Bennington, VT Homes

• 

  

  

  /37

  $1,800,000 Sold Nov 15, 2024

  • 5,699 Sq Ft
  • $316/SF
  • 399 Days On Market

  • 8 Beds
  • 6 Baths
  • Built 1850

  528 Nichols Hill Rd, Dorset, VT 05251

  On an Eastern hillside, between two ridgelines of the Taconic Range, is Goodman Farm. It is reminiscent of an earlier time with two cottages and an antique red barn set at the edge of a spacious hay meadow just outside the village of Dorset. The 187 acres abuts Rupert State Forest with panoramic views, perennial gardens, stone walls and a small pond. Crossing the stone bridge over Goodman Brook

  Story Jenks LandVest, Inc/Woodstock

  528 Nichols Hill Rd, Dorset, VT 05251
• 

  

  

  /16

  Est $690,798 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  21 Peace St, Dorset, VT 05251

  21 Peace St, Dorset, VT 05251
• 

  

  

  /21

  $249,000

  • Land
  • 3.42 Acres
  • $72,807 per Acre

  0 Havoc Hill, Dorset, VT 05253

  Tranquility and Adventure Await on Havoc Hill. Discover 3.42 plus private, wooded acres nestled atop storied Havoc Hill in charming East Dorset, Vermont. Known for its rugged beauty and historic ties to early Vermont logging and farming communities, Havoc Hill offers a rare opportunity to own land rich in character and natural serenity. Set off the picturesque Mad Tom Road, this secluded parcel

  Timothy Apps Four Seasons Sotheby's Int'l Realty

  0 Havoc Hill, Dorset, VT 05253
• 

  

  

  /34

  $325,000 Sold Nov 01, 2024

  • 852 Sq Ft
  • $381/SF
  • 7 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1970

  184 Dorset Hollow Rd, Dorset, VT 05251

  Sweet weekend getaway. Charming Dorset hollow one bedroom one bath updated cottage, close proximity to Barrows House, Dorset Inn, and Dorset playhouse. This one really does have some style: oak veneer flooring throughout, propane gas fireplace in living room, wainscoating walls, ornate hardware on the interior doors, raised panel moldings on ceilings and doors, hunter douglas shades throughout.

  David Halligan Four Seasons Sotheby's Int'l Realty

  184 Dorset Hollow Rd, Dorset, VT 05251
• 

  

  

  /37

  Est $309,574 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,412 Sq Ft

  188 Benedict Rd, East Dorset, VT 05253

  188 Benedict Rd, East Dorset, VT 05253
• 

  

  /25

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft

  393 Morse Hill Rd, East Dorset, VT 05253

  This beautifully maintained home is now available for the first time in 40 years.On the main level, you will find a generously sized eat-in kitchen with granite countertops that opens to a dining room. There are two additional rooms on the main level: a large living room and a bedroom. The main floor also boasts French door that leads out to a spacious deck, perfect for overlooking the

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  393 Morse Hill Rd, East Dorset, VT 05253
• 

  

  /37

  $585,000 Sold Oct 17, 2024

  • 2,690 Sq Ft
  • $217/SF
  • 63 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  2523 Route 30, Dorset, VT 05251

  Embrace being part of the Dorset Village Community while enjoying mountain views and a serene water retreat just minutes from Dorset Village. Nestled on a picturesque 3-acre lot, this charming 2-bedroom house with a 1-bedroom mother-in-law suite offers the perfect combination of seclusion with convenience of nearby amenities. As you approach, palette of colors from vibrant gardens greets you,

  Christine Chovan

  2523 Route 30, Dorset, VT 05251
• 

  

  /16

  Est $556,197 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,129 Sq Ft

  85 Benedict Rd, East Dorset, VT 05253

  85 Benedict Rd, East Dorset, VT 05253
• 

  

  /45

  $3,600,000

  • 4 Beds
  • 3.5 Baths
  • 2,338 Sq Ft

  198 Church St, Dorset, VT 05251

  Nestled in the heart of the iconic Dorset village, just steps from the Dorset Field Club and the beloved local theater, this enchanting historic home has been meticulously renovated, rejuvenated, and reimagined with no expense spared. From the moment you arrive, the home's timeless charm and thoughtful updates are evident. A complete reengineering of the roof and replacement of all major systems

  Adrienne Sherwood Four Seasons Sotheby's Int'l Realty

  198 Church St, Dorset, VT 05251
• 

  

  /39

  $939,000 Sold Oct 11, 2024

  • 4,452 Sq Ft
  • $211/SF
  • 20 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 1786

  3478 Vermont 30, Pawlet, VT 05761

  Elegant five bedroom five bath historic colonial on 0.45 acres located in the heart of Dorset Village, overlooking the Dorset Field Club's golf course nineth green. Recent improvements include: entire exterior professionally painted. Many fine features including: air conditioning multi zones, oversized attached two car garage, multiple fireplaces and woodstove, exposed beams throughout, some 12

  David Halligan Four Seasons Sotheby's Int'l Realty

  3478 Vermont 30, Pawlet, VT 05761
• 

  

  /32

  Est $351,864 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 890 Sq Ft

  5085 Route 30, Dorset, VT 05251

  5085 Route 30, Dorset, VT 05251
• 

  

  /49

  $4,875,000

  • 7 Beds
  • 10 Baths
  • 7,422 Sq Ft

  318 Spring Hill Ln, Dorset, VT 05251

  Welcome to a truly exceptional estate where classic charm and modern craftsmanship unite on 9 secluded acres in the heart of coveted Dorset, Vermont. Meticulously curated with no detail overlooked and no expense spared, this remarkable property features a beautifully renovated 1941 Colonial residence, complemented by a collection of newer luxury companion buildings that together create a one of a

  Richard Slocum Four Seasons Sotheby's Int'l Realty

  318 Spring Hill Ln, Dorset, VT 05251
• 

  

  /23

  $815,000 Sold Oct 10, 2024

  • 2,300 Sq Ft
  • $354/SF
  • 59 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1964

  276 Dorset Rd W, Dorset, VT 05251

  This re-imagined ranch/cape has offers both a one level main living space including the en-suite master and as well as a lower level, family room, two ensuite bedrooms and sliding doors to patio overlooking the headwaters of the Battenkill River and the Green Mountain range. The light filled kitchen has updated appliances, custom cabinetry and butler's pantry/bar. With a partially open concept,

  David Halligan Four Seasons Sotheby's Int'l Realty

  276 Dorset Rd W, Dorset, VT 05251
• 

  

  /27

  Est $1,169,923 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 3,110 Sq Ft

  35 Cheney Rd, Dorset, VT 05251

  35 Cheney Rd, Dorset, VT 05251
• 

  

  /40

  $479,000

  • 4 Beds
  • 3.5 Baths
  • 3,861 Sq Ft

  120 Village St, East Dorset, VT 05253

  Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

  Jill Simon Josiah Allen Real Estate, Manchester Branch Office

  120 Village St, East Dorset, VT 05253
• 

  

  /34

  $650,000 Sold Oct 07, 2024

  • 4,228 Sq Ft
  • $154/SF
  • 35 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  364 Barrows Heights, Dorset, VT 05251

  East House/West House - located on a private 3-acre setting with dramatic views toward Mother Myrick and Equinox Mountains (which can be further enhanced), yet is within walking distance to Dorset Village. Situated on a tranquil private lane, with other well-maintained properties, it feels like you are miles away. Two solidly constructed post and beam buildings offer tremendous value and infinite

  Derryl Lang Four Seasons Sotheby's Int'l Realty

  364 Barrows Heights, Dorset, VT 05251
• 

  

  /35

  Est $629,811 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,161 Sq Ft

  241 Dorset Hollow Rd, Dorset, VT 05251

  241 Dorset Hollow Rd, Dorset, VT 05251
• 

  

  /28

  $750,000

  • 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
• 

  

  /28

  $897,000 Sold Sep 12, 2024

  • 3,082 Sq Ft
  • $291/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1865

  3444 Vermont 30, Pawlet, VT 05761

  Now is your chance to live in the enchanting village of Dorset, Vermont. Close to the village green, this well-maintained 1865 Colonial is within walking distance to the Dorset Playhouse, the Dorset Union Store, and The Dorset Inn. The light-filled home boasts a private bedroom suite with a private bath and a large walk-in closet and laundry. The house’s back section, added in 1910, features a

  Beverly Buber Lakes & Homes Real Estate

  3444 Vermont 30, Pawlet, VT 05761
• 

  

  /27

  Est $603,153 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  2533 Route 30, Dorset, VT 05251

  2533 Route 30, Dorset, VT 05251
• 

  

  /12

  $410,000

  • Land
  • 2.70 Acres
  • $151,852 per Acre

  2937 Dorset Rd W, Dorset, VT 05251

  Prime Buildable Lot in Dorset – Embrace the Best of All Worlds Discover a rare opportunity to own a ready-to-build lot in the heart of Dorset, perfectly positioned to offer unparalleled access to the town's finest attractions. Just moments from scenic hiking trails, the picturesque Dorset Green, and the esteemed Dorset Field Club, this property is your gateway to a lifestyle of outdoor adventure

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  2937 Dorset Rd W, Dorset, VT 05251
• 

  

  /38

  $720,000 Sold Sep 04, 2024

  • 2,052 Sq Ft
  • $351/SF
  • 96 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1985

  191 Maple Hill Ln, Dorset, VT 05251

  In close proximity to the Dorset village is this expertly crafted home with mountain views. This offering comes with so much thoughtful planning on how to live close to amenities, yet have the peace and quiet of the forest as your neighbor. Wood floors throughout the main and second floor of the home, Andersen doors and windows throughout. The main floor hosts a fireplace, wrap around deck, and

  Christiane Carroccio TPW Real Estate

  191 Maple Hill Ln, Dorset, VT 05251
• 

  

  /27

  Est $675,629 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  216 Church St, Dorset, VT 05251

  216 Church St, Dorset, VT 05251
• 

  

  /40

  $1,249,000

  • 4 Beds
  • 6 Baths
  • 4,204 Sq Ft

  842 Dorset Rd W, Dorset, VT 05251

  Spacious luxury contemporary on 15 amazing acres conveniently located on the Dorset West Road. 4 bedrooms including a primary suite on the main floor with adjoining office and huge walk-in closet. Second primary with bath on second floor. Living room with massive stone fireplace and bar area. Well planned and equipped kitchen. Comfortable dining room between living room and kitchen.

  Jill Simon Josiah Allen Real Estate, Manchester Branch Office

  842 Dorset Rd W, Dorset, VT 05251
• 

  

  /37

  $1,300,000 Sold Aug 07, 2024

  • 4,479 Sq Ft
  • $290/SF
  • 109 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 1994

  738 Dorset West Rd, Dorset, VT 05251

  Elegant country contemporary offering 4,479 sqft of luxurious single level living with 5.54 acres on coveted Dorset west road. Designed by renown local architect Tim Clark, and custom built in 1994, this four bedroom six bath home has many fine features including: hardwood flooring, radiant heat, two fireplaces - one wood burning and the other gas, mountain views, private sun deck, and two car

  David Halligan Four Seasons Sotheby's Int'l Realty

  738 Dorset West Rd, Dorset, VT 05251
• 

  

  /15

  Est $391,196 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,171 Sq Ft

  3589 Morse Hill Rd, Dorset, VT 05251

  3589 Morse Hill Rd, Dorset, VT 05251
• 

  

  /48

  $3,275,000

  • 6 Beds
  • 3.5 Baths
  • 3,250 Sq Ft

  73 Pine Rd, Dorset, VT 05251

  This custom-designed modern farmhouse in Dorset, Vermont was completed in 2023. Soaked in natural light, this sunny home may be everything you are looking for. Spectacular mountain and valley views from this private location, yet minutes from all the best of Southern Vermont. Every detail is completely planned and executed - from the Marvin Ultimate windows to the Waterworks bathtub, the finishes

  Christiane Carroccio TPW Real Estate

  73 Pine Rd, Dorset, VT 05251
• 

  /2

  $160,000 Sold May 30, 2025

  • Land
  • 4.49 Acres
  • $35,635 per Acre

  • 42 Days On Market

  0 Kelleher Rd, Dorset, VT 05251

  4.49 acres on a beautiful road in Dorset, Vermont. This setting is ideal for future uses. Near the Manchester town line, the opportunities are endless on this parcel. Approval in place for a four bedroom home.

  Christiane Carroccio TPW Real Estate

  0 Kelleher Rd, Dorset, VT 05251
• 

  

  /31

  Est $742,703 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  161 Dorset Hill Rd, East Dorset, VT 05253

  161 Dorset Hill Rd, East Dorset, VT 05253
• 

  

  /23

  $595,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 2,139 Sq Ft

  62 Dorset Village Ln, Dorset, VT 05251

  Charming Home in Quaint Dorset Village SettingNestled on a gentle knoll above the heart of Dorset Village, this delightful home offers the perfect blend of privacy and convenience. Just a short stroll to village amenities and mere moments from the renowned Pinnacle hiking trails, the location is ideal for those seeking both community charm and outdoor adventure.Brimming with

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  62 Dorset Village Ln, Dorset, VT 05251
• 

  

  /19

  Est $830,932 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,912 Sq Ft

  239 Cheney Rd, Dorset, VT 05251

  239 Cheney Rd, Dorset, VT 05251
• 

  

  /30

  $775,000 Under Contract

  • 3 Beds
  • 4 Baths
  • 2,187 Sq Ft

  379 Owls Head Hill Ln, Dorset, VT 05251

  Contemporary One-Level Retreat on 3.9 Private Acres. Set on nearly 4 peaceful acres, this thoughtfully designed contemporary home offers the perfect blend of style and comfort, all just minutes from area schools, shopping, and amenities. The one-level layout features 3 spacious bedrooms and 4 bathrooms, providing both function and flexibility for everyday living or entertaining. Natural light

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

  379 Owls Head Hill Ln, Dorset, VT 05251
• 

  

  /40

  Est $896,752 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,021 Sq Ft

  93 Peace St, Dorset, VT 05251

  93 Peace St, Dorset, VT 05251
• 

  

  /27

  $595,000 Under Contract

  • 2 Beds
  • 2 Baths
  • 1,416 Sq Ft

  2061 Dorset Rd W, Dorset, VT 05251

  Perched gracefully on a gentle rise, this single level jewel offers a rare blend of architectural simplicity and refined Vermont life. Off one of Dorset's most scenic thoroughfares, Dorset West Road, long admired for its stately homes and pastoral beauty, winds through a landscape steeped in history. Minutes from the Village, where marble sidewalks and iconic homes evoke timeless elegance, the

  Hayleyanne Van Der Kar Four Seasons Sotheby's Int'l Realty

  2061 Dorset Rd W, Dorset, VT 05251
• 

  

  /30

  Est $486,668 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,316 Sq Ft

  705 Route 30, Dorset, VT 05251

  705 Route 30, Dorset, VT 05251
• 

  

  /60

  $555,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 2,031 Sq Ft

  2354 Danby Mountain Rd, Dorset, VT 05251

  Dorset Mountain retreat offering spectacular mountain views of Taconic Mountain Range featuring 7 acres and proximity to year-round outdoor recreation. Snowshoeing, cross country skiing, hiking and mountain biking right here. Fabulous location minutes from Dorset Green. This 3-bedroom, 2-bathroom home is the perfect mountain getaway or a full-time residence offering peace and privacy.The

  Margretta Fischer Wohler Realty Group

  2354 Danby Mountain Rd, Dorset, VT 05251
• 

  

  /24

  Est $869,280 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  3259 Route 30, Dorset, VT 05251

  3259 Route 30, Dorset, VT 05251
• 

  

  /32

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,481 Sq Ft

  3341 Vermont 30, Dorset, VT 05251

  3341 Vermont 30, Dorset, VT 05251
• 

  

  /27

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  177 Dorset West Rd, Dorset, VT 05251

  177 Dorset West Rd, Dorset, VT 05251
• 

  

  /20

  Est $1,227,277 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,500 Sq Ft

  242 Kent Hill Rd, Dorset, VT 05251

  242 Kent Hill Rd, Dorset, VT 05251

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