Bennington County VT Homes for Sale

• 

  

  

  /20

  $649,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  27 Owls Head Hill Ln, Dorset, VT 05251

  Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  27 Owls Head Hill Ln, Dorset, VT 05251
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  /28

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  2023 North Rd, Arlington, VT 05250

  Rare opportunity to own a fully renovated home plus a subdivided, buildable lot with Mount Equinox views. 2023 North Rd offers turnkey living with exceptional future potential, just minutes to Manchester, Stratton, and Bromley. The main home was extensively renovated in Fall of 2025, inside & out. Exterior upgrades include new vinyl siding & trim, all new windows, upgraded insulation, a freshly

  Mandolyn McIntyre Crow Real Broker LLC

  2023 North Rd, Arlington, VT 05250
• 

  

  

  /22

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340

  Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Kimball Hill Rd Unit 1, Winhall, VT 05340
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  /52

  $725,000

  • 3 Beds
  • 4 Baths
  • 2,274 Sq Ft

  490 Barnumville Rd, Manchester Center, VT 05255

  490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries,

  David Shehadi Josiah Allen Real Estate, Inc.

  490 Barnumville Rd, Manchester Center, VT 05255
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  /55

  $10,300,000 New Construction

  • 6 Beds
  • 9 Baths
  • 10,993 Sq Ft

  551 West Fields, Manchester, VT 05254

  Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

  Sunny Breen Josiah Allen Real Estate, Inc.

  551 West Fields, Manchester, VT 05254
• 

  

  /15

  $96,906 New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  10 Cassie Ln, Bennington, VT 05201

  Welcome to 10 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  10 Cassie Ln, Bennington, VT 05201
• 

  

  /58

  $299,000

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

  207 Silver St, Bennington, VT 05201

  Tastefully renovated antique home that retained it character 4 bed 2 bath home with gleaming hardwood floor in through out with Vinyl plank in the bathrooms and Laundry room. The downstairs Ensuite is currently being used as an in home office with private entrance. This would make a great room for a in-law space with private bath and the 3 season sunroom could easily be converted into a

  Dan Mason Perrott Realty

  207 Silver St, Bennington, VT 05201
• 

  

  /25

  $385,000

  • Land
  • 41.1 Acres
  • $9,367 per Acre

  00 Ross Rd, Winhall, VT 05340

  Welcome to 41.1 acres of quintessential Vermont beauty, ideally located between downtown Manchester (11 minutes), Bromley Mountain (6 minutes), and Stratton Mountain (15 mins). This property offers the best of both worlds—easy access to town, ski mountains, and year-round recreation, yet a peaceful and private setting surrounded by nature. The land features a meandering stream, a mix of mature

  David Shehadi Josiah Allen Real Estate, Inc.

  00 Ross Rd, Winhall, VT 05340
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  /12

  $450,000

  • Land
  • 10.26 Acres
  • $43,860 per Acre

  4.1 Pearl Buck Dr, Winhall, VT 05340

  One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

  Kim Morgan-Wohler Wohler Realty Group

  4.1 Pearl Buck Dr, Winhall, VT 05340
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  /28

  $479,000

  • 3 Beds
  • 2.5 Baths
  • 1,392 Sq Ft

  354 New Ireland Rd, Manchester Center, VT 05255

  Cozy Country Getaway Close to It All, Tucked away on 2 private acres and bordered by Bromley Brook, this inviting 3-bedroom, 2.5-bath home offers the perfect balance of quiet country living and easy access to skiing (Bromley 5 miles, Stratton 14 miles) and town. Inside, you will find a spacious living and dining area, and fireplace with a woodstove insert, just right for curling up after a day on

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

  354 New Ireland Rd, Manchester Center, VT 05255
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  /50

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades.This beautifully updated 3-bedroom home is perfectly situated on a desirable corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, with a recent addition of a first-floor primary bedroom and new mudroom back entrance.Step inside to find gleaming hardwood floors and a warm, inviting layout. The dining

  Lindsey Martin Maple Leaf Realty

  113 Main St, Bennington, VT 05201
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  /47

  $625,000 New Construction

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

  682 Fox Hill Rd, Bennington, VT 05201

  Soak up the mountain view from a brand new custom built home. Desirable neighborhood with paved town maintained roads. Just outside of Old Bennington and close to SVMC hospital, downtown restaurants and theaters. An easy commute to Bennington College, 22 minute drive to Williamstown, MA or an hour to Albany Int'l Airport. Nestled at the base of Mount Anthony, hikers will appreciate direct access

  Jenifer Prouty Hoffman Hoffman Real Estate

  682 Fox Hill Rd, Bennington, VT 05201
• 

  

  /20

  $534,900

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  1180 North Rd, East Arlington, VT 05252

  Have your own slice of quintessential Vermont with this 3 acre property at the base of the Green Mountains. A lush, wooded, private property, you will love this 4 bed, 2.5 bath Sunderland home. The 1st floor is an open floor plan with plenty of natural light with a bonus recreational room/office and half bath. The kitchen has granite counters with an updated faucet and oven hood with a butcher

  Jason Saphire www.HomeZu.com

  1180 North Rd, East Arlington, VT 05252
• 

  

  /55

  $495,000

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  935 Old Manchester Rd, Peru, VT 05152

  Cozy Off-Grid Cabin on 10 Private Acres – Peace, Privacy & Ski AccessEscape to your own woodland retreat with this charming 2-bed, 1-bath cabin nestled on 10 serene acres of open meadow and forest. Just 4.5 miles to Bromley Ski & Snowboarding Mountain, this property offers the perfect mix of off-grid living and outdoor adventure.Fully self-sufficient with solar power and propane generator

  Margretta Fischer Wohler Realty Group

  935 Old Manchester Rd, Peru, VT 05152
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  /18

  $300,000

  • 3 Beds
  • 1.5 Baths
  • 1,570 Sq Ft

  940 Gage St, Bennington, VT 05201

  Classic cape with a twist! The eat-in kitchen has plenty of cooking area plus an eat-in area in a windowed alcove. The dining room is large enough for sit downs and the living room is the whole length of the house so movie nights are a go! In the entry side of the house you have a wonderful enclosed porch to serve as a mud room and a sweet sitting porch out front. AND!!!!... there is a fenced in

  Christine Lewis Brattleboro Area Realty

  940 Gage St, Bennington, VT 05201
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  /44

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  475 Sunrise Ln, Arlington, VT 05250

  Discover your private retreat on Beautiful Sunrise Lane! Welcome to "Pine Hollow". This comfortable and inviting home sits on over 6 acres of serene, peaceful landscape, for those seeking a quiet environment and space! Idyllic setting surrounded by pines with complete solitude at the end of a private rd. Enjoy the comfort of generous rooms filled with natural light, ideal for family living and

  Sunny Breen Josiah Allen Real Estate, Inc.

  475 Sunrise Ln, Arlington, VT 05250
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  /33

  $485,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  3 Strattonwald Rd, Winhall, VT 05340

  Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you'll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

  Robin Apps Four Seasons Sotheby's Int'l Realty

  3 Strattonwald Rd, Winhall, VT 05340
• 

  

  /19

  $219,500

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  14 Robinson Ave, Bennington, VT 05201

  Discover this lovely three-bedroom, one-bathroom home featuring 1,254 square feet of finished space, all set on a .24-acre lot. Recent upgrades roughly in the last ten years include blown-in insulation, roof, furnace, and updated kitchen and flooring, making this home both comfortable and stylish. Perfect for families or anyone looking for a cozy place. Minutes from Mt. Anthony Country Club,

  Timothy Corcoran Mahar McCarthy Real Estate

  14 Robinson Ave, Bennington, VT 05201
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  /4

  $14,000

  • Land
  • 1.2 Acres
  • $11,667 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 1.2-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /54

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
• 

  /2

  $425,000

  • Land
  • 3 Acres
  • $141,667 per Acre

  lot B Frost Pond Rd, Dorset, VT 05251

  Private but not remote. Dorset West Road Location nearby Dorset and Manchester. Nice mountain views.Waste water permit in place for 5 BR, 8 person occupancy.

  Charles Mauro Josiah Allen Real Estate, Inc.

  lot B Frost Pond Rd, Dorset, VT 05251
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  /38

  $1,200,000

  • 5 Beds
  • 1 Bath
  • 2,228 Sq Ft

  395 King Hill Rd, Readsboro, VT 05350

  Stunning Mountain & Meadow Views, 135 acres of pristine rolling meadows overlook the Harriman Reservoir, sits a meticulously maintained c. 1770 5 bedroom farmhouse. Welcome to King Hill Farm, this idyllic Vermont homestead has been in the King family for multiple generations. No restrictions, enjoy the peace and quiet of a slight breeze, blue skies and bird songs. Remarkable, one of a kind

  Margretta Fischer Wohler Realty Group

  395 King Hill Rd, Readsboro, VT 05350
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  /4

  $400,000

  • Land
  • 8.01 Acres
  • $49,938 per Acre

  248 French Hollow Rd, Winhall, VT 05340

  Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

  Kim Morgan-Wohler Wohler Realty Group

  248 French Hollow Rd, Winhall, VT 05340
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  /9

  $19,999

  • Land
  • 1.5 Acres
  • $13,333 per Acre

  0 Lebensdorf Ln, Readsboro, VT 05350

  Rectangular building lot in Alpenwald Village. The topography is slightly below road grade but generally flat. Electricity is available at the road. This is a very well maintained development and road system, with lots of privacy and neighbors widely spread out on their own acreage, yet there's still a friendly community feel.

  David White OwnerEntry.com

  0 Lebensdorf Ln, Readsboro, VT 05350
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  /6

  $74,900

  • Land
  • 5.3 Acres
  • $14,132 per Acre

  00 Heartwellville View Rd, Readsboro, VT 05350

  Nestled in the desirable Heartwelleview Road section of Alpenwald, this beautiful 5-acre lot offers the perfect blend of privacy and convenience. The property is partially cleared, making it easy to envision your dream home while still enjoying the natural beauty and tranquility of the surrounding forest. With power already available at the road and septic plans in place, much of the groundwork

  Flex Realty Group Flex Realty

  00 Heartwellville View Rd, Readsboro, VT 05350
• 

  

  /60

  $1,190,000

  • 6 Beds
  • 7 Baths
  • 5,400 Sq Ft

  2001 Depot St, Manchester Center, VT 05255

  LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester’s dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 2 private acres—ideal as a primary home, vacation getaway, or rental investment. With a strong history as a successful

  Steven Bryant TPW Real Estate

  2001 Depot St, Manchester Center, VT 05255
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  /60

  $5,250,000

  • 9 Beds
  • 10 Baths
  • 7,900 Sq Ft

  1184 E Manchester Rd, Manchester, VT 05255

  Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

  Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

  1184 E Manchester Rd, Manchester, VT 05255
• 

  

  /23

  $148,900

  • 4 Beds
  • 2 Baths
  • 1,596 Sq Ft

  4697 Main Rd, Stamford, VT 05352

  Situated on a large 4+acre lot sits this adequately sized home!! 3-4 bedrooms with 1 3/4 bathrooms this home awaits your visions and ideas. With spacious rooms and a functional layout this home has many options. 1 car detached garage and vinyl siding are a plus!

  Dick Thackston R.H. Thackston & Company

  4697 Main Rd, Stamford, VT 05352
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  /32

  $295,000

  • 1 Bed
  • 1.5 Baths
  • 1,680 Sq Ft

  318 North St, Bennington, VT 05201

  A former florist shop for 2 decades, this mixed-use property is now a blank slate ready for your vision. Zoning allows for retail, food/drink/entertainment, gallery or studio, personal or professional services, to multi-family or single-family residential. First floor and basement previously served as retail space, but with the walk-in cooler now removed, the main level feels significantly

  Jenifer Prouty Hoffman Hoffman Real Estate

  318 North St, Bennington, VT 05201
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  /28

  $1,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,363 Sq Ft

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155

  Perfect for the large family! Four bedrooms, Three and a Half Baths, plus a Loft! In highly desirable Rising Bear Lodge, Top Floor, Corner location! Easy walking distance to the Slopes, (Shuttle also available), the Commons' Skating Pond, and the Village Shops and Restaurants. Other amenities include a year round heated Pool, outdoor hot tubs, and a cedar sauna---all comfortably accessible by the

  Edwin Kevil Stratton Real Estate

  43 Middle Ridge Rd Unit 415, Winhall, VT 05155
• 

  

  /45

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  9 Lower Taylor Hill Rd, Winhall, VT 05340

  Come home to your own Vermont playground! Situated on 8.75 private acres at the base of Stratton Mountain Resort access road, this recently renovated single family residence has all the amenities that your family needs. Explore the grounds, play in the Winhall river, hike the surrounding trails, and enjoy the mountain views. Property has easy access to the VAST snowmobile trails directly from the

  Timothy Mich Doddridge Stratton Real Estate

  9 Lower Taylor Hill Rd, Winhall, VT 05340
• 

  

  /40

  $1,025,000

  • 4 Beds
  • 2.5 Baths
  • 3,086 Sq Ft

  19 Roundtree Rd, Bondville, VT 05340

  This rare offering, located in the North Brookwood neighborhood at the Stratton Mountain Resort, presents an opportunity to secure your legacy winter home and enjoy the revenue of a $38,000 seasonal tenant and also benefit from a tax adjustment at closing. Don't overlook the benefits this property offers. Located on Stratton Mountain Resort with shuttle and near the ski trails, this four-bedroom,

  Kim Morgan-Wohler Wohler Realty Group

  19 Roundtree Rd, Bondville, VT 05340
• 

  

  /9

  $27,500

  • Land
  • 1.2 Acres
  • $22,917 per Acre

  0 Bergrucken Ln Unit 5044034, 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 5044034, Stamford, VT 05352
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  /43

  $2,100,000

  • 4 Beds
  • 3 Baths
  • 3,780 Sq Ft

  1228 Skiparee Rd, Pownal, VT 05260

  Welcome to Amara Farm, an equestrian paradise in Southern Vermont. This meticulously planned property offers a 13-stall barn designed with every detail in mind, ensuring comfort and efficiency for both horse and rider. The state-of-the-art indoor arena features GGT footing and a full wall of window providing top-quality conditions for training and performance. Turnout paddocks and outdoor arena

  Christiane Carroccio TPW Real Estate

  1228 Skiparee Rd, Pownal, VT 05260
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  /60

  $579,900

  • 1 Bed
  • 1 Bath
  • 2,529 Sq Ft

  126 Simeon Dean Rd, Shaftsbury, VT 05262

  Horse enthusiasts take notice! Barn Recently renovated w New Electric, 3@12x12 stalls, new Loft & Heated Tack Rm added, or use as desired, Hobby Shop, Antiques, Storage. Wonderful Newly Fenced Pasture & Paddocks & Fencing around house for children or pets. Charming audible Paran Creek from the porch w/nearby adjoining access to serene 6acre Spring Fed Pond. Total of 17.47 acres for your complete

  Denise Byers Green Mountain Premiere Properties

  126 Simeon Dean Rd, Shaftsbury, VT 05262
• 

  

  /27

  $675,000

  • 2 Beds
  • 2 Baths
  • 1,432 Sq Ft

  4928 Main St Unit 2, Manchester Center, VT 05255

  Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

  David Halligan Four Seasons Sotheby's Int'l Realty

  4928 Main St Unit 2, Manchester Center, VT 05255
• 

  

  /33

  $815,000

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  158 Upland Downs Rd, Manchester Center, VT 05255

  This well-maintained home is nestled on an open, sunny lot with mountain views, offering a serene and picturesque setting. The property is in move-in condition and boasts one of Manchester's best locations, providing convenient access to the town, schools, and shops, all just minutes away. It is set back from the road, surrounded by beautifully landscaped lawn, gardens, and a spacious

  Tatsiana Clark Four Seasons Sotheby's Int'l Realty

  158 Upland Downs Rd, Manchester Center, VT 05255
• 

  

  /12

  $399,500

  • Land
  • 2.7 Acres
  • $147,963 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

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  2937 Dorset Rd W, Dorset, VT 05251
• 

  

  /23

  $249,000

  • Land
  • 17.6 Acres
  • $14,148 per Acre

  88 Cedar Ln, Peru, VT 05152

  Tucked away in the heart of the Green Mountains, this stunning 17.60-acre parcel in picturesque Peru, Vermont, is a rare opportunity to create your dream retreat. The land is richly wooded, offering a serene natural setting filled with mature trees and gently rolling terrain that promises a spectacular display of fall foliage—an ever-changing canvas of vibrant reds, oranges, and golds each

  Joe Castaluccio Winhall Real Estate

  88 Cedar Ln, Peru, VT 05152
• 

  

  /40

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,868 Sq Ft

  134 Monument Ave, Bennington, VT 05201

  Sprawling Cape on the Edge of Historic Old Bennington. Welcome to this beautiful and spacious Cape-style home offering warmth, character, and comfort in a highly desirable location. The inviting main level features a large kitchen, a sun-filled living room with a fireplace, and an expansive family room with a dining area-deal for entertaining or relaxing. A private office and a serene primary

  Kelley Mccarthy Mahar McCarthy Real Estate

  134 Monument Ave, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 5