Homes for Sale in 05301

• 

  

  

  /58

  $830,000

  • 5 Beds
  • 5.5 Baths
  • 5,064 Sq Ft

  253 Sugar House Hill Rd, Guilford, VT 05301

  Set on 10.20 beautiful acres in picturesque Guilford, this exceptionally spacious and thoughtfully updated home offers more than 5,000 square feet of finished living space, including approximately 1,715 square feet in the walkout lower level. The main home features five bedrooms, including an expansive primary suite with a walk-in closet and beautifully renovated private bath. At the heart of the

  Kerry Mulverhill

  253 Sugar House Hill Rd, Guilford, VT 05301
• 

  

  

  /34

  $149,900

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft

  14 Deepwood Park, Brattleboro, VT 05301

  Fully remodeled in 2018, this double wide manufactured home looks far newer and nicer than its 1994 age might show. The home is nicely situated on a wide lot well back from the road and it backs up to a nice forest. The kitchen had lots of cabinetry, a center peninsula, wood countertops and a newer stainless side by side refrigerator, microwave, and propane stove. The large dining area abuts the

  Steve Schoppmeyer BHG Masiello Brattleboro

  14 Deepwood Park, Brattleboro, VT 05301
• 

  

  

  /30

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  215 Gilbert Rd, Marlboro, VT 05344

  Looking for a home where privacy, nature and comfortable living come together? This sweet Cape offers a rare opportunity to enjoy nearly 45 acres of serene Vermont land, complete with the soothing sounds of a babbling brook and an abundance of wildlife and natural beauty.Set at the end of a long-deeded right-of-way, the property offers an exceptional sense of privacy and seclusion, with no

  Monica Sumner BHG Masiello Brattleboro

  215 Gilbert Rd, Marlboro, VT 05344
• 

  

  

  /16

  $139,000

  • Land
  • 3.8 Acres
  • $36,579 per Acre

  0 Marlboro Rd Unit 5107996, Brattleboro, VT 05301

  This beautiful, elevated, and sparsely wooded in-town lot features an established shared driveway with power nearby, as well as a woods road running throughout the property. Significant clearing has already been completed, and a substantial amount of firewood remains on the lot.The property will require a septic system and well; however, the neighboring lot has perc'd for an inground

  Victoria Woods Brattleboro Area Realty

  0 Marlboro Rd Unit 5107996, Brattleboro, VT 05301
• 

  

  

  /19

  $804,650

  • 7,120 Sq Ft

  820 & 28 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow, a desirable unit mix, and future potential come together in this well-maintained 8-unit investment package in vibrant Brattleboro. Offered together, the two 4-unit properties feature six spacious 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments, appealing to a broad range of tenants. Pride of ownership is evident throughout, with recent improvements

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 & 28 Western Ave, Brattleboro, VT 05301
• 

  

  /21

  $190,000

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  39 Brookside Dr Unit 5, 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. Newer kitchen cabinets, countertop, flooring, bathroom vanity, vinyl windows and front door. This condo is

  Angela Sherman Brattleboro Area Realty

  39 Brookside Dr Unit 5, Brattleboro, VT 05301
• 

  

  /24

  $120,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  21 Winding Hill, Brattleboro, VT 05301

  Sweet! Taken to a new level, this home has new windows, flooring, bath, etc. Neat as a pin and ready for easy living! Plus...an enclosed porch for rainy day coffee and a sunny deck for every day use. Bedrooms at either end promote privacy or an office away from the main living. The oversized carport is perfect for the changing weather, but doubles as a patio and grilling station. A good choice

  Christine Lewis Brattleboro Area Realty

  21 Winding Hill, Brattleboro, VT 05301
• 

  

  /19

  $499,000

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

  171 Buttonwood Dr, Brattleboro, VT 05301

  Celebrate! You have earned it! A gentle neighborhood for 55 and more, mowing, plowing and shoveling included in the HOA.. Leave the tough stuff for the young at heart! Sit snug as a bug in the sun room and watch it snow, without a care or worry, or run off to play pickle ball in the warm seasons....Want to be snow birding? Perfect set up as the home is easy care inside and out. Park a car in the

  Christine Lewis Brattleboro Area Realty

  171 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /35

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,330 Sq Ft

  205 Wantastiquet Dr, Brattleboro, VT 05301

  Just what you have been waiting for! The perfect spot in the perfect neighborhood! Watch the moon rise over Wantastiquet and the seasons change from your back yard! Listen for spring...when the ice cracks on the river and lets go...and watch the shoots pop to greet a new warm and beautiful summer season. This contemporary raised ranch has a wall of windows to the garden, a lovely little wood

  Christine Lewis Brattleboro Area Realty

  205 Wantastiquet Dr, Brattleboro, VT 05301
• 

  

  /19

  $479,000

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

  162 Buttonwood Dr, Brattleboro, VT 05301

  It has all you wanted! Shiny wood floors to celebrate New England building, plenty of windows to capture every inch of light possible, granite tops on a multitude of cabinets, a step in shower but also a tub for long soaks or the little ones who visit....total one floor living, so rare locally, even no stairs to the direct entry garage. A service that plows, shovels and mows.....a playground for

  Christine Lewis Brattleboro Area Realty

  162 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /17

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,550 Sq Ft

  77 Buttonwood Dr, Brattleboro, VT 05301

  You've earned it.....the right to easy living.....have someone to do the heavy lifting...This community has become a much needed addition to the housing community. All are designed for the 55 and over who are looking for an easy way to settle in. Just think, the snowplowing, shoveling and salting are all taken care of, as well as the summer mowing and hedge trimming. One level living with no

  Christine Lewis Brattleboro Area Realty

  77 Buttonwood Dr, Brattleboro, VT 05301
• 

  

  /27

  $289,000

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  45 Kopkind Rd, Guilford, VT 05301

  Tucked into a peaceful, wooded setting on 2.1 acres in Guilford, just over the Massachusetts border, this cozy 2-bedroom, 1-bath home offers simple Vermont living with plenty of charm. Designed for convenient one-level living, the home features a back deck overlooking the yard surrounded by the quiet of the woods. Several recent improvements add to the home’s comfort and practicality, including a

  Neil Goldberg Brattleboro Area Realty

  45 Kopkind Rd, Guilford, VT 05301
• 

  

  /37

  $615,000

  • 4 Beds
  • 2.5 Baths
  • 2,212 Sq Ft

  354 Orchard St, Brattleboro, VT 05301

  You don't have to wear pearls to live here! This home oozes classic charm, memories of Thanksgivings and every holiday celebrated. The first step in has a welcoming wood stove for winter chill and glass french doors to fling open the first day of spring....Bring them home to the heart of the house with a dining room big enough for a feast...living room with a fireplace....warm hardwood floors, a

  Christine Lewis Brattleboro Area Realty

  354 Orchard St, Brattleboro, VT 05301
• 

  

  /14

  $275,000

  • 1,200 Sq Ft

  752 Butternut Hill Dr, Guilford, VT 05301

  A perfect start! Well, power and driveway are all installed & septic design is available. The building constructed on slab, mostly finished surfaces, cathedral ceiling in the "living room". The interior is already sectioned into 4 rooms, waiting for kitchen and bath fixtures. Seller has plans for a one or 2 unit home build out. Sitting near the end of a quiet country road in no zoning Guilford,

  Christine Lewis Brattleboro Area Realty

  752 Butternut Hill Dr, Guilford, VT 05301
• 

  

  /33

  $110,000

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  77 Hatch School Rd, Brattleboro, VT 05301

  Beautiful country setting! Manufactured home with addition located just off the pavement in Halifax, VT, rural yet central to VT Routes 9 & VT/MA 112 and the outlying towns of Guilford, Marlboro, Whitingham (Jacksonville), Wilmington and Dover, VT. The trustee seller has never occupied the home and has minimal information; financing may be limited due to the home pre-dating 1976. Shown by

  Stephanie Wilde

  77 Hatch School Rd, Brattleboro, VT 05301
• 

  

  /50

  $250,000

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  147 Morningside Dr, Brattleboro, VT 05301

  Easy living. This move-in-ready townhouse comes with snow removal; trash, recycling and compost removal; landscaping; a swimming pool; tennis and pickleball courts; a hiking trail and little libraries included. The seller has refurbished the entire unit by installing beautiful flooring on the first floor and in bathrooms, refinishing cabinets, painting, and cleaning carpeting in order to get the

  Sally Fegley BHG Masiello Brattleboro

  147 Morningside Dr, Brattleboro, VT 05301
• 

  

  /35

  $230,000

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  9 Evergreen Ln, Brattleboro, VT 05301

  **Motivated seller -- offering $5,000 concession to buyers for closing costs** Welcome to Brookside Condominiums! This 2-bedroom, 1.5-bath end-unit townhome offers a comfortable, low-maintenance lifestyle in a convenient Brattleboro location. Natural light fills the living areas throughout, while the thoughtfully designed galley kitchen offers ample cabinet and counter space, a breakfast bar, and

  Ayden Hardy BHG Masiello Keene

  9 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /45

  $1,165,000

  • 4 Beds
  • 2.5 Baths
  • 3,338 Sq Ft

  1472 Carpenter Hill Rd, Guilford, VT 05301

  The Governor Carpenter Homestead, a pivotal piece of American history in Guilford, VT, is now accepting applications for its next Steward. This remarkable property was constructed in 1772 by Benjamin Carpenter, Vermont's first Lieutenant Governor. Lovingly maintained for decades, the residence combines historic integrity with modern functionality. Key features include: Architectural Significance:

  Thomas Dahlin Berkley & Veller Greenwood Country

  1472 Carpenter Hill Rd, Guilford, VT 05301
• 

  

  /35

  $325,000

  New Construction $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 640 Sq Ft

  203 Fairview St, Brattleboro, VT 05301

  PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to this brand NEW, beautiful home, professionally blower-door tested at an exceptional 1.7 providing outstanding airtightness, energy efficiency, & year-round comfort. Completed in July 2026 & designed for low-maintenance living, the home benefits from net-metered solar credits that have offset the owner’s electrical needs, including heating & cooling.

  Kristen Ziter Taylor Brattleboro Area Realty

  203 Fairview St, Brattleboro, VT 05301
• 

  

  /30

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  68 E Bonnyvale Ln, Brattleboro, VT 05301

  Looking for your first home, ready to downsize, or seeking single level living? This one is for you. Set in a peaceful rural location near the end of a quiet dead end road, this single level ranch offers comfort, privacy, and great potential on 6.5+ acres just outside the village of West Brattleboro. Enjoy an in ground swimming pool with a pool house and bathroom - perfect for summer relaxation.

  Dan Normandeau Berkley & Veller Greenwood Country

  68 E Bonnyvale Ln, Brattleboro, VT 05301
• 

  

  /29

  $289,000

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft

  110 Western Ave, Brattleboro, VT 05301

  This in town 4 bedroom, 2 bath home offers the perfect blend of comfort, convenience and versatility. Ideally located close to town amenities, this property provides easy access to shopping, dining, services, schools, parks and everyday essentials while offering a spacious place to call home. Inside you’ll find beautiful wood flooring, inviting living spaces and a layout that provides flexibility

  Wilma Skovinski Berkley & Veller Greenwood Country

  110 Western Ave, Brattleboro, VT 05301
• 

  

  /4

  $182,000

  • 3 Beds
  • 1.5 Baths
  • 1,114 Sq Ft

  23 Williams St, Brattleboro, VT 05301

  Cute as a button! Everyone knows this home painted as pretty as a picture, on the corner lot at the foot of Union Hill. The owners over the years have landscaped and created a magical setting........walk to downtown, coop and the MOOVER! Previous owners did a amazing renovation after Irene. An intown, affordable, vintage home with lots of character. 48 hour notice please in respect of the

  Christine Lewis Brattleboro Area Realty

  23 Williams St, Brattleboro, VT 05301
• 

  

  /27

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,530 Sq Ft

  72 Green Meadow Rd, West Brattleboro, VT 05301

  Nestled in a highly desirable West Brattleboro neighborhood, this well-cared-for home offers a wonderful community lifestyle and the ease of main-level living. The first floor features three bright bedrooms and a full bath - perfect for aging in place. Inside, you'll find classic hardwood floors and a cozy fireplace warming the living room. Step outside to an incredible, private backyard deck

  Thomas Dahlin Berkley & Veller Greenwood Country

  72 Green Meadow Rd, West Brattleboro, VT 05301
• 

  

  /9

  $198,000

  • Land
  • 3.27 Acres
  • $60,550 per Acre

  0 Pleasant Valley Rd, Brattleboro, VT 05301

  It doesn't get better than this! Stunning! Over 3.25 acres in a neighborhood with a wait list, well known hiking trails, near cross country skiing, country club and minutes to downtown. There are 2 lots, the front being mostly wooded with some clearing started and the rear lot with an old horse meadow, stone wall and a bit of height for potential views. Not only is there road frontage on Pleasant

  Christine Lewis Brattleboro Area Realty

  0 Pleasant Valley Rd, Brattleboro, VT 05301
• 

  

  /14

  $249,999

  • Land
  • 29 Acres
  • $8,621 per Acre

  0 Stickney Brook Rd Unit 5101849, Dummerston, VT 05301

  Here's your chance to own 29 acres of wooded Vermont countryside with frontage on both Stickney Brook Road and Hopkins Road, offering flexible access and endless possibilities. Set along one of Dummerston's most picturesque country roads this unique parcel offers privacy, potential and the perfect setting for a private retreat, camp or future homesite. A mix of timber and classic New England

  Lily Gautot Greenwald Realty Group

  0 Stickney Brook Rd Unit 5101849, Dummerston, VT 05301
• 

  

  /27

  $495,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  56 Park Laughton Rd, East Dummerston, VT 05346

  A wonderful Colonial home in Dummerston Village Vermont. Classic layout with a huge primary bedroom with double closets, 2 additional generouslysized bedrooms and a full bath on the second floor. The first floor has a large family room, dining room, a full bath with laundry, and a lovely 1/2 bath. Freshly updated with a new roof, new Anderson windows, new high efficiency furnace, whole house

  Derek Greene Derek Greene

  56 Park Laughton Rd, East Dummerston, VT 05346
• 

  

  /42

  $340,000

  $10K PRICE DROP

  • 2,745 Sq Ft

  120 Western Ave, Brattleboro, VT 05301

  Discover this lovingly cared-for two-unit multi-family property, ideally located in town with convenient access to shopping, restaurants, public transportation, and everyday amenities. Each unit offers a comfortable layout featuring 2 bedrooms and 1 bathroom, making this property an excellent opportunity for owner-occupants, investors, or those seeking rental income. Pride of ownership is evident

  Peggy Winchester ACORN REAL ESTATE GROUP LLC

  120 Western Ave, Brattleboro, VT 05301
• 

  

  /27

  $240,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  11 Evergreen Ln, Brattleboro, VT 05301

  This inviting 2 bedroom, 2-bathroom townhouse is located with privacy but close to Brattleboro amenities. Drive into your one car garage, in addition there is a storage area and laundry room. The second floor has a spacious living room and galley kitchen with eating nook which flows into a dining room and outdoor deck. The third level of this cozy condominium has a full sectional bathroom and 2

  Janet Lucier Barrett & Valley Assoc. Inc

  11 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /17

  $110,000

  • Land
  • 5,227 Sq Ft
  • $916,667 per Acre

  117 * Fuller Dr, Brattleboro, VT 05301

  Nestled just behind 117 Fuller Drive, with privacy and easy access from the street, this property is the perfect spot for the tiny home you have been longing for. Water, sewer, and electric are all at the street, and the seller will help to keep the access accessible :) The subdivision has received preliminary approval from the town, with finalization to be completed prior to sale—giving you

  Rebecca Seymour Brattleboro Area Realty

  117 * Fuller Dr, Brattleboro, VT 05301
• 

  

  /12

  $285,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,050 Sq Ft

  455 S Main St, Brattleboro, VT 05301

  Tucked in near schools, hospital, shopping and a short walk to fishing and a canoe ride. Room enough for a garden, play space and just the right size for new beginnings. Nice sun porch doubles a a mud room, kitchen is huge with room enough for an island, a sweet spot with lots of potential.

  Christine Lewis Brattleboro Area Realty

  455 S Main St, Brattleboro, VT 05301
• 

  

  /14

  $425,000

  $90K PRICE DROP

  • 3,364 Sq Ft

  28 Brook St, Brattleboro, VT 05301

  Strong returns and future potential define this well-maintained 4-unit investment property in vibrant Brattleboro. The building consists of four spacious 2-bedroom, 1-bath apartments, providing a desirable and consistent unit mix. Pride of ownership is evident throughout, making this a turnkey addition to any portfolio. Beyond the existing income, the property offers exciting upside with attic

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  28 Brook St, Brattleboro, VT 05301
• 

  

  /12

  $422,000

  $43K PRICE DROP

  • 3,756 Sq Ft

  820 Western Ave, Brattleboro, VT 05301

  Exceptional cash flow meets classic Vermont charm in this well-maintained 4-unit property in the heart of Brattleboro. The building features a desirable unit mix with two 2-bedroom, 1-bath apartments and two 1-bedroom, 1-bath apartments. Recent improvements include a freshly painted exterior in 2025 and bathroom renovations completed in 2023, reflecting pride of ownership and minimizing near-term

  The Nancy Jenkins Team Nancy Jenkins Real Estate

  820 Western Ave, Brattleboro, VT 05301
• 

  

  /35

  $68,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft

  22 Valley St, Brattleboro, VT 05301

  Welcome to 22 Valley Road, an affordable and easy-to-maintain 2-bedroom, 1-bath mobile home located in Brattleboro’s Tri-Park Cooperative Housing Corporation. This cozy single-level home offers a bright and refreshed interior with natural light, LED lighting, first-floor laundry hookups, and a functional layout that makes great use of the space. The kitchen features an electric range,

  Grayson VanHendrick Flex Realty

  22 Valley St, Brattleboro, VT 05301
• 

  

  /34

  $460,000

  • 3 Beds
  • 2 Baths
  • 1,920 Sq Ft

  216 Ghastly Job Way, Wilmington, VT 05363

  Escape to the beauty of Vermont in this private mountain retreat, ideally situated at the end of a quiet country road. Set on a secluded parcel, this charming getaway boasts sweeping long-range views stretching across the Green Mountains and National Forest to Mount Snow, with easterly vistas toward neighboring Marlboro. Take in spectacular sunsets from the covered front porch or unwind

  Monique White Deerfield Valley Real Estate

  216 Ghastly Job Way, Wilmington, VT 05363
• 

  

  /37

  $285,000

  $14K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  412 Western Ave, Brattleboro, VT 05301

  Move in ready and full of potential, this charming Brattleboro home is ready for its next chapter. The main level features a bright, open concept layout with a spacious kitchen and comfortable living area, creating an ideal space for everyday living and entertaining. Filled with natural light, the living room opens directly onto a private rear deck overlooking a manageable backyard perfect for

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  412 Western Ave, Brattleboro, VT 05301
• 

  

  /30

  $305,000

  $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,607 Sq Ft

  136 Morningside Dr, Brattleboro, VT 05301

  Rare opportunity to enjoy single-level living with all modern conveniences on the main floor in this magnificent condo unit. Featuring a spacious primary bedroom with a walk-in closet and full en-suite bathroom, this home offers comfort and functionality throughout. A second bedroom provides flexibility for guests, a home office, or additional living space. The open-concept kitchen and dining

  Desiree Stango Berkley & Veller Greenwood Country

  136 Morningside Dr, Brattleboro, VT 05301
• 

  

  /55

  $795,000

  $54K PRICE DROP

  • 6 Beds
  • 6.5 Baths
  • 3,877 Sq Ft

  2435 Stage Rd, Guilford, VT 05301

  Only a fortunate few have the privilege of calling Green River Village home - a quintessential Vermont hamlet distinguished by its historic covered bridge, the 1811 timber crib dam, and the iconic wood-spired church proudly perched on the hillside above. Sited next to the bridge, the Green River Bridge House, originally a blacksmith shop, enjoys 300 feet of frontage along the Green River. Built

  John Mcpherson Berkley & Veller Greenwood Country

  2435 Stage Rd, Guilford, VT 05301
• 

  

  /26

  $1,350,000

  • 7,660 Sq Ft

  131,133,141 Green St, Brattleboro, VT 05301

  What an opportunity to own 11 units in 3 separate buildings with a fantastic rental history. Close to downtown, schools, shopping and bus routes. Very well maintained properties with 3 - two bedroom units and 8 one bedroom units. On site laundry for the convenience of tenants. Wonderful features including hardwood floors and large windows for exceptional natural light. Great porches and very

  Susan Bellville Bellville Realty

  131,133,141 Green St, Brattleboro, VT 05301
• 

  

  /44

  $450,000

  $25K PRICE DROP

  • 6 Beds
  • 2.5 Baths
  • 3,682 Sq Ft

  4303 Hinesburg Rd, Brattleboro, VT 05301

  Private! Guilford! This unusual combination of a true log home with an incredible center double sided chimney....a fireplace facing the kitchen/dining and wood stove in the living room, bringing the best of both worlds:... ambiance and warmth. There is a surprise of one more fireplace on the 2nd floor in the charming primary bedroom...use the ensuite for a huge walk in closet. The other half of

  Christine Lewis Brattleboro Area Realty

  4303 Hinesburg Rd, Brattleboro, VT 05301
• 

  

  /48

  $1,650,000

  • 4 Beds
  • 3.5 Baths
  • 3,268 Sq Ft

  161 Depot Rd, Williamsville, VT 05362

  Perched high above the enchanting hills of Newfane, VT, lies a truly one-of-a-kind property. This meticulously crafted home offers an off-grid, private retreat with breathtaking views of the surrounding landscape. Constructed in 2003, the post and beam design incorporates wood and stone harvested from its expansive 219-acre setting, showcasing a harmonious blend of nature and architecture. This

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  161 Depot Rd, Williamsville, VT 05362

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