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$1,350,000
4 Beds 3 Baths 73541775 MLS
Architecturally distinctive and beautifully renovated throughout, this unique home blends historic character with the comfort of modern living. The home offers exceptional curb appeal and privacy with mature evergreens, specialty trees, and an elevated setting. Inside, a central staircase creates a focal point while naturally defining the open concept living and dining rooms, perfect for everyday living and entertaining. The living room is full of natural light, with a large bay of windows and seamlessly connects with the dining room featuring classic wainscoting, and a decorative fireplace. The spacious, thoughtfully updated kitchen offers granite countertops, SS appliances, a breakfast bar island, and laundry. A convenient side entry provides direct access to the first of two driveways, the deck, and the large, private backyard beyond. The deck overlooks a fully fenced backyard that offers the perfect setting for relaxation, recreation, and entertaining. The flexible floor plan is designed to fit a variety of needs with a versatile main level bedroom, a sunny and cheerful space with hardwood floors and direct access to the first of three full bathrooms. The bathroom, also accessible from the hall, offers a dual sink vanity and tiled tub with a shower. A convenient laundry area adds the finishing touch to the main level. Designed with comfort and functionality in mind, the second level features a private primary suite, two additional bedrooms, a family room, and a full family bathroom, all connected by a wide central hallway. The primary bedroom offers a large walk-in closet and an updated bathroom featuring a dual sink vanity and a beautifully tiled shower. The family bedrooms are full of natural light with hardwood floors and ample closets, sharing the family bathroom with a tub and shower. One of the bedrooms also works well as an office if needed. Double French doors open to the inviting family room, where cozy carpeting and a large window overlooking the backyard create the perfect space to relax. Set on a large corner lot with two driveways and a detached two-car garage accessed from quiet Englewood Road, this special property offers a prime location just moments from the Middlesex Fells Reservation, the town center, the commuter rail and Muraco ES. Nothing left to do but move right in.

423 Washington St, 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

$120,000
3 Beds 1 Baths 5094108 MLS
Calling all renovators, dreamers, and HGTV enthusiasts! If you've been looking for a project with great bones and an even better location, 190 Ashuelot Street might be the one. Nestled on 1.4 acres and directly abutting the Ashuelot Rail Trail, this 3-bedroom, 1 bath home is ready for its next chapter. Inside you'll find a large country kitchen, plenty of space to reimagine, and loads of potential. Outside, mature flowering and fruit trees add charm to the yard, while the detached 2-car garage provides room for vehicles, toys, or your next workshop project. Love the outdoors? Step right onto the Rail Trail for walking, biking, snowmobiling, and year-round adventure. Bring your vision, your toolbox, and a little elbow grease—this diamond in the rough is waiting to shine again! Property is being sold as-is. Cash Buyers Only.

190 Ashuelot St, 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

$449,900
3 Beds 2 Baths 5092617 MLS
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

$1,075,000
3 Beds 3 Baths 73519082 MLS
Charming antique Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

$2,695,000
4 Beds 5 Baths 73518621 MLS
Seller to offer a buyer credit paying up to 2% of loan size for buyer at closing that can go to a permanent or temporary rate buydown. European inspired villa blends timeless elegance with modern design. A dramatic curved staircase and soaring architectural details introduce a home designed for both grand entertaining and everyday comfort. Sun-filled living spaces feature handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that create a seamless connection to the outdoors. At the heart of the home is a designer chef’s kitchen w/ bespoke cabinetry, lux appliances, and an adjoining mudroom. Outside, the property transforms into a private resort-like retreat with granite-columned loggia, heated saltwater pool, landscaped grounds w/ irrigation, and multiple entertaining areas. The spa-like primary suite, ensuite guest bedrooms, finished lower level with flexible bonus spaces, and heated driveway/walkways complete this estate.

18 Middlesex St, Winchester

$1,110,000
5 Beds 3 Baths 73515601 MLS
Two-family homes in Winchester are limited, which is exactly why opportunities like this get attention quickly. Whether you are looking for an owner-occupied property with rental income or a solid long-term investment, this one checks the boxes. The larger unit spans the second and third floors, offering three bedrooms, two full baths, and living space that feels more like a single-family home. The first-floor unit includes two bedrooms and one full bath, making it ideal for rental income, extended family, or multi-generational living. Each unit has its own garage space, something tenants and owners always appreciate, plus a long driveway with plenty of additional parking. The layout offers separation, functionality, and strong future potential. Location matters, and this property comes with access to the highly desirable Winchester Public Schools, adding even more long-term value. Investment properties in Winchester do not come along often, especially ones with this much upside.

63-65 Harvard Street, Winchester

$3,995,000
4 Beds 6 Baths 5086956 MLS
One of New England's most unique & premiere properties, a sprawling sanctuary set on over 140 acres with sweeping views of Vermont, Massachusetts, & New York, it offers the ultimate escape from everyday life. A harmonious architectural masterpiece, calibrated with meticulous care. The home is crafted using an alternative construction method from 15 retrofit steel shipping containers reinforced by top grade building components seamlessly blending industrial design with high-end finishes. This unparalleled estate has a private gated entrance that welcomes you, and leads you past a pond with water feature, & basketball court. This private sanctuary presents endless possibilities—luxury residence, event venue, or yoga retreat. Each floor of the residence was thoughtfully designed; the first floor offers seamless indoor/outdoor, open concept living with a chef’s kitchen, living room, guest suite, & mudroom. A floating staircase leads you to the second floor which is counter-leveled creating two 16x10 balconies at the rear of the home, & a 10x8 balcony above the front patio. Enjoy a serene primary suite, two additional en-suite bedrooms, & an office with glass door. The lower level includes a family room, wine room with built-ins, bunk space, full bath, & 4-car tandem garage. A 50x45 raised patio with outdoor kitchen creates effortless entertaining. Every detail was designed to balance function & beauty for all ages & lifestyles. Just 2 hours to Boston, the Seacoast, & Lakes Region. Home being sold fully furnished. Floor Plans and Video available.

398 Scofield Mountain Rd, Winchester

$2,100,000
6 Beds 5 Baths 73510713 MLS
Set back on a tranquil cul-de-sac, this totally gut-renovated Colonial blends high-end modern design with warm organic textures. The heart of the home is a vaulted family room anchored by authentic barn board detailing. This space creates a seamless transition to the oversized private deck for effortless outdoor entertaining. Inside, a designer kitchen featuring a massive gathering island serves as the anchor for the expansive living and dining areas. The primary sanctuary is a true showstopper, featuring soaring ceilings and a boutique-style walk-in closet of legendary proportions. With six bedrooms and spa-inspired baths, there is plenty of space for multiple uses and configurations. From the lower-level recreation room with patio access to the proximity to Wedge Pond and the Middlesex Fells, this home is designed for indoor and outdoor leisure. Enjoy the convenience of nearby local shopping and easy access to the surrounding areas.

6 Ivy Circle, Winchester

$1,150,000
73507899 MLS
A must see Professional Office Condo with Flexible Layout, plenty of Parking and Move-In Ready. Bright, versatile, and move-in ready, this well-appointed office suite is located in the desirable Russell Hill Office Building. The flexible layout features a spacious reception and waiting area, five private offices/exam rooms, a large conference room, staff workspace, kitchenette with dining area, abundant storage, and two restrooms, including a private full in-suite bath. Four offices include sinks, offering flexibility for medical, wellness, legal, accounting, insurance, real estate, financial, consulting, educational, nonprofit, and other professional uses. Furniture is included. The professionally managed, elevator-served building offers on-site parking and handicap-accessible entry. Conveniently located near Winchester Center, Winchester Hospital, Route 38, I-93, and I-95/128. Zoned for medical and professional office use by right. Renovated in 2009,and one recent room renovation.

955 Main St Unit 305, 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

$2,799,000
6 Beds 7 Baths 73500890 MLS
Grand custom-built 6 bedroom / 7 bathroom house in a quiet Winchester neighborhood. This beautiful home welcomes you with a magnificent 18" foyer and features an amazing family room with 18” high coffered ceilings and 3 sides tall and bright windows and a large gourmet kitchen with a big island and double ovens. Traditional living and dining room maintain its good sense of typical New England Colonial style. Curved front stair case add one more layer of beauty. Second floor and third floor offer total 6 bedrooms, suites and walk-in closets. Master bedroom is with cathedral ceilings, a sprawling master closet and an office/sitting area. Smooth flow of the spacious and walk out lower level enables rich life style with billiard room, media room, art room and exercise room -- all designed for a modern lifestyle, with an open layout that is perfect for entertaining. State of the art systems with total 6 heating and cooling zones and central vacuum system.

14 Nassau Drive, Winchester

$3,299,000
7 Beds 8 Baths 73498293 MLS
Ideally situated in one of Winchester's most desirable neighborhoods, 1 Plymouth offers the rare combination of exceptional living space and unmatched convenience just minutes to Winchester Center, top-rated schools, commuter rail access, country clubs, and local amenities.Thoughtfully expanded and rebuilt, this impressive residence features 7 bedrooms, 7 full baths, and 1 half bath, designed to accommodate today's evolving lifestyle. At the heart of the home is a stunning chef's kitchen that flows seamlessly into a fireplaced family room with soaring cathedral ceilings, creating an inviting space for both everyday living and entertaining.What truly sets this property apart is its versatility. A private two-bedroom au pair offers its own living area, office, wet bar, and full bath ideal for extended family, guests, or live-in support. A finished lower level provides valuable additional living and recreation space.Just moments from Mullen Field, and everything Winchester has to offer

1 Plymouth Rd, Winchester

$975,000
2 Beds 2 Baths 73497739 MLS ['83 Church St Condominiums'] BLDG.
Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail. Some photos are virtually staged.

83 Church Street Unit 15, 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

$2,195,000
5 Beds 4 Baths 73496396 MLS
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!

276 High Street, Winchester

$3,200,000
6 Beds 6 Baths 73482275 MLS
Nearing completion! This thoughtfully designed new construction home in prime Winchester locations a must see- a handcrafted labor of love, this home welcomes you with immense curb appeal & showcases stunning living spaces across three finished levels. This 6+ bedroom, 5.5 bath transitional style home blends classic architecture with modern finishes -The main level features an open concept designer kitchen w/vaulted ceilings, skylights, oversized island, sliders to large deck & a fire-placed family room, along with formal living and dining rooms & a FIRST FLOOR bedroom suite! The 2nd floor offers 4 generous BR's including a luxurious primary suite, 2 additional full baths & convenient second floor laundry. The above grade/ walk-out lower level adds exceptional flexibility w/ *Au- pair or In-law suite* media room, home office, exercise room, bedroom & full bath Enjoy all the area has to offer including restaurants, shops, schools, train to Boston, Bike-paths & more! 7 miles from Boston

9 Albamont Road, Winchester

$2,100,000
5075574 MLS
Located in the town of Winchester in southwestern New Hampshire, this portfolio of two non-contiguous forestland parcels totaling 1,002± acres includes a high-quality timber resource, broad ecological attributes, several mountain peaks, and numerous recreational opportunities. In addition, much of the land abuts or is located near thousands of acres of conservation ownerships, enhancing value and providing potential future conservation opportunities. The larger parcel (Gardiner Mountain) is approximately 700 acres with frontage along Route 10. The smaller parcel, at 300 acres, (Cat Den) is located just off Route 119, along the Ashuelot River, though not bordering it. In addition to all its natural resources and recreational amenities, the potential for modest residential or commercial development on portions of the land may also exist. The Winchester Woodlands portfolio offers a diverse range of amenities, as well as near and long-term value drivers, at a scale that is not often found in this region of southern New Hampshire.

00 Rte 10, 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

$115,000
5072791 MLS
Discover a rare opportunity to own 21.2+/- acres of pristine New Hampshire wilderness in the heart of Winchester. This expansive parcel is defined by its stunning frontage along the tranquil Roaring Brook, offering a picturesque and peaceful setting for your future dream home or private getaway. A standout feature of this property is its significant standing timber value; the land has remained untouched by logging for many decades, resulting in a lush forest of mature hardwoods and softwoods ready for immediate investment potential or continued conservation. Nestled in the scenic Monadnock Region, you are perfectly positioned to enjoy the best of the outdoors with easy access to the massive trail systems of Pisgah State Park, the historic local charm of Winchester, and the convenient amenities of nearby Keene. Whether you are looking for a secluded homestead, a recreational retreat, or a savvy land investment, this untouched acreage provides the space and natural resources to make your vision a reality.

525 Richmond Rd, Winchester

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