Bennington, VT Homes

• 

  

  

  /43

  $119,900 Pending

  • Land
  • 26 Acres
  • $4,665 per Acre

  0000 Skiparee Rd, Pownal, VT 05261

  Gorgeous 25.7 acre parcel on a dead end road in Pownal, Vermont. This wooded lot offers many possibilities for a home site. Across a stream and up the logging road there is a large clearing that would offer great privacy, with the mountain behind you and great views to the south and east. A lot of opportunity for outdoors activities, homesteading, livestock and gardening. This lot makes the world

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 392-2133

  0000 Skiparee Rd, Pownal, VT 05261
• 

  

  

  /6

  $33,000 Sold Jul 25, 2025

  • Land
  • 2.50 Acres
  • $13,200 per Acre

  • 11 Days On Market

  0 White Oaks Rd, Pownal, VT 05261

  Nature lovers, rejoice! This 2.5-acre secluded lot, nestled up a dirt mountain road, offers unparalleled privacy and a haven for wildlife. Located in Pownal, between Williamstown, MA, and Bennington, VT, this mostly level lot provides a potential ideal building site. You'll be just minutes away from incredible walking trails, including the Dome Trailhead, Agawam Trail, Broad Brook Trailhead,

  Matt Waddington Hoffman Real Estate

  0 White Oaks Rd, Pownal, VT 05261
• 

  

  

  /22

  Est $280,658 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,048 Sq Ft

  494 Atwood Dr, Pownal, VT 05261

  494 Atwood Dr, Pownal, VT 05261
• 

  

  

  /36

  $199,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1211 Carpenter Hill Rd, Bennington, VT 05201

  Charming, fully furnished woodland retreat on over 3.5 acres with sweeping mountain views. This private getaway features two cozy cabins, each with a sleeping loft, warm wood finishes, and rustic charm. The main cabin includes a vaulted living area with exposed beams, a wood stove, vintage-style kitchen, and a spacious deck with built-in seating.The second cabin offers flexible space for guests,

  

  Peter West

  BISHOP WEST REAL ESTATE

  (802) 278-9529

  1211 Carpenter Hill Rd, Bennington, VT 05201
• 

  

  

  /11

  $163,000 Sold Jul 18, 2025

  • 780 Sq Ft
  • $209/SF
  • 70 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1937

  237 Church St, Pownal, VT 05261

  Cute 2 bedroom, 1 bath home in Pownal with small, easily maintainable lot. convenient to Williamstown and North Adams as well as Bennington. Needs some finishing touches and TLC.

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  237 Church St, Pownal, VT 05261
• 

  

  /36

  Est $693,988 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 7,102 Sq Ft

  134 Grapevine Ln, Pownal, VT 05261

  134 Grapevine Ln, Pownal, VT 05261
• 

  

  /32

  $55,000 Pending

  • 5 Beds
  • 2 Baths
  • 2,204 Sq Ft

  339 S Stream Rd, Pownal, VT 05261

  Built in 1890, this was previously a 9 room home with 5 bedrooms and 2,204 square feet of living space with an attached barn/garage. The property has been 'gutted' and is ready to be renovated from the studs. The foundation needs some work but might be able to be reused and you already have framing and siding to work with along with electrical service to the house. No information is known about

  

  Lisa Friedman

  Great American Dream Realty

  (802) 541-5859

  339 S Stream Rd, Pownal, VT 05261
• 

  

  /16

  $310,000 Sold Jun 27, 2025

  • 1,152 Sq Ft
  • $269/SF
  • 56 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2006

  89 Field Way, Pownal, VT 05261

  Discover your private mountain sanctuary in this charming post-and-beam home with breathtaking views of the Taconic Mountains. Stunning sunrises are visible from the primary bedroom and living area. The versatile loft offers space for a home office, reading nook, or guest accommodation. This unique property seamlessly blends its rustic charm with modern amenities, including solar panels,

  Lori Hurley Four Corner Properties LLC

  89 Field Way, Pownal, VT 05261
• 

  

  /15

  Est $509,897 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,856 Sq Ft

  371 Schenkar Rd, Pownal, VT 05261

  371 Schenkar Rd, Pownal, VT 05261
• 

  

  /59

  $745,000 Under Contract

  • 4 Beds
  • 4 Baths
  • 4,844 Sq Ft

  422 N Mason Hill Rd, Pownal, VT 05261

  At the end of a tree lined drive this country Contemporary awaits you, situated on a private 10 acre parcel with stone walls, mature perennials, and a mix of lawn and woods. The main level enjoys an open floor plan, perfect for entertaining; cooks kitchen with gas range, stainless appliances, pantry cabinets as well as a butler's pantry anchors the space. The two-story fieldstone hearth with

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 483-8151

  422 N Mason Hill Rd, Pownal, VT 05261
• 

  

  /37

  $202,500 Sold Jun 18, 2025

  • 1,912 Sq Ft
  • $106/SF
  • 69 Days On Market

  • 6 Beds
  • 3 Baths
  • Built 1963

  20 Oak Hill School Rd, Pownal, VT 05261

  Check out this excellent investment opportunity! Buyer can keep all units rented as an investment or live in one unit and rent the other two to help cover expenses of homeownership. This three-unit apartment building located in a desirable neighborhood in beautiful Southern VT! This property features a spacious main level unit that has had some updates. Unit has 2-bedrooms and 1 bathroom. Recent

  Floyd Amidon Maple Leaf Realty

  20 Oak Hill School Rd, Pownal, VT 05261
• 

  

  /18

  Est $215,335 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,012 Sq Ft

  9 Palmer Dr, Pownal, VT 05261

  9 Palmer Dr, Pownal, VT 05261
• 

  

  /62

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  679 Middle Pownal Rd, Pownal, VT 05261

  Nestled in the heart of rural Pownal, this beautifully renovated 4-bedroom, 3-bath home offers the perfect blend of modern comfort and peaceful countryside living. Set on 12.1 picturesque acres, the property features a mix of open level land and serene wooded areas, ideal for hobby farming, equestrian use, or simply enjoying nature. Inside, you'll find a spacious and thoughtfully designed layout

  

  Erin Vincent

  BISHOP WEST REAL ESTATE

  (802) 636-6092

  679 Middle Pownal Rd, Pownal, VT 05261
• 

  

  /43

  $401,000 Sold May 23, 2025

  • 2,692 Sq Ft
  • $149/SF
  • 124 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1932

  515 Hillside Dr, Pownal, VT 05261

  Discover Your Perfect Getaway at Verdmont...If you're a nature enthusiast, an exclusive opportunity awaits you at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this prestigious gated club offers nearly 500 acres of pristine wilderness. As a shareholder, you'll have access to a variety of exceptional amenities. *Water and Land Privilege: Enjoy two beautiful

  Kelley Mccarthy Mahar McCarthy Real Estate

  515 Hillside Dr, Pownal, VT 05261
• 

  

  /24

  Est $274,229 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,248 Sq Ft

  382 B Hill Rd, Pownal, VT 05261

  382 B Hill Rd, Pownal, VT 05261
• 

  

  /21

  $175,000

  • Land
  • 18 Acres
  • $9,749 per Acre

  0 U S 7, Pownal, VT 05261

  Beautiful Pownal Valley views from almost wherever you stand on this 17.95 acre parcel. Zoned for commercial use along the road frontage and rural residential in back creates opportunities for different types of development.

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 327-8230

  0 U S 7, Pownal, VT 05261
• 

  

  /42

  $230,500 Sold May 12, 2025

  • 1,144 Sq Ft
  • $201/SF
  • 36 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2009

  225 N Pownal Rd, North Pownal, VT 05260

  Clean and bright one-story home with 3 bedrooms and 2 bathrooms. Easy living with everything all on one level. Semi-open concept living room and kitchen/dining. Tons of cabinets and counter space in the kitchen, an island with seating for two, plus room for a small dining table. Appliances are included, so you can move right in and start cooking. Or step out to the huge back deck to grill

  Jenifer Prouty Hoffman Hoffman Real Estate

  225 N Pownal Rd, North Pownal, VT 05260
• 

  

  /28

  Est $347,090 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,751 Sq Ft

  469 Swallow Hill Rd, Pownal, VT 05261

  469 Swallow Hill Rd, Pownal, VT 05261
• 

  /2

  $20,000

  • Land
  • 3.00 Acres
  • $6,667 per Acre

  0 U S 7, Pownal, VT 05261

  3 acre parcel located behind other parcels. Would be a great place for a hunting "camp", blind or recreation. Right of Way is from 63 Metcalfe Road, Pownal.

  

  Max Squiers

  KW Vermont - Brenda Jones Real Estate Group

  (802) 210-3911

  0 U S 7, Pownal, VT 05261
• 

  

  /59

  $145,000 Sold Apr 25, 2025

  • 3,024 Sq Ft
  • $48/SF
  • 28 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2010

  663 Sweet Rd, Pownal, VT 05261

  If you are looking for a secluded home with views but also close to shopping, dining and activities, this may be the perfect home. This home offers 2 bedrooms, 2 full bathrooms, living room, dining room and laundry on the main level. The 2nd story is ready to be finished with 2additional bedrooms and a family/bonus room that fits buyer’s needs. There is a full walkout basement that provides great

  Floyd Amidon Maple Leaf Realty

  663 Sweet Rd, Pownal, VT 05261
• 

  

  /23

  Est $358,534 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft

  393 Grapevine Ln, Pownal, VT 05261

  393 Grapevine Ln, Pownal, VT 05261
• 

  

  /41

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,542 Sq Ft

  509 Thompson Pond Rd, Pownal, VT 05261

  Discover Your Perfect Getaway at Verdmont If you're a nature enthusiast, a rare and exclusive opportunity awaits at the Verdmont Outing Club. Nestled in the heart of the Green Mountain Preserve, this gated community spans nearly 500 acres of unspoiled wilderness-a true haven for outdoor living.As a shareholder, you'll enjoy a wealth of amenities: Water & Land Privileges: Two stunning

  Kelley Mccarthy Mahar McCarthy Real Estate

  509 Thompson Pond Rd, Pownal, VT 05261
• 

  

  /24

  $385,000 Sold Apr 16, 2025

  • 1,624 Sq Ft
  • $237/SF
  • 50 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1922

  78 Middle Pownal Rd, Pownal, VT 05261

  Gorgeous Farmhouse on 2.3 +/- acres in Pownal. Well decorated, landscaped and maintained. Inside you will find 3 bedrooms, 1 and a half bathrooms, living room, formal dining room and well appointed kitchen. Oozing with charm and features. Main level laundry, 2 mini splits, stamped concrete walkway, sitting porch, rear deck, pond, storage shed and barn. Also has a 2 car detached garage and open

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  78 Middle Pownal Rd, Pownal, VT 05261
• 

  

  /39

  Est $418,789 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,208 Sq Ft

  375 Grapevine Ln, Pownal, VT 05261

  375 Grapevine Ln, Pownal, VT 05261
• 

  

  /34

  $279,900

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft

  3530 Vt Route 346, Pownal, VT 05261

  This historic house, built in 1880, is nestled in the quiet village of North Pownal. It is situated on a large, level lot and offers the timeless charm of yesteryear. The first floor features a roomy kitchen with Kenmore Plus Stainless-Steel appliances, an open-concept living room and dining room, an updated bathroom, and a convenient first-floor laundry room. The back porch has been partially

  Matt Waddington Hoffman Real Estate

  3530 Vt Route 346, Pownal, VT 05261
• 

  

  /27

  $285,000 Sold Apr 03, 2025

  • 2,128 Sq Ft
  • $134/SF
  • 193 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1900

  46 NW Hill Rd, Pownal, VT 05261

  Welcome to this stunning waterfront 1900 Colonial home, boasting three bedrooms and two bathrooms, situated on a charming 0.25 acre lot.The heart of the home is in the kitchen, perfect for entertaining, featuring granite countertops, a beautiful coffee bar, and great waterfront views from the breakfast bar.The family room excudes warmth and charm with a stone wood fireplace built from

  Brooke Thomson Drew Mahar McCarthy Real Estate

  46 NW Hill Rd, Pownal, VT 05261
• 

  

  /38

  Est $346,231 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,176 Sq Ft

  205 W Meadow Ct, Pownal, VT 05261

  205 W Meadow Ct, Pownal, VT 05261
• 

  

  /33

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,666 Sq Ft

  379 Swallow Hill Rd, Pownal, VT 05261

  Welcome home! Tucked away on over 2.6 private and partially wooded acres in the exclusive and tight-knit Swallow Hill neighborhood, this stunning 3-bedroom, 1.5-bath home offers modern comfort and rustic charm in a serene natural setting in Southern Vermont.Step inside to soaring cathedral ceilings, exposed wood beams, and an abundance of Vermont beauty pouring in through large windows.

  Cassie Barbeau Mahar McCarthy Real Estate

  379 Swallow Hill Rd, Pownal, VT 05261
• 

  

  /24

  $148,000 Sold Mar 12, 2025

  • 816 Sq Ft
  • $181/SF
  • 6 Days On Market

  • 1 Bed
  • Built 1900

  354 NW Hill Rd, Pownal, VT 05261

  Welcome to your sanctuary of relaxation. Inside and out, you’ll find welcoming, modern design that perfectly pairs form and function. Inside is stylish and contemporary. The main floor has a renovated kitchen, dining room, living room, full bath, den leading to the deck, and a small staircase to the sleeping loft. The loft has a closet and offers enough room for a dresser and a queen-sized bed.

  Nicholas Charest Maple Leaf Realty

  354 NW Hill Rd, Pownal, VT 05261
• 

  

  /37

  Est $255,618 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,482 Sq Ft

  195 W Meadow Ct, Pownal, VT 05261

  195 W Meadow Ct, Pownal, VT 05261
• 

  

  /49

  $325,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  93 Pace Rd, Bennington, VT 05201

  Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about

  Harvey Roettinger RE/MAX North Professionals

  93 Pace Rd, Bennington, VT 05201
• 

  

  /12

  $53,700 Sold Mar 12, 2025

  • Land
  • 10 Acres
  • $5,301 per Acre

  • 126 Days On Market

  0 Mason Hill Rd N Unit 5016657, Pownal, VT 05261

  If you're looking for a country setting for your future home in Southern Vermont, come check this out! 10 acres close to Bennington and to Williamstown, Massachusetts - easy access to route 7 - and on a quiet country back road in beautiful Pownal Vermont! A gently upsloping parcel with plenty of room for you to build your dream home and create some trails to walk your dog or just enjoy nature or

  Duncan Honig Maple Leaf Realty

  0 Mason Hill Rd N Unit 5016657, Pownal, VT 05261
• 

  

  /38

  Est $269,716 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,156 Sq Ft

  543 Skyboro Rd E, Pownal, VT 05261

  543 Skyboro Rd E, Pownal, VT 05261
• 

  

  /34

  $349,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  224 Burrington Rd, Pownal, VT 05261

  Privately nestled on 5 wooded acres, this charming 3-bedroom, 2-bath home offers a peaceful retreat surrounded by nature. Step into the great room and take in the warmth of the beautiful fireplace or relax in the stunning 603-square-foot insulated, enclosed porch with a wall of windows that make you feel like you're perched in the trees.The lower level offers a fantastic workspace that was

  Kelley Mccarthy Mahar McCarthy Real Estate

  224 Burrington Rd, Pownal, VT 05261
• 

  

  /48

  $395,000 Sold Jan 30, 2025

  • 7,000 Sq Ft
  • $56/SF
  • 94 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1898

  3310 Vt Rte 346, North Pownal, VT 05260

  Former Church Offers So Many Opportunities. What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging?

  Paul Harsch HARSCH ASSOCIATES

  3310 Vt Rte 346, North Pownal, VT 05260
• 

  

  /40

  Est $347,015 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,052 Sq Ft

  46 Grapevine Ln, Pownal, VT 05261

  46 Grapevine Ln, Pownal, VT 05261
• 

  

  /36

  $575,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,982 Sq Ft

  556 Mann Hill Rd S, Pownal, VT 05261

  The simple two-story Vermont farmhouse with its two original barns enjoys views, privacy, serenity, and all the outdoor space one could need to enjoy farming on a small scale or to allow the adjacent farmer to continue haying the large fields. There majority of the land is wooded and offers all sorts of options from leaving nature alone, to trails, to harvesting timber. The house is relatively

  Paul Harsch Harsch Associates

  556 Mann Hill Rd S, Pownal, VT 05261
• 

  

  /46

  $395,000 Sold Jan 30, 2025

  • 6,686 Sq Ft
  • $59/SF
  • 94 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1898

  3310 Vt Route 346, Pownal, VT 05261

  What might be your dream or requirements? This 1889 Church located in the quiet country village of North Pownal, Vermont, could fill them, however big or small. A single family home for all seasons and celebrations? A wedding venue? A place to live and work, rolled into one with plenty of space no matter what you do, from sculpting to computer imaging? This amazing building has so many

  Paul Harsch Harsch Associates

  3310 Vt Route 346, Pownal, VT 05261
• 

  

  /27

  Est $562,955 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,022 Sq Ft

  503 Atwood Dr, Pownal, VT 05261

  503 Atwood Dr, Pownal, VT 05261
• 

  

  /41

  $379,900 Under Contract

  • 2 Beds
  • 3 Baths
  • 1,761 Sq Ft

  653 Skyboro Rd E, Pownal, VT 05261

  Pristine and perfect. This 2 bedroom, 3 bath home is situated on 2 acres in Pownal. Offering Eat-in Kitchen, living room with fireplace, primary bedroom with private bath, secondary bedroom with private bath, basement family room and laundry room and more. Outside a wonderful sitting deck and patio, a heated 2 car detached garage with shop space, well landscaped yard with garden space and shed.

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  653 Skyboro Rd E, Pownal, VT 05261

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