Homes for Sale near Oak Meadow

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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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  /60

  $634,500 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft

  23 Bittersweet Ln, Chesterfield, NH 03466

  Escape the day to day at this picturesque waterfront Cape! Down your private publicly-maintained deadend road, beside the hillside and quaint horse fence, awaits majestic views to envelop you at this park-like setting on the Connecticut River. Your private 3-acre property has over 500’ of riverfront and views with your own beach area and naturally-formed rock jetty. While you’re near to many

  Mary M. Belle Isle EXP Realty

  23 Bittersweet Ln, Chesterfield, NH 03466
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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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  /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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  /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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  /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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  /60

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,726 Sq Ft

  814 Brattleboro Rd, Hinsdale, NH 03451

  Value meets location in this 3-bedroom, 2-bath home, a functional layout, and a long list of big-ticket updates—making it the perfect canvas for your finishing touches. Enjoy peace of mind with a newer roof on house in 2022 & electrical updates completed in 2022/2023. The kitchen was renovated in 2015, including updated walls, wiring, cabinetry, etc. While the windows & interior need some TLC,

  Isabella Luhrs BHG Masiello Keene

  814 Brattleboro Rd, Hinsdale, NH 03451
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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 Fri 5:30PM - 7PM

  • 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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  /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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  /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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  /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
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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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  /20

  $270,000

  • 3 Beds
  • 2 Baths
  • 2,062 Sq Ft

  691 Brattleboro Rd, Hinsdale, NH 03451

  Investor or house-hacker? This 2-unit multifamily delivers $24,000/year in gross income with both tenants paying $1,000/month. Utilities are split, meaning lower operating costs for you. At the $299,999 list price, this property offers a strong 8% cap rate with room to grow and value add potential.Upside opportunities abound: add a third unit, increase bedroom count in existing layouts,

  Andrew Bosco Four Points Real Estate

  691 Brattleboro Rd, Hinsdale, NH 03451
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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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  /12

  $95,000

  • 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
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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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  /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
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  /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
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  /45

  $1,100,000

  • 3 Beds
  • 2 Baths
  • 2,210 Sq Ft

  61 Orchard Rd, Chesterfield, NH 03443

  Continue the legacy of owning the oldest home in Chesterfield with its rich history, bucolic setting of woods, fields, pond and orchard. Well maintained features include beamed ceilings, wide pine floors, slate roof and center chimney. The Custom kitchen has stainless steel appliances, cherry cabinetry and CaesarStone counters. White oak flooring was installed with programmable radiant

  Timothy Keating BHG Masiello Keene

  61 Orchard Rd, Chesterfield, NH 03443
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  /49

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 4,116 Sq Ft

  125 Stage Rd, West Chesterfield, NH 03466

  19+ acres of ultimate privacy surround this spectacular home with timeless details and stunning views, offering a perfect blend of comfort & sophistication. The contractor/owner exquisitely built and maintained the property and thought of everything, starting with the welcoming foyer adorned with Spanish marble. The chef’s kitchen features granite counters, a downdraft gas stove, mesquite

  Ben Prentice Keller Williams Realty Metro-Keene

  125 Stage Rd, West Chesterfield, NH 03466
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  /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
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  /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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  /52

  $114,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  150 Oxbow Rd, Hinsdale, NH 03451

  Bring me back to my former charm and glory.Vaulted ceilings, 2 bedrooms, a fireplaced (currently not operational) living room eagerly awaits a new owner to freshen up this home.The home sits on almost 3 acres of rolling fields. Could be a picturesque setting for your gardens and farmThe property and land is being sold "As - Is"

  Thomas Travers Great Beginnings Real Estate Services, LLC

  150 Oxbow Rd, Hinsdale, NH 03451
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  /26

  $725,000

  • 18 Beds
  • 8 Baths
  • 4,932 Sq Ft

  29 Canal St, Brattleboro, VT 05301

  High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

  Michael Gilman 3GEN Real Estate Inc

  29 Canal St, Brattleboro, VT 05301
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  /29

  $88,900

  • Land
  • 13 Acres
  • $6,984 per Acre

  0 Skyline Dr, Vernon, VT 05354

  12+ Acres of Wooded Vermont Beauty This 12.73-acre parcel in peaceful Vernon, VT offers the ideal blend of privacy, natural beauty, and accessibility. With ample road frontage and electric available at the street, so much potential whether it be a vacation retreat, full time dwelling or investment opportunity. The land features a mix of mature hardwoods and potential

  Morriah Adams BHG Masiello Brattleboro

  0 Skyline Dr, Vernon, VT 05354
• 

  

  /29

  $285,000

  • 4 Beds
  • 1 Bath
  • 1,466 Sq Ft

  625 Plain Rd, Hinsdale, NH 03451

  Welcome to 625 Plain Road, a spacious and charming 4-bedroom home set on a beautiful 1.11-acre open lot in scenic Hinsdale, New Hampshire. This property combines comfort, space, and convenience—perfect for anyone looking to enjoy a quiet country setting while staying close to town amenities. Step inside to find a warm and inviting layout with plenty of natural light. The expansive kitchen is

  Bob Barnard Monadnock Realty Group LLC

  625 Plain Rd, Hinsdale, NH 03451
• 

  

  /51

  $544,400

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

  22 Chestnut St, Brattleboro, VT 05301

  4 condo units being sold together as a great residential package investment opportunity! Rent them, live in one and/or sell them off individually. This offering includes 4 of 5 units in a charming condo development just minutes from downtown, the hospital, shopping, and I-91. Unit 5 has been sold. The property features a large shared yard, off-street parking, and strong rental potential. The

  Erica Reynolds Southern Vermont Realty Group

  22 Chestnut St, Brattleboro, VT 05301
• 

  

  /18

  $425,000

  • 3 Beds
  • 2 Baths
  • 2,074 Sq Ft

  36 Spruce St, Brattleboro, VT 05301

  New Price! $25,000.00 price drop and a revised offering... If you saw this home before you want to take a second look! The 2nd floor is now vacant! ..and ready for owner occupancy. The basement, barn and lower building are empty and ready for all YOUR stuff. Plenty of undercover storage for boats, special vehicles or lots of other toys. A workshop? Home is just right for 2 family use or

  Christine Lewis Brattleboro Area Realty

  36 Spruce St, Brattleboro, VT 05301
• 

  

  /5

  $89,000

  • Land
  • 0.21 Acre
  • $423,810 per Acre

  46-48 Lexington Ave, Brattleboro, VT 05301

  This open, level, in-town building lot is a blank slate awaiting its next chapter. Tucked away in a small neighborhood on a dead-end street, this location offers easy accessibility to shopping, restaurants, public transportation and the interstate. Utilities are readily available, including existing hookups for town water and sewer. A unique opportunity!

  Stephanie Wilde Brattleboro Area Realty

  46-48 Lexington Ave, Brattleboro, VT 05301

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