Homes for Sale near OAK MEADOW SCHOOL

/44
$375,000 Open Sun 2PM - 3:30PM
- 4 Beds
- 2.5 Baths
- 2,132 Sq Ft
156 Sherwood Cir, Brattleboro, VT 05301

YOU CAN GET THERE FROM HERE! NEW ENGLAND CHARM AND FLEXIBLE SPACES...YOUR LUSH RETREAT AWAITS! A short drive to the cultural and foodie hub of southeastern Vermont, this slice of heaven is where your dreams take root. Follow a scenic road to a vibrant green lot where a terraced rock wall dotted with ferns and hostas signals your arrival. A large covered porch invites you to pull up a chair,

Fine Homes Group International Keller Williams Realty-Metropolitan

156 Sherwood Cir, Brattleboro, VT 05301
/26
$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
/38
$465,000
- 3 Beds
- 1.5 Baths
- 1,560 Sq Ft
660 Bonnyvale Rd, Brattleboro, VT 05301

Tucked away on a peaceful 4.3-acre lot surrounded by mature trees, this “wow—worthy” 960 sq ft modern “glass house” (with additional 600+ sq ft of lower level living) on Bonnyvale Road, offers a stylish and serene retreat. Exquisitely designed, it blends indoor ease and simplicity with an outstanding natural setting. The stand-out home features an open-concept layout filled with natural light

Kate Barry EXP Realty

660 Bonnyvale Rd, Brattleboro, VT 05301
/59
$547,000
- 5 Beds
- 4.5 Baths
- 5,850 Sq Ft
628 S Main St, Brattleboro, VT 05301

Absolutely Gorgeous In-Town Home with Exceptional Attention to Detail.This stunning residence offers over 5,000 square feet of meticulously designed living space in the main house, plus a fully separate accessory dwelling with two independent living areas—ideal for extended family, guests, or producing income. Additionally there is a two-car garage with an integrated service pit for

Kerry Mulverhill Brattleboro Area Realty

628 S Main St, Brattleboro, VT 05301
/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
/58
$650,000
- 4 Beds
- 2 Baths
- 3,090 Sq Ft
301 Maple St, Brattleboro, VT 05301

How sweet it is! It is the perfect time to own this home, as the season turns to spring all the extraordinary effort in design and creating the hardscape and gardens come to life in bursts of bloom, enchanting ribbons of perfume and delightful fragrant nooks. Perfect set up for home office on first floor or tuck away in a sweet 2nd floor option with lots of room to work in private. Out back, in

Christine Lewis Brattleboro Area Realty

301 Maple St, Brattleboro, VT 05301
/26
$450,000
- 3 Beds
- 1.5 Baths
- 2,262 Sq Ft
1142 Western Ave, Brattleboro, VT 05301

You choose! Such a versatile property...invest in 2 rentals...live in either unit and rent the other...maybe develop the barn into another unit, home business, workshop..(check with Zoning). Just short of an acre (.86) the land is the big, big seller....the huge, mostly level back yard is already lush with flourishing fruit trees and blueberry bushes. There is a garage/gardening shed for your

Christine Lewis Brattleboro Area Realty

1142 Western Ave, Brattleboro, VT 05301
/13
$450,000
- 3 Beds
- 2 Baths
- 2,074 Sq Ft
36 Spruce St, Brattleboro, VT 05301

You choose! This amazing property can be used as one of the grand ladies of the neighborhood...just open a door or two and repurpose the kitchen...what a nice laundry room it would make...or use as is with 2 flats, live in 1 and have a bit of income from the other...What else, you might ask! There is a rear section of the house ready to be reclaimed, and a barn attached that could also be built

Christine Lewis Brattleboro Area Realty

36 Spruce St, Brattleboro, VT 05301
/19
$299,000
- 3 Beds
- 1 Bath
- 1,500 Sq Ft
85 Crosby St, Brattleboro, VT 05301

Charming 1950s Gem! Step into timeless warmth and character with this delightful 3-bedroom, 1-bath home. This lovingly cared for home features beautiful rock maple hardwood floors, solid wood doors, and rich original woodwork that speak to its enduring craftsmanship. Recent updates blend vintage charm with modern comfort, including fresh interior and exterior paint, standing seam metal roof,

Karen Hoppe Berkley & Veller Greenwood Country

85 Crosby St, Brattleboro, VT 05301
/18
$325,000
- 3 Beds
- 1 Bath
- 1,174 Sq Ft
138 Cedar St, Brattleboro, VT 05301

Welcome to this adorable 3-bedroom, 1-bath ranch-style home nestled in one of Brattleboro's most sought-after neighborhoods! Built in 1956, this lovingly cared for gem perfectly blends classic character with modern comfort. Many recent upgrades including CertainTeed Monogram vinyl siding and trim, freshly painted interior walls and so much more. The kitchen features a sleek Whirlpool glass top

Claire Renaud Berkley & Veller Greenwood Country

138 Cedar St, Brattleboro, VT 05301
/29
$109,900
- 3 Beds
- 2 Baths
- 1,064 Sq Ft
26 Cedar St, Hinsdale, NH 03451

Well maintained 3 bedroom, 2 bathroom home with open concept living room/kitchen area. Fully applianced kitchen with stainless steel appliances and lovely kitchen island. Master bedroom and bathroom on one end and the other additional bedrooms on the other. Paved driveway and a shed for storage. Park approval required!

Dick Thackston R.H. Thackston & Company

26 Cedar St, Hinsdale, NH 03451
/24
$349,999
- 3 Beds
- 1.5 Baths
- 1,073 Sq Ft
12 Breezy Knoll, Hinsdale, NH 03451

This adorable cape has been lovingly renovated and is totally move in ready. The current owners have spared no expense getting this 3 bedroom & 1.5 bath ready for its new owners. New septic, siding and roof are some of the big items but certainly not all. Join us Sunday June 22nd for an Open House 12-2, or schedule a private showing today - no delays!

Anna Thackston Vylla Home

12 Breezy Knoll, Hinsdale, NH 03451
/8
$170,000
- Land
- 18 Acres
- $9,290 per Acre
0 Gibson Rd, Brattleboro, VT 05301

This just doesn't happen, a large parcel,18+ acres, in a desirable Brattleboro location. Just up the road the Brattleboro Country Club. Here you'll find stonewalls, small, intriguing streams and mature hard and softwoods. It's the pine trees, however that take center stage, some of them stretching up over 100 feet. If the acreage isn't quite enough there's an adjacent parcel on the market as

Bill Hickok Berkley & Veller Greenwood Country

0 Gibson Rd, 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
/23
$345,000
- 4 Beds
- 2 Baths
- 1,550 Sq Ft
122 Marlboro Ave, Brattleboro, VT 05301

122 Marlboro Avenue is in a highly sought out, in-town neighborhood known for its peace and quiet, friendly neighbors, and super-convenient location. This solid, 3-4 bedroom, 2 bath home sits attractively on a sunny and level lot and comes with an oversized garage and attached workshop (and potential to add additional living space). This home provides a completely renovated and modernized

Stephanie Peduzzi-Baker Brattleboro Area Realty

122 Marlboro Ave, Brattleboro, VT 05301
/20
$299,999
- 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
/5
$100,000
- 1 Bed
- 1 Bath
- 700 Sq Ft
39 Brookside Dr Unit 7, Brattleboro, VT 05301

Ready for a redo, this home is priced right for anyone who is handy with freshening, light carpentry (flooring) and other minor skills. Worth the effort to find an affordable option to renting or living with Mom! 48 hour a must for notice. This condo is located in a prime location with quick, easy access to I91 and a stones throw to the Whetstone Brook, Farmers Market and Living Memorial Park.

Christine Lewis Brattleboro Area Realty

39 Brookside Dr Unit 7, Brattleboro, VT 05301
/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
/9
$179,000
- Land
- 14 Acres
- $12,990 per Acre
0 E Orchard St Unit 5046918, Brattleboro, VT 05301

Here's an excellent opportunity to have a larger parcel of land, 13+ acres, in Brattleboro, not only in town but right across the street from the Brattleboro Country Club! This property has not been available for over 35 years and now it's ready for your building plans. This wooded lot features a mature mix of hard and softwoods including some true giants. There's a stream coursing through it

Bill Hickok Berkley & Veller Greenwood Country

0 E Orchard St Unit 5046918, Brattleboro, VT 05301
/12
$100,000
- 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 and public access. The town of Hinsdale is family friendly and perfect for nature lovers. It borders Connecticut River for 13 miles and can boasts a preferred Pisgah State Park trailhead. From this home, it is only a five mile drive to Brattleboro and 22 miles to Keene. The home is a split level

Jessie Carpenter Keller Williams Realty Metro-Keene

48 Robbins St, Hinsdale, NH 03451
/29
$290,000
- 3 Beds
- 1 Bath
- 1,392 Sq Ft
403 Tyler Hill Rd, Vernon, VT 05354

Welcome to this sweet and inviting 3-bedroom, 1-bath home, beautifully updated around 2015 and ready for new memories! Nestled on a generous lot, this home offers both comfort and functionality with a bright, open layout and thoughtful improvements throughout.Enjoy relaxing or entertaining on the deck overlooking a spacious yard with a babbling brook—perfect for peaceful mornings or summer

Kerry Mulverhill Brattleboro Area Realty

403 Tyler Hill Rd, Vernon, VT 05354
/50
$318,000
- 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
/60
$729,000
- 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
/58
$859,000
- 3 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
$995,000
- 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 passing stonewalls & lovely properties on hundreds of acres of ridgetop, you'll find this gracious & energy efficient home that's a mere 10 minutes from downtown Brattleboro. Building materials have been harvested from it's 51-1/2 acre forest with streams, ponds. Rooms are thoughtfully designed & filled with light from the abundant

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
/33
$334,500
- 3 Beds
- 1.5 Baths
- 1,848 Sq Ft
49 Hampshire Cir, Brattleboro, VT 05301

Cute home at the end of the cul-de-sac. Large front deck with a slider that leads into a newly refinished kitchen, dining area and living room. A half bath with laundry complete the first floor. Two bedrooms upstairs with a full bath. First floor has a door that leads out back to another large deck. The third bedroom and family room in the walkout basement. Open house Saturday 6/21/25 from

Darlene Conca Keller Williams Realty Metro-Keene

49 Hampshire Cir, Brattleboro, VT 05301
/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
/45
$1,250,000
- 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, a pond and former orchard. The home's historic features have been well maintained; exhibiting beamed ceilings, wide board floors and paneling from the hurricane of 1938. The chef in the family will love the updated kitchen centered around an island, its large gas range with

Timothy Keating BHG Masiello Keene

61 Orchard Rd, Chesterfield, NH 03443
/14
$30,000
- 3 Beds
- 1.5 Baths
- 924 Sq Ft
3 Gateway Dr, Hinsdale, NH 03451

Got some skills? Got people? Maybe you are the one to take this home in need of rehab, do the work and have a sweet home, in a coop park, and beat the rap of apartments. This is worth looking into, but please be prequalified for a rehab loan in the park, or proof of funds for cash. It is not everyone's home, but is worth the consideration. Buyers must be park approved.

Christine Lewis Brattleboro Area Realty

3 Gateway Dr, Hinsdale, NH 03451
/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
/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
/28
$239,000
- 3 Beds
- 1.5 Baths
- 1,531 Sq Ft
316 Putney Rd, Brattleboro, VT 05301

Convenient Location & Low Maintenance Living! Enjoy easy access to shopping, public transportation and waterfront with scenic trails. The backyard is just the right size for enjoying nature and a little fresh air. This charming home combines classic character with practical updates featuring a standing seam roof, vinyl windows and aluminum siding. Inside, the home radiates its original charm

Kerry Mulverhill Brattleboro Area Realty

316 Putney Rd, Brattleboro, VT 05301
/16
$488,875
- 5 Beds
- 4 Baths
- 3,064 Sq Ft
176 High St, Brattleboro, VT 05301

Unique opportunity to invest in your own home and have revenue from 2 apartments. Located close to all that Brattleboro has to offer for unique shopping, art, theater and lots of dining venues. The 1st floor apartment has over 1500 square feet of living space with 2+ bedrooms and two bathrooms, its own covered porch and expansive deck. Additionally, there is a spacious eat in kitchen, large

Susan Bellville Bellville Realty

176 High St, Brattleboro, VT 05301
/29
$329,000
- 4 Beds
- 2 Baths
- 1,548 Sq Ft
11 Maple St, Brattleboro, VT 05301

Charming and well-built Cape-style home featuring 4 bedrooms and 2 full baths. The updated kitchen boasts tiled floors, generous counter space, and modern finishes—perfect for the home chef. Just off the kitchen, the dining room includes a sliding door that opens to the backyard and patio, ideal for indoor-outdoor entertaining.Beautiful hardwood floors run throughout the home—no carpet here.

Monica Sumner BHG Masiello Brattleboro

11 Maple St, Brattleboro, VT 05301
/22
$325,000
- 3 Beds
- 1 Bath
- 1,104 Sq Ft
62 Lawton Dr, Brattleboro, VT 05301

Everything deserves a second chance, and this home found the right owner to love and recreate it in a stunning new life. Anyone who has looked at this home in the past few years, has to come back to see the shine....the fresh new look....the simplicity of move right in. Not only is this home refreshed stem to stern, it has new windows, siding, shingles, kitchen, bath.....and on and on! Tuck

Christine Lewis Brattleboro Area Realty

62 Lawton Dr, Brattleboro, VT 05301
/26
$745,000
- 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
/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

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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.