Homes for Sale in 05301

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  /30

  $579,000

  • 4 Beds
  • 2 Baths
  • 2,656 Sq Ft

  204 Meeting House Ln, Brattleboro, VT 05301

  Your Dream Home Awaits on Meetinghouse Lane! Nestled in the desirable and quiet neighborhood of Meetinghouse Lane, this contemporary home offers both privacy & charm. Surrounded by mature trees, the property feels like a peaceful retreat, while still being conveniently located. A paved driveway leads to an oversized two-car garage, connected to the house by a convenient breezeway. The expansive

  Desiree Stango Berkley & Veller Greenwood Country

  204 Meeting House Ln, Brattleboro, VT 05301
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  /40

  $795,000

  • 3 Beds
  • 5 Baths
  • 2,663 Sq Ft

  1194 Ames Hill Rd, Brattleboro, VT 05301

  Welcome to The Appleshed. Starting as a storage structure within an old apple orchard, to a gentleman's hunting/fishing camp, to the cherished family home it is today, this property has had many lives and grown into a beloved gathering place for generations. Now it’s ready for its next chapter. Set on 63.8 acres with a babbling brook and breathtaking views of Mount Monadnock, this is a true

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  1194 Ames Hill Rd, Brattleboro, VT 05301
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  /40

  $489,000

  • 5 Beds
  • 3 Baths
  • 2,917 Sq Ft

  3550 Coolidge Hwy, Guilford, VT 05301

  This lovely property has classic character and charm with modern updates and upgrades making this a truly comfortable place to call home! There's the main house with attached garage as well as the accessory in-law suite/apartment/accessory living space for longer term guests to stay that provides privacy from your main home. There's the nicely sized barn for parking, animals or storage which

  A.J. Bellville Bellville Realty

  3550 Coolidge Hwy, Guilford, VT 05301
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  /60

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 3,685 Sq Ft

  155 Hillwinds N, Brattleboro, VT 05301

  Situated in Brattleboro’s premier, rural neighborhood, this much-loved home is a masterclass in thoughtful design, meticulous construction, & refined living. A grand dbl-door foyer welcomes you into a soaring entry hall that flows seamlessly into a sunken, dbl-height ceiling LR - complete w/ granite-surround FP, custom blt-ins, & crowned by a dramatic balcony overlook. Light pours in from every

  Dan Normandeau Berkley & Veller Greenwood Country

  155 Hillwinds N, Brattleboro, VT 05301
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  /60

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,315 Sq Ft

  23 Meeting House Ln, Brattleboro, VT 05301

  First Time on the Market – Premier Brattleboro Location!Nestled on one of the most desirable lots in one of Brattleboro’s finest neighborhoods, this well-maintained home is being offered for sale for the very first time! Custom-built by the current owner in 1970 with attention to detail, this spacious ranch offers comfort, functionality, and an impressive list of amenities.Perfect for

  Bert Inman RE/MAX Town & Country

  23 Meeting House Ln, Brattleboro, VT 05301
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  /47

  $995,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

  Melissa Nebelski Skihome Realty

  6036 Jacksonville Stage Rd, Guilford, VT 05301
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  /53

  $475,000

  • 3 Beds
  • 3 Baths
  • 2,463 Sq Ft

  1591 Higley Hill, Marlboro, VT 05344

  Wonderful home on 11.2 acres in a peaceful setting on Higley Hill in Marlboro. The main level boasts a beautiful family room addition with lots of windows and a gas fireplace, galley kitchen with stainless appliances, dining area, 3/4 bath with laundry, living room with gas stove, 3/4 bath with sitting area and a primary bedroom with ensuite full bath. A loft area that can be used as a bedroom or

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  1591 Higley Hill, Marlboro, VT 05344
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  /27

  $550,000

  • 3 Beds
  • 3 Baths
  • 3,148 Sq Ft

  672 E Orchard St, West Brattleboro, VT 05301

  You can't beat this location, overlooking the Brattleboro Country Club golf course. This home was built circa 1919, and has many cool vintage features such as retro curved metal kitchen cabinets and baths. Generous rooms include a large living room with two field-stone fireplaces, a spacious family room. This is a 3 bedroom house with 3 full bathrooms, but it's really about how you configure

  John Hatton Berkley & Veller Greenwood Country

  672 E Orchard St, West Brattleboro, VT 05301
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  /60

  $649,000

  • 3 Beds
  • 2 Baths
  • 2,731 Sq Ft

  49 Tyler St, Brattleboro, VT 05301

  Rare opportunity to own this iconic Queen-Anne Victorian in Brattleboro’s coveted Tyler Street neighborhood. A remarkable and extremely rare blend of country and in-town living. Extraordinary and stunning views of the Connecticut River & Mount Wantastiquet. Lovingly cared for by the same owner for the past 29 yrs. This home sits proudly on the expansive 0.85-acre corner lot, in the core of

  Dan Normandeau Berkley & Veller Greenwood Country

  49 Tyler St, Brattleboro, VT 05301
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  /52

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,023 Sq Ft

  6940 Coolidge Hwy, Guilford, VT 05301

  Located just north of the Massachusetts border, this home with two car detached garage is conveniently just 15 minutes from both Greenfield and Brattleboro.As you step inside to the mudroom you'll enter the coziest of kitchens radiating warmth and character. Featuring a wood stove, a stunning brick hearth with beehive oven, wooden beams adding rustic charm, while a cathedral ceiling keeps the

  Rebecca Seymour Brattleboro Area Realty

  6940 Coolidge Hwy, Guilford, VT 05301
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  /58

  $599,000

  • 4 Beds
  • 2 Baths
  • 3,090 Sq Ft

  301 Maple St, Brattleboro, VT 05301

  This is IT! Summer is here! The gardens are ablaze, the deck is perfect for the evening sip of something cool and there is open sky for sightings like the strawberry moon and shooting stars. Treat yourself to your own spa....the sweet spot is the oversized salt pool, surrounded by lush greenery for privacy and an apron for sunning. Add some of your own fun and you will stay at home,

  Christine Lewis Brattleboro Area Realty

  301 Maple St, Brattleboro, VT 05301
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  /20

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,178 Sq Ft

  17 Winter Ct, Brattleboro, VT 05301

  Classic Ranch Style Home! Just starting out or thinking of downsizing? This could be the one! Nestled in a sweet neighborhood, this charming ranch offers easy one-level living just minutes from downtown shopping, schools, and recreation. Set on a manageable 0.2 acre lot, this home features a bright enclosed porch/bonus room perfect for morning coffee, reading, or relaxing year-round. Continuing

  Liz LaVorgna Berkley & Veller Greenwood Country

  17 Winter Ct, Brattleboro, VT 05301
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  /2

  $300,000

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  109 Central St, Brattleboro, VT 05301

  Bright Sunny, south facing! 2 stacked flats just perfect for multi generational living! Inside access with both formal front stair and back utility stairs, so easy for caring for family members, or a plan for aging in place with a care giver. Rent one or both for a money maker. This owner is owner occupying both flats. Plenty of off street parking, a sweet side porch and just a bit of a yard

  Christine Lewis Brattleboro Area Realty

  109 Central St, Brattleboro, VT 05301
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  /34

  $299,900 Open Sat 10PM - 11:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,025 Sq Ft

  35 Hillcrest Terrace, Brattleboro, VT 05301

  Open House August 1, 5:30-7:00 and August 2, 10-11:30. Welcome to 35 Hillcrest Terrace, a well-loved home owned by the same family for over 20 years, perfectly situated in one of Brattleboro’s most convenient neighborhoods. Just moments from Memorial Park, this charming property offers easy access to recreation, walking trails, and town amenities while providing a peaceful, residential

  Morriah Adams BHG Masiello Brattleboro

  35 Hillcrest Terrace, Brattleboro, VT 05301
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  /28

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,213 Sq Ft

  5704 Coolidge Hwy, Guilford, VT 05301

  Tucked back off the road, equidistant between Brattleboro, Vermont and Bernardston, MA, this “cute-as-a-button,” chalet-influenced cape is an excellent opportunity for a cozy, 3-bedroom home or an Airbnb, on a 7.9-ac lot in beautiful Guilford, Vermont. Nice mix of sun and shade. Excellent gardening spot. High-speed internet available. Single-level living is possible, with a first-floor

  Dan Normandeau Berkley & Veller Greenwood Country

  5704 Coolidge Hwy, Guilford, VT 05301
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  /35

  $399,000

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  1469 Higley Hill Rd, West Marlboro, VT 05363

  Cozy Log Cabin with Sunny Addition, Small Pond & Sugar House on 5 Acres in Marlboro, VermontThis inviting log cabin blends classic Vermont charm with a thoughtfully designed, light-filled addition—offering comfort, space, and versatility on 5 peaceful acres. Tucked away on a quiet dirt road in a desirable Marlboro neighborhood, the property features a small pond and a traditional sugar house,

  Melissa Nebelski Skihome Realty

  1469 Higley Hill Rd, West Marlboro, VT 05363
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  /51

  $425,000

  • 4 Beds
  • 2 Baths
  • 2,445 Sq Ft

  17 Tinker Hill Rd, Guilford, VT 05301

  This one is the right one! So very special, nestled in the countryside just waiting.... So many options to choose from...a first floor main bedroom is perfect for aging in place, an x gen who still lives at home, in-law suite...or...perfect for an Air B&B. The other main bedroom features a walk out to the upper gardens, vaulted ceilings, room for a private getaway or reading nook. Plenty of

  Christine Lewis Brattleboro Area Realty

  17 Tinker Hill Rd, Guilford, VT 05301
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  /31

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,568 Sq Ft

  321 Leonard Rd, Dummerston, VT 05301

  Get ready for your new favorite property. Located in highly-desirable West Dummerston, just 10 minutes from downtown Brattleboro, this energy-efficient Unity high performance home is waiting for you. It’s a very cozy 3-bedroom, 2 full bathroom single-level home on 0.88 acres. Built of pre-fabricated components in factory-controlled conditions, this house is just some solar panels away from

  John Hatton Berkley & Veller Greenwood Country

  321 Leonard Rd, Dummerston, VT 05301
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  /2

  $90,000

  • 3 Beds
  • 1 Bath
  • 1,030 Sq Ft

  93 Clark St, Brattleboro, VT 05301

  An affordable opportunity for a new beginning, for both you and the home! Located in an evolving neighborhood where a new generation is investing, walk to downtown. This corner lot has off street parking, a bit of yard for some planting or sunning, and what the current owner has used as a workshop. This one will take cash or a rehab loan, but is being occupied so systems are working. Please,

  Christine Lewis Brattleboro Area Realty

  93 Clark St, Brattleboro, VT 05301
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  /2

  $89,000

  • 4 Beds
  • 3 Baths
  • 2,108 Sq Ft

  321 Williams St, Brattleboro, VT 05301

  Great opportunity for starting or expanding your investment portfolio. Good rental income and affordable property. Nice location. Good parking for tenants and private porches. Minimal yard maintenance.

  Susan Bellville Bellville Realty

  321 Williams St, Brattleboro, VT 05301
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  /16

  $259,900

  • Land
  • 29 Acres
  • $8,901 per Acre

  1270 Melendy Hill Rd, Guilford, VT 05301

  A rare find! This amazing land has long range views, privacy and close to everything! There is a right of way for egress, and will be perfect for an off grid tuck away cabin or primary. A small meadow is part of the 2 acre exemption for house site, just at the end of the existing drive...easy to get to and just the beginning of the land. Mostly Black Birch, Sugar Maple and Hemlock, there is

  Christine Lewis Brattleboro Area Realty

  1270 Melendy Hill Rd, Guilford, VT 05301
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  /10

  $175,000

  • Land
  • 8 Acres
  • $21,875 per Acre

  680 W River Rd, Brattleboro, VT 05301

  8 acres only 2 miles from Brattleboro situated across the road from the West River. Existing gated gravel driveway is in. Gravel on site and road roughed into a high plateau with designs for SIX 1-2 bedroom cottages. Topographical survey, septic design plans and other existing engineering are complete which make this an attractive option for someone looking to develop a parcel into a cottage

  Chris Long BHG Masiello Brattleboro

  680 W River Rd, Brattleboro, VT 05301
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  /18

  $176,500

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  15 Lynwood Dr, Brattleboro, VT 05301

  This is absolutely NOT your ordinary Mobile Home! The original steel frame is the only remaining component of the mobile home. Completely rebuilt from the floor up with wood framing, windows, doors and insulation. This fully fenced leased lot has two sheds, a 1 car garage building with tons of storage and a workshop building with its own mini-split for heat and AC. The tastefully renovated

  Chris Long BHG Masiello Brattleboro

  15 Lynwood Dr, Brattleboro, VT 05301
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  /9

  $80,250

  • Land
  • 3.10 Acres
  • $25,887 per Acre

  0 E Orchard St Unit 5047716, Brattleboro, VT 05301

  A rare opportunity to purchase a lot in a highly desirable Brattleboro neighborhood. This 3+ acre wooded parcel features a mature pine forest with additional hardwoods intermixed, stonewalls and even a small stream. It's the location that makes this property unique. Just up the road from the Brattleboro Country Club on a quiet street that gives quick access to all that Brattleboro and the

  Bill Hickok Berkley & Veller Greenwood Country

  0 E Orchard St Unit 5047716, Brattleboro, VT 05301
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  /38

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 2,862 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362
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  /34

  $265,000

  • 2 Beds
  • 1 Bath
  • 1,137 Sq Ft

  199 Depot Rd, Williamsville, VT 05362

  Nestled on 12.4 acres of wooded privacy, this raised ranch at 199 Depot Road offers the best of Vermont living—peaceful, scenic, and just minutes from the village of Newfane. With 2 bedrooms and 1 full bath across 1,137 square feet, this well-maintained home features warm wood accents, abundant natural light, and an open-concept living and dining area that feels bright and inviting.Large

  Kate Barry EXP Realty

  199 Depot Rd, Williamsville, VT 05362
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  /11

  $250,000

  • Land
  • 18 Acres
  • $13,889 per Acre

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301

  Tucked in the gently rolling hills of Vermont, this is a sweet spot to build your new home. Located on a class 3 privately maintained road, there are power poles the length of the road with fiber optics ready for the streamers or work at home folks. Build on the road for a short drive and utility ease, or take the secluded route and tuck away in the forest. The acreage is an educated guess and

  Christine Lewis Brattleboro Area Realty

  0 Melendy Hill Rd Unit 5046973, Guilford, VT 05301
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  /47

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,222 Sq Ft

  1082 W River Rd, Brattleboro, VT 05301

  Welcome to 1082 West River Road — a peaceful, well-located gem just minutes from downtown Brattleboro. This charming home offers the perfect blend of convenience, outdoor space, and natural beauty. Set on a spacious lot with a large, open yard, there's room to garden, gather, or simply relax and enjoy the Vermont seasons. The private river access makes it easy to enjoy kayaking, swimming, or

  Kate Barry EXP Realty

  1082 W River Rd, Brattleboro, VT 05301
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  /51

  $949,000

  • 5 Beds
  • 8 Baths
  • 7,430 Sq Ft

  925 Hinesburg Rd, Brattleboro, VT 05301

  Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

  Christine Lewis Brattleboro Area Realty

  925 Hinesburg Rd, Brattleboro, VT 05301
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  /24

  $279,900

  • 3 Beds
  • 2 Baths
  • 1,183 Sq Ft

  4322 Augur Hole Rd, Brattleboro, VT 05301

  Super location! Easy access to Rt 9 and Rt 30 but tucked into nearly a level acre in a lovely country setting. You can tell the previous occupants loved their gardens and a bit of work would restore the blooms to full glory. The pool is a bonus but is waiting for some care to get up and running...The home has emerged from a fun loving schoolhouse filled with learning and joy to a cozy,

  Christine Lewis Brattleboro Area Realty

  4322 Augur Hole Rd, Brattleboro, VT 05301
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  /59

  $859,000

  • 4 Beds
  • 3.5 Baths
  • 3,212 Sq Ft

  104 Juniper Ridge Rd, Brattleboro, VT 05301

  Welcome to Juniper Ridge! Where you will find superior craftsmanship, a private haven, and neighbors only one can dream of. As you enter the foyer of this custom built home, you'll feel its character & elegance with vaulted ceilings, arched doorways, terracotta tile and balconies lined with bookshelves. The home was built with attention to the flow, energy and natural light. The kitchen has

  Kristen Ziter Taylor Brattleboro Area Realty

  104 Juniper Ridge Rd, Brattleboro, VT 05301
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  /60

  $895,000

  • 3 Beds
  • 3 Baths
  • 2,258 Sq Ft

  266 Ursa Ridge Rd, Dummerston, VT 05301

  This home is living art, tucked away at the end of the road of lovely homes & hundreds of acres ridgetop, yet only 10 minutes from downtown Brattleboro. Built by a craftsman this home is gracious & energy efficient. Building materials have been harvested from it's 51-1/2 acre woodland. Rooms are thoughtfully designed awash with natural light. Walk up the covered, stone walkway to enter the

  Randi Ziter Brattleboro Area Realty

  266 Ursa Ridge Rd, Dummerston, VT 05301
• 

  

  /18

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  164 Chestnut St, Brattleboro, VT 05301

  Just right for new beginnings! This raised ranch affords the new home buyer a cozy place to start with a big, level yard with lots of flowering shrubs to look pretty when you drive up, and a perfect spot for ball in the back! The dead end street is a bit safer for bikes and strolls than others and creates a nice comfortable neighborhood for smiling greetings. With an eat in kitchen with

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
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  /42

  $415,000

  • 3 Beds
  • 1.5 Baths
  • 2,433 Sq Ft

  183 Bear Hill Rd, Dummerston, VT 05301

  Discover a hidden gem nestled deep in the woods—a rustic retreat that’s entirely off-grid and 100% solar powered. Perfect for nature lovers, creative spirits, or anyone seeking serenity and self-sufficiency.This one-of-a-kind property features a charming main house with a two-bedroom loft attached, currently used for short-term rentals. The main cabin exudes classic Adirondack charm with

  Kate Barry EXP Realty

  183 Bear Hill Rd, Dummerston, VT 05301
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  /5

  $139,900

  • Land
  • 1.30 Acres
  • $107,615 per Acre

  00 Creamery Rd, Guilford, VT 05301

  Just in time! Unbelievable! A high rolling meadow of your very own! Build the new home, the one you have been waiting for all your life, on this beautifully cared for sweet spot in the Vermont countryside community of Guilford. The boundaries are easy to find, one being right up to the edge of an old stone wall, the others marked with posts. Pick the high point and have a local view of old

  Christine Lewis Brattleboro Area Realty

  00 Creamery Rd, Guilford, VT 05301
• 

  

  /13

  $79,000

  • Land
  • 3.69 Acres
  • $21,409 per Acre

  0 Honeycomb Hill, Marlboro, VT 05301

  On the privately maintained road of Honeycomb Hill sits this 3.69 acre lot. The wooded parcel has young tree growth and slopes gently. There are three areas that are fairly level and open and may be suitable building sites. Just 30 minutes to Mt. Snow, 25 minutes to Brattleboro and 15 minutes to Harriman Reservoir, this conveniently located parcel offers easy access to all of Southern Vermont's

  Laura D'Angelo Berkley & Veller Greenwood Country

  0 Honeycomb Hill, Marlboro, VT 05301
• 

  

  /41

  $265,000

  • 4 Beds
  • 1 Bath
  • 1,612 Sq Ft

  178 Parsons Rd, Wilmington, VT 05363

  Charming Cape-style home set on 1.7 beautifully landscaped acres, featuring a detached two-car garage. The expansive yard includes established gardens, a BBQ area, a barn, and two additional sheds in need of some TLC. Located just 4 miles from downtown Wilmington, you’ll enjoy easy access to shopping, dining, and year-round outdoor activities like skiing, golfing, hiking, biking, and boating. The

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  178 Parsons Rd, Wilmington, VT 05363
• 

  

  /23

  $1,150,000

  • 6,442 Sq Ft

  69-71 Elliot St, Brattleboro, VT 05301

  Prime commercial opportunity in the heart of downtown Brattleboro. This mixed-use property features seven residential apartments on the upper levels and five ground-floor commercial units. Two retail spaces have direct frontage on Elliot Street, offering strong visibility, while three others open onto the Harmony Lot pedestrian area, a centrally located public parking and business zone. The

  Erica Reynolds Southern Vermont Realty Group

  69-71 Elliot St, Brattleboro, VT 05301
• 

  

  /34

  $399,000

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

  1637 Adams Brook Rd, Marlboro, VT 05301

  Tucked away in the rolling hills of Marlboro, Vermont, this off-the-grid house sits on 8 plus acres of forest and meadowland, offering a perfect blend of rustic charm and sustainable living. Powered by a newer 48V Schneider solar power system, with a backup propane generator, the home is a self-sufficient sanctuary far from the hustle of modern life. An open concept floor plan offers much

  Kassie Rubico Berkley & Veller Greenwood Country

  1637 Adams Brook Rd, Marlboro, VT 05301
• 

  

  /16

  $488,875

  • 5 Beds
  • 4 Baths
  • 3,064 Sq Ft

  176 High St, Brattleboro, VT 05301

  Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

  Susan Bellville Bellville Realty

  176 High St, Brattleboro, VT 05301

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