Bennington County VT Homes for Sale with Basement

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  /17

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 1,368 Sq Ft

  21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255

  THE PROGRAM: Purchase Price Assistance/ Mortgage Payment Reduction:Eligibility Requirements: * Vermont Residency or Residency at time of Purchase * First Time Vermont Homebuyer * Household Income at or Below $178,735* * Qualify for a Bank Mortgage * 10% Down Payment The developer will offer Gifted Equity and Paid Points at closing that will reduce the purchase price of the real estate and

  Britt Wohler

  21 Jameson Flats Unit Duplex Unit B, Manchester, VT 05255
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  /25

  $289,000

  • 7 Beds
  • 6 Baths
  • 5,712 Sq Ft

  136 North St, Bennington, VT 05201

  Downtown mixed-use investment opportunity located on North Street near the Four Corners intersection of Routes 7 and 9 in the heart of Bennington. The property features six total units, including four residential apartments (three two-bedroom units and one one-bedroom unit) and two street-level commercial storefronts with direct North Street frontage providing strong visibility for retail,

  Jeffrey Dorman

  136 North St, Bennington, VT 05201
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  /60

  $979,000

  • 4 Beds
  • 3.5 Baths
  • 5,248 Sq Ft

  41-43 Cranberry Hill Rd, Winhall, VT 05340

  This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with

  Jamie Luke TPW Real Estate

  41-43 Cranberry Hill Rd, Winhall, VT 05340
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  /37

  $399,000

  • 3 Beds
  • 1 Bath
  • 1,663 Sq Ft

  446 Highland Ave, Manchester Center, VT 05255

  Looking for a unique opportunity for equity growth? This is it! Location, location, location. Highly desirable Highland Avenue is one of those rare streets with character homes that is literally only a few walking blocks to town. If you are lucky enough to own this charming 3- bedroom home offering 1,663 sq ft of living space, you will enjoy easy access to the library, local shops, coffee spots,

  Sunny Breen Josiah Allen Real Estate, Inc.

  446 Highland Ave, Manchester Center, VT 05255
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  /49

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 2,139 Sq Ft

  94 Murray Hill Woods Rd Unit 64, Manchester, VT 05255

  "The Maisonette of Murray Hill"...if you are searching for elements such as unique layouts, high ceilings, move in ready and to unwind in luxury...then come discover a one-of-a kind completely and luxuriously renovated Murray Hill Woods Rd condo! This stunning condo features breathtaking views, and is the only one with an extended deck and private stairs leading to a spacious patio for Al Fresco

  Sunny Breen Josiah Allen Real Estate, Inc.

  94 Murray Hill Woods Rd Unit 64, Manchester, VT 05255
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  /52

  $1,100,000 Open Sun 11AM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 4,279 Sq Ft

  3 Linscott Rd, Winhall, VT 05340

  Welcome home! This property is MOVE IN READY ! This exceptional contemporary is just minutes from the Stratton base lodge. Meticulously maintained and thoughtfully updated, this home is ideal for you and your guests! Designed for both relaxation and entertaining, the open-concept floor plan ensures everyone can gather with ease. Two spacious living areas provide wonderful flexibility for

  Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

  3 Linscott Rd, Winhall, VT 05340
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  /15

  $169,000

  • 2 Beds
  • 1 Bath
  • 748 Sq Ft

  415 County St, Bennington, VT 05201

  The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated finishes. From the moment you step into the entrance that was converted from a front porch into a versatile mudroom or home office—you’ll feel the quality. The layout is a

  Lori Hurley Four Corner Properties LLC

  415 County St, Bennington, VT 05201
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  /21

  $215,000

  • 2 Beds
  • 1 Bath
  • 938 Sq Ft

  55 Eden Way Unit 3, Bennington, VT 05201

  Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge community! Meticulously maintained and thoughtfully cared for, this home offers effortless one-level living with nothing left to do but unpack. Step inside to discover a freshly painted interior complemented by new flooring and carpeting throughout. The bright and inviting kitchen features beautiful cabinetry and

  Angela Bevin Maple Leaf Realty

  55 Eden Way Unit 3, Bennington, VT 05201
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  /51

  $1,795,000

  • 3 Beds
  • 3 Baths
  • 5,228 Sq Ft

  2167 Myers Rd, Shaftsbury, VT 05262

  Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

  Kelley Mccarthy Mahar McCarthy Real Estate

  2167 Myers Rd, Shaftsbury, VT 05262
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  /26

  $199,000

  • 4 Beds
  • 2 Baths
  • 1,980 Sq Ft

  210 Division St, Bennington, VT 05201

  Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

  Lilli West Maple Leaf Realty

  210 Division St, Bennington, VT 05201
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  /46

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 6,129 Sq Ft

  1035 Holy Smoke Rd, Shaftsbury, VT 05262

  Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

  Lori Hurley Four Corner Properties LLC

  1035 Holy Smoke Rd, Shaftsbury, VT 05262
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  /39

  $895,000

  • 4 Beds
  • 4 Baths
  • 2,673 Sq Ft

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

  Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

  Mike England Michael England Real Estate

  F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
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  /38

  $949,000

  • 4 Beds
  • 3 Baths
  • 3,252 Sq Ft

  E1 Rock Ridge Rd, Winhall, VT 05155

  Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

  Christine Chovan

  E1 Rock Ridge Rd, Winhall, VT 05155
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  /52

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 4,650 Sq Ft

  20 Blackberry Ln, Peru, VT 05152

  Welcome to Bromley Village. This spacious 5 bedroom, 5 bath house offers everything you need to ensure the comfort of your group whether it’s large or small. The heart of this home is the magnificent great room with 20 foot ceilings, wood burning fireplace, slate floors, dining area and corner bar. The gourmet kitchen with red cabinets, soapstone counters, and top of the line appliances (Sub

  David Citron RE/MAX Four Seasons

  20 Blackberry Ln, Peru, VT 05152
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  /45

  $995,000

  • 13 Beds
  • 12 Baths
  • 8,594 Sq Ft

  2759 Vt Route 11, Peru, VT 05152

  Your private Vermont resort awaits! Perfect for multi-generational living or a co-ownership vacation compound, this 9.5-acre estate offers historic charm with massive capacity. Located minutes from premier skiing at Bromley, Stratton, and Magic. Highlights include, Main Residence: Beautifully renovated 1835 farmhouse with 4 beds, 3 baths, modern kitchen, and deck.Guest Wings: Two additions

  Gregory Cutler Four Seasons Sotheby's Int'l Realty

  2759 Vt Route 11, Peru, VT 05152
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  /60

  $5,600,000

  • 5 Beds
  • 5.5 Baths
  • 4,674 Sq Ft

  1060 Upper Hollow Rd, Dorset, VT 05251

  'MOONLIGHT REFLECTIONS ON AN UPPER HOLLOW SANCTUARY'... This stunning rare estate sits on 66 secluded acres of unspoiled beauty, offering breathtaking sweeping views of two luminous ponds, where moonlight reflections shimmer across the water each evening, creating a truly magical feeling. Inside you will find a contemporary open layout anchored by a dramatic stone fireplace, perfect for cozy

  Sunny Breen Josiah Allen Real Estate, Inc.

  1060 Upper Hollow Rd, Dorset, VT 05251
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  /58

  $1,495,000

  • 7 Beds
  • 5.5 Baths
  • 6,392 Sq Ft

  16 West Rd, Bennington, VT 05201

  Elegant and stately, this distinguished 1910 home is beautifully set in the heart of Old Bennington, Vermont. Thoughtful renovations began in 2000, carefully preserving the home’s historic character while enhancing comfort and functionality throughout. Offering over 6,000 square feet of gracious living space, the residence features seven bedrooms, six baths, and six fireplaces, with timeless

  Kelley Mccarthy Mahar McCarthy Real Estate

  16 West Rd, Bennington, VT 05201
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  /23

  $120,000

  • 2 Beds
  • 1 Bath
  • 880 Sq Ft

  818 Old Depot Rd, Shaftsbury, VT 05262

  Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway, vacation rental, or full-time home. New vinyl siding, a recent metal roof, and newer furnace. Enjoy

  Lisa Friedman Great American Dream Realty

  818 Old Depot Rd, Shaftsbury, VT 05262
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  /37

  $829,000

  • 4 Beds
  • 3 Baths
  • 2,797 Sq Ft

  13 Betty Johnson Ln, Bondville, VT 05340

  Experience the magic of Vermont in every season with this stunning four-bedroom, three-bathroom home directly on Stratton Mountain. Your ultimate year-round retreat. Nestled in the heart of Vermont, this property boasts two cozy fireplaces, perfect for warming up after a day of winter adventures or enjoying a crisp autumn evening. With two distinct living areas, you'll find the ideal spaces for

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  13 Betty Johnson Ln, Bondville, VT 05340
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  /31

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  109 Evergreen Dr, Bennington, VT 05201

  House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201
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  /47

  $269,900

  • 3 Beds
  • 1.5 Baths
  • 900 Sq Ft

  2092 N Bennington Rd, North Bennington, VT 05257

  Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  2092 N Bennington Rd, North Bennington, VT 05257
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  /58

  $1,950,000

  • 9 Beds
  • 7 Baths
  • 6,956 Sq Ft

  1086 West Rd, Bennington, VT 05201

  Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

  Kelley Mccarthy Mahar McCarthy Real Estate

  1086 West Rd, Bennington, VT 05201
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  /50

  $750,000

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

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340

  WAKE UP TO UNPRECEDENTED MOUNTAIN VIEWS once called Terra Bella with ownership over four decades and now this can be the Winhall/Stratton residence you have been searching for. From the moment you drive in you are captivated with incredible scenery off prestigious Pearl Buck Drive. Offered on 3.5 acres.The main level boasts newly refinished oak floors, two bedrooms, a den or living area with

  Terry Hill Berkshire Hathaway HomeServices Stratton Home

  57 Pearl Buck Dr Unit 33, Bondville, VT 05340
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  /25

  $1,425,000

  • 3 Beds
  • 2.5 Baths
  • 2,560 Sq Ft

  1058 Granger Hollow Rd, North Bennington, VT 05257

  A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

  Andrea Kaplan Four Seasons Sotheby's Int'l Realty

  1058 Granger Hollow Rd, North Bennington, VT 05257
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  /51

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  281 Old County Ln, Readsboro, VT 05350

  Nestled on more than two acres of beautifully maintained countryside and mature forest, this renovated 1892 farmhouse blends New England charm with peaceful seclusion and easy access to local attractions. Just 15 minutes from Mass MoCA, 25 minutes from Mount Snow, and close to hiking and ATV trails, it’s perfect for outdoor enthusiasts. Inside, you’ll find a warm and thoughtfully updated home

  Melissa Nebelski Real Broker LLC

  281 Old County Ln, Readsboro, VT 05350
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  /27

  $290,000

  • 4 Beds
  • 2 Baths
  • 2,190 Sq Ft

  196 Granger Hollow Rd, North Bennington, VT 05257

  Currently being used as a primary home with in-law rental 2nd home, this property could easily transition into a 2 unit multifamily with 2 separate houses with your tenants paying all utilities responsible for their own plowing and yard upkeep. This quiet country location has 2 homes located on its 2 acres. The main home is a 3 bedroom ranch featuring a large eat-in kitchen opening into a large

  Steve Schoppmeyer BHG Masiello Brattleboro

  196 Granger Hollow Rd, North Bennington, VT 05257
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  /25

  $975,000

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

  Marek Kovac TPW Real Estate

  124 Elm St, Bennington, VT 05201
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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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  /52

  $675,000

  • 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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  /20

  $524,900

  • 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
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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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  /24

  $471,000

  • 3 Beds
  • 2 Baths
  • 1,357 Sq Ft

  102 Mccormick Ln, Sunderland, VT 05250

  Built in 2003, the home's open-concept design is highlighted by a bright and airy living/dining/kitchen area, where large windows flood the space with abundant natural light. A cozy pellet stove provides warmth and ambiance for those crisp Vermont evenings. The functional layout features two comfortable bedrooms and a full bathroom on the main level, while the private primary ensuite bedroom

  Dana Kingsley Josiah Allen Real Estate, Inc.

  102 Mccormick Ln, Sunderland, VT 05250
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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
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  /34

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  114 Colebrook Rd, East Arlington, VT 05252

  This is an unfinished home that needs the right owner to complete it to its fullcapacity.Set off on a private road this home is set on a beautiful, secluded, wooded lot.Access to major highways and schools

  David White OwnerEntry.com

  114 Colebrook Rd, East Arlington, VT 05252
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  /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
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  /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
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  /56

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 3,059 Sq Ft

  466 3 Maple Dr, Manchester, VT 05254

  Welcome to Three Maple Drive, a beautifully crafted, brand-new single-family home nestled in a quiet and scenic location in Manchester, Vermont. Built in 2023 with impeccable attention to detail, this 3,059 sq ft modern farmhouse seamlessly blends luxury, comfort, and timeless design—all set on a private 3.85-acre lot with gorgeous mountain views. This home features three spacious bedroom suites,

  David Shehadi Josiah Allen Real Estate, Inc.

  466 3 Maple Dr, Manchester, VT 05254
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  /43

  $1,895,000

  • 6 Beds
  • 5.5 Baths
  • 5,178 Sq Ft

  144 Taconic Rd, Manchester, VT 05255

  “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

  Tom Deck Josiah Allen Real Estate, Inc.

  144 Taconic Rd, Manchester, VT 05255
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  /32

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 2,696 Sq Ft

  130 Ipan Rd, North Bennington, VT 05257

  Tucked away on a private road, this stunning brick colonial offers over 30 acres of peaceful Vermont countryside-yet is less than 2 miles from the Village of North Bennington and Bennington College. A classic barn and separate studio provide endless possibilities for hobbies, storage, or creative space. The main level features a spacious living room with a fireplace, warm pine floors, and plenty

  Kelley Mccarthy Mahar McCarthy Real Estate

  130 Ipan Rd, North Bennington, VT 05257
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  /34

  $349,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  This inviting in-town home has been nearly completely renovated with only a few more touches to be brought by the new owner, blending fresh updates with classic comfort. Inside, you’ll find 3 bedrooms and a full bath, plus a bonus room that could serve as a 4th bedroom with a half-bath. An additional room with its own separate entrance is ideal for a small home business. The convenient attached

  Cassie Barbeau Mahar McCarthy Real Estate

  89 Merson St, Woodford, VT 05201

Showing Results 41 - 80, Page 2 of 3