Homes for Sale near St. Michael Catholic School

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  /47

  $550,000

  • 4 Beds
  • 4 Baths
  • 2,372 Sq Ft

  187 Hillwinds Rd, Brattleboro, VT 05301

  Welcome home! Four bedroom, 4-bathroom home with dedicated office space is located in one of the area’s most desirable communities. Just minutes from Brattleboro, it offers the perfect blend of convenience, comfort, and outdoor living, with walking trails right nearby. The bright, open layout is ideal for everyday living and entertaining, featuring a welcoming kitchen, dining, and living area. A

  Claire Renaud Berkley & Veller Greenwood Country

  187 Hillwinds Rd, Brattleboro, VT 05301
• 

  

  

  /3

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  24 Dogwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  24 Dogwood Dr, Brattleboro, VT 05301
• 

  

  

  /3

  $560,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  162 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  

  /3

  $585,000

  • 2 Beds
  • 2 Baths
  • 1,775 Sq Ft

  161 Buttonwood Dr, Brattleboro, VT 05301

  BLACK MOUNTAIN ESTATES - where your next chapter begins. Welcome to Brattleboro’s premier 55+ active lifestyle community, where nature, connection, & comfort converge. For the first time, a limited number of homes are available for purchase as we transition to a Planned Community. Surrounded by majestic pines, a private nature trail, & open green space, residents enjoy a serene setting just 1

  Dan Normandeau Berkley & Veller Greenwood Country

  161 Buttonwood Dr, Brattleboro, VT 05301
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  /39

  $625,000

  • 5 Beds
  • 4 Baths
  • 3,748 Sq Ft

  58 Oak St, Brattleboro, VT 05301

  Come experience the elegance and charm of this stunning in-town retreat! Close to the town common and vibrant downtown Brattleboro—home to fine dining, galleries, quaint shops, and live music venues. Step inside the main house and be welcomed by a country kitchen featuring a large island, ideal for gatherings. The home exudes Victorian character with soaring ceilings, hardwood floors, and

  Rebecca Seymour Brattleboro Area Realty

  58 Oak St, Brattleboro, VT 05301
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  /41

  $449,500

  • 3 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  785 Brattleboro Rd, Hinsdale, NH 03451

  Easy access to Hinsdale and Brattleboro. This home features a large formal living room, dining room, office space and a new large handicap bath on the first floor. Large bedrooms, full bath and laundry on the second floor. A newer screen room for bug free enjoyment outside and a large private deck outback for those sun filled days. Two sheds and an oversize garage to help with storage. Don't

  Darlene Conca Keller Williams Realty Metro-Keene

  785 Brattleboro Rd, Hinsdale, NH 03451
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  /36

  $442,500

  • 4 Beds
  • 3.5 Baths
  • 2,794 Sq Ft

  87 Orchard St, Brattleboro, VT 05301

  Pleasant and comfortable! This inviting home offers four bedrooms, three and a half bathrooms, a choice of primary bedroom with ensuite bath on the first floor or on the second. Enjoy a pleasant open flow living, kitchen and dining with hard wood floors for entertaining or hosting your next book club. The first floor offers a cheerful step saver kitchen with a pantry, gas range and views to the

  Jim Bellville Bellville Realty

  87 Orchard St, Brattleboro, VT 05301
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  /49

  $750,000

  • 4 Beds
  • 2 Baths
  • 2,875 Sq Ft

  136 Cross Rd, West Chesterfield, NH 03466

  OPEN HOUSE 9/6 From 11-1pm. Versatile Property Perfect for Single or Multi-Generational Living – West Chesterfield, NH. Discover this rare opportunity to own a lovingly maintained property in sought-after West Chesterfield, NH. Owned and cared for by the same family for over 40 years, this unique offering is ideal for single or multi-generational living. The main home features four spacious

  Robert Ingham Coldwell Banker Realty Center Harbor NH

  136 Cross Rd, West Chesterfield, NH 03466
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  /37

  $849,000

  • 4 Beds
  • 4 Baths
  • 3,600 Sq Ft

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam home in coveted Hillwinds. Tucked along a birch-lined drive, this exceptional post-and-beam home is set on 11+ acres of landscaped grounds with lawns, stone walls, gardens, and mixed woodland in the desirable Hillwinds community. Enjoy direct trail access and easy proximity to downtown and the Country Club. Step inside the striking custom-designed interior through a covered

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
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  /44

  $475,000

  • 4 Beds
  • 3 Baths
  • 3,314 Sq Ft

  76 Spruce St, Brattleboro, VT 05301

  Sweet! The perfect location...intown...backing up to the retreat trail system...and has a beautiful front porch and private back deck. This has been a much loved home, ready for a new generation to create their own music and harmony of life. The rooms are large, comfortable with lots of windows, real wood paneling reflecting the era, high ceilings, enough room to work from home (even an office

  Christine Lewis Brattleboro Area Realty

  76 Spruce St, Brattleboro, VT 05301
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  /60

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 3,415 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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  /46

  $379,000

  • 4 Beds
  • 2 Baths
  • 1,446 Sq Ft

  155 Oak Grove Ave, Brattleboro, VT 05301

  All work has been done for you on this beautiful, 1932 period home. 4 bedrooms, 2 full baths, set in a high demand, desirable neighborhood. Manicured, corner lot with classical perennial plantings, two covered porches, a slate roof, and detached double garage. There are 20+ upgraded, insulated windows, with antique reproduction filling the home with natural light. Hardwood floors predominate.

  Kristen Ziter Taylor Brattleboro Area Realty

  155 Oak Grove Ave, Brattleboro, VT 05301
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  /30

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  1089 Marlboro Rd, Brattleboro, VT 05301

  The one you have been waiting for! This traditional New England cape with a twist checks all the boxes! Remodeled in the 90's, it has a cook's delight for a kitchen with tons of cabinets and lots of countertops for baking prep...cookies and breads are a must!. The first floor was expanded to almost double the size of the living room, adding a fireplace and a main bedroom. Again in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /19

  $84,500

  • 3 Beds
  • 1 Bath
  • 1,490 Sq Ft

  7 Nichols Dr, Guilford, VT 05301

  This two story home offers 3 bedrooms/1 bathroom with 1,490 sq. ft. of living space. The property sits on a 0.50 acre lot. The first floor has a kitchen with wooden cabinets and granite countertops, wood flooring and a carpeted living room. A dedicated laundry area is also included. The property features a barn in the backyard for storage. Exterior highlights include a covered front entry,

  Derek Greene Derek Greene

  7 Nichols Dr, Guilford, VT 05301
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  /25

  $99,000

  • 2 Beds
  • 1 Bath
  • 732 Sq Ft

  313 Plain Rd, Hinsdale, NH 03451

  Looking for an affordable home with potential? This mobile home sits on 0.4 acres of owned land—no park fees here! A full basement and a solid asphalt roof set the stage for equity-building improvements. Here’s a chance to live inexpensively while upgrading over time. Located in the friendly town of Hinsdale, you’ll enjoy small-town charm with local shops, schools, and dining nearby. Just minutes

  Bob Barnard Monadnock Realty Group LLC

  313 Plain Rd, Hinsdale, NH 03451
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  /24

  $279,000

  • 3 Beds
  • 1 Bath
  • 912 Sq Ft

  91 Carriage Hill Rd, Brattleboro, VT 05301

  This charming split-level home offers 3 bedrooms and a full bathroom, complete with a single-bay garage in the desirable Carriage Hill neighborhood. Hardwood floors extend through the living room, hall, and bedrooms, adding warmth and character. The living room features a lovely picture window with opening side windows, perfect for letting in a refreshing breeze and natural light.The lower level

  Rebecca Seymour Brattleboro Area Realty

  91 Carriage Hill Rd, Brattleboro, VT 05301
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  /32

  $425,000

  • 3 Beds
  • 1.5 Baths
  • 1,655 Sq Ft

  155 Upper Dummerston Rd, Brattleboro, VT 05301

  Great location! This 3-bedroom Colonial, built in 1920 (when houses were well-built) on Upper Dummerston Road is up the road from the Brattleboro Country Club and its golf course, cross country skiing, trails, and the West River. On a comfortable 0.75 level acres, this property is private but only 10 minutes from the center of town. Lots of windows bring in lots of light. Generous living room,

  John Hatton Berkley & Veller Greenwood Country

  155 Upper Dummerston Rd, Brattleboro, VT 05301
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  /20

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  172 Franklin Rd, Vernon, VT 05354

  Fantastic opportunity! This split level has 3 floors to finish for lots of living! Or, choose to begin with the first floor that has living/dining/kitchen/full bath and bedroom. It needs work, but an easy way to get started. 4 Possible bedrooms (town says 3, appraiser says 4), The basics are here, sheetrock up and partially mudded, good sized bedrooms, lots of windows and kitchen has been

  Christine Lewis Brattleboro Area Realty

  172 Franklin Rd, Vernon, VT 05354
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  /14

  $50,000

  • 4 Beds
  • 2 Baths
  • 1,120 Sq Ft

  18 Springbrook St, Hinsdale, NH 03451

  Great price! A little cosmetics will go a long way to spruce this one up! 4 bedrooms and 2 baths is an unusual event in the parks, so best grab it while you can! Big yard, with lots of planting just waiting for recovery...open concept living/dining/kitchen.....applianced....Truly affordable. Buyers must be park approved. Please be sure buyers are prequalified with lender who lends in parks

  Christine Lewis Brattleboro Area Realty

  18 Springbrook St, Hinsdale, NH 03451
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  /38

  $549,900

  • 3 Beds
  • 2 Baths
  • 2,476 Sq Ft

  458 Bonnyvale Rd, Brattleboro, VT 05301

  PRICE REDUCTION! THE 4.875 ACRE LOT NEXT DOOR HAS BEEN REMOVED FROM SALE. Welcome to this inviting West Brattleboro home, perfectly situated just 1 mile from Route 9 and 2 miles from I-91 on 1.95 private acres. Relax by the in-ground pool, soak in the jacuzzi tub, or enjoy your own blueberry bushes, raspberry bushes, and beautifully maintained flower and vegetable gardens. Recent updates include

  Kelsea McAuliffe Greenwald Realty Group

  458 Bonnyvale Rd, Brattleboro, VT 05301
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  /29

  $345,000

  • 4 Beds
  • 2 Baths
  • 2,408 Sq Ft

  78-80 Central St, Brattleboro, VT 05301

  Charming Two-Unit Multi-Family on Quiet In-Town Street – Ideal for Investors or Owner-Occupants! Tucked away on a peaceful side street yet just minutes from shopping, dining, and public transportation, this two-family property offers the perfect blend of convenience and comfort. The current owners have updated all the electrical in both units. Each unit features spacious, light-filled

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78-80 Central St, Brattleboro, VT 05301
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  /58

  $568,000

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

  192 Western Ave, Brattleboro, VT 05301

  Timeless 1855 classic with historic charm just minutes to downtown Brattleboro. Step back in time with this beautifully preserved home, offering a rare blend of vintage character and modern comfort. Featuring three bedrooms and two bathrooms, this home is perfect for those who appreciate craftsmanship and history. Thoughtful updates complement the historic features without compromising

  Claire Renaud Berkley & Veller Greenwood Country

  192 Western Ave, Brattleboro, VT 05301
• 

  

  /24

  $585,000

  • Land
  • 67.63 Acres
  • $8,650 per Acre

  932 Middle Rd, Dummerston, VT 05301

  Discover the perfect blend of peace, privacy, and potential on this 67.63-acre privately owned parcel of land. Nestled in a scenic and serene setting, this expansive property is a rare opportunity to build your dream home, estate, or getaway retreat. Two picturesque ponds – ideal for fishing, wildlife watching, or just enjoying the view. The main home site has amazing mountain views and sits

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  932 Middle Rd, Dummerston, VT 05301
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  /25

  $189,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  22 Chestnut St Unit 1, Brattleboro, VT 05301

  Welcome to 22 Chestnut Street, Unit #1 — a charming and fully furnished first-floor condo nestled in the lovely Chestnut Street neighborhood. This spacious 2-bedroom, 1-bath unit features a thoughtfully updated bathroom with a clawfoot tub and separate shower, a cozy mudroom entryway, and a sunny side porch that conveys with the unit — perfect for morning coffee or evening relaxation. The kitchen

  Erica Reynolds Southern Vermont Realty Group

  22 Chestnut St Unit 1, Brattleboro, VT 05301
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  /16

  $160,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  16 Hillcrest St, Hinsdale, NH 03451

  Better than new!! This special home, built in 2017 has had many upgrades to meet the owners standard of excellence! Start with granite kitchen countertops and bathroom sink tops, matching stainless steel appliances, and new vinyl flooring. The wall joining strips were removed, plastered, the wall freshly painted and crown molding added. There is also a new section of deck for additional

  Christine Lewis Brattleboro Area Realty

  16 Hillcrest St, Hinsdale, NH 03451
• 

  

  /20

  $279,900

  • 4 Beds
  • 2 Baths
  • 1,733 Sq Ft

  1177 Western Ave, Brattleboro, VT 05301

  So much to offer! This 4 bedroom 2 bath has plenty of room for all! It features a large kitchen with lots of counter space and the laundry tucked in for easy access while you cook and bake. The deck overlooks the lower yard where the solar panels live and the perfect spot for the above ground swimming pool (needs a liner). Huge lot, lots of off street parking and on the MOOVER line for non

  Christine Lewis Brattleboro Area Realty

  1177 Western Ave, Brattleboro, VT 05301
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /3

  $150,000

  • Land
  • 3.86 Acres
  • $38,860 per Acre

  00 Orchard Rd, Chesterfield, NH 03443

  A rare find in Chesterfield. 4+/- acres of mostly open land situated on a quiet country road. Long road frontage assures privacy and allows for your choice of driveway access. Located about 3 miles from Rt 9 and close to Chesterfield Elementary, this spot provides convenience to Keene, Brattleboro and Hinsdale. And is close to Spofford Lake and Pisgah Park.

  Timothy Keating BHG Masiello Keene

  00 Orchard Rd, Chesterfield, NH 03443
• 

  

  /16

  $259,900

  • Land
  • 29.2 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
• 

  

  /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
• 

  

  /9

  $80,250

  • Land
  • 3.1 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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  /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
• 

  

  /12

  $80,000

  • 2 Beds
  • 1 Bath
  • 832 Sq Ft

  48 Robbins St, Hinsdale, NH 03451

  Thicket Hill Cooperation sits on a quiet hillside adjacent to the Connecticut River Reservoir. The town of Hinsdale is family friendly and perfect for nature lovers. It borders Connecticut River for 13 miles and boasts a popular Pisgah State Park access. From this home, it is only a five mile drive to Brattleboro and 22 miles to Keene. The home is a split level inside with an open concept

  Jessie Carpenter Keller Williams Realty Metro-Keene

  48 Robbins St, Hinsdale, NH 03451
• 

  

  /51

  $899,800

  • 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
• 

  

  /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
• 

  

  /42

  $399,000

  • 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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