Windham County VT Homes for Sale

• 

  

  

  /41

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1137 Upper Dummerston Rd, Brattleboro, VT 05301

  Elegant and charming cape with an enchanting, exceptional garden that will impress even the seasoned green thumb. This magnificent home is solar equipped; the owner has had no electric bills for 3 years and the solar agreement may be transferred to the new buyer. Classic Vermont timeless style throughout features gorgeous archways, built-ins, and oak flooring. The kitchen is spacious with a

  Kristen Ziter Taylor Brattleboro Area Realty

  1137 Upper Dummerston Rd, Brattleboro, VT 05301
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• 

  

  

  /20

  $190,000

  • Land
  • 30.1 Acres
  • $6,312 per Acre

  0 Schoolhouse Rd, Jamaica, VT 05343

  Parcel 2 is a forested 30-acre property situated on Schoolhouse Road in Jamaica, Vermont. From the intersection of Schoolhouse and South Hill Roads, the road winds around a sharp bend and climbs a short hill before reaching the majority of the property, which lies along the north side of the road. A weathered stone wall is found along the entire length of the road frontage, hinting at the land's

  Thom Milke Fountains Land Inc.

  0 Schoolhouse Rd, Jamaica, VT 05343
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  /11

  $120,000

  • Land
  • 10.2 Acres
  • $11,765 per Acre

  0 S Hill Rd, Jamaica, VT 05343

  The South Jamaica Parcels consist of two contiguous lots situated along South Hill Road and Schoolhouse Road in South Jamaica, Vermont. Each parcel offers an excellent building opportunity, featuring level, buildable terrain and the convenience of power already available at the street making them ideal, low-hassle sites for a future home.Parcel I is a 10-acre building site located on

  Thom Milke Fountains Land Inc.

  0 S Hill Rd, Jamaica, VT 05343
• 

  

  

  /54

  $300,000

  • 4 Beds
  • 1.5 Baths
  • 1,632 Sq Ft

  28 Pine St, Bellows Falls, VT 05101

  **Open House Sunday 8/23 from 11am-1pm**Classic Charm Meets Comfortable Family Living in Bellows Falls!Step into the charm of yesteryear with this well-maintained home in the heart of historic Bellows Falls. Filled with character and timeless appeal, this inviting property offers the warmth and space that makes a house feel like home.With 4 bedrooms and 1.5 baths, there’s

  Jonathan Griffus BHG Masiello Keene

  28 Pine St, Bellows Falls, VT 05101
• 

  

  

  /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
• 

  

  /29

  $224,900

  • 2 Beds
  • 1 Bath
  • 1,017 Sq Ft

  1892 US Rt 5, Dummerston, VT 05346

  Local history suggests this charming Dummerston bungalow may have begun its life as a one-room schoolhouse. Offering 1,017 square feet of living space, the home features two bedrooms, a full bath, a dedicated dining area, and a separate laundry room. Its warm wood details and practical single-level layout provide an inviting starting point for restoration and personalization.Outside, the

  Linda Benoit Highland Realty

  1892 US Rt 5, Dummerston, VT 05346
• 

  

  /37

  $215,000

  • 2,690 Sq Ft

  56 Atkinson St, Town of Rockingham, VT 05101

  Located in the village of Bellows Falls, this 2-unit multi family is available for an investor OR for an owner-occupied buyer to live on the first floor. The photos include what the lower unit looked like when it was vacant as well as current pictures. The basement was recently insulated/weatherized by SEVCA and the seller has installed a new oil tank and a new furnace. The second bedroom in the

  Heather Gleim CENTURY 21 North East

  56 Atkinson St, Town of Rockingham, VT 05101
• 

  

  /38

  $393,900

  • 2 Beds
  • 2 Baths
  • 1,024 Sq Ft

  8 Deer Creek Unit E, Dover, VT 05356

  Located at the base of Mount Snow, Deer Creek offers a prime setting just an easy walk across Handle Road to the Sundance Base Lodge, home to two new chairlifts—including a high-speed detachable 6-pack. Recently painted, this 2-bedroom plus loft, 2-bath condo features all-new flooring, a convenient ski locker one floor down from the unit, and an in-home washer and dryer. The open-concept living,

  Donna Brown Skihome Realty

  8 Deer Creek Unit E, Dover, VT 05356
• 

  

  /49

  $299,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  21 Lawrence Davis Dr, Wilmington, VT 05363

  NEW 2025 MANUFACTURED HOME ON 1.4 ACRES IN WILMINGTON! Enjoy the perfect blend of privacy, convenience, and value in this immaculate 3-bedroom, 2-bath double-wide manufactured home offering approximately 1,300 square feet of comfortable one-level living. Set on 1.4+/- acres on a quiet dead-end road, this property offers a peaceful setting while remaining just a short drive to downtown Wilmington

  Donald Koelsch Deerfield Valley Real Estate

  21 Lawrence Davis Dr, Wilmington, VT 05363
• 

  

  /59

  $390,000

  • 2 Beds
  • 3 Baths
  • 1,614 Sq Ft

  116 Green Meadow Rd, Brattleboro, VT 05301

  Welcome to 116 Green Meadow Road, where a unique shared-meadow setting offers the feel of country living with the convenience of Brattleboro nearby. Built in 1981 and situated on a manageable .25-acre lot, this home overlooks a beautiful 22-acre meadow. The current owner holds 20 shares in the meadow, providing shared ownership, recreational use and a voice in its stewardship. Purchase of the 20

  Carol Slocum Keller Williams Realty Metro-Keene

  116 Green Meadow Rd, Brattleboro, VT 05301
• 

  

  /9

  $49,000

  • Land
  • 2.01 Acres
  • $24,378 per Acre

  0 Penny Ave Unit 5104876, Stratton, VT 05155

  Discover the perfect setting for your Vermont getaway on this 2.01-acre wooded lot, ideally situated between Stratton Mountain and Mount Snow. A beautiful stream meanders through the property, creating a peaceful natural setting and adding to the character of this special parcel.Surrounded by mature woods, the property offers a wonderful opportunity to create your own Vermont retreat.

  Jamie Wylie Stratton Real Estate

  0 Penny Ave Unit 5104876, Stratton, VT 05155
• 

  

  /58

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,856 Sq Ft

  59 Colonial Ridge Rd, Dover, VT 05356

  Located in the highly desirable Dover Hills, this beautifully maintained, custom-built 4-bedroom, 2-bath chalet offers the perfect combination of Vermont charm, comfort, and convenience. Set on a private 2-acres with easy paved access, the property is just a short drive to Mount Snow, the VAST snowmobile trail system, Harriman Reservoir, shopping, dining, and all the amenities of West Dover.

  Donald Koelsch Deerfield Valley Real Estate

  59 Colonial Ridge Rd, Dover, VT 05356
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  /35

  $725,000

  • 2 Beds
  • 2 Baths
  • 1,071 Sq Ft

  771 Stratton Mountain Access Rd Unit 472, Stratton, VT 05360

  Hang up your keys for the weekend and enjoy one of Stratton’s most convenient locations. Walk to the slopes and Stratton Village for skiing, dining, shopping, and year-round activities. This quiet, top-floor end unit at Long Trail House is filled with natural light and offers wide mountain views, including the front face of Stratton. The desirable two-bedroom, two-bath layout is an ideal choice

  Cheyanne Pugliese

  771 Stratton Mountain Access Rd Unit 472, Stratton, VT 05360
• 

  

  /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
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  /33

  $499,000

  • 2 Beds
  • 2 Baths
  • 3,320 Sq Ft

  5855 Windham Hill Rd, West Townshend, VT 05359

  Bring your vision to life on 33.34 acres in the scenic hills of Windham, Vermont. This partially completed home offers a rare opportunity to finish a thoughtfully designed residence surrounded by open meadows, established trails, and an idyllic rural setting.Designed with a 4 bedroom septic system, the home is ready for the next owner to complete the interior and exterior finishes. The

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  5855 Windham Hill Rd, West Townshend, VT 05359
• 

  

  /50

  $596,000

  • 3 Beds
  • 2.5 Baths
  • 3,325 Sq Ft

  194 Coolidge St, Westminster, VT 05158

  Dramatic two-story foyer flaunting elegance and craftsmanship.The kitchen is designed with custom cabinetry, generous workspace, 5burner DCS range, skylight, and dining area.The living room features a beautiful gas fireplace and a Honduran Mahogany entertainment center. oversized Low-E Andersen windows filled w/light. In the evenings, customized recessed lighting.On the first

  Derek Greene Derek Greene

  194 Coolidge St, Westminster, VT 05158
• 

  

  /47

  $1,995,000

  • 6 Beds
  • 6.5 Baths
  • 5,545 Sq Ft

  420 Ray Hill Rd, Wilmington, VT 05363

  This impressive 6-bedroom, 7-bath farm-style timber frame home, built by Davis Frame and featured on their website as “The Great White Barn,” sits on 3.51 acres just minutes from the Hermitage Club, Mount Snow, downtown Wilmington, lakes, hiking, golf, and VAST trails. Formerly known by its previous owners as “La Maison de Pommes” (House of Apples) for its old apple orchard setting, the home was

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  420 Ray Hill Rd, Wilmington, VT 05363
• 

  

  /26

  $539,000

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft

  67 Heritage Dr, Dover, VT 05356

  Absolutely charming cedar chalet nestled in the Dover Hills just a short drive from the Mount Snow ski resort. This recently renovated home sits on a private wooded corner lot with winter views of the sunsets and ski trails. Conveniently accessible off a paved road and near the snowmobile trail access. Inside you are treated to a charming open concept living area with vaulted ceiling and exposed

  Adam Palmiter Berkley & Veller Greenwood/Dover

  67 Heritage Dr, Dover, VT 05356
• 

  

  /12

  $645,000

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  776 Stratton Mountain Access Rd Unit 1102, Stratton, VT 05155

  Immaculate two bedroom, two bath ski in, ski out condominium steps from the snow front and Stratton Village Square with its shops and restaurants. Mudroom and full laundry facilities, serve through kitchen, two ensuite baths. One of Stratton resort's most sought after properties. Sold furnished, turnkey. Excellent rental potential.

  John Sikes Stratton Real Estate

  776 Stratton Mountain Access Rd Unit 1102, Stratton, VT 05155
• 

  

  /43

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft

  96 Lower Bartonsville Rd, Chester, VT 05143

  This tastefully updated ranch-style home is set on a unique one-acre parcel with a convenient location to the Williams River. Three bedrooms and two baths, thoughtfully updated interior with inviting living spaces and the convenience of one level living. A full basement provides valuable additional space and could be finished to create a family room, home office, recreation area, or even a gym.

  Jessica Citera Cummings & Co

  96 Lower Bartonsville Rd, Chester, VT 05143
• 

  

  /34

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,296 Sq Ft

  170 River Rd, Jamaica, VT 05343

  Charming cape style modular home set on a beautiful, level 3.67 acre parcel. The expansive yard is framed by a stunning mountain backdrop that gives the entire property a peaceful, protected feel. Inside, you’ll find a bright and welcoming three bedroom, one and a half bath layout with plenty of natural light and comfortable living spaces. Mudroom entryway offers nice closet space and washer

  Julie Lowe Lowe's Real Estate, LLC

  170 River Rd, Jamaica, VT 05343
• 

  

  /35

  $245,000

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

  9 Evergreen Ln, Brattleboro, VT 05301

  **Open House Sunday 8/23/26 from 1-3pm** 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 an easy flow into the dining area.

  Ayden Hardy BHG Masiello Keene

  9 Evergreen Ln, Brattleboro, VT 05301
• 

  

  /26

  $519,000

  • 2 Beds
  • 2.5 Baths
  • 1,537 Sq Ft

  4B Newfane Cir, Dover, VT 05356

  Welcome to effortless mountain living in the sought-after Greenspring community of West Dover, where comfort, convenience, and four-season recreation come together just minutes from Mount Snow. This beautifully updated 2-bedroom, 2.5-bath townhome is designed for both relaxing getaways and easy everyday living. Each spacious bedroom features its own private ensuite bath, offering comfort and

  Mike Masters Four Seasons Sotheby's Int'l Realty

  4B Newfane Cir, Dover, VT 05356
• 

  

  /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
• 

  

  /25

  $375,000

  • 4 Beds
  • 2.5 Baths
  • 2,066 Sq Ft

  313 Dover Rd, Newfane, VT 05362

  Step back in time while enjoying the comforts of today in this classic 1800s post-and-beam Cape set on 2 peaceful acres in the Vermont countryside. Rich in character and timeless charm, this 4-bedroom, 3-bath home showcases the warmth and craftsmanship of a bygone era with exposed beams, inviting living spaces, and room for family and guests. Outside, you’ll find established perennial gardens,

  Claire Renaud Berkley & Veller Greenwood Country

  313 Dover Rd, Newfane, VT 05362
• 

  

  /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
• 

  

  /44

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,611 Sq Ft

  279 Westminster Rd, Putney, VT 05346

  Built in 1962, this inviting home perfectly balances peaceful country living with convenient access to local amenities, including excellent public and private schools. Near to an extensive network of hiking, cross country skiing and mountain bike trails offering spectacular views. Whether seeking a peaceful retreat or an outdoorsy lifestyle, this property in a welcoming community has it all. Home

  Jonathan Minerick

  279 Westminster Rd, Putney, VT 05346
• 

  

  /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
• 

  

  /27

  $40,000

  • 2 Beds
  • 3 Baths
  • 1,008 Sq Ft

  358/360 Qtr. 3 89 Grand Summit Way, Dover, VT 05356

  Trailside, best ski in/out mountain location. A really comfortable end unit sleep 8. Unit 360 includes a kitchenette, comfortable living room setting, a sleep sofa, and a bedroom ensuite on the second level with a king size bed. Unit 358 boasts 2 queen size beds, a full bathroom, and a covered deck with views of the main base and mountain trails to enjoy skiers on the slopes, summer and fall

  Sheila Joyce-Albano Skihome Realty

  358/360 Qtr. 3 89 Grand Summit Way, Dover, VT 05356
• 

  

  /27

  $249,900

  • 2 Beds
  • 1.5 Baths
  • 2,184 Sq Ft

  6 Church St, Wilmington, VT 05363

  Located in the heart of Wilmington, this charming two bedroom, one and a half bath home offers an excellent opportunity to create something truly special. Just a short walk to shops, restaurants, and everything downtown has to offer, the location is hard to beat. The home features an attached garage with potential unfinished space above, offering endless possibilities for expansion, a home

  Julie Lowe Lowe's Real Estate, LLC

  6 Church St, Wilmington, VT 05363
• 

  

  /56

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  7 Cross St, Newfane, VT 05345

  This is your chance to be part of the historic and lively community in the center of Newfane.This home underwent a complete overhaul in the early 2000s, including a new slate roof, a relocated fireplace for a more practical layout, a reinforced stone foundation with a poured concrete floor, new windows, boiler, cement clapboard, and new kitchen countertops. The main level features radiant

  Victoria Woods Brattleboro Area Realty

  7 Cross St, Newfane, VT 05345
• 

  

  /51

  $715,000

  • 3 Beds
  • 3.5 Baths
  • 2,895 Sq Ft

  106 Westminster Rd W, Putney, VT 05346

  Set on 25.8± scenic acres, this 3-bedroom, 3½-bath historic barn conversion offers long views across meadows to the surrounding hills within walking distance of Putney Village. It is a rare Putney combination: genuine privacy & room to explore, w/ village shops, food, arts, Putney Central School, and the town pool nearby. This property features approximately 2,300 sq ft of living space, with 595

  A.J. Bellville Bellville Realty

  106 Westminster Rd W, Putney, VT 05346
• 

  

  /52

  $769,900

  • 4 Beds
  • 2.5 Baths
  • 6,232 Sq Ft

  4 Signal Pine Rd, Putney, VT 05346

  Discover one of Putney Village's most distinctive properties. A beautifully converted 1909 brick schoolhouse that was transformed into a remarkable residence. Rich in architectural character, this 4-Bedroom, 2.5-Bath home showcases soaring 12-foot ceilings, oversized historic windows, exposed brick, hardwood floors, and expansive open spaces filled with natural light. The upper two floors offer a

  Cliff Leinonen Four Seasons Sotheby's Int'l Realty

  4 Signal Pine Rd, Putney, VT 05346
• 

  

  /35

  $699,000

  • 7 Beds
  • 5 Baths
  • 3,409 Sq Ft

  633 635 Route 100 Hwy, Dover, VT 05360

  A rare opportunity for a family retreat or investment property! This unique offering includes two beautifully fully furnished and updated homes with direct snowmobile trail access and just minutes from Mount Snow.Both homes were extensively remodeled, including new roofs, windows, doors, kitchen cabinets, and each includes a new private hot tub. With an excellent rental history, this

  Lisa Mirando Deerfield Valley Real Estate

  633 635 Route 100 Hwy, Dover, VT 05360
• 

  

  /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
• 

  

  /13

  $335,000

  • Land
  • 79.3 Acres
  • $4,224 per Acre

  00 Dover, Newfane, VT 05351

  Discover an amazing opportunity to own approximately 79 acres of wooded land in Southern Vermont, offering privacy, natural beauty, and endless possibilities just minutes from a charming Vermont village. Located near Mount Snow and Brattleboro, this expansive parcel is ideal for those seeking a private retreat, recreational property, or the perfect setting to build a Vermont getaway.The

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  00 Dover, Newfane, VT 05351
• 

  

  /24

  $229,000

  • 2 Beds
  • 1 Bath
  • 876 Sq Ft

  8 Novice Village Rd, West Dover, VT 05356

  Offered for the first time in nearly 50 years, this two bedroom chalet with a sleeping loft is perfectly suited as a ski retreat, weekend getaway, or renovation project in the heart of Dover. The main level offers an open concept kitchen, dining, and living area anchored by a cozy wood burning fireplace, ideal for unwinding after a day on the slopes. Two bedrooms and a full bathroom round out

  Megan Quinn Southern Vermont Realty Group

  8 Novice Village Rd, West Dover, VT 05356
• 

  

  /29

  $599,000

  • 5 Beds
  • 2 Baths
  • 2,350 Sq Ft

  9282 Vt Route 100, Whitingham, VT 05361

  This Vermont Country Farmhouse has been recently completed renovated and is ready for turn key enjoyment. The property consists of 41+ acres with tremendous exposure and easy main road access, extensive pasture which could easily be used for farming, a 42x48 post and beam barn, multiple out buildings ideal for workshops and storage, and a location with easy access to Harriman Reservoir and not

  Adam Palmiter Berkley & Veller Greenwood/Dover

  9282 Vt Route 100, Whitingham, VT 05361
• 

  

  /4

  $299,000

  • Land
  • 57.76 Acres
  • $5,177 per Acre

  0 Vt Route 100 S Unit 5103450, Jamaica, VT 05343

  Discover the possibilities with this exceptional 57+ acre parcel in the Town of Jamaica, Vermont, where no local zoning provides incredible flexibility for your vision. Ideally located just minutes from Stratton Mountain, Mount Snow, and within easy reach of Bromley, Magic Mountain, Manchester, and Brattleboro, this property offers the perfect balance of privacy, recreation, and convenience.

  Julie Lowe Lowe's Real Estate, LLC

  0 Vt Route 100 S Unit 5103450, Jamaica, VT 05343
• 

  

  /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

Showing Results 41 - 80, Page 2 of 12