Windsor County VT Homes for Sale

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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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  /48

  $1,695,000

  • 4 Beds
  • 2.5 Baths
  • 3,542 Sq Ft

  353 Cabot Rd, Woodstock, VT 05091

  "BLISS HOUSE" Privately nestled on a picturesque hillside just minutes from the Woodstock Village Green, this beautifully renovated residence offers exceptional privacy, sweeping long-range mountain views, open meadows, mature gardens, a swimming pool, hot tub, and the perfect blend of Vermont charm and modern comfort. A thoughtful renovation transformed the kitchen and dining areas into a

  John Snyder Snyder Donegan Real Estate Group

  353 Cabot Rd, Woodstock, VT 05091
• 

  

  

  /58

  $569,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,924 Sq Ft

  530 West Rd, Barnard, VT 05031

  Set just up West Road in Barnard, this inviting Cape-style home offers a classic Vermont setting: a peaceful wooded backdrop, warm interior character, and easy access to village life, Silver Lake, and the outdoors. The Barnard General Store and Silver Lake, with the town hall, town library, and newly constructed fire station, are nearby. West Road also serves as a way to head toward the

  Eric Johnston Four Seasons Sotheby's Int'l Realty

  530 West Rd, Barnard, VT 05031
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  /38

  $1,599,000

  • 4 Beds
  • 3.5 Baths
  • 3,456 Sq Ft

  96 Echo View Dr, Plymouth, VT 05056

  Experience the perfect blend of luxury, comfort, and Vermont charm in this exceptional 3,456-square-foot home. Built with superior craftsmanship andmeticulous attention to detail, this residence reflects a commitment to quality where every finish was carefully selected and thoughtfully executed. No detail wasoverlooked, with premium materials and high-end finishes throughout, creating a home that

  Gail Beardmore Engel & Volkers Okemo

  96 Echo View Dr, Plymouth, VT 05056
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  /58

  $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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  /60

  $29,000,000

  $10M PRICE DROP

  • 2 Beds
  • 7 Baths
  • 9,950 Sq Ft

  650 Francis Rd, Barnard, VT 05031

  Set on 400+/- acres in Barnard, Vermont, Monsalvat Farm is a legacy estate where rolling pastures, stone walls, forests, and mountain views reflect the state’s timeless character. Settled in 1793, the land carries generations of stewardship, elevated by one of the finest residences in the country—an architectural masterpiece complemented by historic and companion structures that are carefully

  Chris Lang

  650 Francis Rd, Barnard, VT 05031
• 

  

  /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
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  /15

  $205,000

  $32K PRICE DROP

  • Land
  • 221 Acres
  • $928 per Acre

  0 New Boston Rd, Thetford, VT 05074

  The ownership is selling their property in two separate parcels, divided by the town line. The +/-60-acre Strafford parcel is well-suited for 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 significant frontage

  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
• 

  

  /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
• 

  

  /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
• 

  

  /30

  $3,500,000

  • 4 Beds
  • 3 Baths
  • 2,571 Sq Ft

  58 Lakeshore Dr, Ludlow, VT 05149

  One-of-a-kind Lake Rescue sanctuary with 179 feet of shoreline, stone walls, perennial gardens, apple trees, and a sprawling flat lawn perfect for games and gatherings. Offering exceptional flexibility, this special setting on 4.35 acres has the potential to become a family compound, multi-generational retreat, or income-producing investment. A 3-bedroom septic permit is already in place,

  Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

  58 Lakeshore Dr, Ludlow, VT 05149
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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
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  /27

  $125,000

  • Land
  • 3.82 Acres
  • $32,723 per Acre

  0 Berry Patch Ln Unit 5099902, Ludlow, VT 05149

  Build your Vermont dream home on this beautiful 3.82-acre parcel in a peaceful South Hill setting. Just under five miles from downtown Ludlow and Okemo, this shovel-ready property offers the perfect blend of privacy and convenience. A 4-bedroom wastewater permit has already been filed with the State of Vermont, and power is available at the road, making it easy to begin your building plans. The

  Kevin Barnes William Raveis Real Estate Vermont Properties

  0 Berry Patch Ln Unit 5099902, Ludlow, VT 05149
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  /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
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  /34

  $100,000

  • 2 Beds
  • 3 Baths
  • 1,367 Sq Ft

  506/508 Qtr I Adams House, Ludlow, VT 05149

  Adams House Unit 506/508 QII: Quarter ownership. This 2 Bedroom, 3 Bathroom lock-out style unit that sleeps 8 in Adams House is in an excellent location. When you park in the heated garage, you find yourself only steps away from the unit which is located on the first floor. A very short walk down the hall and you pass the owners locker location. The gas fireplace will warm your spirits and make

  Michael Normyle Mary W. Davis Realtor & Assoc., Inc.

  506/508 Qtr I Adams House, Ludlow, VT 05149
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  /41

  $350,000

  • 2 Beds
  • 1.5 Baths
  • 1,092 Sq Ft

  143 Ascutney St, Windsor, VT 05089

  Open House 8/8/2026 11am-1pm. Welcome to 143 Ascutney Street, a well-maintained 2-bedroom, 1.5-bath home offering 1,092 square feet of comfortable living space. Thoughtfully cared for over the years, this home features a functional layout with bright living areas, an eat-in kitchen, and the convenience of a first-floor half bath. Outside, enjoy a manageable yard that's easy to maintain while

  Evan Russell Real Broker LLC

  143 Ascutney St, Windsor, VT 05089
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  /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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  /17

  $85,000

  • Land
  • 11.51 Acres
  • $7,385 per Acre

  00 Chaos Turnpike, Cavendish, VT 05142

  This Hideaway is Just down the country lane to Knapp Ponds/Knapp Brook Wildlife Management Area. Forgotten by the owners for the last 30 years, this lot has a mix of timber, stone wall & sloping mountain terrain. 475 feet frontage along the Class 3 road and only a short hike to the ponds. Boat ramps for fishing and hunting access.

  Alexandra Eatmon Kelley Real Estate, Inc.

  00 Chaos Turnpike, Cavendish, VT 05142
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  /44

  $729,000

  $20K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,018 Sq Ft

  51 High St, Ludlow, VT 05149

  Welcome to 51 High Street: an immaculate, turnkey village home just steps from the Okemo shuttle stop, offering effortless access to Okemo Mountain Resort and all that Ludlow has to offer. This inviting residence features five bedrooms and 2.5 baths, thoughtfully updated for comfortable year-round living. The renovated kitchen shines with classic soapstone countertops and a charming Jøtul

  McLaughlin Team Mary W. Davis Realtor & Assoc., Inc.

  51 High St, Ludlow, VT 05149
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  /29

  $65,000

  • 1 Bath
  • 390 Sq Ft

  243 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149

  Jackson Gore Inn Unit 243 Qtr. IV: Quarter ownership. Centrally located Jackson Gore studio unit with beautiful slope views and easy access to all resort amenities. This inviting studio comfortably sleeps four and features a queen-size bed and a queen sofa bed, along with one full bathroom. Enjoy the convenience of being just steps from dining, skiing, the fire pit, the Round House, the outdoor

  Laurene Skinner Mary W. Davis Realtor & Assoc., Inc.

  243 Qtr. I V Jackson Gore Inn, Ludlow, VT 05149
• 

  

  /31

  $875,000

  • 3 Beds
  • 3.5 Baths
  • 2,194 Sq Ft

  3755 Quechee Main St Unit 1B, Quechee, VT 05059

  Spacious Coach Road end-unit condominium offering exceptional privacy and outdoor space in a desirable location at the end of Coach Road on the western edge of Quechee Lakes. The open floor plan is flooded with natural light, while the fabulous kitchen layout flows easily into the dining and living areas. An expanded patio with direct access from the dining room creates a wonderful extension of

  Derek Cosentino Four Seasons Sotheby's Int'l Realty

  3755 Quechee Main St Unit 1B, Quechee, VT 05059
• 

  

  /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
• 

  

  /13

  $215,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059

  Welcome to easy living in Quechee Lakes! This charming 2-bedroom condo offers a cozy, traditional style that feels warm and inviting from the moment you arrive. Neat, tidy, and well-maintained, it's the perfect retreat for year-round enjoyment or a convenient getaway. As part of the Quechee Lakes community, you'll have access to an outstanding array of amenities, including championship golf,

  Kasia Butterfield Coldwell Banker LIFESTYLES - Quechee

  122 Quechee Hollow Ln Unit 4E, Hartford, VT 05059
• 

  

  /36

  $299,000

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft

  29 Markham Ln, Weston, VT 05161

  This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

  Catherine Cairns Maple Leaf Real Estate

  29 Markham Ln, Weston, VT 05161
• 

  

  /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
• 

  

  /25

  $269,500

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft

  1211 Skitchewaug Trail, Springfield, VT 05156

  Just listed is this nice home that has had multiple improvements in the last two years! 2 bedrooms have been added, the kitchen and bathroom have been remodeled, all new roof and siding, large new deck, a new chicken house, and more! It's in a good location in Springfield, on a paved state maintained road with easy access to I-91 at either exit 7 or exit 8, making it a convenient spot to get to

  Glenn Olney Barrett and Valley Associates Inc.

  1211 Skitchewaug Trail, Springfield, VT 05156
• 

  

  /24

  $199,000

  $16K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,075 Sq Ft

  112 Merrill St, Springfield, VT 05156

  This sweet Cape is the perfect place to start your homeownership journey or to simplify your lifestyle with comfortable, easy living. The main level features an inviting open-concept kitchen, dining, and living area, creating a bright and functional space for everyday living and entertaining. Upstairs, you'll find two cozy bedrooms that offer privacy away from the general living area. The full

  Chelsea Richardson Barrett and Valley Associates Inc.

  112 Merrill St, Springfield, VT 05156
• 

  

  /36

  $510,000

  $25K PRICE DROP

  • 6 Beds
  • 4 Baths
  • 4,933 Sq Ft

  2 Pine St, Windsor, VT 05089

  Come see and appreciate this recently rejuvenated and extraordinary home that includes 6 bedrooms and 4 bathrooms as well as a 2 car garage! Located just off the downtown village area, this unique property features historical charm and character with vintage woodwork, custom wood floors, high ceilings, spacious rooms and the nooks and crannies a classic home has to offer! Relax on the rear porch

  Susan Bellville Bellville Realty

  2 Pine St, Windsor, VT 05089
• 

  

  /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
• 

  

  /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
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  /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
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  /60

  $1,199,000

  $51K PRICE DROP

  • 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
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  /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
• 

  

  /31

  $795,000

  $50K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,282 Sq Ft

  3755 Quechee Main St Unit 9A, Quechee, VT 05059

  The perfect combination of feeling like a single family home but with the convenience and ease of townhouse living! Enjoy a park like setting with wonderful landscaping and stone walls throughout. Walk, bike or golf cart to the Quechee Club and Lake Pineo. Located adjacent to the 13th fairway of the Highland golf course. On site there is a beautiful in ground pool and two tennis courts for that

  Barbara Ruel Coldwell Banker LIFESTYLES - Quechee

  3755 Quechee Main St Unit 9A, Quechee, VT 05059
• 

  

  /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
• 

  

  /46

  $599,000

  • 3 Beds
  • 3.5 Baths
  • 2,203 Sq Ft

  44 Freeman Rd Unit B2, Cavendish, VT 05153

  Unique opportunity to own a spacious three-bedroom townhouse at The Castle, one of the area's most sought-after luxury resort communities. Offering exceptional quality and amenities unlike any other in the region, residents enjoy year-round access to an Aveda spa, heated outdoor saltwater pool, tennis courts, a fully equipped fitness center with sauna and locker rooms, and an outdoor hot tub.

  Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

  44 Freeman Rd Unit B2, Cavendish, VT 05153
• 

  

  /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

Showing Results 41 - 80, Page 2 of 14