266

Bennington County VT Homes for Sale

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  • /20

    $399,000

    • 3 Beds
    • 2 Baths
    • 1,225 Sq Ft

    16B Bromley Knolls Rd Unit B, Winhall, VT 05340

    TURN-KEY VERMONT MOUNTAIN RETREAT JUST MINUTES FROM BROMLEY & STRATTON!Beautifully renovated in 2021, this fully furnished 3-bedroom, 2-bath condominium offers the perfect combination of Vermont charm, modern comfort, and year-round recreation. Located just one minute from Bromley Mountain and approximately ten minutes from Stratton, this property is ideally situated for skiing, hiking,

    Jason Saphire www.HomeZu.com

    16B Bromley Knolls Rd Unit B, Winhall, VT 05340
  • /41

    $910,000

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,031 Sq Ft

    7 Roundtree Rd, Winhall, VT 05340

    Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes, this property offers the best of Stratton living in every season.Step

    Bob Maisey Berkshire Hathaway HomeServices Stratton Home

    7 Roundtree Rd, Winhall, VT 05340
  • /45

    $490,642

    $8K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,708 Sq Ft

    145 Oberdorf Rd, Readsboro, VT 05350

    Welcome to Alpenwald Village, a peaceful mountain community in scenic Readsboro, Vermont. This charming 4 bedroom chalet sits on 2 private acres and offers the perfect blend of comfort, style, and access to Vermont’s four-season lifestyle. Whether you're searching for a full-time residence or the ideal vacation getaway, this beautifully updated home delivers. Step inside to discover thoughtful

    Evan Russell Real Broker LLC

    145 Oberdorf Rd, Readsboro, VT 05350
  • /60

    $695,000

    • 4 Beds
    • 2 Baths
    • 1,614 Sq Ft

    515 Quarry Rd, Bennington, VT 05201

    Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

    Vicki Wilson Maple Leaf Real Estate

    515 Quarry Rd, Bennington, VT 05201
  • /60

    $5,575,000

    • 7 Beds
    • 9.5 Baths
    • 9,915 Sq Ft

    159 Winhall Hollow Rd, Bondville, VT 05340

    Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line. A sweeping private drive sets the tone for an extraordinary arrival; open meadows, a serene pond, and beautifully preserved grounds before revealing the 9915 SF residence itself and massive barn. There's an immediate sense of

    Kim Morgan-Wohler Wohler Realty Group

    159 Winhall Hollow Rd, Bondville, VT 05340
  • /34

    $249,900

    $50K PRICE DROP
    • 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
  • /48

    $2,950,000

    $335K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 6,900 Sq Ft

    68 Green Peak Orchard S, East Dorset, VT 05253

    Welcome to Green Peak Orchard in Dorset, Vermont, where timeless architecture and exceptional craftsmanship define this custom Greek Revival residence on 9.9 private acres. Surrounded by mature landscaping, stone walls, and slate terraces, this remarkable home blends classic New England elegance with modern comfort. Designed with meticulous attention to detail, the home features wide-plank

    Carol O`Connor Four Seasons Sotheby's Int'l Realty

    68 Green Peak Orchard S, East Dorset, VT 05253
  • /28

    $750,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,610 Sq Ft

    3622 Dorset West Rd, Dorset, VT 05251

    Unique Dorset West Road offering....This rare opportunity beckons creativity,craft, and charm! Begs all those ready, willing and able to renovate, keeping the existing home, whilst enjoying life in an extremely beautiful and desirable location. Enjoy the beautiful framed in mountain views from most interior living spaces and from the back patio/yard. This 6.6 acre rolling property boasts

    Sunny Breen Josiah Allen Real Estate, Inc.

    3622 Dorset West Rd, Dorset, VT 05251
  • /15

    $825,000

    • Land
    • 77.6 Acres
    • $10,631 per Acre

    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

    Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

    Trent Stephens Wohler Realty Group

    0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
  • /4

    $80,000

    • 4 Beds
    • 2 Baths
    • 1,465 Sq Ft

    107 Lyons St, Bennington, VT 05201

    Situated on a peaceful dead-end street, this home offers tremendous potential for investors, contractors, or buyers looking to create their dream home. The property features 3 bedrooms, with the possibility of a fourth, along with 2 bathrooms, providing a highly desirable layout and ample living space. With some vision, care, and updates, this home can be transformed into a beautiful residence in

    Max Squiers KW Vermont - Brenda Jones Real Estate Group

    107 Lyons St, Bennington, VT 05201
  • /60

    $1,495,000

    Open Sat 11AM - 1PM
    • 5 Beds
    • 5 Baths
    • 5,029 Sq Ft

    20 Blackberry Ln, Peru, VT 05152

    Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous

    Dylan Gage Bromley Real Estate

    20 Blackberry Ln, Peru, VT 05152
  • /37

    $375,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    291 Springhill Rd, Bennington, VT 05201

    Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons.

    Faith Rhodes Maple Leaf Real Estate

    291 Springhill Rd, Bennington, VT 05201
  • /40

    $59,900

    • Land
    • 40,075 Sq Ft
    • $65,109 per Acre

    14 The Ln, Stamford, VT 05352

    Escape to the beauty of VT with this unique cabin in charming Stamford VT. This is a beautiful almost 1 acre lot that has direct frontage on the North Branch of the Hoosic River. It is mostly cleared & level & has a quaint pathway leading down to the river, to enjoy nature. The property includes a cozy 16x10 cabin with solar powered battery system for lights and to plug things into. with 2

    Susan Colvin Monarch Realty

    14 The Ln, Stamford, VT 05352
  • /12

    $64,000

    $11K PRICE DROP
    • Land
    • 13.01 Acres
    • $4,919 per Acre

    3 W Hill Dr, Readsboro, VT 05350

    Discover the potential of this 13-acre parcel in scenic Readsboro offering RR (Rural Residential) zoning and endless possibilities. With gently rolling terrain and potential for views, this property is ideal for a private home or possible subdivision. Aerial photos and videos available! Enjoy a true outdoor lifestyle with nearby access to skiing, hiking, fishing, boating, snowmobile trails, and

    Derek Greene Derek Greene

    3 W Hill Dr, Readsboro, VT 05350
  • /8

    $65,000

    • Land
    • 1.24 Acres
    • $52,419 per Acre

    2041 East Rd, Bennington, VT 05201

    Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life. Perk test were positive for a inground leaching system, results available.

    Dan Mason Perrott Realty

    2041 East Rd, Bennington, VT 05201
  • /8

    $15,500

    • Land
    • 1.2 Acres
    • $12,917 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    The land lots on Heartwelleville View Road offer an idyllic setting for your dream home or getaway retreat. These lots are perfectly situated less than 30 minutes from the renowned Mt. Snow, providing easy access to world-class skiing and snowboarding. Just 20 minutes away, you can explore the vibrant cultural scene of North Adams and the acclaimed MASS MoCA.Outdoor enthusiasts will

    Colt Hazell Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /60

    $1,900,000

    • 6 Beds
    • 6 Baths
    • 5,704 Sq Ft

    751 Main Rd, Stamford, VT 05352

    Step into the most amazing Victorian house you will ever see! Built in 1880, you will feel like you've walked back in time. Beautiful architecture and woodwork. The house was built by John Tudor, a Welsh immigrant who had made a fortune as a mill owner in northern Vermont and settled in Stamford. There is a stunning 3 floor Post & Beam Barn built in 2000 with a 2 car garage built-in. Barn also

    Michael Jarvis United Country Real Estate Mike Jarvis Group Inc

    751 Main Rd, Stamford, VT 05352
  • /37

    $875,000

    • 3 Beds
    • 2 Baths
    • 2,000 Sq Ft

    155 Brookman Rd, Pownal, VT 05261

    Gorgeous setting for this newly constructed home built in 2025, offering breathtaking views from the expansive front porch on 10+/- private acres. Thoughtfully designed with quality craftsmanship throughout, the custom kitchen features beautiful cabinetry, a large center island, gas range, and classic farmhouse sink, all open to the inviting living room with a cozy gas fireplace. The stunning

    Kelley Mccarthy Mahar McCarthy Real Estate

    155 Brookman Rd, Pownal, VT 05261
  • /60

    $1,495,000

    $300K PRICE DROP
    • 17 Beds
    • 20 Baths
    • 14,861 Sq Ft

    3888 Vermont Route 7a, Shaftsbury, VT 05262

    The historic Arlington Inn & Spa is the centerpiece of scenic Arlington, Vermont. It features a tavern, restaurant and massage spa room. There are 15 guest rooms in 3 buildings, and an antique event barn on over 3.5 beautifully landscaped acres. This unique property can easily be configured in many creative ways. It could remain as an inn with a restaurant and bar. It could become a restaurant

    Vicki Wilson Maple Leaf Real Estate

    3888 Vermont Route 7a, Shaftsbury, VT 05262
  • /15

    $115,000

    $30K PRICE DROP
    • Land
    • 2.9 Acres
    • $39,655 per Acre

    Lot 3 Route 11 30, Winhall, VT 05340

    Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

    Laura Beckwith Josiah Allen Real Estate, Inc.

    Lot 3 Route 11 30, Winhall, VT 05340
  • /60

    $1,195,000

    Open Sat 11AM - 2PM $200K PRICE DROP
    • 2 Beds
    • 3.5 Baths
    • 3,873 Sq Ft

    181 Route 11, Winhall, VT 05340

    Perched on 6.3 private acres with sweeping views of Mt. Equinox, this custom post-and-beam home offers a rare combination of craftsmanship, energy efficiency, and natural beauty. Bordering the Green Mountain National Forest on two sides and located just minutes from Manchester, Bromley, and Stratton, the property delivers a secluded mountain retreat without sacrificing convenience. Built in 2012,

    Jonathan Minerick

    181 Route 11, Winhall, VT 05340
  • /8

    $23,999

    $4K PRICE DROP
    • Land
    • 2.4 Acres
    • $10,000 per Acre

    00 Heartwellville View Rd, Readsboro, VT 05350

    The land lots on Heartwelleville View Road offer an idyllic setting for your dream home or getaway retreat. These lots are perfectly situated less than 30 minutes from the renowned Mt. Snow, providing easy access to world-class skiing and snowboarding. Just 20 minutes away, you can explore the vibrant cultural scene of North Adams and the acclaimed MASS MoCA.Outdoor enthusiasts will

    Colt Hazell Flex Realty

    00 Heartwellville View Rd, Readsboro, VT 05350
  • /50

    $499,000

    • 4 Beds
    • 2 Baths
    • 2,144 Sq Ft

    5131 Main Rd, Stamford, VT 05352

    Set on 2.85 acres with beautiful mountain views, this 4-bedroom, 2-bath Colonial offers space, comfort, and classic Vermont charm in the heart of Stamford. The home features 2,144 finished square feet with a welcoming layout that includes a bright living room, family room, dining area, and a spacious kitchen with warm cabinetry, an arched window, and great flow for everyday living or

    Colt Hazell Flex Realty

    5131 Main Rd, Stamford, VT 05352
  • /27

    $609,000

    • 4 Beds
    • 3 Baths
    • 1,650 Sq Ft

    60 Hilltop Rd Unit 60, Winhall, VT 05340

    Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

    Timothy Apps Four Seasons Sotheby's Int'l Realty

    60 Hilltop Rd Unit 60, Winhall, VT 05340
  • /6

    $22,000

    • Land
    • 1.13 Acres
    • $19,469 per Acre

    0 Rue Madeline Rd Unit 8, Readsboro, VT 05350

    1.1 acre lot conveniently located off Vermont Route 100 in Readsboro. Approximately half the property is cleared, offering a great start for a future homesite or recreational retreat. Enjoy easy access to the VAST trail system. With selective tree clearing, the property may offer scenic mountain views. Pictures show both the current state and what's under it before it got a little over grown.

    Erica Hale Ridgeline Real Estate

    0 Rue Madeline Rd Unit 8, Readsboro, VT 05350
  • /37

    $1,600,000

    • 5 Beds
    • 5 Baths
    • 4,700 Sq Ft

    212 Taconic Rd, Manchester, VT 05255

    Set on coveted Taconic Road in the heart of Manchester Village, this beautifully renovated five-bedroom home seamlessly blends timeless Vermont charm with modern comfort. Thoughtfully reimagined from top to bottom, every detail has been carefully considered, resulting in a home that is both inviting and functional.Filled with natural light, the spacious floor plan centers around a beautifully

    Carol O`Connor Four Seasons Sotheby's Int'l Realty

    212 Taconic Rd, Manchester, VT 05255
  • /14

    $450,000

    $50K PRICE DROP
    • Land
    • 21.2 Acres
    • $21,226 per Acre

    56 Lower Taylor Hill Rd, Winhall, VT 05340

    Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont living. Rolling terrain, mature woodland, and natural clearings create an exceptional setting for a private Vermont retreat, with the potential for Bromley Mountain views depending on house placement and design.Supported by a

    Kevin Moran Four Seasons Sotheby's Int'l Realty

    56 Lower Taylor Hill Rd, Winhall, VT 05340
  • /32

    $350,000

    • 2,586 Sq Ft

    110 Short St, Bennington, VT 05201

    Secure a smart, low-maintenance income property featuring four well-kept units—two 2-bedroom and two 1-bedroom—on a dead-end road. This is turnkey living for tenants and hassle-free ownership for you. Three of the four units have dedicated washer/dryer hookups and each unit is fully separated utilities (electric, gas or oil, hot water), so tenants manage their own bills and turnover is smooth.

    William Paquin Maple Leaf Real Estate

    110 Short St, Bennington, VT 05201
  • /23

    $269,000

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft

    1806 Bosley Hill Rd, Readsboro, VT 05350

    This Contemporary Chalet sit on a quiet rural town maintained road.The property is a tasteful blend of woodland and grassy yard with gardens. You can enter from the garage ,above ground , and walk up an interior staircase to the the next level. There is also a half bath and laundry room and plenty of room for side-by-sides, snowmobiles and seasonal gear!On the second level there is a very

    Janet Boyd Boyd Real Estate

    1806 Bosley Hill Rd, Readsboro, VT 05350
  • /15

    $115,000

    • Land
    • 1 Acre
    • $115,000 per Acre

    75 Sylvan Ridge Rd, Winhall, VT 05340

    Your Vermont adventure starts here. This 0.90 - acre parcel offers a fantastic location between Stratton, Bromley, and Magic Mountains, with easy access to the year round recreation, dining, and shopping of Manchester. The current owner cleared and leveled the building site and excavated and built a driveway. There is a Waste Water Permit for a 4 bedroom home in place. Electric service is readily

    Lisa Sullivan Four Seasons Sotheby's Int'l Realty

    75 Sylvan Ridge Rd, Winhall, VT 05340
  • /20

    $475,000

    $24K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 9,000 Sq Ft

    425 Main St, Bennington, VT 05201

    15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

    Chris Long BHG Masiello Brattleboro

    425 Main St, Bennington, VT 05201
  • /43

    $499,900

    $50K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 3,105 Sq Ft

    193 Finley Dr, Bennington, VT 05201

    Set on 3.11 peaceful acres with mountain views and a wonderful sense of privacy, 193 Finley Drive offers the rare combination of one-floor living, generous finished space, and excellent garage capacity in a convenient Bennington location. This 2-bed/3-bath home features a thoughtful main-level layout, with each bedroom offering direct access to a 3/4 bathroom. The primary bath also includes

    Jenifer Prouty Hoffman Hoffman Real Estate

    193 Finley Dr, Bennington, VT 05201
  • /60

    $3,500,000

    • 6 Beds
    • 5.5 Baths
    • 3,690 Sq Ft

    123 Nichols Rd, Landgrove, VT 05148

    HIGH-QUALITY NEW CONSTRUCTION | 123 Nichols Hill Road, Peru, VermontRarely does an opportunity like this come to market in Peru, Vermont, a brand new, high-quality, luxury residence offering the perfect combination of refined construction, privacy, expansive mountain views, a private pond, and a beautifully renovated guest house. The main residence was thoughtfully designed for both

    Britt Wohler

    123 Nichols Rd, Landgrove, VT 05148
  • /85

    $1,200,000

    • 3 Beds
    • 2.5 Baths
    • 2,874 Sq Ft

    1996 N Pownal Rd, Pownal, VT 05261

    Uncommonly Superb View -- A Vermont Meadow RetreatTucked quietly into a broad meadow and surrounded by lush Vermont landscape, this property enjoys one of those rare, completely unspoiled western vistas: a full, harmonious sweep of the Taconic Mountain ridgeline, framed perfectly within human scale. The almost 40 acre setting--meadow bordered by deep woodland--creates a sense of arrival,

    Paul Harsch HARSCH ASSOCIATES

    1996 N Pownal Rd, Pownal, VT 05261
  • /2

    $58,000

    • Land
    • 20,908 Sq Ft
    • $120,833 per Acre

    33 Asa's Way, Bennington, VT 05257

    This lot in beautiful North Bennington is ready to go! Building plans have been drawn up and available to come with the property for an approx. 2200 sq ft 3 bed, 2 bath home with decks facing the mountains. This lot has the electric, water, and sewer available at the street. Beyond having school choice for the elementary it also boasts being the second highest elevation lot in the development,

    William Paquin Maple Leaf Real Estate

    33 Asa's Way, Bennington, VT 05257
  • /22

    $232,500

    • 3 Beds
    • 2 Baths
    • 1,582 Sq Ft

    903 Gage St, Bennington, VT 05201

    You can make this home your own! With a little TLC, this charming 3 bedroom, 2 bath, Cape has the potential to become the perfect home. Featuring a large, level yard, a two-car, detached garage, with attached outdoor room, mudroom to the kitchen, wood floors, fireplace (condition unknown) and with this central location, it offers endless possibilities. Whether you are looking to renovate,

    Pauline Green

    903 Gage St, Bennington, VT 05201
  • /57

    $2,275,000

    $25K PRICE DROP
    • 9 Beds
    • 8 Baths
    • 5,512 Sq Ft

    288 Cedar Ln, Peru, VT 05152

    Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be

    Jessica Citera Cummings & Co

    288 Cedar Ln, Peru, VT 05152
  • /39

    $1,450,000

    $125K PRICE DROP
    • 4 Beds
    • 5.5 Baths
    • 4,530 Sq Ft

    527 Sleighbell Ln, Manchester Center, VT 05255

    Set on over 11.5 private acres, this custom-built Colonial offers the kind of comfort, craftsmanship, and peace of mind that’s increasingly hard to find. Thoughtfully designed and maintained since it was built in 2004, this home blends timeless style with practical features for everyday living. With over 4,300 square feet, the layout provides generous space without feeling overwhelming. The home

    David Halligan Four Seasons Sotheby's Int'l Realty

    527 Sleighbell Ln, Manchester Center, VT 05255
  • /4

    $20,000

    • Land
    • 1.2 Acres
    • $16,667 per Acre

    0 Bergrucken Ln Unit 377, Stamford, VT 05352

    Trade city sirens for wind-rustled maples on this gently wooded 1.2-acre lot tucked inside Alpenwald Village. Alpenwald, although deed restricted, the light protective covenants keep the area tidy without cramping your architectural imagination. Think A-Frame, modern farmhouse, or a passive solar cottage. Beyond the lot is access to trails that lace through the Green Mountain National Forest.

    Kelly Agrillo Southern Vermont Realty Group

    0 Bergrucken Ln Unit 377, Stamford, VT 05352
  • /60

    $4,995,000

    • 5 Beds
    • 6.5 Baths
    • 7,455 Sq Ft

    440 Marcia Ln, Dorset, VT 05251

    A rare opportunity awaits at this exceptional Dorset Hollow estate, privately situated at the end of exclusive Marcia Lane. Perched high on Dorset Mountain across 16.74 acres, the property captures breathtaking long-range views of Owls Head, Equinox Mountain, and beyond.Built in 2005 by renowned craftspeople, this 7,451-square-foot, five-bedroom, seven-bath estate has undergone a

    David Halligan Four Seasons Sotheby's Int'l Realty

    440 Marcia Ln, Dorset, VT 05251

Showing Results 161 - 200, Page 5 of 7

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