Bennington, VT Homes

• 

  

  

  /60

  $1,600,000

  • 5 Beds
  • 4.5 Baths
  • 4,243 Sq Ft

  397 Fern Hill, Dorset, VT 05251

  Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-3043

  397 Fern Hill, Dorset, VT 05251
• 

  

  

  /59

  $4,500 per month

  • 3 Beds
  • 4 Baths
  • 2,308 Sq Ft
  • House for Rent

  1728 Vermont 30, Dorset, VT 05251

  Escape to Cody Cottage, a charming 3 bed, 3 bath home perfect for outdoor enthusiasts and families alike! Nestled next to the scenic Dorset Quarry, this cozy retreat offers easy summer swimming and breathtaking mountain views. Vaulted ceiling in the living room with dining that opens to the updated kitchen with 2 seat island. 1st Floor has the primary bedroom with en suite bath, a guest bedroom

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 694-4997

  1728 Vermont 30, Dorset, VT 05251
• 

  

  

  /29

  $350,000 Sold Jun 10, 2025

  • 1,362 Sq Ft
  • $257/SF
  • 46 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  297 Mad Tom Rd, East Dorset, VT 05253

  Adorable Cape-style gem nestled beside the enchanting Mad Tom Brook. This bright and sunny 1.5-story home captures the essence of Vermont living, natural beauty, timeless charm, and thoughtfully updated comfort. Step inside to discover a charming interior that blends classic New England character with modern upgrades. The newly updated kitchen is appointed with elegant soapstone countertops and

  Sandy Reavill Real Broker LLC

  297 Mad Tom Rd, East Dorset, VT 05253
• 

  

  

  /32

  Est $1,614,588 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,507 Sq Ft

  40 Nims, Dorset, VT 05251

  40 Nims, Dorset, VT 05251
• 

  

  

  /47

  $1,500,000

  • Land
  • 39 Acres
  • $38,890 per Acre

  500 Nims Rd, Dorset, VT 05251

  This Majestic and Private 38 + acre parcel located nearby the Dorset Village, is tucked away on an elevated and prepped site which just happens to be one of the most dreamy and picturesque estate quality lands offered in all of Dorset. Just a mile from the Dorset Green and perched up on a knoll with nothing less than amazing mountain views to the south, east and the north. Absolutely stunning

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 634-4776

  500 Nims Rd, Dorset, VT 05251
• 

  

  /31

  $6,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,340 Sq Ft
  • House for Rent

  294 Green Peak Orchard S, Dorset, VT 05253

  Escape to a stunning summer/winter retreat in Southern Vermont, featuring 4 spacious bedrooms and 3.5 baths. Nestled in the heart of nature, this property offers breathtaking mountain views, perfect for relaxation and outdoor adventures. Open-concept living/kitchen area with plenty of seating, a wood burning fireplace, and panoramic mountain views. Kitchen is fully equipped with modern

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 644-7034

  294 Green Peak Orchard S, Dorset, VT 05253
• 

  

  /18

  $949,900 Sold Jun 02, 2025

  • 1,736 Sq Ft
  • $547/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1954

  168 Meadow Ln, Dorset, VT 05251

  A true village gem !!! One level living.Totally renovated in 2020. Gutted to the studs. All new--wiring, plumbing, insulation, sheet rock, roofing, windows, kitchen and baths. Beautiful bright sun room. On over an acre of land.Walk to the theater, library, restaurants, general store.This is a must see. Extremely charming and turn key.All dimensions are approximate.

  Charles Mauro Josiah Allen Real Estate, Inc.

  168 Meadow Ln, Dorset, VT 05251
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  /40

  Est $3,050,709 Not Listed For Sale

  • 5 Beds
  • 7.5 Baths
  • 8,700 Sq Ft

  440 Marcia Ln, Dorset, VT 05251

  440 Marcia Ln, Dorset, VT 05251
• 

  

  /60

  $2,475,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,975 Sq Ft

  341 Danby Mountain Rd, Dorset, VT 05251

  Spectacular Dorset 24 acre Architect Designed Estate conveniently located 1.3 miles from the Dorset Green boasting level stone walled perennial gardens, meadows and woodlands, water ways and pond with established walking paths meandering throughout this compound creating ideal indoor - outdoor transitions to be embraced quietly amongst song birds and completely away from all hustle and bustle!

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 255-8663

  341 Danby Mountain Rd, Dorset, VT 05251
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  /37

  $9,000 per month

  • 3 Beds
  • 3 Baths
  • 1,980 Sq Ft
  • House for Rent

  3093 Route 30, Dorset, VT 05251

  Wonderful Dorset Village Historic Colonial, private and completely protected by the established vintage tree line that buffers the neighbors and Route 30. Walk to Village location, this property has been fully renovated with updated kitchen and baths. The house is warm and welcoming with front and side covered porch entrance while the rear screened porch creates an expansive summer room to the

  

  Laura Beckwith

  Josiah Allen Real Estate, Inc.

  (802) 520-2909

  3093 Route 30, Dorset, VT 05251
• 

  

  /57

  $800,000 Sold May 30, 2025

  • 3,390 Sq Ft
  • $236/SF
  • 77 Days On Market

  • 2 Beds
  • 4 Baths
  • Built 2005

  3149 Morse Hill Rd, Dorset, VT 05251

  Nestled in the scenic town of Dorset, this exquisite three-bedroom, four-bathroom home offers a perfect blend of comfort and sophistication. This latest addition to the market graces a generous 2,144 square feet of meticulously designed living space. Upon entry, you'll be greeted by an astonishingly modern sweet kitchen, boasting granite countertops, pretty white cupboards, a two tier bar and

  Nancy Greenwood Watson Realty & Associates

  3149 Morse Hill Rd, Dorset, VT 05251
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  /40

  Est $2,580,054 Not Listed For Sale

  • 4 Beds
  • 5.5 Baths
  • 4,711 Sq Ft

  674 Dorset Hollow Rd, Dorset, VT 05251

  674 Dorset Hollow Rd, Dorset, VT 05251
• 

  

  /43

  $1,550,000

  • 5 Beds
  • 4.5 Baths
  • 4,219 Sq Ft

  7 Timberbrook N, Dorset, VT 05251

  Modern Elegance Surrounded by Mountain Serenity. Stunning 5-bedroom, 4.5-bath home nestled on 4.7 acres, just minutes from Dorset Green and Manchester Village. Blending modern design with traditional warmth, the property features energy-efficient geothermal heating & cooling and solar power. Expansive windows and French doors frame mountain views, the deck is perfect for entertaining. The main

  Margretta Fischer Wohler Realty Group

  7 Timberbrook N, Dorset, VT 05251
• 

  

  /29

  $665,000 Sold May 09, 2025

  • 1,716 Sq Ft
  • $388/SF
  • 51 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  147 Spring Hill Ln, Dorset, VT 05251

  Come see this charming 3 bedroom cottage, nestled on private road with stunning mountain views. Perched atop a hill, this home offers a peaceful retreat with beautiful scenery. The spacious primary bedroom features an ensuite bath and extensive closet space, while two additional bedrooms provide perfect guest rooms or office space. At the heart of the home, the inviting living room boasts large

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  147 Spring Hill Ln, Dorset, VT 05251
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  /33

  Est $475,724 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,020 Sq Ft

  885 Mad Tom Rd, East Dorset, VT 05253

  885 Mad Tom Rd, East Dorset, VT 05253
• 

  

  /57

  $2,429,000

  • 7 Beds
  • 6.5 Baths
  • 6,358 Sq Ft

  349 Kent Hill Rd, Dorset, VT 05251

  Located in the heart of Dorset Village, just a short walk to the town green, this stunning 7-bedroom, 7-bath residence, built in 1928, is a rare find. Set on 4 hill top acres, the property exudes timeless elegance, blending the charm of its historic roots with thoughtful modern updates. Inside, you will discover a captivating blend of warmth and sophistication. The gourmet kitchen, the heart of

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  349 Kent Hill Rd, Dorset, VT 05251
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  /45

  $593,000 Sold Mar 18, 2025

  • 2,986 Sq Ft
  • $199/SF
  • 99 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1860

  109 Mad Tom Rd, East Dorset, VT 05253

  Discover timeless charm blended with modern comfort in this enchanting 4-bedroom, 2-bath home nestled amidst Vermont's scenic beauty. This residence boasts a newly painted exterior with a classic wrap-around porch that invites you to enjoy leisurely moments soaking in East Dorset's small town lifestyle complete with restored marble sidewalks. Step inside to a welcoming parlor where wood flooring

  Julie Citron RE/MAX Four Seasons

  109 Mad Tom Rd, East Dorset, VT 05253
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  /40

  Est $385,325 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 6,096 Sq Ft

  319 Tower Rd, Dorset, VT 05251

  319 Tower Rd, Dorset, VT 05251
• 

  

  /43

  $1,495,000

  • 5 Beds
  • 4.5 Baths
  • 4,219 Sq Ft

  7 Timberbrook N, Dorset, VT 05251

  Modern Elegance Surrounded by Mountain Serenity. Stunning 5-bedroom, 4.5-bath home nestled on nearly 2 acres, just minutes from Dorset Green and Manchester Village. Blending modern design with traditional warmth, the property features energy-efficient geothermal heating & cooling and solar power. Expansive windows and French doors frame mountain views, the deck is perfect for entertaining. The

  Margretta Fischer Wohler Realty Group

  7 Timberbrook N, Dorset, VT 05251
• 

  

  /21

  $451,150 Sold Jan 03, 2025

  • 875 Sq Ft
  • $516/SF
  • 37 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1968

  77 Dorset Hollow Rd, Dorset, VT 05251

  Location, Location, Location! Nestled in the heart of Dorset, just steps from the charming Dorset Green, this delightful home sits on a spacious double lot. This cape features a living area that is conveniently located on the first floor, featuring two bedrooms, a generously sized living room, and a cozy kitchen that opens onto a large deck overlooking the backyard. A sizable mudroom connects the

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  77 Dorset Hollow Rd, Dorset, VT 05251
• 

  

  /38

  Est $735,008 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,678 Sq Ft

  96 Mount Aeolus Ln, East Dorset, VT 05253

  96 Mount Aeolus Ln, East Dorset, VT 05253
• 

  

  /40

  $1,800,000

  • 5 Beds
  • 4.5 Baths
  • 3,436 Sq Ft

  59 Church St, Dorset, VT 05251

  Exceptional Dorset Church St. offering. Spacious c 1850s Italianate with Greek Revival features in remarkable condition with new roof, windows, refinished floors, A/C. Spacious, bright eat-in kitchen large parlor living room with fireplace, dining room. First floor master suite, bright well-appointed eat-in kitchen and updated bathrooms. 4-5 bedrooms, Large level yard, stone walled terraces

  R. Diedrich August Wohler Realty Group

  59 Church St, Dorset, VT 05251
• 

  

  /7

  $290,000 Sold Dec 09, 2024

  • Land
  • 4.19 Acres
  • $69,212 per Acre

  • 74 Days On Market

  3131 Dorset Rd W, Dorset, VT 05251

  Discover the perfect blend of privacy and convenience with this exceptional 4.19-acre approved building lot, located at the end of Church Street just steps away from Dorset's Village. The location is an idea setting for a dream home with privacy, views and easy access to Dorset's shopping, restaurants and theater. This property comes with an approved wastewater permit for a 4-bedroom residence,

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  3131 Dorset Rd W, Dorset, VT 05251
• 

  

  /40

  Est $1,602,961 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,555 Sq Ft

  1092 Nichols Hill Rd, Dorset, VT 05251

  1092 Nichols Hill Rd, Dorset, VT 05251
• 

  

  /43

  $1,975,000

  • 4 Beds
  • 4.5 Baths
  • 5,696 Sq Ft

  376 Windward Hill, Dorset, VT 05251

  Welcome to 376 Windward Hill, a stunning Southern Vermont estate with breathtaking views of the Taconic and Green Mountain Ranges. Spanning 12 acres, the property features a private trout pond and tranquil waterfall, creating a serene atmosphere.Inside, the home combines timeless elegance with modern comfort. Herringbone brick and hardwood floors lead to the expansive living room, highlighted

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  376 Windward Hill, Dorset, VT 05251
• 

  

  /40

  $1,115,000 Sold Dec 06, 2024

  • 4,000 Sq Ft
  • $279/SF
  • 94 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2002

  170 Owls Head Hill Ln, Dorset, VT 05251

  Complete privacy on 4+ acres. Magnificent grand 2 story entry greets your guests with a wrought iron staircase. Living and family room with vaulted ceilings share a stone fireplace open to both sides. Eat-in kitchen with custom cabinetry and center island has a pass thru double cabinet pantry with wine fridge and storage leading to the formal dining room. Wide pine floors in excellent

  Julie Citron RE/MAX Four Seasons

  170 Owls Head Hill Ln, Dorset, VT 05251
• 

  

  /6

  Est $764,135 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,703 Sq Ft

  18 Lane Rd, Dorset, VT 05251

  18 Lane Rd, 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
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  /46

  $1,050,000 Sold Dec 05, 2024

  • 4,200 Sq Ft
  • $250/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1986

  443 Owl's Head Hill Ln, Dorset, VT 05251

  HOME AND HEARTH, MOUNTAIN AND MEADOW IN WONDERFUL DORSET! All the joys of Vermont are yours in this excellent quality expanded Classical Cape gracing almost five glorious Dorset acres. Passing the wooded glen, flower garden and front patio, you enter the vaulted-ceilinged kitchen/family/dining room, with acacia wood underfoot. After noticing the recently updated kitchen appliances, proceed to the

  Lawrence Zupan EXP Realty

  443 Owl's Head Hill Ln, Dorset, VT 05251
• 

  

  /40

  Est $1,269,815 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 4,090 Sq Ft

  89 Windward S, Dorset, VT 05251

  89 Windward S, Dorset, VT 05251
• 

  

  /45

  $1,390,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,165 Sq Ft

  92 Barrows Heights, Dorset, VT 05251

  A rare offering in Dorset Village. Set on nearly four private acres just a short stroll from the Dorset Village Green, this masterfully restored 1931 Saltbox Colonial blends timeless New England charm with elevated modern living. Renovated in 2020, the home offers over 3,000 square feet of sunlit, versatile rooms for work, play, or rest; ideal as a full-time residence or refined seasonal

  Katherine Zilkha Four Seasons Sotheby's Int'l Realty

  92 Barrows Heights, Dorset, VT 05251
• 

  

  /35

  $670,000 Sold Dec 02, 2024

  • 2,924 Sq Ft
  • $229/SF
  • 47 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 1981

  1489 Route 30, Dorset, VT 05251

  Nestled on 3.20 private acres, this beautifully updated home offers three bedrooms, four baths, and a perfect blend of modern comfort and natural beauty. From the moment you step into the fabulous entranceway, with its custom lighting and hand-crafted woodwork, you’ll feel the unique charm that defines this home. Two new mini splits offering AC is such a perk! The main level features an open

  Margretta Fischer Wohler Realty Group

  1489 Route 30, Dorset, VT 05251
• 

  

  /39

  Est $1,240,890 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,611 Sq Ft

  951 Nichols Hill Rd, Dorset, VT 05251

  951 Nichols Hill Rd, Dorset, VT 05251
• 

  

  /58

  $1,790,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 6,165 Sq Ft

  75 Church St, Arlington, VT 05250

  Picture Postcard Perfect! Built in harmony with nature, filled with color and warmth, spectacular floor plan including a very impressive great room, gorgeous first floor primary bedroom, great finished lower level. Not to mention within walking distance to the Dorset Inn, Dorset Field Club, and all the amenities of lovely Church Street! The future owner will certainly be lucky to take stewardship

  Sunny Breen Josiah Allen Real Estate, Inc.

  75 Church St, Arlington, VT 05250
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  /7

  $410,000 Sold Nov 23, 2024

  • Land
  • 5 Acres
  • $78,695 per Acre

  • 14 Days On Market

  737 Squirrel Hollow Rd, Dorset, VT 05253

  --- Premiere Building Lot with Driveway Built and Septic Installed --- Just minutes to Manchester and Dorset, this 5.21-acre building lot offers breathtaking mountain views and a peaceful Vermont setting. The property has been thoughtfully cleared, the driveway built and the septic system installed. Currently permitted for a 4BR main house with 1BR guest house, this septic system has the capacity

  Cheyanne Pugliese

  737 Squirrel Hollow Rd, Dorset, VT 05253
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  /40

  Est $585,695 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  601 Peace St, Dorset, VT 05251

  601 Peace St, Dorset, VT 05251
• 

  

  /60

  $1,375,000 Under Contract

  • 3 Beds
  • 4 Baths
  • 2,088 Sq Ft

  393 Red Tail Ln, Dorset, VT 05251

  Stunning contemporary design with elevated mountain views, three bedrooms, four bathrooms, on 11.52 secluded acres in Dorset Hollow. Many recent improvements including: propane baseboard heat, mini-splits for a/c, kitchen redesign, and screened in porch. This home offers an open floor plan with floor to ceiling windows, wood burning fireplace, access to rear sundeck, and wonderful unobstructed

  David Halligan Four Seasons Sotheby's Int'l Realty

  393 Red Tail Ln, Dorset, VT 05251
• 

  

  /32

  $380,000 Sold Nov 22, 2024

  • 1,332 Sq Ft
  • $285/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1905

  567 Kirby Hollow Rd, Dorset, VT 05251

  Fabulous Dorset location! 1905 Farm House on Kirby Hollow Road only minutes to Dorset Green. Four bedroom, three bath with a lovely little brook. Absolutly dreamy setting. A single family that once served as a two family home offers so many options. This home needs TLC. The foundation needs some work. Update the kitchen(s) and baths to your taste and make the home your own. Harwood floors

  Margretta Fischer Wohler Realty Group

  567 Kirby Hollow Rd, Dorset, VT 05251
• 

  

  /23

  Est $495,538 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,722 Sq Ft

  30 Owls Head Hill Ln, Dorset, VT 05251

  30 Owls Head Hill Ln, Dorset, VT 05251
• 

  

  /50

  $1,275,000 Under Contract

  • 4 Beds
  • 5 Baths
  • 3,610 Sq Ft

  3360 Dorset Rd W, Dorset, VT 05251

  Exceptional Dorset Contemporary with Classic Craftsmanship & Modern ComfortsSet on 1.86 peaceful acres abutting Dorset Field Club property, this beautifully maintained four-bedroom, five-bath contemporary home offers privacy, elegance, and an ideal Vermont lifestyle. Surrounded by nature and just moments from Dorset Village, this property blends timeless design with thoughtful updates,

  David Halligan Four Seasons Sotheby's Int'l Realty

  3360 Dorset Rd W, Dorset, VT 05251

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