Windham County VT Homes for Sale

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  /59

  $675,000

  $25K PRICE DROP

  • 6,144 Sq Ft

  2170 N Main St, Londonderry, VT 05148

  For more than 20 years, this mixed-use property has been consistently operated and maintained by the same owner—an indicator of stability, reliability, and proven performance. The building features three distinct income channels: a fully equipped small-town diner with loyal local traffic, a well-established general market serving the community’s daily needs, and two rental apartments above that

  Jessica Ackley

  2170 N Main St, Londonderry, VT 05148
• 

  

  

  /45

  $1,475,000

  • 7 Beds
  • 6 Baths
  • 6,292 Sq Ft

  53 Hickory Ridge Rd, Putney, VT 05346

  Hickory Ridge House is a Federal masterpiece: a definitive piece of Vermont history. Elegant and expansive, the home’s soul is rooted in the 19th century, while its heart beats with 21st-century innovation. The interiors are a masterclass in "refined rustic" design, with original features such as antique wood floors, 12-over-12 windows, crown moldings, and wood-burning fireplaces throughout the

  Thomas Dahlin Berkley & Veller Greenwood Country

  53 Hickory Ridge Rd, Putney, VT 05346
• 

  

  

  /7

  $279,000

  • Land
  • 45 Acres
  • $6,200 per Acre

  Lot 0 Saddada Rd, Whitingham, VT 05361

  Lovely pastoral parcel of land in Whitingham Vermont with mountain views. This parcel sits conveniently on the MA border for easy access into the Deerfield Valley or Heath area. The 45 acre parcel is about half pasture and half mature woodlands, with easy access of the quiet country road, old stone walls, views of the mountains to the west, and a serene setting.

  Michael Purcell Berkley & Veller Greenwood/Dover

  Lot 0 Saddada Rd, Whitingham, VT 05361
• 

  

  

  /8

  $95,000

  $25K PRICE DROP

  • Land
  • 15 Acres
  • $6,333 per Acre

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301

  Hillside building lot deeded for one beautiful home, with a straight-ahead view of inspiring mountains and valleys to the south. The property is moderately sloped near the road but more flat at the highest elevation, with benches of level ground at intervals up and down the land. A network of hiking trails is blazed across the property, but the easiest way to view the high ground is what remains

  David White OwnerEntry.com

  0 Carpenter Hill Rd Unit 5090787, Guilford, VT 05301
• 

  

  

  /36

  $1,295,000

  $20K PRICE INCREASE

  • 5 Beds
  • 3.5 Baths
  • 3,040 Sq Ft

  4427 W Hill Rd S, Jamaica, VT 05343

  One-of-a-kind luxury lodge offering the comfort and amenities of a five-star retreat with the warmth and charm of a Vermont mountain home. The house provides all the space your friends and family could want—an expansive open layout perfect for gatherings, along with plenty of cozy, private spots for quiet moments. Enjoy movie nights in the 11-foot home theater, or relax in front of one of two

  Carrie Mathews Winhall Real Estate

  4427 W Hill Rd S, Jamaica, VT 05343
• 

  

  /11

  $174,000

  • Land
  • 15 Acres
  • $11,600 per Acre

  491 Whitneyville Rd, Halifax, VT 05358

  Tucked away along a quiet, town-maintained deadend road, this private 15-acre parcel offers a rare combination of seclusion, character, and natural beauty. Set high on a peaceful knoll, the property features an old homesite's stone foundation, open meadow areas, and several mature apple trees that hint at the land’s past, also a drilled well.A gentle babbling brook traces one boundary, adding

  Leslie Fraser Four Seasons Sotheby's Int'l Realty

  491 Whitneyville Rd, Halifax, VT 05358
• 

  

  /42

  $1,150,000

  • 4 Beds
  • 1 Bath
  • 1,972 Sq Ft

  2245 Burrington Hill Rd, Whitingham, VT 05361

  Lovely 1800s vintage dairy farm on 100+ acres in the heart of Whitingham Vermont, just a short driving to nearby country villages, lakes, skiing, and more. Conveniently just over the MA border sits this amazing property which has been in the same family for 2 generations. Nestled on the crest of rolling pasture, you are treated to long range three state mountain views including Mount Monadnock to

  Michael Purcell Berkley & Veller Greenwood/Dover

  2245 Burrington Hill Rd, Whitingham, VT 05361
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  /42

  $675,000

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  54 Main St, Grafton, VT 05146

  This home IS quintessential Grafton Vermont! Built c. 1850 this stately 4 over 4 colonial served as the Parsonage for the Grafton Church as it is still referred to this day. Privately owned for nearly 30 years this handsome home is ready for new stewardship. Spacious and sturdy, this vintage gem offers plenty of space and has been updated for today’s lifestyle. The first floor offers open concept

  Jessica Landers Barrett and Valley Associates Inc.

  54 Main St, Grafton, VT 05146
• 

  

  /22

  $399,000

  • 9 Beds
  • 4 Baths
  • 3,286 Sq Ft

  19 Canal St, Brattleboro, VT 05301

  Located in the heart of Brattleboro, this fully occupied and consistently high-performing investment property offers an outstanding opportunity for investors seeking strong cash flow and steady rental demand. Currently configured with 9 individual rentable rooms, the property has been successfully exclusively rented to The New England Center for Circus Arts students for years and maintains an

  Karen Hoppe Berkley & Veller Greenwood Country

  19 Canal St, Brattleboro, VT 05301
• 

  

  /59

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,345 Sq Ft

  52 Ruth Way, Wilmington, VT 05363

  Welcome to this inviting 4-bedroom, 3-bathroom home nestled on a tranquil street, cherished by one family for nearly two decades. This residence exudes warmth and comfort, offering the perfect blend of functionality and charm. As you step through the covered front door, a cozy mudroom/entry area sets the tone for the welcoming atmosphere throughout the home. The spacious living room is ideal for

  Donna Brown Skihome Realty

  52 Ruth Way, Wilmington, VT 05363
• 

  

  /27

  $69,000

  $6K PRICE DROP

  • Land
  • 1 Acre
  • $69,000 per Acre

  170 Maple Dr, Wardsboro, VT 05355

  This one-acre parcel at 170 Maple Drive in the Snow Mountain Farms community offers the perfect opportunity to start your Vermont dream home. The property already has a state-issued 4-bedroom wastewater permit in place, making it ready for your 2026 build. Located on a town-maintained road with a quiet cul-de-sac setting, this lot provides both easy access and privacy. Driveway is in, lot is

  Chris Lowe Lowe's Real Estate, LLC

  170 Maple Dr, Wardsboro, VT 05355
• 

  

  /9

  $165,000

  • Land
  • 1.9 Acres
  • $86,842 per Acre

  Lot A Sweet Pond Rd, Guilford, VT 05301

  Beautiful open 1.9-acre parcel on scenic Sweet Pond Road in Guilford, VT. Featuring open pastureland, generally level terrain, and excellent southern exposure, this property offers a wonderful opportunity for a primary residence, homestead, recreation property, or investment. A classic stone wall borders the western edge, adding timeless Vermont character. Buyers to verify utility availability

  Erica Reynolds Southern Vermont Realty Group

  Lot A Sweet Pond Rd, Guilford, VT 05301
• 

  

  /43

  $679,000

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  148 Townshend Rd, Grafton, VT 05146

  This circa 1860 Greek Revival home is one of Grafton Village’s gems, blending historic character with recent, thoughtful renovations. A sweeping backyard framed by rugged stone walls adds to the property’s appeal, while established perennials and a welcoming side porch create an inviting entrance. The delightful country kitchen flows into the formal dining room and living room, where a propane

  Heidi Bernier Berkley & Veller Greenwood Country

  148 Townshend Rd, Grafton, VT 05146
• 

  

  /39

  $2,195,000

  • 4 Beds
  • 4 Baths
  • 3,524 Sq Ft

  392 Lake Raponda Rd, Wilmington, VT 05363

  A rare opportunity for true year-round enjoyment. This is a remarkable chance to own a home on a motorboat lake - with a private dock - just minutes from both the Mount Snow and Hermitage Club ski resorts, hiking, biking, and snowmobile trails, and the charming village of Wilmington, Vermont. Lake Raponda stands apart from the other lakes in the area in one important way: because larger boats

  Adam Palmiter Berkley & Veller Greenwood/Dover

  392 Lake Raponda Rd, Wilmington, VT 05363
• 

  

  /22

  $595,000

  • 4 Beds
  • 2 Baths
  • 1,430 Sq Ft

  9 Mountain Acres Rd, Jamaica, VT 05343

  Completely renovated and move-in ready, this stunning mountain home offers the perfect blend of comfort and convenience. The full interior renovation includes a brand-new kitchen and bathroom (as well as an updated second bath) , updated bedrooms, new doors, fresh paint, and beautiful new flooring throughout. A propane fireplace adds warmth and charm, while a newly installed mini-split system

  Carrie Mathews Winhall Real Estate

  9 Mountain Acres Rd, Jamaica, VT 05343
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  /42

  $499,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  147 Gilbert Rd, Guilford, VT 05301

  This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting

  Monica Sumner BHG Masiello Brattleboro

  147 Gilbert Rd, Guilford, VT 05301
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  /60

  $1,165,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,632 Sq Ft

  350 Sunset Lake Rd, Newfane, VT 05301

  Experience the timeless charm of Vermont living at this beautifully renovated farmhouse estate sitting on 92 acres in Newfane Vermont. Originally restored and thoughtfully updated, this exceptional antique farmhouse seamlessly blends historic character with modern comfort and convenience. Unlike many older homes, this property features expansive rooms, high ceilings, wood floors, abundant natural

  Keith Nowak Four Seasons Sotheby's Int'l Realty

  350 Sunset Lake Rd, Newfane, VT 05301
• 

  

  /19

  $135,000

  $50K PRICE DROP

  • Land
  • 16.05 Acres
  • $8,411 per Acre

  00 E Hill Rd, Wardsboro, VT 05355

  Discover your private Vermont sanctuary on this heavily wooded 16.05-acre parcel on East Hill Road in Wardsboro. This pristine property is bordered by the year-round Wardsboro Brook, which serves as a scenic natural boundary and offers an extensive fly fishing area, while the diverse forest canopy provides an unlimited, sustainable source of firewood. The heavy lifting is already done with a

  Steve Lawrence KW Vermont-Stowe

  00 E Hill Rd, Wardsboro, VT 05355
• 

  

  /24

  $350,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,830 Sq Ft

  4850 Vermont Route 100, Wardsboro, VT 05355

  Dual charming updated cottages located conveniently between Mount Snow and Stratton with easy access off a paved public road for peace of mind and tremendous rentability. The current owners have lovingly updated these 2 cape style homes. One partially burned down and has been completely rebuilt and just completed. That larger home features an open concept kitchen and dining area, large great room

  Adam Palmiter Berkley & Veller Greenwood/Dover

  4850 Vermont Route 100, Wardsboro, VT 05355
• 

  /2

  $149,000

  • Land
  • 16.74 Acres
  • $8,901 per Acre

  9 Brown Rd, Wilmington, VT 05363

  Nice private almost 17 acre site with driveway, dug well, dug pond, sitework and ski area and Mountain views. Log cabin or post and beam home is a great fit. VAST snowmobile trail runs through the property. Beautiful bright and sunny exposure.

  Mark Yule BHG Masiello Brattleboro

  9 Brown Rd, Wilmington, VT 05363
• 

  

  /34

  $695,000

  $170K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 2,481 Sq Ft

  1871 W Hill Rd, Townshend, VT 05353

  Welcome to your fully furnished chalet-style escape in Townshend, Vermont. Tucked away at the end of a private drive on 10 partially cleared, usable acres, this 2-bedroom, 2-bathroom home offers the perfect blend of comfort and Vermont charm. With four separate sleeping areas, there's plenty of space. The first-floor primary suite provides a private retreat with its own ensuite bathroom. Above, a

  Kim Meeker Southern Vermont Realty Group

  1871 W Hill Rd, Townshend, VT 05353
• 

  

  /43

  $549,900

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  1 Bucket Ln, Dover, VT 05356

  NEW PRICE! Exceptional Value in Vermont’s Ski Country! This beautifully renovated classic chalet just became an even better opportunity! Offering the perfect blend of rustic Vermont charm and modern updates, this home features vaulted ceilings, exposed beams, a dramatic floor-to-ceiling brick fireplace, gorgeous remodeled kitchen with quartz countertops, and an expansive deck ideal for

  Linda Benoit Highland Realty

  1 Bucket Ln, Dover, VT 05356
• 

  

  /7

  $399,000

  • Land
  • 30 Acres
  • $13,300 per Acre

  Lot X Tyanoga Rd, Whitingham, VT 05361

  Spectacular opportunity to own a rare waterfront building lot on Lake Sadawga in Southern Vermont. This lot sits on a private dead end corner with southern exposure, private lake frontage including an earthen dam, and easy access along this pristine, natural lake. There is additional frontage along Stimpson Hill Road. The lake offers tremendous fishing, kayaking, canoeing, water sports, and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  Lot X Tyanoga Rd, Whitingham, VT 05361
• 

  

  /38

  $1,850,000

  • 6 Beds
  • 6 Baths
  • 4,154 Sq Ft

  3 Slopeside Rd, West Dover, VT 05356

  Trailside luxury in a class of its own. This stunning home was taken down to the frame and should be considered new construction — positioned immediately trailside at Mount Snow with a private ski trail connecting directly to the magic carpet at Carinthia for full-season ski access. Ski to and from your mudroom door and never worry about shuttles or parking again.Professionally designed and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  3 Slopeside Rd, West Dover, VT 05356
• 

  

  /57

  $850,000

  • 5 Beds
  • 4 Baths
  • 3,218 Sq Ft

  4880 Pikes Falls Rd, Jamaica, VT 05343

  Welcome to your perfect four-season retreat nestled just minutes from Stratton Mountain Ski Resort. This authentic 5-bedroom, 4-bathroom log cabin plenty of space throughout, with ample natural light and that signature Vermont charm and cozy ambiance. A large kitchen, combined with an open dining area and expansive wrap around deck, offer a multitude of opportunities for seasonal gatherings no

  Mike England Michael England Real Estate

  4880 Pikes Falls Rd, Jamaica, VT 05343
• 

  

  /40

  $825,000

  • 5 Beds
  • 1 Bath
  • 1,224 Sq Ft

  6036 Jacksonville Stage Rd, Guilford, VT 05301

  Imagine 216 acres of rolling fields, serene woodlands, and a glowing sugarbush tucked along a quiet country dirt road near the Massachusetts border in Halifax, just a short drive to Brattleboro and Wilmington. Held by the same family for generations, this timeless Southern Vermont property includes a farmhouse, barns, and several outbuildings ,many ready for restoration, reimagining, or

  Melissa Nebelski Real Broker LLC

  6036 Jacksonville Stage Rd, Guilford, VT 05301
• 

  

  /11

  $139,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 128 Sq Ft

  1 N Ridge Rd, Town of Rockingham, VT 05101

  Tiny home living in a big way! Enjoy the conveniences of public sewer and water on a quiet plot of land close to I-91 and five minutes to the Amtrack station. This property is well cared for and maintained. All you need to do is either move in or start renting it out for extra income. This adorable home generates over $20,000 per year as an Airbnb, or you can get up to $1500/mo in long term

  Amanda Cota The Thomas Group of Northern New England, LLC

  1 N Ridge Rd, Town of Rockingham, VT 05101
• 

  

  /30

  $599,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  48 Upper Highlands, Dover, VT 05356

  Unique opportunity to own an updated and woodsy chalet just up from the slopes of Mt Snow, yet also with direct snowmobile trail access. This 5 bedroom, 2 bath home has been tastefully renovated while maintaining the charm and character befitting a Vermont retreat ski home. The interior features an open concept living space with vaulted great room, wood burning fireplace, natural woodwork and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  48 Upper Highlands, Dover, VT 05356
• 

  

  /28

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,510 Sq Ft

  49 West Rd, Wilmington, VT 05363

  Lovely renovated chalet at the bottom of the Chimney Hill community with easy access to trails, hiking, lakes, and nearby Mount Snow. This lovely private parcel sits in the easily accessible lower section with nice seclusion and views out the rear, affording nice privacy yet with all the conveniences of community living. The interior boasts an open concept living space with natural light and

  Adam Palmiter Berkley & Veller Greenwood/Dover

  49 West Rd, Wilmington, VT 05363
• 

  

  /29

  $449,000

  • 3 Beds
  • 2.5 Baths
  • 1,842 Sq Ft

  15B Snow Tree Ln Unit Clovers B, Dover, VT 05356

  Lovely updated townhome in the Snowtree development adjacent to the base area at Mount Snow. Take the Snowtree shuttle to the mountain or access via the walking bridge to the magic carpet at the tubing hill. If you don't ski you can still easily access the mountain without worrying about parking. Ideal for the ski season, but also summer festivals, hiking, biking, and more. Unlike the condos with

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15B Snow Tree Ln Unit Clovers B, Dover, VT 05356
• 

  

  /19

  $469,000

  • 2 Beds
  • 2.5 Baths
  • 1,912 Sq Ft

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363

  Beautiful condo on the side of Haystack mountain at the beautiful exclusive Hermitage Club Ski Resort. Enjoy sunrise views out your living room windows in this immaculate 2 bedroom, 2.5 bath unit. Walk in from the spacious mudroom entry to a living area with wood burning fireplace, deck overlooking the view, tremendous light and views, kitchen with breakfast bar, updated appliances, and gas

  Adam Palmiter Berkley & Veller Greenwood/Dover

  15 Haymaker Ln Unit 6D, Wilmington, VT 05363
• 

  

  /24

  $299,900

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,192 Sq Ft

  1329 Newfane Rd, Wardsboro, VT 05355

  Nature lovers rejoice! Escape to the charm of rural Vermont with this rustic cottage retreat, privately set on a secluded 1-acre lot surrounded by woods and nature. Tucked away in a peaceful setting, this inviting home offers warmth, character, and the simple beauty of country living. The first floor features an open floor plan with hardwood floors and natural woodwork throughout, a cozy

  Matt Waddington Hoffman Real Estate

  1329 Newfane Rd, Wardsboro, VT 05355
• 

  

  /14

  $50,000

  • Land
  • 12,632 Sq Ft
  • $172,414 per Acre

  41 Country Club Rd, Wilmington, VT 05363

  Set on 0.29 acres along a quiet dead-end, town-maintained paved road, this property offers a convenient and peaceful setting. The driveway is already in place, electric underground service is on site, and a natural spring is located on the property. Nearby access to the VAST Trails. Included in the sale is a 2015 Jayco Eagle Premier RV, providing comfortable seasonal living or a ready-made

  Jennifer Hovey-Densmore Deerfield Valley Real Estate

  41 Country Club Rd, Wilmington, VT 05363
• 

  

  /16

  $260,000

  • 1 Bed
  • 1 Bath
  • 512 Sq Ft

  319 River Rd S, Putney, VT 05346

  Looking for the simple life in tiny home living, or maybe just a good basecamp to explore the outdoors? Look no further! This unique property is conveniently located just a couple miles outside the bucolic village of Putney off a main road, with easy access to I-91. With 33 acres of rolling woods and local valley views there's plenty of land to explore and play with, while the cozy little home

  Courtney Doubleday EXP Realty

  319 River Rd S, Putney, VT 05346
• 

  

  /39

  $550,000

  • Land
  • 99.4 Acres
  • $5,533 per Acre

  188 Rattlesnake Mountain Rd, Townshend, VT 05353

  Townshend, Vermont sits in the heart of the West River Valley, minutes from Grafton, Londonderry, and Brattleboro. The property borders Vermont Route 30 and offers easy access to two of southern Vermont's premier ski resorts and the broader four-season recreational economy. A rare opportunity to own nearly 100 acres of productive Vermont forestland in one of Windham County's most scenic corridors

  Mike England Michael England Real Estate

  188 Rattlesnake Mountain Rd, Townshend, VT 05353
• 

  

  /36

  $389,000

  • 7 Beds
  • 5 Baths
  • 3,460 Sq Ft

  733 Vermont 121, Westminster, VT 05101

  This 5-unit multi-family property presents a strong investment opportunity with steady, long-term tenants and consistent on-time rental history. Meticulously cared for over the years, the property features updated systems, public water, a double lot, and ample parking for tenants and guests alike. Current rents are below today’s market rates, offering clear opportunity for future income growth

  Morriah Adams BHG Masiello Brattleboro

  733 Vermont 121, Westminster, VT 05101
• 

  

  /54

  $498,750

  $46K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  1488 Hartley Hill Rd, Putney, VT 05346

  Welcome to this spacious contemporary home located on the desirable Hartley Hill Road, conveniently situated near Saxtons River, Bellows Falls, Putney, and I-91. Built in 2008, this well-maintained home offers quality craftsmanship including a brand new roof installed April 2026, high-end utilities, and modern comforts throughout. The finished, walk-out lower level features radiant heat, abundant

  Chelsea Richardson Barrett and Valley Associates Inc.

  1488 Hartley Hill Rd, Putney, VT 05346
• 

  

  /34

  $799,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,550 Sq Ft

  25 Yeaw Rd, Dover, VT 05341

  Enjoy year-round living in this handsome contemporary home set on over 12 acres of picturesque land, featuring open meadows, a gentle stream, a large pond, mixed woodland, and beautifully maintained gardens. Bright and inviting, the home offers a spacious layout designed for both comfort and entertaining. There is an attached 3 bay garage above which is a huge heated bonus room with storage

  Robert Doyle Berkley & Veller Greenwood Country

  25 Yeaw Rd, Dover, VT 05341
• 

  

  /44

  $65,000

  • Land
  • 36,154 Sq Ft
  • $78,313 per Acre

  123 High Top Rd, Wilmington, VT 05363

  Section B - new to market! Oversized building lot with new perc tests show it is suitable for a 3-bedroom single family home. Lot may support a larger home; buyer would have to pursue this option at their own cost. As an owner of an undeveloped lot in CHOA, you are entitled to all the recreation amenities in the Resort, including year-round swimming at the exclusive member-only clubhouse, located

  Sigrid Pickering Chimney Hill Realty

  123 High Top Rd, Wilmington, VT 05363
• 

  

  /50

  $1,800,000

  • 4 Beds
  • 5 Baths
  • 4,853 Sq Ft

  95 Middletown Rd, South Londonderry, VT 05155

  One-of-a-Kind Vermont Lifestyle PropertyHome, Income & Creative Opportunity Welcome to an exceptional Southern Vermont offering that blends refined country living with rare income and lifestyle flexibility. Set on 2.4 picturesque acres in South Londonderry, this beautifully restored 1865 property is first and foremost a warm and inviting 4-bedroom home—rich in character, thoughtfully updated,

  Eric Nathan Nathan Auction & Real Estate Inc.

  95 Middletown Rd, South Londonderry, VT 05155

Showing Results 241 - 280, Page 7 of 12