Bennington County, VT Homes

/7
$55,000
- Land
- 22,215 Sq Ft
- $107,843 per Acre
24 Asa's Way, Bennington, VT 05257

Build your future in the heart of North Bennington at 24 Asa's Way. This 0.51 acre corner lot offers a rare opportunity to create a custom home in a well established neighborhood surrounded by beautifully maintained properties. With mountain views and underground utilities already in place, the setting combines natural beauty with modern convenience.Public water and sewer are available,

Brooke Thomson Drew

Mahar McCarthy Real Estate

24 Asa's Way, Bennington, VT 05257
/26
$20,000 Per Month
- 3 Beds
- 3.5 Baths
- 1,994 Sq Ft
- Condo for Rent
39 Sage Hill Rd Unit 25, Manchester, VT 05255

WINTER SEASONAL RENTAL: 12/1/26 to 3/31/2027Location is everything, and Torbank’s condominiums are the perfect choice! Just minutes from the heart of Manchester, Southern Vermont’s premier destination, you’ll have easy access to boutique shopping, dining, medical services, and year-round activities. In the winter, enjoy the convenience of nearby skiing at Bromley Mountain Ski Resort and

Kristin Comeau

TPW Real Estate

39 Sage Hill Rd Unit 25, Manchester, VT 05255
/36
$277,737

Sold Feb 18, 2026

109 Watershed Rd, Woodford, VT 05201
- 3 Beds
- 2 Baths
- 1,782 Sq Ft
- Built 1992
Last Sold Summary
- 7% Below List Price
- $156/SF
- 9 Days On Market
Last Listing Agent Faith Rhodes Maple Leaf Real Estate

109 Watershed Rd, Woodford, VT 05201

/22
Est $461,887

Not Listed For Sale

163 Vt Route 30, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,590 Sq Ft
- Built 1970
163 Vt Route 30, Winhall, VT 05340

Last Sold Summary
- 13 Days On Market
Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

/40
$305,000

Pending
- 3 Beds
- 2.5 Baths
- 1,378 Sq Ft
61 E Branch Farms Unit 1, Manchester Center, VT 05255

East Branch Farms is in the most convenient location! This 3 bedroom and 2 and a half bath condo is ready for its next owners. Wood floors on the main level and new granite countertops in the kitchen. Full basement with both interior and exterior access for workshop space or extra storage. Located at the edge of lovely Manchester VT it is privately screened from the road with views of soaring

Alison Cummings

Cummings & Co

61 E Branch Farms Unit 1, Manchester Center, VT 05255
/6
$1,050

Total Monthly Price
- 2 Beds
- 1 Bath
- 100 Sq Ft
- Condo for Rent
110 Short St Unit 3, Bennington, VT 05201

2 bed 1 bath unit. First, last, security required at least signing. Credit and background checks required. No smoking. No pets.

110 Short St Unit 3, Bennington, VT 05201
/11
$162,500

Sold Sep 04, 2026

905 County St, Bennington, VT 05201
- 4 Beds
- 2 Baths
- 2,643 Sq Ft
- Built 1920
Last Sold Summary
- 5% Above List Price
- $61/SF
- 14 Days On Market
Current Estimated Value $163,622

Last Listing Agent Max Squiers KW Vermont - Brenda Jones Real Estate Group

905 County St, Bennington, VT 05201

/19
Est $217,053

Not Listed For Sale

42 Colvin Ave, Shaftsbury, VT 05262
- 3 Beds
- 1 Bath
- 952 Sq Ft
- Built 1964
42 Colvin Ave, Shaftsbury, VT 05262

Last Sold Summary
- 28 Days On Market
Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

/13
$229,000
- Land
- 0 Sq Ft
468 Skyboro Rd, Pownal, VT 05261

835+ FEET OF ROAD FRONTAGE 10+ ACRES - SUBDIVISION POTENTIAL!Developer and investor opportunity in Pownal, Vermont! This 10+ acre parcel offers approximately 835.9 feet of road frontage on Skyboro Road, providing valuable flexibility for evaluating potential homesites, and future development. The combination of acreage and exceptional road frontage creates an opportunity to explore

Sheryl Morehouse

BISHOP WEST REAL ESTATE

468 Skyboro Rd, Pownal, VT 05261
/24
$3,200 Per Month
- 4 Beds
- 2 Baths
- 1,950 Sq Ft
- House for Rent
78 Franklin Rd, Manchester, VT 05255

WINTER RENTAL ONLY! 11/15/26 to 4/15/27'Tis the season, well, almost. Winter is just around the corner, and this classic, 1920s Vermont home awaits your stay. This traditional Manchester Village home is fully furnished and ready for your Winter Season rental. Just 20 minutes from Bromley Mountain Ski Resort and 35 minutes to Stratton Ski ResortTurn off your electronics, curl up with a

Kristin Comeau

TPW Real Estate

78 Franklin Rd, Manchester, VT 05255
/18
$238,000

Sold Aug 13, 2026

19 Winhall Condo Rd Unit 1, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,020 Sq Ft
- Built 1978
Last Sold Summary
- 4% Below List Price
- $233/SF
- 28 Days On Market
Last Listing Agent Cheyanne Pugliese

19 Winhall Condo Rd Unit 1, Winhall, VT 05340

/49
Est $605,412

Not Listed For Sale

199 North Rd, Shaftsbury, VT 05262
- 3 Beds
- 2 Baths
- 3,278 Sq Ft
- Built 1970
199 North Rd, Shaftsbury, VT 05262

Last Sold Summary
- 7 Days On Market
Last Listing Agent Timothy Corcoran Mahar McCarthy Real Estate

/5
$55,000
- Land
- 20,908 Sq Ft
- $114,583 per Acre
29 Asa's Way, Bennington, VT 05257

Build your dream home at 29 Asa's Way, ideally situated at the top of the hill in a desirable North Bennington neighborhood. This 0.48 acre lot offers a level, build friendly setting with beautiful mountain views, providing the perfect backdrop for your future home.Public water and sewer are available, along with underground utilities, making for a smooth and efficient building process.

Brooke Thomson Drew

Mahar McCarthy Real Estate

29 Asa's Way, Bennington, VT 05257
/17
$1,895 Per Month
- 2 Beds
- 1 Bath
- 850 Sq Ft
- Townhouse for Rent
61 Luge Run, East Dorset, VT 32751

Property Id: 2912257 Newly renovated downstairs apartment in historic East Dorset, quiet location as upstairs tenants seldom home. 2 Bedrooms, one bath. Gas fireplace. Located on part of the original Mad Tom Apple Orchard from the turn of the 20th century. Fenced back field boards horses at the moment but they will be gone in November. Manchester Center is 10 minutes away and there is a

61 Luge Run, East Dorset, VT 32751
/38
$437,000

Sold Sep 03, 2026

60 Murray Hill Heights Rd Unit 23, Manchester, VT 05255
- 3 Beds
- 2.5 Baths
- 1,596 Sq Ft
- Built 1980
Last Sold Summary
- 3% Below List Price
- $274/SF
- 10 Days On Market
Last Listing Agent Kristin Comeau TPW Real Estate

60 Murray Hill Heights Rd Unit 23, Manchester, VT 05255

/53
Est $640,000

Not Listed For Sale

23 Mechanic St, North Bennington, VT 05257
- 4 Beds
- 2.5 Baths
- 2,456 Sq Ft
- Built 1870
23 Mechanic St, North Bennington, VT 05257

Last Sold Summary
- 40 Days On Market
Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

/31
$595,000
- Land
- 23.62 Acres
- $25,191 per Acre
3213 West Rd, Bennington, VT 05201

Some properties offer acreage, some offer breathtaking views, very few offer both along with a rich history worth preserving and a future waiting to be imagined. For generations, this rare south-facing farm has looked across the valley enjoying sunlight from dawn until dusk & panoramic views that are exceptional! More than productive farmland, it became a place where neighbors and families

Monique Geannelis

Mahar McCarthy Real Estate

3213 West Rd, Bennington, VT 05201
/16
$5,500 Per Month
- 4 Beds
- 3 Baths
- 2,400 Sq Ft
- Townhouse for Rent
556 Equinox On the Battenkill Unit J-11, Manchester, VT 05254

SUMMER RENTAL 2027 - EQUINOX ON THE BATTENKILLThere is so much to offer! This sought-after four-bedroom EOB townhome is now available for a summer seasonal rental. EOB amenities include tennis, pickleball, pool, and clubhouse privileges. Enjoy all that Manchester and the Mountains have to offer. We have the Manchester Music Festival, The Vermont Summer Festival, the Dorset Theatre, the

Kristin Comeau

TPW Real Estate

556 Equinox On the Battenkill Unit J-11, Manchester, VT 05254
/28
$585,000

Sold Mar 12, 2026

550 Finbars Forest Rd, Manchester Center, VT 05255
- 3 Beds
- 2 Baths
- 1,958 Sq Ft
- Built 1999
Last Sold Summary
- 14% Below List Price
- $299/SF
- 142 Days On Market
Current Estimated Value $601,686

Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

550 Finbars Forest Rd, Manchester Center, VT 05255

/47
Est $286,817

Not Listed For Sale

120 Imperial Ave, Bennington, VT 05201
- 4 Beds
- 2.5 Baths
- 2,404 Sq Ft
- Built 1895
120 Imperial Ave, Bennington, VT 05201

Last Sold Summary
- 114 Days On Market
Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

/60
$995,000
- 5 Beds
- 5 Baths
- 4,126 Sq Ft
238 Seminary Ave, Manchester, VT 05254

Manchester Village LivingExperience the charm of village life in this expansive Victorian home and guest cottage, ideally located in the heart of Manchester Village. Rich in character and architectural detail, the home features original woodwork, soaring ceilings, generously sized rooms, and timeless New England appeal—enhanced by a new roof, windows and heating system.The spacious main

Margretta Fischer

Wohler Realty Group

238 Seminary Ave, Manchester, VT 05254
/20
$4,000 Per Month
- 4 Beds
- 3 Baths
- 2,688 Sq Ft
- Condo for Rent
67 Valley Pass, Manchester, VT 05255

Welcome to 67 Valley Pass Road, where your new Vermont home awaits. This stylish split level ranch has been meticulously maintained and is move in ready. Offering 4 bedrooms and 3 full bathrooms, the home features a spacious primary suite with a private en suite bathroom. The upper level boasts an updated open concept kitchen and dining area with an easy flowing layout, perfect for everyday

67 Valley Pass, Manchester, VT 05255
/39
$215,000

Sold Jul 21, 2026

215 Orchard St, Pownal, VT 05261
- 2 Beds
- 1 Bath
- 988 Sq Ft
- Built 1953
Last Sold Summary
- 2% Below List Price
- $218/SF
- 37 Days On Market
Current Estimated Value $215,605

Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

215 Orchard St, Pownal, VT 05261

/35
Est $241,012

Not Listed For Sale

115 Jefferson Ave, Bennington, VT 05201
- 2 Beds
- 2 Baths
- 1,554 Sq Ft
- Built 1930
115 Jefferson Ave, Bennington, VT 05201

Last Sold Summary
- 83 Days On Market
Last Listing Agent Kelley Mccarthy Mahar McCarthy Real Estate

/52
$685,000

$95K PRICE DROP Under Contract
- 4 Beds
- 4.5 Baths
- 3,423 Sq Ft
85 Limerick Ln Unit A & B, Arlington, VT 05250

Seller is offering a credit to buyers of $5000 towards closing costs at closing.• Battenkill River Frontage – Enjoy direct access to the Battenkill River, 8 shared acres, and a prime location just minutes from Manchester’s shopping, dining, skiing, biking, and hiking.• Spacious & Flexible – Light-filled 4-bedroom, 5-bath home with quality finishes, a private apartment, multiple

Margretta Fischer

Wohler Realty Group

85 Limerick Ln Unit A & B, Arlington, VT 05250
/20
$2,500 Per Month
- 3 Beds
- 2 Baths
- 1,635 Sq Ft
- Condo for Rent
293 Barnumville Rd, Manchester, VT 05255

3 bed, 2 bath house. Great location right in Manchester with all the amenities! Eat in kitchen with dishwasher, living room, garage, basement, washer & dryer, screened in back porch, backyard, perennial flower garden, walking distance to Manchester Center. House comes furnished except for the kitchen...must bring all kitchenware/necessities. Enjoy lunch/dinner or working from home on the

293 Barnumville Rd, Manchester, VT 05255
/17
$59,900

Sold Jul 31, 2026

0 Sunset Hill Rd Unit B, Pownal, VT 05261
- Land
- 2.38 Acres
- $25,168 per Acre
Last Sold Summary
- 20% Below List Price
- 227 Days On Market
Last Listing Agent Terri Edgerley Edge Realty Vermont

0 Sunset Hill Rd Unit B, Pownal, VT 05261

/33
Est $398,782

Not Listed For Sale

60 Knoll Crest Ln, Bennington, VT 05201
- 4 Beds
- 2 Baths
- 2,072 Sq Ft
- Built 1948
60 Knoll Crest Ln, Bennington, VT 05201

Last Sold Summary
- 22 Days On Market
Last Listing Agent Moira Spivey Four Seasons Sotheby's Int'l Realty

/3
$45,000

Pending
- Land
- 3.67 Acres
- $12,262 per Acre
0 Grapevine Ln Unit 5109674, Pownal, VT 05261

A rare land opportunity in Pownal!3.67 acres on a beautiful, peaceful road with so many possibilities. Whether you’ve been dreaming of building your own home or you’re looking for a private piece of Vermont land to enjoy for hunting, recreation, or simply having a place of your own, this property is worth taking a look at.On-site well and septic will be needed.This property hasn’t

Brooke Thomson Drew

Mahar McCarthy Real Estate

0 Grapevine Ln Unit 5109674, Pownal, VT 05261
/6
$950 Per Month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Condo for Rent
103 County St Unit 2, Bennington, VT 05201

Property Id: 810906 1 bedroom apartment is located on second floor.Month to month lease where tenants pay for their utilities such as heat electric etc..

103 County St Unit 2, Bennington, VT 05201
/48
$295,000

Sold Jul 22, 2026

166 Cardinal Ln, Bennington, VT 05201
- 3 Beds
- 2 Baths
- 2,753 Sq Ft
- Built 1964
Last Sold Summary
- $107/SF
- 16 Days On Market
Current Estimated Value $303,218

Last Listing Agent Monique Geannelis Mahar McCarthy Real Estate

166 Cardinal Ln, Bennington, VT 05201

/38
Est $680,403

Not Listed For Sale

359 Hickory Hill Rd, Bennington, VT 05201
- 3 Beds
- 2.5 Baths
- 2,184 Sq Ft
- Built 2004
359 Hickory Hill Rd, Bennington, VT 05201

Last Sold Summary
- 71 Days On Market
Last Listing Agent Brooke Thomson Drew Mahar McCarthy Real Estate

/38
$299,000

$26K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,829 Sq Ft
89 Merson St, Woodford, VT 05201

Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

Brooke Thomson Drew

Mahar McCarthy Real Estate

89 Merson St, Woodford, VT 05201
/57
$4,000 Per Month
- 3 Beds
- 2.5 Baths
- 1,906 Sq Ft
- Townhouse for Rent
55 Murray Hill Woods Unit 49, Manchester, VT 05255

This lovely 3-bedroom plus loft, 2.5-bath condominium comfortably sleeps up to 8 people and is conveniently located in Manchester, within walking distance of shops, restaurants, and local amenities. The home features a fully renovated kitchen with stainless steel appliances, a 4-seat breakfast bar, and beautiful wood floors throughout the main living area. The inviting living room offers a cozy

Laura Beckwith Josiah Allen Real Estate, Inc.

55 Murray Hill Woods Unit 49, Manchester, VT 05255
/60
$825,000

Sold Jul 24, 2026

1731 Three Maple Dr, Manchester Center, VT 05255
- 4 Beds
- 3.5 Baths
- 3,237 Sq Ft
- Built 1971
Last Sold Summary
- 6% Below List Price
- $255/SF
- 23 Days On Market
Current Estimated Value $839,379

Last Listing Agent David Citron RE/MAX Four Seasons

1731 Three Maple Dr, Manchester Center, VT 05255

/19
Est $267,332

Not Listed For Sale

20 Rockwood St, Bennington, VT 05201
- 3 Beds
- 1 Bath
- 1,070 Sq Ft
- Built 1990
20 Rockwood St, Bennington, VT 05201

Last Sold Summary
- 4 Days On Market
Last Listing Agent Vicki Wilson Maple Leaf Real Estate

/33
$249,000

$50K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,408 Sq Ft
8 West St, Bennington, VT 05201

Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

Brooke Thomson Drew

Mahar McCarthy Real Estate

8 West St, Bennington, VT 05201
/26
$1,750

Total Monthly Price
- 3 Beds
- 1 Bath
- 1,500 Sq Ft
- Condo for Rent
9 Mechanic St Unit B, North Bennington, VT 05257

9 Mechanic St Unit B, North Bennington, VT 05257
/30
$345,750

Sold Oct 21, 2025

374 Overlea Rd, North Bennington, VT 05257
- 3 Beds
- 2 Baths
- 1,753 Sq Ft
- Built 1948
Last Sold Summary
- 5% Below List Price
- $197/SF
- 58 Days On Market
Current Estimated Value $346,361

Last Listing Agent Gregory Cutler Four Seasons Sotheby's Int'l Realty

374 Overlea Rd, North Bennington, VT 05257

/57
Est $206,782

Not Listed For Sale

100 Webb St, Bennington, VT 05201
- 3 Beds
- 1 Bath
- 1,416 Sq Ft
- Built 1943
100 Webb St, Bennington, VT 05201

Last Sold Summary
- 75 Days On Market
Last Listing Agent Lindsey Martin Maple Leaf Real Estate

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