Homes for Sale near Oak Grove School

• 

  

  

  /23

  $500,000

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft

  137 Pleasant Valley Rd, Brattleboro, VT 05301

  This is IT! If you are looking for an incredible small home...not tiny...but compact and just the right size, this is it. Timber framing at it's best gives you an open concept, live in every inch, light filled, high quality charming home. Nestled in a wildflower meadow, with plenty of room for a homestead garden, enough open sky for stargazers, big and flat enough for your own cross country ski

  Christine Lewis Brattleboro Area Realty

  137 Pleasant Valley Rd, Brattleboro, VT 05301
• 

  

  

  /36

  $479,000

  • 4 Beds
  • 2.5 Baths
  • 1,887 Sq Ft

  230 Western Ave, Brattleboro, VT 05301

  This beautifully renovated in-town home blends character, comfort, and convenience. From the welcoming front porch to the shaded backyard and new deck, every space has been thoughtfully updated. The sunny kitchen offers granite countertops, stainless steel appliances, and a well-planned pantry, while the living room is anchored by a handsome Italian pellet stove; efficient, warm, and the perfect

  John Hatton Berkley & Veller Greenwood Country

  230 Western Ave, Brattleboro, VT 05301
• 

  

  

  /48

  $575,000

  • 5 Beds
  • 2.5 Baths
  • 2,406 Sq Ft

  231 Chesterfield Rd, Hinsdale, NH 03451

  Welcome to this spacious five-bedroom, three-bath residence that perfectly blends comfort, practicality, and versatility. Set on a picturesque lot with rolling hills, this property has been home to cows, horses, and chickens, making it an excellent choice for those seeking a small farm or hobby homestead. The property includes a barn and a detached two-car garage with radiant heating, offering

  Megan Manley North New England Real Estate Group

  231 Chesterfield Rd, Hinsdale, NH 03451
• 

  

  

  /32

  $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
• 

  

  

  /34

  $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
• 

  

  /32

  $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
• 

  

  /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
• 

  

  /47

  $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 miss

  Carol Slocum Keller Williams Realty Metro-Keene

  785 Brattleboro Rd, Hinsdale, NH 03451
• 

  

  /58

  $515,000

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

  301 Maple St, Brattleboro, VT 05301

  Fall is here! The leaves are turning, the mums are in cheerful blooming mode and soon it will be time to cozy in with the woodstove! But...not quite yet, there are still plenty of days for the sun filled deck, blooms galore and strolls around your own private gardens. This sweet home has the great construction of the 1800's...loved and cared for by generations of Vermonters who have added,

  Christine Lewis Brattleboro Area Realty

  301 Maple St, Brattleboro, VT 05301
• 

  

  /17

  $209,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  75 Mather Rd, Brattleboro, VT 05301

  Great Location, Great opportunity! Currently, a 1-bedroom, 1-bath home sits back on a desirable, pleasant country road. It is a larger lot than most, and with vision, here is an opportunity to start home ownership, downsize to a one-level with efficient living space. Use an investment or create your small Vermont getaway. This sweet spot is ready for your vision and ideas. This property is in

  Kristen Ziter Taylor Brattleboro Area Realty

  75 Mather Rd, Brattleboro, VT 05301
• 

  

  /30

  $336,000

  • 3 Beds
  • 1.5 Baths
  • 1,663 Sq Ft

  122 Meetinghouse Rd, Hinsdale, NH 03451

  Welcome to this charming and cozy 3-bedroom, 1.5-bathroom home where comfort meets functionality. Perfect for those looking for space to live, gather, and grow! The heart of the house is the large, bright kitchen, offering ample granite counter space for cooking and casual gatherings. This space flows seamlessly from the dining room into the large living room.The main level conveniently hosts

  Cassie Eaton H. G. Johnson Real Estate

  122 Meetinghouse Rd, Hinsdale, NH 03451
• 

  

  /19

  $190,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  39 Brookside Dr Unit 3, Brattleboro, VT 05301

  Desirable 2 bedroom, 1 bath low maintenance, affordable home. Your spacious living/dining area has sliders looking out to the woods and a small yard space. Upstairs are 2 large bedrooms and a full bath. The lower level is a 465 square foot basement for extra storage with washer/dryer hookup. The entire interior has been freshly painted, new kitchen cabinets, countertop, new flooring, new bathroom

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 3, Brattleboro, VT 05301
• 

  

  /24

  $29,900

  • 2 Beds
  • 1 Bath
  • 684 Sq Ft

  97 Glen St, Brattleboro, VT 05301

  Finally!! Affordable!! This just right sized home is tucked into the 55 and older park for peace and quiet. Along the brook, the damaged homes have been removed and replaced with open green space with a gentle park like feel. There is an awning over the stairs, an added pitched roof, spacious front end kitchen/dining with several windows and some built-ins. Located in one of the 3 parks, making

  Angela Sherman Brattleboro Area Realty

  97 Glen St, Brattleboro, VT 05301
• 

  

  /18

  $279,500

  • 3 Beds
  • 1 Bath
  • 1,212 Sq Ft

  75 Hinsdale Heights, Hinsdale, NH 03451

  Nestled in a family friendly neighborhood this well maintained 3 bedroom ranch house is move in ready...recent interior paint accents lovely wood floors..,basement has a large family room adjacent to full service laundry room...oversized garage and shed for additional storage..spacious backyard is nicely landscaped...walking distance to local schools and local park/playground. minutes to Vermont

  Curtiss Thornbrugh HKS Associates, Inc.

  75 Hinsdale Heights, Hinsdale, NH 03451
• 

  

  /59

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  290 Guilford St, Brattleboro, VT 05301

  This meticulously maintained 3-bedroom, 2-bath ranch surprises with its spacious layout and thoughtfully designed interior. The kitchen is a dream for those who love to cook, featuring quartz countertops, slate flooring, solid hardwood soft-close cabinetry, a dedicated baking station, and access to the nearly 700 sq. ft. back deck—perfect for entertaining. The open main living area features

  Kate Barry EXP Realty

  290 Guilford St, Brattleboro, VT 05301
• 

  

  /24

  $400,000

  • 5 Beds
  • 3 Baths
  • 2,254 Sq Ft

  85 Stockwell Dr, Brattleboro, VT 05301

  Motivated Seller! Sweet! This 5 bedroom /3 bath home is located in one of our most sought after neighborhoods, is newly remodeled, has 2 pellet stoves for economical heat and a nice back deck. Lots of opportunities to garden, relax in a hammock or play with pets. Flexible floor plan is perfect for at home workers, multigenerational living and aging in place. Hop the MOOVER and take a ride

  Christine Lewis Brattleboro Area Realty

  85 Stockwell Dr, Brattleboro, VT 05301
• 

  

  /60

  $415,000

  • 6 Beds
  • 2 Baths
  • 2,048 Sq Ft

  58-60 Frost Place, Brattleboro, VT 05301

  Back on the market - Unit 58 is now Vacant! Located in the heart of downtown Brattleboro, Vermont's vibrant southern hub, recently dubbed "one of the best small towns in America". This turnkey income generator features two 3 bedroom units, one with a successful Airbnb rental history, completely renovated in 2018, with in-unit washer/dryer. Enter through the mudroom with generous built-in storage.

  Lily Gautot Greenwald Realty Group

  58-60 Frost Place, Brattleboro, VT 05301
• 

  

  /30

  $369,000

  • 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. Aging in place is easy

  Christine Lewis Brattleboro Area Realty

  1089 Marlboro Rd, Brattleboro, VT 05301
• 

  

  /36

  $414,500

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

  87 Orchard St, Brattleboro, VT 05301

  SELLER IS RELOCATING. It is time to pass the keys to the next owner and move closer to family. Welcome to one of the most highly sought after neighborhoods in Brattleboro – Orchard St.This spacious modern contemporary home is conveniently located just minutes from I-91 and downtown Brattleboro. There is plenty of space with four large bedrooms, 3 full baths, and wonderful open concept living

  Jim Bellville Bellville Realty

  87 Orchard St, Brattleboro, VT 05301
• 

  

  /47

  $715,000 Open Sat 12PM - 2PM

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

  136 Cross Rd, West Chesterfield, NH 03466

  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 bedrooms and two full bathrooms,

  Robert Ingham Coldwell Banker Realty Center Harbor NH

  136 Cross Rd, West Chesterfield, NH 03466
• 

  

  /20

  $225,000

  • 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
• 

  

  /37

  $849,000

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

  5 Hillwinds N, Brattleboro, VT 05301

  Elegant Post-and-Beam!!! Tucked along a birch-lined drive, this exceptional home is set on 11 acres of landscaped grounds with lawns, stone walls, gardens, and 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 porch that opens into a marble floored foyer

  Robert Doyle Berkley & Veller Greenwood Country

  5 Hillwinds N, Brattleboro, VT 05301
• 

  

  /44

  $425,000

  • 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
• 

  

  /14

  $40,000

  • 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
• 

  

  /29

  $310,000

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

  78-80 Central St, Brattleboro, VT 05301

  MOTIVATED SELLER: 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,

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  78-80 Central St, Brattleboro, VT 05301
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /30

  $629,000

  • 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

  $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
• 

  

  /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
• 

  

  /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

  $309,900

  • 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 sliders

  Christine Lewis Brattleboro Area Realty

  164 Chestnut St, Brattleboro, VT 05301
• 

  

  /45

  $898,000

  • 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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