Cheshire, NH Homes

/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
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/45
$401,000 Sold Jul 01, 2025
- 4,981 Sq Ft
- $81/SF
- 5 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1839
108 Westmoreland Rd, Spofford, NH 03462

Nestled on 21 sprawling acres, this estate, formerly known as "The Maples- Bed & Breakfast" offers a unique blend of historical charm and modern luxury. This large property has a true New England feel and features multiple screened-in porches, perfect for enjoying the natural surroundings. The first floor is designed for seamless living, boasting a large open living room, primary bedroom suite, a

Todd Bassler Greenwald Realty Group

108 Westmoreland Rd, Spofford, NH 03462

/34
Est $541,873 Not Listed For Sale
- 2 Beds
- 3 Baths
- 2,500 Sq Ft
1245 Black Mountain Rd, Brattleboro, VT 05301

1245 Black Mountain Rd, Brattleboro, VT 05301

/2
$300,000
- 4 Beds
- 2 Baths
- 1,808 Sq Ft
109 Central St, Brattleboro, VT 05301

Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

Christine Lewis Brattleboro Area Realty

109 Central St, Brattleboro, VT 05301
/28
$514,500 Sold Jun 30, 2025
- 2,676 Sq Ft
- $192/SF
- 6 Days On Market
- 4 Beds
- 2 Baths
- Built 1888
2 Streeter Hill Rd, West Chesterfield, NH 03466

Located in West Chesterfield, this 1888 farmhouse is beautifully maintained and designed for modern comforts - it could be the perfect place to build your future! Settled on a hilltop corner, this property is ideally positioned between both Brattleboro, VT and Keene, NH in a peaceful country setting. The 1.6 acre lot offers a sprawling front yard with lush garden beds and a fully-enclosed private

Megan Manley North New England Real Estate Group

2 Streeter Hill Rd, West Chesterfield, NH 03466

/23
Est $544,928 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,294 Sq Ft
50 Knapp Rd, Dummerston, VT 05301

50 Knapp Rd, Dummerston, VT 05301

/2
$90,000
- 3 Beds
- 1 Bath
- 1,030 Sq Ft
93 Clark St, Brattleboro, VT 05301

An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

Christine Lewis Brattleboro Area Realty

93 Clark St, Brattleboro, VT 05301
/55
$450,000 Sold Jun 30, 2025
- 2,407 Sq Ft
- $187/SF
- 28 Days On Market
- 3 Beds
- 2 Baths
- Built 1976
164 Poocham Rd, Westmoreland, NH 03467

For Sale: Spacious Post & Beam Contemporary on Nearly 12 Acres in Sought-After WestmorelandEscape to the charm and tranquility of this beautiful post and beam contemporary home, nestled on 11.89 private acres in highly desirable Westmoreland. Brimming with character, this spacious residence features wide pine floors, exposed beamed ceilings, and a generous living room warmed by a brand-new

Nancy Proctor BHG Masiello Keene

164 Poocham Rd, Westmoreland, NH 03467

/22
Est $279,379 Not Listed For Sale
- 2 Beds
- 1 Bath
- 864 Sq Ft
1075 Middle Rd, Brattleboro, VT 05301

1075 Middle Rd, Brattleboro, VT 05301

/3
$150,000
- Land
- 3.86 Acres
- $38,860 per Acre
00 Orchard Rd, Chesterfield, NH 03443

A rare find in Chesterfield. 4+/- acres of mostly open land situated on a quiet country road. Long road frontage assures privacy and allows for your choice of driveway access. Located about 3 miles from Rt 9 and close to Chesterfield Elementary, this spot provides convenience to Keene, Brattleboro and Hinsdale. And is close to Spofford Lake and Pisgah Park.

Timothy Keating BHG Masiello Keene

00 Orchard Rd, Chesterfield, NH 03443
/27
$285,000 Sold Jun 27, 2025
- 1,243 Sq Ft
- $229/SF
- 4 Days On Market
- 3 Beds
- 1.5 Baths
- Built 2004
707 Oxbow Rd, Hinsdale, NH 03451

First time on the market in almost 28 years. One level living at its best. This ranch home sits on an acre lot at the end of a quiet road. The nice yard allows for a garden, a fire pit and a quiet deck off the dining room for you to enjoy your morning coffee. This home has 3 bedrooms and one and a half baths. Also offers a full unfinished basement and a two-car garage. There are hiking and

Peggy Winchester ACORN REAL ESTATE GROUP LLC

707 Oxbow Rd, Hinsdale, NH 03451

/29
Est $592,696 Not Listed For Sale
- 3 Beds
- 2 Baths
- 3,768 Sq Ft
18 Miller Rd, East Dummerston, VT 05346

18 Miller Rd, East Dummerston, VT 05346

/10
$175,000
- Land
- 8 Acres
- $21,875 per Acre
680 W River Rd, Brattleboro, VT 05301

8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

Chris Long BHG Masiello Brattleboro

680 W River Rd, Brattleboro, VT 05301
/40
$312,000 Sold Jun 27, 2025
- 960 Sq Ft
- $325/SF
- 59 Days On Market
- 1 Bed
- 1 Bath
- Built 2006
63 Winter Bell Dr, Dummerston, VT 05346

Who hasn't dreamed of owning a sweet log cabin home in beautiful VT with a large covered porch, easterly views and sunsets into the NH mountains? Located right between exit 3 Brattleboro and exit 4 Putney, this property has 3.38 mainly-open acres of land in a country setting, but close to town and a stone's throw to the wonderful Walker Farm stand, You will really appreciate the convenience of

Stephanie Peduzzi-Baker Brattleboro Area Realty

63 Winter Bell Dr, Dummerston, VT 05346

/23
Est $271,309 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,539 Sq Ft
380 S Main St, Brattleboro, VT 05301

380 S Main St, Brattleboro, VT 05301

/18
$275,000
- Land
- 0.68 Acre
- $404,412 per Acre
36 Canal St, Spofford, NH 03462

Build Your Dream Retreat in the Heart of the Spofford Lake District! Welcome to 36 Canal Street, a picturesque and buildable 0.68-acre lot with existing well, perched above the scenic Partridge Brook, fed by Spofford Lake. This rare offering is tucked into one of the region’s most sought-after lake communities—just minutes from the town beach, boat launch, and all the recreational fun

Kelsey Malloy Keller Williams Realty Metro-Keene

36 Canal St, Spofford, NH 03462
/60
$610,470 Sold Jun 24, 2025
- 3,282 Sq Ft
- $186/SF
- 0 Days On Market
- 3 Beds
- 3 Baths
- Built 1995
36 Split Oak Cir, Chesterfield, NH 03443

Welcome to your dream log home, where rustic charm meets modern luxury! Nestled on a picturesque 1.34-acre lot, this stunning Crockett Log home promises to be your ultimate escape. From the moment you step inside, the soaring cathedral ceilings and open-concept living space will take your breath away. Whether you're hosting dinner or preparing a quiet meal, the kitchen’s elegant granite

Josh Greenwald Greenwald Realty Group

36 Split Oak Cir, Chesterfield, NH 03443

/24
Est $495,573 Not Listed For Sale
- 4 Beds
- 1.5 Baths
- 1,592 Sq Ft
89 Oak Grove Ave, Brattleboro, VT 05301

89 Oak Grove Ave, Brattleboro, VT 05301

/45
$950,000
- 3 Beds
- 2 Baths
- 2,210 Sq Ft
61 Orchard Rd, Chesterfield, NH 03443

Continue the legacy of owning the oldest home in Chesterfield with its rich history, bucolic setting of woods, fields, pond and orchard. Well maintained features include beamed ceilings, wide pine floors, slate roof and center chimney. The Custom kitchen has stainless steel appliances, cherry cabinetry and CaesarStone counters. White oak flooring was installed with programmable radiant

Timothy Keating BHG Masiello Keene

61 Orchard Rd, Chesterfield, NH 03443
/55
$400,000 Sold Jun 20, 2025
- 1,837 Sq Ft
- $218/SF
- 63 Days On Market
- 3 Beds
- 1 Bath
- Built 1974
121 Pond Brook Rd Unit 4-A001, West Chesterfield, NH 03466

Versatile cape, on a beautiful 6 acre lot w/a greenhouse & south facing 3 season sunroom. Very special land, tended for over 40 years, now filled w/herb gardens, garden beds, blueberry patch & fruit trees. Custom built stone walkways & walls compliment the peaceful setting. New windows & natural woodwork. Livingroom w/hardwood flooring, chair rail, picture window & mini-split. KIT & Dining area

Connie Joyce RE/MAX Town & Country

121 Pond Brook Rd Unit 4-A001, West Chesterfield, NH 03466

/14
Est $316,052 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,492 Sq Ft
131 Oak Grove Ave, Brattleboro, VT 05301

131 Oak Grove Ave, Brattleboro, VT 05301

/23
$1,150,000
- 6,442 Sq Ft
69-71 Elliot St, Brattleboro, VT 05301

Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

Erica Reynolds Southern Vermont Realty Group

69-71 Elliot St, Brattleboro, VT 05301
/50
$584,000 Sold Jun 13, 2025
- 2,242 Sq Ft
- $260/SF
- 25 Days On Market
- 4 Beds
- 3 Baths
- Built 1880
890 River Rd, Westmoreland, NH 03467

Located in the peaceful town of Westmoreland, NH, this established 6-acre mini farm is set in the heart of the fertile Connecticut River Valley, renowned for its rich, productive soils.This well maintained 4-bedroom, 3-bath Colonial home, originally built in 1880, has been thoughtfully upgraded over the years to blend classic charm with modern comfort. Inside, you’ll find spacious living areas, a

Alison Fissette Alset Realty LLC

890 River Rd, Westmoreland, NH 03467

/24
Est $283,391 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,514 Sq Ft
94 Fuller Dr, Brattleboro, VT 05301

94 Fuller Dr, Brattleboro, VT 05301

/16
$488,875
- 5 Beds
- 4 Baths
- 3,064 Sq Ft
176 High St, Brattleboro, VT 05301

Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

Susan Bellville Bellville Realty

176 High St, Brattleboro, VT 05301
/33
$386,250 Sold Jun 12, 2025
- 1,617 Sq Ft
- $239/SF
- 49 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1880
33 Frost Place, Brattleboro, VT 05301

Whether you're seeking a smart investment or a beautifully appointed primary residence, this exceptional offering in the heart of Brattleboro, VT, is not to be missed. Fully renovated by the current owners, this charming home offers far more than it's modest exterior suggests.Step onto the inviting screened porch — the perfect spot to unwind during warmer months or transition comfortably from the

Keith Nowak Four Seasons Sotheby's Int'l Realty

33 Frost Place, Brattleboro, VT 05301

/24
Est $320,087 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,500 Sq Ft
62 Highland St, Brattleboro, VT 05301

62 Highland St, Brattleboro, VT 05301

/52
$95,000
- 2 Beds
- 1 Bath
- 840 Sq Ft
150 Oxbow Rd, Hinsdale, NH 03451

Bring me back to my former charm and glory.Vaulted ceilings, 2 bedrooms, a fireplaced (currently not operational) living room eagerly awaits a new owner to freshen up this home.The home sits on almost 3 acres of rolling fields. Could be a picturesque setting for your gardens and farmThe property and land is being sold "As - Is"

Thomas Travers Great Beginnings Real Estate Services, LLC

150 Oxbow Rd, Hinsdale, NH 03451
/18
$169,000 Sold Jun 09, 2025
- 980 Sq Ft
- $172/SF
- 15 Days On Market
- 2 Beds
- 2 Baths
- Built 1999
682 Oxbow Rd, Hinsdale, NH 03451

Tucked into your own little niche, with lilacs and azaleas getting ready for spring, this is a very affordable home for the starter. Having one floor living, it is also perfect for downsizing. The huge front deck can seat a crowd.....the town road is paved...you CAN get there from here.....the open concept is perfect for using every bit of space, every day....bird watching from the kitchen sink

Christine Lewis Brattleboro Area Realty

682 Oxbow Rd, Hinsdale, NH 03451

/25
Est $246,013 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,033 Sq Ft
88 Washington St, Brattleboro, VT 05301

88 Washington St, Brattleboro, VT 05301

/26
$725,000
- 18 Beds
- 8 Baths
- 4,932 Sq Ft
29 Canal St, Brattleboro, VT 05301

High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

Michael Gilman 3GEN Real Estate Inc

29 Canal St, Brattleboro, VT 05301
/55
$427,000 Sold May 30, 2025
- 4,140 Sq Ft
- $103/SF
- 6 Days On Market
- 8 Beds
- 4 Baths
- Built 1850
73 Main St, Chesterfield, NH 03466

Step into a rare opportunity to own a piece of Chesterfield's rich history. Located in the heart of town, this beautifully preserved building sits directly on the scenic Catsbane Brook, offering tranquil water views, a peaceful back yard and a large deck. With its generous layout, high ceilings, and large windows that fill the space with natural light, this one-of-a-kind building is perfect for

Kelsey Malloy Keller Williams Realty Metro-Keene

73 Main St, Chesterfield, NH 03466

/30
Est $333,669 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,540 Sq Ft
20 Washington St, Brattleboro, VT 05301

20 Washington St, Brattleboro, VT 05301

/51
$1,525,000
- 3 Beds
- 2 Baths
- 2,498 Sq Ft
46 N Shore Rd, Chesterfield, NH 03462

Ultimate Lakeside Living at Spofford Lake. Experience luxury and comfort in this meticulously renovated, turn-key home on the prestigious Spofford Lake. Professionally Designed for year-round enjoyment, every detail has been carefully considered so you can move in and start making memories from day one. Full interior and exterior painting delivers a modern, cohesive look. All floors have been

Nancy Proctor BHG Masiello Keene

46 N Shore Rd, Chesterfield, NH 03462
/26
$207,000 Sold May 27, 2025
- 1,512 Sq Ft
- $137/SF
- 28 Days On Market
- 3 Beds
- 2 Baths
- Built 1920
9 Garden Dr, Brattleboro, VT 05301

***Offers due by Monday 4/28 at 3:00" Looking for an affordable home within walking distance to downtown Brattleboro? Come see this 8 room, 3+ bed, 2 full bath home. The 2nd floor has been updated with beautiful refinished floors, recent paint, updated bath and walkup attic with spray foam insulation. The 1st floor needs updates and repairs, but could shine as nicely as the 2nd floor! Replacement

Sue Beaudet EXP Realty

9 Garden Dr, Brattleboro, VT 05301

/27
Est $223,745 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 900 Sq Ft
10 Washington St, Brattleboro, VT 05301

10 Washington St, Brattleboro, VT 05301

/29
$285,000
- 4 Beds
- 1 Bath
- 1,466 Sq Ft
625 Plain Rd, Hinsdale, NH 03451

Welcome to 625 Plain Road, a spacious and charming 4-bedroom home set on a beautiful 1.11-acre open lot in scenic Hinsdale, New Hampshire. This property combines comfort, space, and convenience—perfect for anyone looking to enjoy a quiet country setting while staying close to town amenities. Step inside to find a warm and inviting layout with plenty of natural light. The expansive kitchen is

Bob Barnard Monadnock Realty Group LLC

625 Plain Rd, Hinsdale, NH 03451
/19
$345,000 Sold May 27, 2025
- 2,736 Sq Ft
- $126/SF
- 16 Days On Market
- 6 Beds
- 4 Baths
- Built 1890
99 Clark St, Brattleboro, VT 05301

High cash flow well maintained 4plex located in quaint Brattleboro neighborhood within proximity to the vibrant downtown, listed at a deep-value 11% cap rate. This 100% occupied building has 2x 2br and 2x1br, and a net operating income of ~38K with significant upside based on rents over 20% below market. A new owner can step into to yield over a 15% cash on cash return starting year 1, and

Michael Gilman 3GEN Real Estate Inc

99 Clark St, Brattleboro, VT 05301

/17
Est $300,899 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,927 Sq Ft
18 Central St, Brattleboro, VT 05301

18 Central St, Brattleboro, VT 05301

/10
$185,000
- 3 Beds
- 3 Baths
- 3,370 Sq Ft
148 Elliot St, Brattleboro, VT 05301

Spring Price Reduction! 3 One bedroom units and 4 single room occupancy units (SROs) w a shared bathroom and dishwashing area. Newer shingle roof on rear addition. The unfinished basement is spray foam insulated with a vapor barrier. Recent fire and safety inspection. Building needs a hands-on owner willing to take on some maintenance and improvements. Solid returns with opportunity to enhance

Steve Schoppmeyer BHG Masiello Brattleboro

148 Elliot St, Brattleboro, VT 05301

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