋅ 2 Baths ⋅ 5112930 MLS
When you look for a good family home, I hope you're lucky enough to find one like this! Same owners for the past 35yrs, mountains of updates and improvements, and investment! From the plumbing, heating system, 200A electrical, hot water, appliances, siding and so much more! (see the disclosures) The icing on the cake is the 24x36' garage with two full stories! You'll walk into a large sunroom, then step into a big family kitchen, with doorways to the office and living room. A full ADA bath on the first floor has a large step in shower, whirlpool tub and laundry! Beautiful floors throughout, replacement windows and tall ceilings will make you feel right at home. The garage is absolutely amazing, has dedicated electrical service, GOBS of storage or hobby space! (Garage was $75k) This is an affordable family home in a quiet setting that you can move into with confidence and pride.

44 Gunn Mountain Rd, Winchester
200 Swanton St Unit 717, Winchester
$349,900
1 Beds ⋅ 1 Baths ⋅ 73500952 MLS ⋅ ['The Parkview Condominium'] BLDG.
Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for dining and entertaining. Large living room with a glass slider leading to a private balcony overlooking a view of beautifully landscaped grounds. Unit also includes 1 parking space, storage space in the basement, and on-site laundry room. Condo fee includes; heat. hot water, electric, A/C, water/sewer, landscape, & snow removal. Other amenities include gated entry, on-site management, plus the swimming pool with picnic/BBQ area. minutes away from town center, shops, restaurants, bus stop, & the commuter rail t-stop. Close to outdoor trails, major highways, and easy access to the city of Boston

200 Swanton St Unit 717, Winchester
63 Shore Rd Unit 12, Winchester
$345,000
1 Baths ⋅ 73582003 MLS
Excellent opportunity to own your own office condo at Judkin Green in downtown Winchester. This garden office condo consists of 625 square feet of open space with 1 private bathroom and storage room. Turn this office into your own! Other businesses include accountants, insurance, mortgage lenders, dentists/medical, and more. Excellent location- close to other businesses, restaurants, shops, parking, and commuter rail. Last two photos are AI generated.

63 Shore Rd Unit 12, Winchester
20 Arthur St Unit 20, Winchester
$329,900
2 Beds ⋅ 1 Baths ⋅ 73587970 MLS
Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

20 Arthur St Unit 20, Winchester
235 Ashuelot St, Winchester
$315,000
2 Beds ⋅ 1 Baths ⋅ 5114398 MLS
If you love spending time outdoors and entertaining, this is one you'll want to see! Welcome to 235 Ashuelot Street in Winchester, NH, where comfortable living meets an awesome backyard setup! Inside, you'll find two bedrooms, a full bathroom, and a comfortable, functional layout with living and dining spaces on the main floor. Downstairs, the partially finished basement offers a bonus room and plenty of additional space to make your own! Whether you're looking to create a family room, home office, workout area, or even add a second bathroom, there's plenty of potential to customize the space to fit your needs. But wait until you see the outdoor space! The covered pavilion takes outdoor entertaining to another level, complete with a mounted TV, ambient perimeter lighting, and plenty of room for comfortable seating. Whether you're catching the big game, hosting friends for a summer cookout, or relaxing with your favorite show on a warm evening, this space is designed to be enjoyed. Rain or shine, this is a space you'll want to use! Beyond the expansive deck, the spacious 0.69-acre lot offers plenty of room for outdoor activities, while the oversized shed provides tons of clean, dry storage space for all your tools, equipment, and seasonal items. As an added bonus, solar panels help keep energy costs down, allowing you to spend less on utilities and more on the things you enjoy! *Showings begin at the OPEN HOUSE 10/17/26 from 11AM-1PM!*

235 Ashuelot St, Winchester
000 Burt Hill Rd, Winchester
$310,000
5100318 MLS
An extraordinary opportunity awaits on Burt Hill Road in Winchester, New Hampshire. Spanning a massive 118 +/- contiguous acres, this expansive wooded parcel offers an unbeatable blend of privacy, natural beauty, and strategic location. Situated directly at New Hampshire’s southwestern border, the property provides the ultimate tax-friendly NH lifestyle while remaining exceptionally accessible for Massachusetts commuters and weekenders alike. The land features a beautiful tapestry of rolling hills and mature forest. With a bit of clearing, the high elevations yield the potential for absolutely breathtaking, panoramic views of the surrounding Monadnock region. For the immediate investor or homesteader, the property holds significant timber value that could be harvested to offset initial costs or create custom clearings for your dream estate and 1 acre has been set out for building in the current use plan so no additional tax for buyer on that. Whether you are looking to build a private family compound, establish an off-grid sanctuary, or explore a larger project, the canvas is yours. With town approvals, this substantial acreage holds excellent potential for the future. Don't miss out on one of the largest available tracts in the area.

000 Burt Hill Rd, Winchester
73 Ashuelot Main St, Winchester
$299,000
3 Beds ⋅ 1 Baths ⋅ 5107206 MLS
Price Reduction, Motivated Seller. Welcome to this beautifully renovated single-family home featuring 3 bedrooms and thoughtful new updates throughout. This move-in-ready property offers a comfortable and inviting layout, making it an excellent choice for a first-time homebuyer or anyone looking for a great starter home. With its fresh updates and welcoming atmosphere, this home is ready for its next owner to make it their own. Situated across the road from the Ashuelot River come take a look for yourself.

73 Ashuelot Main St, Winchester
292 Richmond Rd, Winchester
$290,000
5077669 MLS
INVESTORS WANTED. This property is just a few minutes away from downtown Winchester. 4 units are occupied. Tenants pay on time and would like to stay. Some have been here for many years. Property needs some repairs. The mostly open 3 acre parcel offers the tenants plenty of space for outdoor activities. Showings are limited due to tenants works schedules. Property is being sold without further repairs. *This will need a CASH BUYER*. Please allow 48 hr notice. Weekend showings only.

292 Richmond Rd, Winchester

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