Brattleboro, VT Homes for Sale

/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/13
$80,000
- 2 Beds
- 1 Bath
- 949 Sq Ft
7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301

This is a well cared for and improved affordable home. The airy open concept of the main space makes for a feeling of spaciousness. The primary bedroom has direct access to the full bath and laundry. The attached enclosed porch offers additional seasonal living space, The large corner lot offers good garden space and storage in the good sized storage shed.

David Brown Berkley & Veller Greenwood Country

7 Stonewall Dr Unit 60159.s07, Brattleboro, VT 05301
/25
$269,000
- 5 Beds
- 4 Baths
- 2,376 Sq Ft
50 Grove St, Brattleboro, VT 05301

New to the market, this well-maintained 3-unit property is a fantastic opportunity for both investors and owner-occupants. Located just minutes from downtown, it offers convenience, value, and flexibility. One unit is currently on a month to month and move-in ready, making it ideal for someone looking to live on-site or set their own rental terms. The other two units are occupied by long-term,

Kate Barry EXP Realty

50 Grove St, Brattleboro, VT 05301
/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
/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
/20
$249,000
- 6 Beds
- 2 Baths
- 1,968 Sq Ft
14-16 Valley St, Brattleboro, VT 05301

Perfectly situated on a quiet street close to downtown, stores, and schools, this well cared for duplex is a rare opportunity for owner-occupants or investors alike. Each spacious unit offers 3 bedrooms and 1 full bath, with a host of updates and energy-efficient upgrades throughout. Many recent upgrades include Solar panels, Finished and insulated attics, Partially finished basements, Gas

Claire Renaud Berkley & Veller Greenwood Country

14-16 Valley St, Brattleboro, 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
/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
/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
/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
/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
/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
/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
/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
/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
/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
/5
$315,000
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
412 Western Ave, Brattleboro, VT 05301

The cutest house on the block! Only 1 house from the famous deli for eats, right near the entrance to I 91, both north and south for travel or work and 2 minutes away from Memorial Park with all it offers....skating, ball games, pools, sliding, skiing. Plus it has a great back yard, 2 levels of decks and a front porch to add to the package. This 1860's Mansard is so sweet, filled with character

Christine Lewis Brattleboro Area Realty

412 Western Ave, Brattleboro, VT 05301
/12
$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
/60
$1,338,000
- 4 Beds
- 3.5 Baths
- 3,400 Sq Ft
1845 Hatch School Rd, Brattleboro, VT 05301

Welcome to our Contemporary Farmhouse with 100 private acres yet only 5 miles to Wilmington Center and 14 miles to Mount Snow Ski Resort. Harriman Reservoir is close for summer boating, water sports and picnics. Nestled in the heart of nature, the property offers numerous possibilities, including a well-appointed home, a working farm, various business opportunities and/or investment potential. As

Richard Caplan Deerfield Valley Real Estate

1845 Hatch School Rd, Brattleboro, VT 05301
/54
$2,490,000
- 7 Beds
- 7.5 Baths
- 6,518 Sq Ft
1324 Middle Rd, Brattleboro, VT 05301

Truly a rare and remarkable property. This custom home was lovingly designed and constructed in 2005 with a clear vision for bringing the Vermont scenery in, while maintaining the rustic charm befitting a country estate. The main house features gorgeous exposed timber frame construction throughout, natural wood flooring, paneling, and trim, extensive artisan stonework inside and out, including 3

Adam Palmiter Berkley & Veller Greenwood/Dover

1324 Middle Rd, 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
/5
$680,000
- Studio
- 5,540 Sq Ft
50 Terrace St, Brattleboro, VT 05301

SUPERB OPPORTUNITY to acquire one of Brattleboro’s nicest multi-family, investment properties!! Situated in one of THE BEST neighborhoods in Brattleboro, Vermont, this sweet, money-maker offers 7 units on a quiet street that is SOOO close to downtown Brattleboro. What every investor dreams of!!! Location, quality condition and build, spacious unit size, superb level, off-street parking, and

Dan Normandeau Berkley & Veller Greenwood Country

50 Terrace St, Brattleboro, VT 05301
/2
$90,000
- Land
- 1.97 Acres
- $45,685 per Acre
24 Summit Cir, West Brattleboro, VT 05301

Gorgeous building lot nestled into a prime development on a wooded hillside in Southern Vermont. The 1.97 wooded lot is minutes to downtown Brattleboro, yet private and rural!

Claire Renaud Berkley & Veller Greenwood Country

24 Summit Cir, West Brattleboro, VT 05301
/10
$59,900
- Land
- 0.25 Acre
- $239,600 per Acre
203 Fairview St, Brattleboro, VT 05301

In-town lots are few and far between these days but are such a great option! Design your own low inpact, energy efficient home, your dream home! This is your spot! This neighborhood is friendly and convenient to schools, Memorial Park, shopping, hospitals and just minutes to 91. The .25 acre lot is cleared and ready to go with easy access to town water and sewer. House site is set back from the

Rebecca Seymour Brattleboro Area Realty

203 Fairview St, Brattleboro, VT 05301
/15
$75,000
211 High St, Brattleboro, VT 05301

Here's a great opportunity! Formerly a 2 unit multi-family, this is currently a shell ready for your finishing! This property will need everything ... heating, electrical, plumbing, exterior work and full interior finishing. Very convenient to downtown, some off street parking but nicely sited above the road. Please do NOT park in the driveway.

A.J. Bellville Bellville Realty

211 High St, Brattleboro, VT 05301
/5
$380,000
- 6 Beds
- 4 Baths
- 3,264 Sq Ft
25 Cottage St, Brattleboro, VT 05301

Sweet neighborhood. This would be a great location for an owner to live in one unit and rent the other 3. Lots of character! Great investment possibility. Close to Hospital, nursing homes, shopping, interstate for travel. Plenty of off street parking

Christine Lewis Brattleboro Area Realty

25 Cottage St, Brattleboro, VT 05301
/9
$250,000
- Land
- 3.79 Acres
- $65,963 per Acre
000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301

Easy to build!!! The land is open, so no fuss with a lot of prep. Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

Christine Lewis Brattleboro Area Realty

000 Fort Dummer Heights Unit 1 and 2, Brattleboro, VT 05301
/2
$150,000
- Land
- 2.05 Acres
- $73,171 per Acre
00 Fort Dummer Heights Unit 2, Brattleboro, VT 05301

Beautiful high meadow, in a nice little neighborhood tucked up against the state park, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor cooperation.

Christine Lewis Brattleboro Area Realty

00 Fort Dummer Heights Unit 2, Brattleboro, VT 05301
/3
$125,000
- Land
- 1.75 Acres
- $71,429 per Acre
0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301

Manicured into a beautiful high meadow, in a nice little neighborhood....sunny with views, what more could you want? Easy to build!!! The land is open, so no fuss with a lot of prep. This land has gone thru several transitions and plans for development by it's builder owner, but we now have the simplest! There are potentially a couple of options for hooking to town sewer with neighbor

Christine Lewis Brattleboro Area Realty

0 Fort Dummer Heights Unit 1 4934976, Brattleboro, VT 05301
/5
$270,000
- 6 Beds
- 2 Baths
- 2,112 Sq Ft
556 S Main St, Brattleboro, VT 05301

What a great way to start your home ownership! A tenant can help with the monthly expenses letting you build your own reserves and take a bit of pressure off the cost of home ownership! This 2 family has two-3 bedroom units, a nice yard and off street parking. Check it out and see for yourself...please respect the 48 hour notice for tenants, mask up! No interior photos due to tenant privacy.

Christine Lewis Brattleboro Area Realty

556 S Main St, Brattleboro, VT 05301

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.