Vintage homes for sale & real estate in Bennington County, VT

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ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
This neat and tidy single story home has been completely renovated from top to bottom, offering comfort, efficiency, and style. Updates include all new metal roof, vinyl siding, thermopane windows, propane hot-air heating system with heat pump central air conditioning, appliances, kitchen cabinets, counters, and hardwood flooring. Also updated plumbing, fiber optic internet, new electrical with a 200-amp panel, and a standby propane generator—move-in ready with nothing left to do. The home features 2 bedrooms, a spacious full bath, an open living and dining room flowing seamlessly into the kitchen, a separate laundry room, and a convenient mudroom entry. Two inviting screened porches

$269,000

2 beds1 bath1,400 sq ft

3264 Route 153, West Rupert, VT 05776

Metal roof • Fiber optic internet • Vinyl siding

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ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
Captivating French Provincial architecture is the hallmark of this 6,800 sq. ft 1866 Manor House occupying a commanding and picturesque view over 94 acres of pristine pastoral fields and the distant Taconic Mountain Range. The timeless and beautifully proportioned interiors feature extensive molding, solid oak flooring, eight fireplaces, nine bedrooms, seven baths, country kitchen and adjoining pantry, formal dining and living rooms. The private estate includes a three car garage, 3 bedroom caretakers cottage, artist studio and gunite heated in-ground pool. Set on the outskirts of the historic town of Bennington offering shopping, live theatre, restaurants, horseback riding and proximity to

$1,950,000

9 beds6 baths6,956 sq ft

1086 West Rd, Bennington, VT 05201

Solid oak flooring • Extensive molding • Eight fireplaces

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
New Price! Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light graces this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining area just off the eat-in kitchen. The first floor laundry room, full bathroom, and a second bedroom round out the first floor. The second level features two additional bedrooms, a second bath and an office/ bonus space. Easy first-floor living and comfortable family flow. The full poured concrete base

$389,000

4 beds2 baths2,368 sq ft

263 Elm St, Shaftsbury, VT 05262

Large level backyard • New buderus boiler • Mountain view

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income. This well-maintained property boasts a number of recent updates, including a modern septic system. The fully fenced-in yard offers privacy and security, while the level lot ensures easy maintenance and ample parking for both tenants and guests. Located just far enough from the hustle and bustle of downtown Manchester, yet convenie

$549,000

2 beds2 baths3,478 sq ft

142 Mt Aeolus Rd, Manchester Center, VT 05255

Level lot • Modern septic system • Residential rental

ABOUT THIS HOME
Vintage Home for sale in Bennington County, VT:
Charming Downtown Victorian - Income Opportunity Meets Timeless Style Tucked behind the classic facade of this downtown Bennington gem lies an incredible opportunity-for homeowners and investors alike. Located in the heart of downtown on a street known for both professional and residential appeal, this Victorian-style duplex offers versatility, character, and reliable income potential. Each unit-one upstairs, one downstairs-offers over 1,140 square feet of well-maintained and tastefully furnished living space. All utilities are separate for each unit. Currently operating as a successful Airbnb with consistent 5-star reviews, this property is truly turnkey, ready to welcome guests or new own

$279,900

5 beds2 baths2,294 sq ft

218 Union St, Bennington, VT 05201

Separate utilities • Short term rentals • Turnkey property

Property at 3309 3321 Main St, Manchester, VT 05254, 11 beds, 7.5 baths

$1,300,000

11 beds7.5 baths9,560 sq ft

3309 3321 Main St, Manchester, VT 05254

Property at 2984 VT Route 153, Pawlet, VT 05761, 4 beds, 1 bath

$69,900

4 beds1 bath1,500 sq ft

2984 VT Route 153, Pawlet, VT 05761

Property at 24 VT Route 11, Londonderry, VT 05148, 6 beds, 7 baths

$895,000

6 beds7 baths5,764 sq ft

24 VT Route 11, Londonderry, VT 05148

Property at 6982 Main St, Readsboro, VT 05350, 9 beds

$250,000

9 beds— baths3,810 sq ft

6982 Main St, Readsboro, VT 05350

Property at 2 Cold Spring Rd, North Bennington, VT 05257, 5 beds, 2 baths

$725,000

5 beds2 baths2,424 sq ft

2 Cold Spring Rd, North Bennington, VT 05257

Property at 636 Tunnel St, Readsboro, VT 05350, 4 beds, 3 baths

$499,999

4 beds3 baths3,504 sq ft

636 Tunnel St, Readsboro, VT 05350

Property at 636 Dexter Rd, Shaftsbury, VT 05262, 4 beds, 3 baths

$985,000

4 beds3 baths2,462 sq ft

636 Dexter Rd, Shaftsbury, VT 05262

Property at 395 King Hill Rd, Readsboro, VT 05350, 5 beds, 1 bath

$1,200,000

5 beds1 bath2,228 sq ft

395 King Hill Rd, Readsboro, VT 05350

Property at 3888-3904 VT Route 7A, Arlington, VT 05250, 17 beds, 19 baths

$1,745,000

17 beds19 baths14,861 sq ft

3888-3904 VT Route 7A, Arlington, VT 05250

Property at 190 VT Route 11 #1, Peru, VT 05152, 3 beds, 2 baths

$625,000

3 beds2 baths1,894 sq ft

190 VT Route 11 #1, Peru, VT 05152

Property at 25 Mountain Haunts Rd, Bondville, VT 05340, 6 beds, 6.5 baths

$2,999,000

6 beds6.5 baths6,650 sq ft

25 Mountain Haunts Rd, Bondville, VT 05340

Property at 15 Wind Hill Rd, Manchester Center, VT 05255, 5 beds, 2 baths

$4,000,000

5 beds2 baths3,347 sq ft

15 Wind Hill Rd, Manchester Center, VT 05255

Property at 137-139 Park St, Bennington, VT 05201, 5 beds, 3 baths

$249,000

5 beds3 baths2,184 sq ft

137-139 Park St, Bennington, VT 05201

Property at 254 Union St, Bennington, VT 05201, 4 beds, 2 baths

$295,000

4 beds2 baths1,792 sq ft

254 Union St, Bennington, VT 05201

Property at 14 Robinson Ave, Bennington, VT 05201, 3 beds, 1 bath

$219,500

3 beds1 bath1,254 sq ft

14 Robinson Ave, Bennington, VT 05201

Property at 1677 Barnumville Rd, Manchester Center, VT 05255, 4 beds, 2.5 baths

$1,350,000

4 beds2.5 baths4,634 sq ft

1677 Barnumville Rd, Manchester Center, VT 05255

Property at 303-305 Gage St, Bennington, VT 05201, 6 beds, 2 baths

$225,000

6 beds2 baths2,112 sq ft

303-305 Gage St, Bennington, VT 05201

Property at 527 Benson Rd, Manchester Center, VT 05255, 5 beds, 4 baths

$4,975,000

5 beds4 baths6,998 sq ft

527 Benson Rd, Manchester Center, VT 05255

Property at 32-34 Sage St, North Bennington, VT 05257, 5 beds, 2 baths

$190,000

5 beds2 baths1,478 sq ft

32-34 Sage St, North Bennington, VT 05257

Property at 162 Highland Ave, Manchester Center, VT 05255, 5 beds, 3 baths

$599,000

5 beds3 baths3,836 sq ft

162 Highland Ave, Manchester Center, VT 05255

Property at 236-240 Grandview St, Bennington, VT 05201

$99,000

— beds— baths— sq ft

236-240 Grandview St, Bennington, VT 05201

Property at 2937 Dorset West Rd, Dorset, VT 05251

$399,500

— beds— baths— sq ft

2937 Dorset West Rd, Dorset, VT 05251

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Vintage Homes for Sale in Bennington County

There are currently 68 vintage homes for sale in Bennington County at a median listing price of $550K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Bennington County stay on the market for 87 days. This map is refreshed with the newest listings in Bennington County every 15 minutes.

In the past month, 38 homes have been sold in Bennington County. In addition to houses in Bennington County, there were also 30 condos, 1 townhouse, and 11 multi-family units for sale in Bennington County last month. Find your dream home in Bennington County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Bennington County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Bennington County. If you're looking to sell your home in the Bennington County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Bennington County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Sun Dec 14 2025 on the search page

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