Bennington County VT Homes for Sale

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  /12

  $1,295,000

  • Land
  • 52 Acres
  • $24,904 per Acre

  0 Montgomery Rd, Pownal, VT 05261

  A rare opportunity to own one of the most extraordinary parcels in the region. High Meadows Farm encompasses sweeping open meadows, mature woodlands, and truly breathtaking 360-degree views stretching from Mount Greylock to the south, Mount Anthony to the north, the Taconic Ridge to the west, and Dome and Pine Cobble to the east. Wander a secluded birch-lined pathway, discover a magnificent

  Ann Greenwood ALTON & WESTALL REAL ESTATE AGENCY, LLC

  0 Montgomery Rd, Pownal, VT 05261
• 

  

  

  /10

  $125,000

  • Land
  • 5.77 Acres
  • $21,664 per Acre

  0 East Rd, Shaftsbury, VT 05262

  Set along scenic East Road in Shaftsbury, this 5.77-acre wooded parcel offers a beautiful opportunity to create a private Vermont homesite in one of the area’s most appealing rural settings. The land is currently wooded, allowing the next owner to decide how much to clear for a driveway, yard, gardens, or building site, with potential for a mountain view to the north with selective clearing.

  Jenifer Prouty Hoffman Hoffman Real Estate

  0 East Rd, Shaftsbury, VT 05262
• 

  

  

  /49

  $650,000

  • 5 Beds
  • 3 Baths
  • 5,524 Sq Ft

  81 Honeysuckle Ln, North Bennington, VT 05257

  Nestled on 9.89 secluded acres in North Bennington, this exceptional 4-bedroom, 3-bath home offers the perfect blend of character, comfort, and versatility. The sprawling residence features a beautiful interior highlighted by stunning post-and-beam cathedral ceilings and inviting living spaces designed for both everyday living and entertaining. The heart of the home is the large open space

  Kelley Mccarthy Mahar McCarthy Real Estate

  81 Honeysuckle Ln, North Bennington, VT 05257
• 

  

  

  /42

  $3,900,000

  • 5 Beds
  • 7 Baths
  • 11,736 Sq Ft

  2236 River Rd, Manchester, VT 05254

  Set on more than 18 picturesque acres along desirable River Road in Manchester Village, this extraordinary, converted farm offers a rare blend of historic character, modern comfort, & endless possibilities. Thoughtfully transformed into a multi-use residential compound, the property features four distinct living, working, & entertaining spaces, each with its own personality and purpose.

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

  2236 River Rd, Manchester, VT 05254
• 

  

  

  /52

  $850,000

  $120K PRICE DROP

  • 6 Beds
  • 8 Baths
  • 5,764 Sq Ft

  24 Vt Route 11, Londonderry, VT 05148

  Some properties simply hold stories within their walls. Formerly the beloved Nordic Inn, this iconic Landgrove property has been thoughtfully reimagined into a gathering place designed for modern Vermont living while honoring its rich history of hospitality, adventure, and connection. Inside, six ensuite bedrooms, spa-inspired baths, multiple fireplaces, a chef’s kitchen, sun-filled all-season

  Nancy Jensen Four Seasons Sotheby's Int'l Realty

  24 Vt Route 11, Londonderry, VT 05148
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  /37

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14 Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

  Julie Citron RE/MAX Four Seasons

  14 Marisa Ln, Dorset, VT 05251
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  /26

  $2,300,000

  • 5 Beds
  • 3.5 Baths
  • 3,332 Sq Ft

  241 High Hill Rd, Manchester Center, VT 05255

  Perched on a hillside in one of the area's most sought-after in-town locations, this special property offers a rare combination of privacy, breathtaking mountain views, and a picturesque pond, all just moments from local shops, restaurants, and amenities. Surrounded by established landscaping and filled with natural light, the home captures the beauty of its setting through expansive windows on

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

  241 High Hill Rd, Manchester Center, VT 05255
• 

  

  /19

  $182,000

  $13K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,590 Sq Ft

  176 Glen Ave, Readsboro, VT 05350

  Charming and spacious 3-bedroom, 1-bath home situated on approximately 1.90 acres, offering warm character and generous living space. Beautiful wood floors flow throughout the home, complemented by fresh paint, making this property truly move-in ready.The expansive wrap-around porch is a standout feature, perfect for enjoying quiet mornings, relaxing afternoons, or entertaining family and

  Cassandra Ehrlich BHG Masiello Brattleboro

  176 Glen Ave, Readsboro, VT 05350
• 

  

  /41

  $939,000

  • 5 Beds
  • 6 Baths
  • 3,031 Sq Ft

  3191 Vermont 30, Dorset, VT 05251

  Dorset Village Investor's choice! Village Commercial... Currently Presenting a 5 unit, 3030 SF residence that can not be reproduced locally. This building has been lifted and a full (includes a small crawl) poured concrete foundation installed... dry as can be... clean as any basement can be hoped for! There are a mix of one bedrooms and studios... The configuration can be easily altered to

  Laura Beckwith Josiah Allen Real Estate, Inc.

  3191 Vermont 30, Dorset, VT 05251
• 

  

  /16

  $495,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255

  Breathtaking views of Mount Equinox await from the privacy of this three-bedroom, 2.5-bath end unit condominium, ideally located just minutes from town and the ski mountains. The top floor features a bright loft filled with natural light and a convenient half bath. The spacious living room opens to a private deck with stunning mountain views and includes a cozy wood-burning fireplace.The

  Northshire Sales Group Real Broker LLC

  14 Vaughn Farm Rd Unit 1, Manchester Center, VT 05255
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  /38

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,786 Sq Ft

  14A Marisa Ln, Dorset, VT 05251

  Welcome to your next chapter in the charming heart of Vermont, where easy living meets thoughtful design in this beautifully crafted one-level duplex townhouse. If you've been dreaming of a home that eliminates stairs from your daily routine while still delivering style and substance, your search ends here. Step inside and discover an open floor plan that feels both spacious and inviting across

  Julie Citron RE/MAX Four Seasons

  14A Marisa Ln, Dorset, VT 05251
• 

  

  /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.

  397 Fern Hill, Dorset, VT 05251
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  /41

  $1,425,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,931 Sq Ft

  932 Mcnamara Rd, Dorset, VT 05251

  It's SUMMER in Dorset and Manchester Vermont and this home screams opportunity ! NEW ROOF and exterior maintenance all updated for new owner! Situated in a most beautiful 5.4 acre setting of mature trees, landscaping and privacy, tucked away at the end of a gently curved, tree-lined drive. Located just over the Manchester Dorset town line, where Three Maple Drive becomes MacNamara, you'll

  Britt Wohler

  932 Mcnamara Rd, Dorset, VT 05251
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  /9

  $374,900

  • Land
  • 2.31 Acres
  • $162,294 per Acre

  0 Wall St, Winhall, VT 05340

  Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away from the bustle of the resort. Totaling 2.31 acres, this land is situated high on River Road where neighboring homes enjoy spectacular views of Stratton. Conceptual rendering showing the potential view is based on the current

  Cheyanne Pugliese

  0 Wall St, Winhall, VT 05340
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  /28

  $159,000

  $30K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 760 Sq Ft

  1675 Vermont 9, Searsburg, VT 05363

  Welcome to Peaceful Pines, your cottage in the woods near the entrance to the Green Mountain National Forest. The charming two-bedroom cottage/camp was lovingly maintained. Key updates include a completely rebuilt chimney and masonry work, a wood stove ( in addition to baseboard heat) to take the chill out of those fall and winter evenings, T11 siding, a newer roof, and a private back deck with

  Jacki Murano Southern Vermont Realty Group

  1675 Vermont 9, Searsburg, VT 05363
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  /38

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  25 Benson Fuller Dr, Bondville, VT 05340

  Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway feels like. From the moment you step inside, the design does exactly what a great contemporary home should: it steps back and lets nature take center stage. Massive, soaring windows act as living art pieces, framing sweeping,

  Robin Apps Four Seasons Sotheby's Int'l Realty

  25 Benson Fuller Dr, Bondville, VT 05340
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  /38

  $309,900

  $15K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft

  2 Pine Rd, Bennington, VT 05201

  Bright 3 bedroom, 1 and a half bath home in Bennington. Close to the hospital and offering kitchen, formal dining room, living room, and 2 main level bedrooms. Upstairs a loft office area and another bedroom. The basement is partially finished with laundry, family room and half bath. Outside there is a great deck with a separate, heated sun room and 2 car detached garage. A must see home in a

  Brenda Jones KW Vermont - Brenda Jones Real Estate Group

  2 Pine Rd, Bennington, VT 05201
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  /43

  $439,000

  • 4 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  96 Twitchell Hill Rd, Shaftsbury, VT 05262

  Some homes simply have a way of making you slow down. Built in 1863, the original Twitchell Farmhouse is one of them. Rich in history and craftsmanship, this beautifully maintained four-bedroom, 2.5-bath home offers the warmth and authenticity that only a true Vermont farmhouse can provide. Original hardwood floors, handcrafted woodwork by a master carpenter, and thoughtful updates create a home

  Daire Gibney Barrett and Valley Associates Inc.

  96 Twitchell Hill Rd, Shaftsbury, VT 05262
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  /46

  $1,599,000

  • 6 Beds
  • 5.5 Baths
  • 5,568 Sq Ft

  144 High Meadow Rd, Winhall, VT 05340

  Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated kitchen and expanded finished lower level, this home is ready for mountain living and endless entertaining! Designed with multiple gathering rooms and fireplaces, you'll enjoy apres ski with and an incredible open floor plan. Game

  Kim Morgan-Wohler Wohler Realty Group

  144 High Meadow Rd, Winhall, VT 05340
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  /23

  $329,900

  $20K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  773 Oberdorf Rd, Readsboro, VT 05350

  Discover cozy mountain living in this charming Alpenwald chalet, where rustic character meets thoughtful modern updates. Nestled among the trees, this inviting retreat offers a bright, open floor plan filled with natural light from expansive windows and sliding glass doors. Recently remodeled, the kitchen and both full bathrooms bring a fresh, updated feel, while a comfortable bar area adds the

  Sean Taylor Moresi Real Estate Partners

  773 Oberdorf Rd, Readsboro, VT 05350
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  /15

  $125,000

  • Land
  • 1.18 Acres
  • $105,932 per Acre

  510 Center St, Pownal, VT 05261

  Discover the potential of this scenic 1.18 acre parcel situated on a quiet street directly across from the town offices. Offering beautiful views and the convenience of town sewer, this property presents an excellent opportunity to build the home you've been dreaming of. Whether you're planning a year-round residence or a peaceful retreat, the generous lot provides plenty of space to create your

  Angela Bevin Maple Leaf Real Estate

  510 Center St, Pownal, VT 05261
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  /37

  $269,900

  $19K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,146 Sq Ft

  109 County St, Bennington, VT 05201

  Welcome to your like-new home in the heart of Bennington! Within easy walking distance of the vibrant downtown district, this beautifully renovated 4-bedroom, 2-bath New Englander has been completely transformed into a truly turnkey property. Nearly every aspect of the home has been updated, allowing you to enjoy the benefits of modern, low-maintenance living from day one.Extensive

  Angela Bevin Maple Leaf Real Estate

  109 County St, Bennington, VT 05201
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  /40

  $5,900,000

  $1M PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft

  515 W Fields Rd, Manchester, VT 05254

  Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

  Sunny Breen Josiah Allen Real Estate, Inc.

  515 W Fields Rd, Manchester, VT 05254
• 

  

  /47

  $845,000

  • 5 Beds
  • 5.5 Baths
  • 3,875 Sq Ft

  1629 Mann Hill Rd N, Pownal, VT 05261

  Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this stunning modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors and cozy alcoves create warmth and charm throughout, while original beams in the living room add a touch of history and authenticity. The spacious layout offers 5 bedrooms, each with

  Kelley Mccarthy Mahar McCarthy Real Estate

  1629 Mann Hill Rd N, Pownal, VT 05261
• 

  

  /10

  $245,000

  $97K PRICE DROP

  • Land
  • 28.5 Acres
  • $8,596 per Acre

  11 Old County Rd E, Londonderry, VT 05148

  A rare opportunity to own a wooded hillside property with potential southern and western views on a quiet country road in the much coveted village of Landgrove. Priced below the town assessment, the land is in current use, affording a tax savings, with a state permit for a 4-bedroom house. Enjoy all the elements of a Vermont country setting including a mix of mature hardwoods and softwoods,

  Steve Stettler Four Seasons Sotheby's Int'l Realty

  11 Old County Rd E, Londonderry, VT 05148
• 

  

  /56

  $2,200,000

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

  312 Beartown Rd, Manchester Center, VT 05255

  Set on 24 private acres with sweeping mountain views, 312 Beartown Road offers a sense of complete escape while remaining moments from Manchester.Filled with natural light, the four-bedroom residence is thoughtfully designed to capture its extraordinary setting. Every room is oriented to the outdoors, with expansive windows that keep the Vermont landscape always in view. The chef's kitchen

  Christiane Carroccio TPW Real Estate

  312 Beartown Rd, Manchester Center, VT 05255
• 

  

  /38

  $775,000

  • 4 Beds
  • 4 Baths
  • 3,520 Sq Ft

  12 Stratton Ridge Rd, Winhall, VT 05340

  First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the dead end of a private road, the setting offers privacy along with a true Vermont feel—quiet and peaceful.Inside, the home features a bright, open layout with abundant natural light and warm woodwork throughout, creating an

  Carrie Mathews Winhall Real Estate

  12 Stratton Ridge Rd, Winhall, VT 05340
• 

  

  /54

  $495,000

  • 4 Beds
  • 2.5 Baths
  • 3,312 Sq Ft

  498 Townline Rd, Bennington, VT 05201

  If you are seeking privacy and serenity, look no further. Your private drive will lead you to your home on the hill with no neighbors in sight. You will enjoy this peaceful spot, yet you are just 5 miles to downtown Bennington. 52+ acres that include open land perfect for kids, animals, gardens, sledding, or all of the above. The blueberry bushes are big producers. This home was built by the

  Betty McEnaney Diamond Realty

  498 Townline Rd, Bennington, VT 05201
• 

  

  /12

  $299,999

  • Land
  • 10.05 Acres
  • $29,851 per Acre

  00 Garden Loop Rd, Winhall, VT 05340

  The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

  David White OwnerEntry.com

  00 Garden Loop Rd, Winhall, VT 05340
• 

  

  /45

  $275,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  951 Gage St, Bennington, VT 05201

  This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

  Dan Mason Perrott Realty

  951 Gage St, Bennington, VT 05201
• 

  

  /31

  $1,200,000

  • 1 Bath
  • 950 Sq Ft

  109 Winhall Hollow Rd, Winhall, VT 05340

  Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home—it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling

  Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

  109 Winhall Hollow Rd, Winhall, VT 05340
• 

  

  /38

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,288 Sq Ft

  1 Beaver St, Bondville, VT 05340

  Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minutes to Bromley, and 12 minutes to Manchester, you’ll enjoy easy access to skiing, dining, shopping, and year-round recreation.Inside, the home features a spacious living room filled with natural light, creating a warm and

  Carrie Mathews Winhall Real Estate

  1 Beaver St, Bondville, VT 05340
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  /36

  $359,000

  $40K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,938 Sq Ft

  100 McCarthy Acres, North Bennington, VT 05257

  Nearly Lakefront Living in the Heart of North Bennington!Come for the space—stay for the location! This spacious home offers over 2,500 sq. ft. of living space, including 5 bedrooms, 3 full bathrooms, a large home office in the finished basement, and a versatile 250 sq. ft. bonus room attached to one of the upstairs bedrooms. The original garage has been thoughtfully transformed into a 600

  Nicholas Charest Maple Leaf Real Estate

  100 McCarthy Acres, North Bennington, VT 05257
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  /32

  $575,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,234 Sq Ft

  202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255

  This Eagle Rise Condo with three bedrooms and two & half baths is in an exclusive residential area accessed off scenic Manchester West Road. The Condo offers an open floor plan design, central air, propane baseboard hot water heat, hardwood floors and elevated deck. Recent improvements include new kitchen w/ granite counter tops, hickory cabinets with soft close drawers & doors, stainless steel

  David Halligan Four Seasons Sotheby's Int'l Realty

  202 Eagle Rise Rd Unit 16, Manchester Center, VT 05255
• 

  

  /22

  $430,000

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  13 Golden Triangle Rd, Winhall, VT 05340

  The ideal opportunity in a prime location, minutes from Stratton Mountain, Bromley Mountain, and the charming town of Manchester, this 5-bedroom, 2-bathroom home has what you need for your primary Vermont residence or a quiet place to getaway. The spacious living room and dining area is complimented by a wrap around porch. This home is low maintenance and setup well for those who want a

  Mike England Michael England Real Estate

  13 Golden Triangle Rd, Winhall, VT 05340
• 

  

  /42

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,814 Sq Ft

  1153 King Hill Rd, Readsboro, VT 05350

  This recently updated 1920s Vermont farmhouse features 4 bedrooms, 2 full bathrooms, and a versatile loft space on just over 8 acres! Large, updated windows showcase mountain views and allow natural light to fill every room, highlighting the home's charming original details alongside modern updates. The first floor has two bedrooms, both full bathrooms, first floor laundry, as well as TWO

  Casey Scott Southern Vermont Realty Group

  1153 King Hill Rd, Readsboro, VT 05350
• 

  

  /56

  $925,000

  • 3 Beds
  • 4.5 Baths
  • 3,718 Sq Ft

  171 Mending Walls Rd, Manchester Center, VT 05255

  Looking for "NEW"? This residence is as close to new construction as it gets, having been thoughtfully gutted to the studs and tastefully renovated across all three levels. The stunning new quartz island kitchen features all new stainless appliances, new soft gray cabinetry, and an open-concept design flowing seamlessly into the dining room, living room and main-level office. A dramatic two-story

  Laura Beckwith Josiah Allen Real Estate, Inc.

  171 Mending Walls Rd, Manchester Center, VT 05255
• 

  

  /11

  $260,000

  • Land
  • 3.3 Acres
  • $78,788 per Acre

  0 Mountain Haunts Unit 5099438, Winhall, VT 05340

  The 3.3-acre parcel of land located on Mt Haunts Road in Winhall has received approval for the construction of a four-bedroom residence, presenting an outstanding opportunity for prospective homeowners. This exceptional site boasts views of Stratton Mountain Resort, allowing residents to monitor the mountain's snow conditions from the comfort of their own home each morning, as well as enjoy views

  Mike England Michael England Real Estate

  0 Mountain Haunts Unit 5099438, Winhall, VT 05340
• 

  

  /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
• 

  

  /34

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,343 Sq Ft

  760 W Mountain Rd, Shaftsbury, VT 05262

  Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

  Kelley Mccarthy Mahar McCarthy Real Estate

  760 W Mountain Rd, Shaftsbury, VT 05262

Showing Results 121 - 160, Page 4 of 7