Cheshire, NH Homes

/60
$649,000
- 3 Beds
- 2 Baths
- 2,731 Sq Ft
49 Tyler St, Brattleboro, VT 05301

Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

Dan Normandeau Berkley & Veller Greenwood Country

49 Tyler St, Brattleboro, VT 05301
/18
$2,295 per month
- 2 Beds
- 1 Bath
- 1,400 Sq Ft
- Condo for Rent
131 Frost St Unit 2, Brattleboro, VT 05301

Applications must be received prior to showings- Rent includes Wifi, snow removal from driveway, water/sewer - Tenants pays electric and Oil (at owners rate)- Large, light filled 3 bedroom first floor apartment in a 2 unit building. - In unit W/D included - Large and quiet back yard- Garage included with dedicated driveway - Ample storage with back barn/workshop- Pets

131 Frost St Unit 2, Brattleboro, VT 05301
/34
$425,000 Sold Aug 14, 2025
- 1,596 Sq Ft
- $266/SF
- 2 Days On Market
- 3 Beds
- 2 Baths
- Built 1977
194 Paine Rd, Westmoreland, NH 03467

This warm and welcoming home offers the perfect blend of comfort, convenience and energy efficiency. Located in Westmoreland, this 3 bedroom/2 bath, full dormered cape is set on 7.7 idyllic acres that include established perennial beds, garden space, a tranquil backyard stream, fruit trees, berry bushes and wooded acres to hike and explore. The home features an energy efficient heat pump system

Gina Paight Greenwald Realty Group

194 Paine Rd, Westmoreland, NH 03467

/20
Est $608,665 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,704 Sq Ft
193 Valley Park Dr, Spofford, NH 03462

193 Valley Park Dr, Spofford, NH 03462

/49
$895,000
- 4 Beds
- 2.5 Baths
- 4,116 Sq Ft
125 Stage Rd, West Chesterfield, NH 03466

19+ acres of ultimate privacy surround this spectacular home with timeless details and stunning views, offering a perfect blend of comfort & sophistication. The contractor/owner exquisitely built and maintained the property and thought of everything, starting with the welcoming foyer adorned with Spanish marble. The chef’s kitchen features granite counters, a downdraft gas stove, mesquite

Ben Prentice Keller Williams Realty Metro-Keene

125 Stage Rd, West Chesterfield, NH 03466
/13
$2,350 per month
- 2 Beds
- 1 Bath
- 600 Sq Ft
- Apartment for Rent
4 Elliot St Unit 8, Brattleboro, VT 05301

The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

Peggy Winchester ACORN REAL ESTATE GROUP LLC

4 Elliot St Unit 8, Brattleboro, VT 05301
/38
$239,000 Sold Aug 14, 2025
- 1,056 Sq Ft
- $226/SF
- 13 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1988
81 Morningside Commons, Guilford, VT 05301

The moment you step into this condo, you notice its unique features and feel a sense of calm. In the living room, you’ll enjoy the “Anywhere” ethanol fireplace for its ambience and extra heat - with no connections, venting or emissions to worry about! The kitchen has been carefully redone, with expanded cabinetry and improvements to the layout and lighting, including a custom display cabinet and

Victoria Woods Brattleboro Area Realty

81 Morningside Commons, Guilford, VT 05301

/39
Est $482,990 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,691 Sq Ft
1044 Plain Rd, Hinsdale, NH 03451

1044 Plain Rd, Hinsdale, NH 03451

/18
$425,000
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
36 Spruce St, Brattleboro, VT 05301

New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

Christine Lewis Brattleboro Area Realty

36 Spruce St, Brattleboro, VT 05301
/13
$1,500 per month
- 1 Bed
- 1 Bath
- 750 Sq Ft
- Condo for Rent
98 High St Unit 3, Brattleboro, VT 05301

Property Id: 120577Charming, light, 1bedroom apartment is just a three-minute walk from downtown Brattleboro. The 3rd floor apartment is located in a grand Victorian house that includes a turret, front porch, and two third-floor outside decks. There is also a fenced-in patio with garden space in the back.The apartment has 4 rooms with a spacious central hallway and is suitable

98 High St Unit 3, Brattleboro, VT 05301
/28
$180,000 Sold Aug 12, 2025
- 1,531 Sq Ft
- $118/SF
- 70 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1941
316 Putney Rd, Brattleboro, VT 05301

Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

Kristen Ziter Taylor Brattleboro Area Realty

316 Putney Rd, Brattleboro, VT 05301

/36
Est $323,683 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,667 Sq Ft
35 Pierce Rd, Chesterfield, NH 03462

35 Pierce Rd, Chesterfield, NH 03462

/45
$400,000 Pending
- 2 Beds
- 1 Bath
- 1,027 Sq Ft
247 N Shore Rd, Spofford, NH 03462

Two bedroom cottage with shared lake access set off the road with a great floor plan. The front windows wrap around the sides to provide great natural lignt and fresh air. You are welcomed with an open deck, covered entry and deck for extended living. The kitchen has a portable island, great storage and counter space that is open to the living area. The dining area has a passthrough from the

Sandy Cormier Greenwald Realty Group

247 N Shore Rd, Spofford, NH 03462
/10
$1,800 per month
- 1 Bed
- 1 Bath
- 535 Sq Ft
- Apartment for Rent
215 Main St Unit 204, Brattleboro, VT 05301

Recently renovated One bedroom apartment on the second floor. This one-bedroom apartment has bright sun lit rooms, with additional locking storage in the building, along with an elevator to get to the second floor for the onsite laundry facilities. This is intown living at its best. Photos are virtually staged

Peggy Winchester ACORN REAL ESTATE GROUP LLC

215 Main St Unit 204, Brattleboro, VT 05301
/20
$490,000 Sold Aug 07, 2025
- 2,400 Sq Ft
- $204/SF
- 52 Days On Market
- 3 Beds
- 3 Baths
- Built 1880
21 Howard St, Brattleboro, VT 05301

This beautiful Victorian home is just a short stroll from vibrant Brattleboro and has access to a huge town trail network. Nicely landscaped and has a partially fenced yard for pets or children. The house has lovely Victorian detailing and includes 3 covered porches. The formal entry has hardwood flooring, period staircase, stained glass window and a 3/4 bath. The adjacent front parlor includes

Robert Doyle Berkley & Veller Greenwood Country

21 Howard St, Brattleboro, VT 05301

/40
Est $652,893 Not Listed For Sale
- 3 Beds
- 4 Baths
- 2,752 Sq Ft
30 White Birch Dr, Chesterfield, NH 03443

30 White Birch Dr, Chesterfield, NH 03443

/58
$525,000 Under Contract
- 4 Beds
- 2 Baths
- 2,284 Sq Ft
384 Gulf Rd, West Chesterfield, NH 03466

Spacious Chalet on 2.93 Peaceful Acres in Chesterfield, NH.Plenty of room for a large family or a perfect weekend retreat awaits on 2.93 serene acres, along a quintessential country road in highly desirable Chesterfield, NH. This well-maintained and expanded chalet offers over 2,200 square feet of living space across three levels.Highlights include cathedral ceilings, warm wood

Alison Fissette Alset Realty LLC

384 Gulf Rd, West Chesterfield, NH 03466
/12
$2,200 per month
- 2 Beds
- 1 Bath
- 790 Sq Ft
- Apartment for Rent
4 Elliot St Unit 6, Brattleboro, VT 05301

The National, featuring this 2 Bedroom apartment with bright sunlit rooms, amazing hardwood floors and views of downtown and the mountain. Coin operated Laundry is on site and off street parking is available in the parking garage. The building is pet friendly

Peggy Winchester ACORN REAL ESTATE GROUP LLC

4 Elliot St Unit 6, Brattleboro, VT 05301
/22
$365,000 Sold Aug 01, 2025
- 543 Sq Ft
- $672/SF
- 3 Days On Market
- 1 Bed
- 1 Bath
- Built 1998
263 Welcome Hill Rd, Chesterfield, NH 03466

Nestled away from the hustle and bustle of city life, there lies a breathtaking piece of land, a sanctuary of natural beauty spanning 108 acres. This recreational haven features a charming, seasonal cabin that offers a nice mix of rustic charm for those seeking privacy. You'll be in awe as you walk in this 1 bedroom private get-a-way. And yes, it offers a full kitchen, 3/4 bath, living room, and

Todd Bassler Greenwald Realty Group

263 Welcome Hill Rd, Chesterfield, NH 03466

/40
Est $605,625 Not Listed For Sale
- 4 Beds
- 2 Baths
- 2,928 Sq Ft
25 Pine Tree Cir, Spofford, NH 03462

25 Pine Tree Cir, Spofford, NH 03462

/60
$634,500 Under Contract
- 3 Beds
- 2 Baths
- 1,448 Sq Ft
23 Bittersweet Ln, Chesterfield, NH 03466

Escape the day to day at this picturesque waterfront Cape! Down your private publicly-maintained deadend road, beside the hillside and quaint horse fence, awaits majestic views to envelop you at this park-like setting on the Connecticut River. Your private 3-acre property has over 500’ of riverfront and views with your own beach area and naturally-formed rock jetty. While you’re near to many

Mary M. Belle Isle EXP Realty

23 Bittersweet Ln, Chesterfield, NH 03466
/12
$2,000 per month
- 1 Bed
- 1 Bath
- 535 Sq Ft
- Apartment for Rent
215 Main St Unit 203, Brattleboro, VT 05301

This amazing apartment is available immediately. The view from the large windows in the kitchen and living room are of downtown Brattleboro. Recently renovated this space offers shared living room and kitchen with a large one bedroom apartment. The building has designated off street parking, and elevator in the building, along with laundry facilities and additional storage as well. Schedule

Peggy Winchester ACORN REAL ESTATE GROUP LLC

215 Main St Unit 203, Brattleboro, VT 05301
/18
$335,000 Sold Jul 30, 2025
- 1,174 Sq Ft
- $285/SF
- 36 Days On Market
- 3 Beds
- 1 Bath
- Built 1956
138 Cedar St, Brattleboro, VT 05301

Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

Claire Renaud Berkley & Veller Greenwood Country

138 Cedar St, Brattleboro, VT 05301

/13
Not Listed For Sale
0 Middle Rd, Brattleboro, VT 05301

0 Middle Rd, Brattleboro, VT 05301

/37
$499,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,024 Sq Ft
46 Poplar Commons, Dummerston, VT 05301

Nestled in the heart of Vermont, this charming Cape Cod-style home offers the perfect blend of country living and modern convenience. With 3 spacious bedrooms and 2.5 baths, it's designed for both comfort and functionality. The home boasts a large sunroom, perfect for enjoying Vermont's scenic beauty year-round, and a screened-in porch for those warm summer evenings. The outdoor deck provides an

Josh Greenwald Greenwald Realty Group

46 Poplar Commons, Dummerston, VT 05301
/16
$6,700 per month
- 4 Beds
- 2.5 Baths
- 4,823 Sq Ft
- House for Rent
18 Namaschaug Landing, Spofford, NH 03462

A RENTAL LIKE NO OTHER!!! WELCOME TO THE LAKE! You're going to absolutely love this stunning “Lake Life Dream Home”. This executive level, meticulously maintained home overlooks gorgeous Spofford Lake, in Chesterfield, N.H. You’ll have over 100 ft. of incredible lakefront to enjoy all your favorite summer watersport activities, expansive deck, stone patio, lake front gazebo, dock, included. The

Todd Bassler Greenwald Realty Group

18 Namaschaug Landing, Spofford, NH 03462
/26
$347,000 Sold Jul 25, 2025
- 1,435 Sq Ft
- $242/SF
- 22 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1890
157 Pine St, Brattleboro, VT 05301

Be impressed by this stately in-town Victorian home with an airy and open-concept feel, handsome historical features, and many thoughtful and attractive upgrades. Enter this lovely home loaded with charm and character and be prepared to be wowed with high ceilings and the gorgeous hardwood floors! A highlight of the house is an attractive kitchen with appealing custom cabinetry, granite and

Stephanie Peduzzi-Baker Brattleboro Area Realty

157 Pine St, Brattleboro, VT 05301

/12
Est $569,546 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,400 Sq Ft
58 Oak St, Brattleboro, VT 05301

58 Oak St, Brattleboro, VT 05301

/53
$449,000 Under Contract
- 3 Beds
- 2.5 Baths
- 2,157 Sq Ft
132 Poocham Rd, West Chesterfield, NH 03466

Wonderful log home in low tax, and very convenient, Chesterfield! Set in a private and pretty country setting on over 5 acres, this lovely home is just minutes from either Keene or Brattleboro. Walk onto the very well built front porch you get a sense of what awaits you inside. Step inside into the cathedral ceiling great room you will immediately feel at home. Open concept, wood floors, a large

Bert Inman RE/MAX Town & Country

132 Poocham Rd, West Chesterfield, NH 03466
/2
$185,000 Sold Jul 18, 2025
- 2,562 Sq Ft
- $72/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 1870
17 Thomas St, Brattleboro, VT 05301

Large 2 unit apartment building on a quiet one way street and is an easy stroll to downtown Brattleboro. There is a partially fenced yard, off street parking, 2 covered porches and shed off the rear of this home. Each spacious unit provides 2 bedrooms, bath, living room and kitchen (the lower unit also has a dining room). Full basement with newer boilers and tenants pay for heat, electric and

Robert Doyle Berkley & Veller Greenwood Country

17 Thomas St, Brattleboro, VT 05301

/20
Est $281,288 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
149 Canal St, Brattleboro, VT 05301

149 Canal St, Brattleboro, VT 05301

/29
$445,000
- 4 Beds
- 3 Baths
- 2,121 Sq Ft
487 River Rd, Westmoreland, NH 03467

Absolutely amazing location with 12.58 acres of land!!!! Situated in lovely Westmoreland sits this 2200+/- square ranch style home. Features 4 bedrooms, 3 bathrooms, 2 fireplaces and tons of room to roam!!! Don't miss this opportunity!

Dick Thackston R.H. Thackston & Company

487 River Rd, Westmoreland, NH 03467
/25
$349,000 Sold Jul 15, 2025
- 1,503 Sq Ft
- $232/SF
- 42 Days On Market
- 4 Beds
- 1.5 Baths
- Built 1928
6 Willow St, Brattleboro, VT 05301

This home truly has it all and is conveniently located on one Brattleboro's most charming streets. Close to shopping, restaurants, and downtown yet tucked away from it all. The large fenced lot has good exposure for gardening. Inside the home you will find 3 bedrooms and a fabulous renovated attic, complete with custom cabinetry and shelving. Enjoy indoor/outdoor entertaining with french-door

John Hatton Berkley & Veller Greenwood Country

6 Willow St, Brattleboro, VT 05301

/30
Not Listed For Sale
- 8 Beds
- 4 Baths
- 3,854 Sq Ft
100 Frost St, Brattleboro, VT 05301

100 Frost St, Brattleboro, VT 05301

/51
$389,000
- 3 Beds
- 2 Baths
- 1,550 Sq Ft
84 Brook St, Chesterfield, NH 03466

Looking to downsize? Looking for that perfect first home? Or anything in-between! This 3 bedroom, 2 bath, home is open and bright, and best of all, single level! The location could not be prettier, sitting by the brook it's a perfect spot to dip your toes in the cool water on a hot summer day, or just listen to the sound of the water from the stone patio. The kitchen, dining area, and living

Rebecca Seymour Brattleboro Area Realty

84 Brook St, Chesterfield, NH 03466
/4
$164,500 Sold Jul 14, 2025
- Land
- 108 Acres
- $1,527 per Acre
- 12 Days On Market
0 Stones Mill Rd Unit 5045865, Chesterfield, NH 03443

A surveyed 107.7-acre tract of land abutting the 13,000+acre Pisgah State Park is an ideal location for anyone looking to enjoy the outdoors whether for hunting, hiking or camping. Streams and a nearby pond offer wildlife viewing year-round. The serene setting offers a natural escape from the everyday hustle and bustle of the city as you reconnect with nature and everything it has to offer.

Fred Blais Blais & Associates, Realtors

0 Stones Mill Rd Unit 5045865, Chesterfield, NH 03443

/34
Est $210,726 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,000 Sq Ft
766 Us Route 5, Dummerston, VT 05301

766 Us Route 5, Dummerston, VT 05301

/23
$249,000
- 2 Beds
- 2 Baths
- 864 Sq Ft
45 Blakeslee St, Brattleboro, VT 05301

Charming Sun-Filled Cape on Corner Lot.This sweet and practical 2-bedroom, 2-bathroom Cape offers timeless appeal and everyday comfort on a sunny corner lot. Built in 1942, the home retains its original charm with 3-over-1 windows, built-ins throughout, and even a vintage ironing board cabinet. Inside, enjoy wood floors, a spacious eat-in kitchen with generous counter space, and a bright

Liz LaVorgna Berkley & Veller Greenwood Country

45 Blakeslee St, Brattleboro, VT 05301
/29
$269,000 Sold Jul 07, 2025
- 2,242 Sq Ft
- $120/SF
- 65 Days On Market
- 4 Beds
- 2 Baths
- Built 1890
27 Horton Place, Brattleboro, VT 05301

Outstanding Investment Opportunity Near Downtown Brattleboro. Just minutes from the vibrant Brattleboro town center, this versatile two-unit property offers unmatched convenience and strong potential for investors or owner-occupants alike. Enjoy close proximity to shopping, dining, and professional services, as well as Brattleboro Memorial Hospital, local schools, and several parks for year-round

Patrice Schneider Southern Vermont Realty Group

27 Horton Place, Brattleboro, VT 05301

/19
Est $442,588 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,074 Sq Ft
125 Dummerston Station Rd, East Dummerston, VT 05346

125 Dummerston Station Rd, East Dummerston, VT 05346

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