Windsor County VT Homes for Sale with Acreage

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  /52

  $849,000

  • 4 Beds
  • 4.5 Baths
  • 4,009 Sq Ft

  320 Old Bow Rd, Springfield, VT 05156

  Tucked away on a private road in Weathersfield, this property offers nearly 14 acres of open land, big sky, and clear views of Ascutney Mountain. A good portion of the land has already been cleared and is currently home to farm animals, so there is a head start here if that lifestyle appeals to you. You can keep it going as it is, expand into something more, or simply enjoy the open land for the

  

  Patrick Kelley

  Real Broker LLC

  (802) 392-2795

  320 Old Bow Rd, Springfield, VT 05156
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  /41

  $195,000

  • Land
  • 3.41 Acres
  • $57,185 per Acre

  119 Advent Hill Rd, Hartland, VT 05048

  Perched high in the scenic hills of Hartland, this exceptional 3.41 acre parcel offers the perfect balance of privacy, sunshine, and sweeping Vermont beauty. Fully surveyed, the property features a selectively cleared and thoughtfully laid out open house site, positioned to capture big vistas overlooking abutting fields and pastureland. In a neighborhood with multi-million dollar homes nearby,

  

  John Bassette

  Bassette Real Estate Group

  (802) 523-2987

  119 Advent Hill Rd, Hartland, VT 05048
• 

  

  

  /60

  $349,900

  • 4 Beds
  • 2 Baths
  • 1,546 Sq Ft

  295 Spencer Hollow Rd, Springfield, VT 05156

  First time ever for sale! This delightful country home has been with the same family since it was built. Expanded cape style home is full of wonderful natural light, hardwood and tile floors, natural woodwork, built-in China cabinet, 3 bedrooms and full bath on the main floor and a fourth bedroom and 3/4 bath on the second floor along with a bonus room. Ceiling fans throughout the home keep the

  

  Julie Buffum

  Buffum Realty

  (802) 481-3424

  295 Spencer Hollow Rd, Springfield, VT 05156
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  /60

  $475,000

  $20K PRICE DROP

  • 3,036 Sq Ft

  7868 Pomfret Rd, North Pomfret, VT 05053

  CASH FLOW POSITIVE - PRICE REDUCTION! A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c.1830. This 3-story New Englander offers charm, character, and a solid income stream on 1.84 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office

  

  John Bassette

  Bassette Real Estate Group

  (802) 215-9321

  7868 Pomfret Rd, North Pomfret, VT 05053
• 

  

  

  /5

  $139,000

  • 2,144 Sq Ft

  73 Union St, Springfield, VT 05156

  Nice sized in-town home and yard with large 2 car garage and shed. Lots of room for your toys. The home is currently a 2-unit home but was originally a single-family home and could be changed back into a one family without a lot of effort. Home does need some work so cash buyers only please. This could be your chance to get into rental business. Lots of possibilities for this home.Home is

  

  Julie Buffum

  Buffum Realty

  (802) 423-2965

  73 Union St, Springfield, VT 05156
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  /47

  $1,790,000

  $105K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,708 Sq Ft

  196 Cowdrey Outlook, Bethel, VT 05032

  For the first time in over half a century, this extraordinary 100+ acre estate-level property in Barnard is being offered for sale. Cherished by the same family for generations, the property presents a rare opportunity to own one of Vermont’s most scenic and versatile landscapes. Commanding long-range mountain views define the setting, while several picturesque spring-fed ponds, rolling meadows,

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  (802) 284-4197

  196 Cowdrey Outlook, Bethel, VT 05032
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  /52

  $599,000

  • 4 Beds
  • 3 Baths
  • 3,428 Sq Ft

  583 Hawk Spur Rd, Plymouth, VT 05056

  Looking for a property with HUGE equity possibilities?? Your dream mountain retreat perfectly nestled between Okemo/Vail and Killington awaits! This contemporary diamond in the rough boasts mountain views and sits on a double lot in the desirable Hawk resort area. You will fall in love with the floods of natural light that bring the outdoors in. This home is ready for your ideas and finishes

  

  Lisa Kelley

  Cummings & Co

  (802) 988-7969

  583 Hawk Spur Rd, Plymouth, VT 05056
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  /3

  $170,000

  • Land
  • 10.04 Acres
  • $16,932 per Acre

  00 Will Dean Rd, Springfield, VT 05156

  Nice piece of land with some selected clearing done but more could be done with the potential of views. Land is both clear and wooded, level and sloping. Located on a quiet gravel road with a mix of single-family homes and small farms it is the perfect reflection of rural Vermont. Just minutes to I91and downtown Springfield makes this a great spot to set down roots.

  

  Julie Buffum

  Buffum Realty

  (802) 327-7566

  00 Will Dean Rd, Springfield, VT 05156
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  /41

  $325,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,332 Sq Ft

  397 River St, Chester, VT 05143

  Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops

  

  Lisa Kelley

  Cummings & Co

  (802) 392-0114

  397 River St, Chester, VT 05143
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  /49

  $2,195,000

  • 3 Beds
  • 3 Baths
  • 2,997 Sq Ft

  9671 Vt Route 12, Barnard, VT 05031

  SPRING HILL FARM – A Storied Vermont Estate with Timeless Appeal. Set amidst the rolling hills of Barnard, Vermont, Spring Hill Farm is a distinguished country estate where historic charm and thoughtful stewardship come together across 207 acres of beautifully maintained landscape. Anchoring the property is a stately brick residence dating to 1795, offering a refined sense of heritage and

  

  Susan Hickey

  Snyder Donegan Real Estate Group

  (802) 300-4226

  9671 Vt Route 12, Barnard, VT 05031
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  /44

  $824,900

  $25K PRICE DROP

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

  117 Horseshoe Dr, Brownsville, VT 05037

  Experience Vermont living at its finest in this custom-built home, thoughtfully designed by the builder for exceptional energy efficiency and year-round comfort. Perfect as a relaxing getaway, this property offers expansive sleeping spaces ideal for hosting family and friends. Spend your days exploring the nearby VAST Trail system or Ascutney Mountain, and your evenings unwinding by the

  Katie Ladue Gilbert BHHS Verani Upper Valley

  117 Horseshoe Dr, Brownsville, VT 05037
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  /54

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 1,972 Sq Ft

  207 Hartness Way, Hartford, VT 05001

  Are you looking for the ideal energy efficient property, perhaps perfect as a 2nd home or investment opportunity? The Sellers have paid less than $3,300 per year covering all utilities for this premium energy efficient home. Discover the perfect blend of comfort, efficiency, and adventure in this beautifully designed, sunny and bright newer-build home, nestled within Vermont's coveted Quechee

  Tyler Hall BHHS Verani Upper Valley

  207 Hartness Way, Hartford, VT 05001
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  /60

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 5,127 Sq Ft

  114 Oak Ridge Way, Woodstock, VT 05091

  See the property specific website with video, 3-D tour and more. Set against the timeless beauty of Woodstock’s rolling countryside, this exceptional estate offers a rare blend of refined luxury and pastoral charm. Thoughtfully designed for both elegant entertaining and everyday comfort, the four-bedroom, four-bath residence centers around a stunning gourmet kitchen—complete with a Sub-Zero

  Tami Sullivan Snyder Donegan Real Estate Group

  114 Oak Ridge Way, Woodstock, VT 05091
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  /50

  $1,399,000

  $49K PRICE INCREASE

  • 4 Beds
  • 3.5 Baths
  • 3,720 Sq Ft

  145 the Plateau, Windsor, VT 05089

  "The Plateau", originally part of the Kennedy Biscuit Co. (Nabisco) family estate, is nestled on a plateau at the end of a private road which greets you with open fields, mature trees, beautiful gardens, and a protected front-and-center view of Mt. Ascutney to the West and the Connecticut River to the East. This private peaceful setting includes an inground pool for those hot summer days, and two

  Dan Noble Snyder Donegan Real Estate Group

  145 the Plateau, Windsor, VT 05089
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  /60

  $479,000

  Open House 6/27

  • 3 Beds
  • 3 Baths
  • 2,676 Sq Ft

  64 Maple St, Chester, VT 05143

  Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area

  Betsy Adamovich Real Broker LLC

  64 Maple St, Chester, VT 05143
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  /33

  $1,895,000

  • 2 Beds
  • 2.5 Baths
  • 2,944 Sq Ft

  2394 Fletcher Hill Rd, Woodstock, VT 05091

  Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

  John Snyder Snyder Donegan Real Estate Group

  2394 Fletcher Hill Rd, Woodstock, VT 05091
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  /60

  $2,350,000

  $145K PRICE DROP

  • 5 Beds
  • 9 Baths
  • 7,322 Sq Ft

  1497 Bowman Rd, Barnard, VT 05068

  Circa 1799 Vermont cape, thoughtfully restored and expanded to over 7,300 finished square feet on 12.5 private acres, minutes to Silver Lake and Woodstock village. Five bedrooms, nine baths, and a layout that balances everyday living with the ability to host. Original materials carry throughout, including wide pine floors, skim-coat plaster walls, hand-carved paneling, and period hardware, giving

  Richard Higgerson Higgerson & Company

  1497 Bowman Rd, Barnard, VT 05068
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  /58

  $3,100,000

  • 5 Beds
  • 6 Baths
  • 4,843 Sq Ft

  66 Hollow Farm Rd, Woodstock, VT 05071

  CURTIS HOLLOW FARM- Exceptional estate on the western edge of Woodstock offering 105 diverse acres bordering Calvin Coolidge State Forest. The updated main house features 5 bedrooms and 4 baths, filled with abundant natural light and thoughtfully designed for both large gatherings and quiet retreat spaces. The open-concept main level includes a spacious living room with picture windows

  David Donegan Snyder Donegan Real Estate Group

  66 Hollow Farm Rd, Woodstock, VT 05071
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  /60

  $2,195,000

  $255K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 5,625 Sq Ft

  16 Olcott Rd, Norwich, VT 05055

  16 OLCOTT ROAD- Elegant, spacious, and immaculate reproduction colonial constructed by premier builder Douglas Gest in an idyllic location minutes to Norwich Village yet privately set with lovely westerly views. This gorgeous home is well-appointed, bright, and has fine finish work at every turn. The main level flows effortlessly from a spacious kitchen and pantry to open concept dining and

  David Donegan Snyder Donegan Real Estate Group

  16 Olcott Rd, Norwich, VT 05055
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  /52

  $1,395,000

  $100K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,648 Sq Ft

  1522 Barnard Rd, Woodstock, VT 05091

  Just 2 miles from Woodstock Village, this gracious brick Cape on 6 open acres offers the perfect blend of privacy, comfort, and classic Vermont charm. Thoughtfully expanded and beautifully maintained, the home features a chef’s kitchen that opens seamlessly to a spacious gathering room designed for entertaining and everyday living. Multiple fireplaces—including a wood-burning and gas-ready—add

  Keri Cole Williamson Group Sothebys Intl. Realty

  1522 Barnard Rd, Woodstock, VT 05091
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  /16

  $3,150,000

  • Land
  • 506 Acres
  • $6,225 per Acre

  Markham Mountain, Andover, VT 05143

  Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

  Story Jenks LANDVEST

  Markham Mountain, Andover, VT 05143
• 

  

  /15

  $237,000

  • Land
  • 221 Acres
  • $1,072 per Acre

  0 New Boston Rd, Thetford, VT 05074

  IntroductionThe ownership is selling their property in two separate parcels, divided by the town line. The +/-60 acre Strafford parcel is well suited to future home development with paved town road frontage and roadside electric service. The +/-220 acre Thetford parcel is well suited to a camp or seasonal off-grid home development with beautiful local views.Both parcels have

  John Latham Fountains Land

  0 New Boston Rd, Thetford, VT 05074
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  /24

  $217,500

  • Land
  • 94 Acres
  • $2,314 per Acre

  6416 Vermont 107, Stockbridge, VT 05772

  Nestled among natural streams in the rolling hills of Vermont’s Green Mountains, this remarkable 94-acre parcel offers sweeping views overlooking the White River. Rich with potential for residential use or future development, the property includes a private septic system and a drilled well already in place. With 670 feet of frontage along VT Route 107, the land provides convenient access while

  Kate Jarvis Williamson Group Sothebys Intl. Realty

  6416 Vermont 107, Stockbridge, VT 05772
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  /41

  $725,000

  $70K PRICE DROP

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

  115 Prior Rd, Cavendish, VT 05142

  Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral

  Glenn Olney Barrett and Valley Associates Inc.

  115 Prior Rd, Cavendish, VT 05142
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  /17

  $53,000

  • Land
  • 1.5 Acres
  • $35,333 per Acre

  2-66 Goshawk Dr, Plymouth, VT 05056

  Dreaming of building your own Vermont-style home but hoping to find an affordable parcel? This lot at Hawk Resort is the perfect opportunity. With power and other utilities already on site and the ability to connect to the community septic system, you’ll be well on your way to breaking ground on your dream home. Tucked among the trees in a peaceful natural setting, this property offers privacy

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  2-66 Goshawk Dr, Plymouth, VT 05056
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  /25

  $115,000

  • Land
  • 10 Acres
  • $11,500 per Acre

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056

  Ten-acre wooded parcel with potential views located near the top of Great Roaring Brook Rd. The topography is rolling too steep with multiple buildings sites, rock crop outs, and streams throughout. A wonderful opportunity to design and build your Vermont dream home. Located between Ludlow and Woodstock with equal distance to Killington and Okemo Ski areas. Close to Lake Rescue and Echo Lake for

  Terry Davis Williamson Group Sothebys Intl. Realty

  S-1C Great Roaring Brook Rd, Plymouth, VT 05056
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  /39

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,308 Sq Ft

  76 Goldthwaite Rd, Chester, VT 05143

  Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

  Gary Coger Four Seasons Sotheby's Int'l Realty

  76 Goldthwaite Rd, Chester, VT 05143
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  /36

  $95,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149

  Experience Vermont's Premier Mountain Living Without Full Ownership Costs. Step directly onto Okemo's slopes from your slopeside retreat at Jackson Gore. This condo-tel quarter-share gives you deeded ownership of 13 weeks annually (25% of the year)—at a fraction of the cost of whole ownership. You own one of four deeded interests in this unit. You receive every fourth week on a rotating schedule,

  Rachael Lange Lange & Lange

  224 QIV Jackson Gore Inn Unit 224 QIV, Ludlow, VT 05149
• 

  

  /12

  $199,000

  • Land
  • 29 Acres
  • $6,862 per Acre

  00 Vermont 12, Barnard, VT 05031

  A beautiful and private 29 acre building lot on a mountainside in an area of Barnard populated by estate properties. A road to the potential building site is in and soil testing for septic will be completed as soon as snow clears. Views of the valley and local mountains currently cleared and can be expanded with additional clearing. The location is a short drive to Woodstock, a shorter drive to

  Stan Butler Four Seasons Sotheby's Int'l Realty

  00 Vermont 12, Barnard, VT 05031
• 

  

  /3

  $175,000

  • Land
  • 12.51 Acres
  • $13,989 per Acre

  377 Coach Rd, Chester, VT 05143

  Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

  Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

  377 Coach Rd, Chester, VT 05143
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  /36

  $500,000

  • 3 Beds
  • 3 Baths
  • 2,122 Sq Ft

  1138 Bethel Mountain Rd, Rochester, VT 05767

  Set on 4.7± acres along scenic Bethel Mountain Road, this mountain-view property offers the kind of Vermont experience that you're yearning for. With a swimming pond, expansive outdoor living spaces, detached three-car garage, and easy access to some of the state’s best outdoor recreation, this is a home designed to be enjoyed in every season. The setting is exceptional. Long-range mountain views

  William Brokhof Vermont Backcountry Real Estate

  1138 Bethel Mountain Rd, Rochester, VT 05767
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  /29

  $530,000

  • 3 Beds
  • 2.5 Baths
  • 4,020 Sq Ft

  28 Fairview Terrace, Royalton, VT 05068

  This 3-bedroom, 2.5-bath home is full of potential, with the option to create an auxiliary dwelling for added flexibility. The current owner saw the promise in this gem and has already invested in the important updates: fresh exterior paint, a brand-new septic system, a new roof, upgraded electrical, and other quality improvements. With much of the essential work complete, the next owner has the

  Wendie Wright Coldwell Banker LIFESTYLES - Hanover

  28 Fairview Terrace, Royalton, VT 05068
• 

  

  /4

  $169,000

  • Land
  • 15.4 Acres
  • $10,974 per Acre

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091

  Instant Equity in Woodstock! Bring your vision to life on this exceptional parcel of raw land, nestled in one of Vermont’s most coveted and quintessential communities. Offered below its current town-assessed value and backed by a recent independent appraisal valuation, this property delivers significant instant equity from day one. Whether you envision a private, tucked-away country estate or a

  Chelsea Bevis KW Vermont Woodstock

  0 Iver Johnson Way Unit 5095630, Woodstock, VT 05091
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  /12

  $79,000

  • Land
  • 2.53 Acres
  • $31,225 per Acre

  Lot #4 Meadow Rd, Ludlow, VT 05149

  Private 2.53+/- acre state approved building lot located at the end of a dead-end, private road. Positioned at the south end of Ludlow off East Hill Road, this lot offers easy access to town amenities and the Okemo Ski Area. Possible views of Okemo with clearing.

  Andre Menard Mary W. Davis Realtor & Assoc., Inc.

  Lot #4 Meadow Rd, Ludlow, VT 05149
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  /20

  $85,000

  • Land
  • 3.99 Acres
  • $21,303 per Acre

  00 Simonsville Rd, Andover, VT 05143

  ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for

  Geralyn Donohue Four Seasons Sotheby's Int'l Realty

  00 Simonsville Rd, Andover, VT 05143
• 

  

  /6

  $195,000

  • Land
  • 1 Acre
  • $195,000 per Acre

  Lot 48 Partridge Rd, Ludlow, VT 05149

  1.01+/- acres. Lot 48. Ready to build. Prestigious neighborhood, some lots with views of Okemo Slopes with clearing. Very convenient to the village and Okemo Mountain Resort. This property is owned by a Vermont licensed real estate agent.

  Boris Lavanovich Mary W. Davis Realtor & Assoc., Inc.

  Lot 48 Partridge Rd, Ludlow, VT 05149
• 

  

  /60

  $1,250,000

  • 3 Beds
  • 4 Baths
  • 3,123 Sq Ft

  292 Hard Rd, Hartford, VT 05001

  Rooted in the traditions of New England architecture and thoughtfully built for modern living, this colonial reproduction occupies a special place within Quechee Lakes, Vermont's premier four-season community.Inspired by a Connor Historic Federal farmhouse design and constructed by one of the region's most respected builders, the home reflects a level of craftsmanship that is increasingly

  Richard Higgerson Higgerson & Company

  292 Hard Rd, Hartford, VT 05001
• 

  

  /41

  $1,576,000

  • 9,455 Sq Ft

  14 Summarsell Dr Unit 16, Hartland, VT 05048

  This charming converted farmstead features two primary buildings on one parcel, combining classic Vermont character with solid investment returns. The property offers a diverse mix of one-, two-, and four-bedroom apartments, plus one commercial unit currently leased to a local bath and body company. Additional income comes from a three-bay garage, a shed, and a storage container — all fully

  Loren Wehmeyer Tesla Realty Group, LLC

  14 Summarsell Dr Unit 16, Hartland, VT 05048
• 

  

  /20

  $599,000

  $190K PRICE DROP

  • Land
  • 33 Acres
  • $18,152 per Acre

  00 Olcott Rd Unit 189, Norwich, VT 05055

  This 33-acre estate-quality parcel is offered with conceptual drawings and a fully permitted four-bedroom wastewater system design, presenting an exceptional opportunity to build in a prime Upper Valley location. Overlooking and bordering conserved land, the property is located just 1.5 miles from the center of Norwich, Vermont. Its close proximity to downtown Hanover, NH, and Dartmouth College,

  Richard Higgerson Higgerson & Company

  00 Olcott Rd Unit 189, Norwich, VT 05055
• 

  

  /48

  $2,500,000

  • 6 Beds
  • 6 Baths
  • 7,019 Sq Ft

  5518 Vermont 12, Barnard, VT 05031

  This gracious 1796 Brick Federal homestead was transformed into a popular gathering spot more than 60 years ago. The Barnard Inn has long been considered among the finest dining and hospitality venues in Vermont. It is currently operated as an event destination by the chef-owner and his family. Now, with children grown and off on their own paths, it is time to pass stewardship of the historic

  Laird Bradley Williamson Group Sothebys Intl. Realty

  5518 Vermont 12, Barnard, VT 05031

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