5-Bedroom Homes for Sale in Windham County VT

/56
$350,000
- 6 Beds
- 4.5 Baths
- 3,042 Sq Ft
2072 N Main St, Londonderry, VT 05148

Rare Mixed-Use Opportunity in Downtown Londonderry, VT – Live, Work, or Invest! Unlock the full potential of this versatile and beautifully situated property in the heart of Londonderry’s vibrant downtown district. With major West River frontage, expansive lawn space, and prime visibility on North Main Street, this unique listing offers endless possibilities — perfect for residential, commercial,

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6058

2072 N Main St, Londonderry, VT 05148
/41
$8,950,000
- 6 Beds
- 10 Baths
- 13,393 Sq Ft
370 Fischer Ln, Jamaica, VT 05343

Accessible, but miles from the everyday. Camp Endo’s mountain kingdom is minutes from Stratton Mtn. with a 21st century take on a mountain timberframe home, and 417+/- acres threaded with trails and ridgelines. Ski your own glades and rip the eight miles of custom-designed mountain biking terrain, or just pause to enjoy the vast views. The house reimagines a rustic lodge with classic wood, bark

Dia Jenks LandVest, Inc/Woodstock

370 Fischer Ln, Jamaica, VT 05343
/44
$829,000
- 5 Beds
- 2.5 Baths
- 3,102 Sq Ft
1410 Haven Hill Rd, South Londonderry, VT 05155

This beautiful Timber frame home on an 8.1 acre lot is located a few miles from the base of Stratton, Bromley, and Magic Mountain making it a versatile investment. Whether a seasonal prospect or primary home, being next door to Gale Meadow Pond provides a wonderful destination to walk, hike, fish, or just paddle. This home has a private, beautiful yard with its own pond, stream, and firepit just

Amy Carson Lowe's Real Estate, LLC

1410 Haven Hill Rd, South Londonderry, VT 05155
/37
$730,000
- 5 Beds
- 3 Baths
- 2,275 Sq Ft
341 Under the Mountain Rd, Londonderry, VT 05148

Escape to this idyllic 1800s cape-style farmhouse nestled on a quiet dirt road in a peaceful country setting, just minutes from three popular ski areas. Set on 44 private acres with a scenic pond, this unique property offers the perfect blend of historic character and modern comfort, making it ideal for a family getaway, vacation rental, or year-round home. Inside, you'll find surprisingly

Andy Reed Four Seasons Sotheby's Int'l Realty

341 Under the Mountain Rd, Londonderry, VT 05148
/55
$789,000
- 5 Beds
- 3.5 Baths
- 2,848 Sq Ft
516 Rockingham Hill Rd, Bellows Falls, VT 05101

This charming vintage cape set on 6.6 acres is the perfect blend of classic character and modern updates. The home offers 5 bedrooms, 4 baths and spacious common rooms including a lovely three season room just perfect for morning coffee or unwinding at the end of the day. There is a separate entrance in the garage leading to the second floor which offers an opportunity for a private space for

Wilma Skovinski Berkley & Veller Greenwood Country

516 Rockingham Hill Rd, Bellows Falls, VT 05101
/47
$985,000
- 6 Beds
- 4.5 Baths
- 3,500 Sq Ft
5825 Vermont 30, Townshend, VT 05353

Equine Estate with 21 acres. 6+ Beds, 5 Baths! Unique and versatile property has been operated as a 501(c)(3) equine rescue facility since 2005. 3-bedroom MAIN HOUSE with attached 1-bedroom accessory unit, ideal for guests, staff, income. MAIN BARN w/8 box stalls and wash stall. Hay elevator, automatic water, heated tack rooms, office with a deck overlooking the public forest. The “CARRIAGE

Jacki Murano Southern Vermont Realty Group

5825 Vermont 30, Townshend, VT 05353
/33
$799,000
- 5 Beds
- 2.5 Baths
- 3,064 Sq Ft
32 Old Town Rd, Dover, VT 05356

Tucked away on a country road in Dover, Vermont, this inviting five bedroom, three bathroom home offers the perfect blend of comfort, functionality, and outdoor enjoyment. Set on a scenic open lot with a tranquil pond and open views, the property includes a spacious inlaw apartment on the walkout lower level ideal for guests, extended family, or potential rental income.The main home features

Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

32 Old Town Rd, Dover, VT 05356
/40
$1,695,000
- 7 Beds
- 7.5 Baths
- 8,364 Sq Ft
251 Pratt Bridge Rd, Jamaica, VT 05343

Cold Moon Farm: Where Dreams Take Root! Ever imagine waking up to mountain vistas & the gentle sound of contented goats? This legendary Vermont property, makes that dream a reality. This once-in-a-lifetime offering is brimming with possibilities, whether you crave a sprawling family haven, a luxurious personal retreat, or a chance to revive the farm's celebrated B&B. Prepare to be Enchanted! An

TG Glazer Winhall Real Estate

251 Pratt Bridge Rd, Jamaica, VT 05343
/47
$995,000
- 5 Beds
- 1 Bath
- 1,224 Sq Ft
6036 Jacksonville Stage Rd, Guilford, VT 05301

Welcome to a rare and breathtaking slice of Vermont. This expansive 216-acre farm offers a beautiful mix of open pastures, mature woodlands, fruit trees, berry bushes, and a small section of scenic wetlands – a true haven for nature lovers and outdoor enthusiasts seeking peace and space in every direction. Set along a quiet dirt road near the Massachusetts border, with the added convenience of

Melissa Nebelski Skihome Realty

6036 Jacksonville Stage Rd, Guilford, VT 05301
/31
$947,000
- 5 Beds
- 3 Baths
- 3,015 Sq Ft
100 Mowing Way, Wilmington, VT 05363

Impeccably maintained golf course home nestled in the Vermont mountains just 5 miles from lakes, ski resorts, and scenic trails. Perfect for entertaining or quiet enjoyment, this elegant property combines luxury and comfort in a stunning natural setting. The soaring great room features beamed ceilings, radiant heated hickory floors, and a gas fireplace flanked by built ins. A chefs dream kitchen

Leslie Fraser Four Seasons Sotheby's Int'l Realty

100 Mowing Way, Wilmington, VT 05363
/60
$899,000
- 5 Beds
- 4.5 Baths
- 5,000 Sq Ft
42 Blackberry Ln, Jamaica, VT 05343

Idyllic, Picturesque, Expansive, Vast Family Farm with outbuildings and Large Farmhouse! Known to some as Sweet Berry Farm the blueberries and blackberries are plentiful along with many other productive fruits trees, a grove of 20 mature apple trees with many over 30 years old, , flowers and veggies in the gardens. This location just off of Route 30 is perfect for ALL of your Vermont dreams and

Steve Goldfarb Deerfield Valley Real Estate

42 Blackberry Ln, Jamaica, VT 05343
/51
$949,000
- 5 Beds
- 8 Baths
- 7,430 Sq Ft
925 Hinesburg Rd, Brattleboro, VT 05301

Hidden away, this secluded 18 acre rolling landscape of quiet meadow and woodland is minutes to town, easy access to I-91. Skiing, lakes, river/water fun, hiking/biking Or, stay at home in south facing sanctuary designed for easeful living and enjoy the shimmering pool, huge gourmet kitchen with Viking range and 2 walk-in pantries, creating wonderful memories for friends and family. Plenty of

Christine Lewis Brattleboro Area Realty

925 Hinesburg Rd, Brattleboro, VT 05301
/49
$1,350,000
- 5 Beds
- 3.5 Baths
- 3,516 Sq Ft
732 Under the Mountain Rd, South Londonderry, VT 05155

Londonderry’s Under the Mountain Road is one of the area’s most beautiful roads, meandering along the edge of Glebe Mountain (home to Magic Mtn) and thousands of acres of conserved land. Here you’ll find “Fairmount”, featuring one of the best panoramic views in southern Vermont overlooking the West River Valley and majestic Green Mountains between Stratton and Bromley. The 1810 farmhouse was

Claudia Harris Mary Mitchell Miller Real Estate

732 Under the Mountain Rd, South Londonderry, VT 05155
/53
$989,000
- 5 Beds
- 6 Baths
- 4,900 Sq Ft
10 14 Wiswall Hill Rd, Newfane, VT 05345

Welcome to 2 exceptional homes set on 8 acres of meadows w/ stone walls, woodland, and frontage on the Smith Brook. The contemporary barn conversion was architect designed & boasts an impressive Great Room with soaring ceilings, exposed post & beams, and gas fireplace. Patio doors open onto a huge deck, offering views of the in-ground pool and serene surroundings. The dining room, crafted from

Robert Doyle Berkley & Veller Greenwood Country

10 14 Wiswall Hill Rd, Newfane, VT 05345
/40
$849,000
- 5 Beds
- 3.5 Baths
- 3,436 Sq Ft
67 Castle Hill Rd, Wilmington, VT 05363

Rare opportunity to own a meticulous 1830s vintage farmhouse, completely turn-key with extensive updates, renovations, and modern amenities. Conveniently located just outside the country village of Wilmington for shopping and great dining options, a short drive to the Mount Snow ski resort, and just up the street from the Lake Whitingham boat launch and beach areas, for true four season

Adam Palmiter Berkley & Veller Greenwood/Dover

67 Castle Hill Rd, Wilmington, VT 05363
/53
$449,000
- 6 Beds
- 3 Baths
- 2,500 Sq Ft
29 Mountainview Loop, Dover, VT 05356

Spacious Multi-Unit Home Less Than a Mile from Mount Snow!Located just minutes from one of Vermont’s most popular ski destinations, this versatile property offers two separate living units and plenty of room for guests, rental income, or multi-generational living.The first-floor unit features a spacious great room layout with a full kitchen, dining area, and cozy living room complete with

Richard Caplan Deerfield Valley Real Estate

29 Mountainview Loop, Dover, VT 05356
/51
$389,000
- 6 Beds
- 2 Baths
- 2,787 Sq Ft
225 Church Ave, Bellows Falls, VT 05101

Welcome to Your Dream of a Fully Renovated Victorian Treasure! This stunning Victorian, built in 1903, has been lovingly renovated by its current owner, preserving the original charm while blending modern amenities. Every surface has been meticulously restored, combining classic elegance with today’s comforts. Sitting on the largest lot in the neighborhood, this home overlooks the Saxtons River,

Daire Gibney Barrett and Valley Associates Inc.

225 Church Ave, Bellows Falls, VT 05101
/40
$489,000
- 5 Beds
- 3 Baths
- 2,917 Sq Ft
3550 Coolidge Hwy, Guilford, VT 05301

This lovely property has classic character and charm with modern updates and upgrades making this a truly comfortable place to call home! There's the main house with attached garage as well as the accessory in-law suite/apartment/accessory living space for longer term guests to stay that provides privacy from your main home. There's the nicely sized barn for parking, animals or storage which

A.J. Bellville Bellville Realty

3550 Coolidge Hwy, Guilford, VT 05301
/46
$2,250,000
- 6 Beds
- 5.5 Baths
- 4,588 Sq Ft
71 Overlook Dr, Dover, VT 05356

Enjoy stunning views, privacy, and access, from a rare offering of a home at the Peaks at Mt Snow. This luxury community sits above the Greenspring development, directly across from the ski slopes at Mount Snow, with access to all the great amenities including club house, gym, indoor pool and hot tub, pickleball courts, game room, on site management company, and direct shuttle service from your

Adam Palmiter Berkley & Veller Greenwood/Dover

71 Overlook Dr, Dover, VT 05356
/24
$499,000
- 7 Beds
- 2 Baths
- 1,124 Sq Ft
45 Blue Brook Rd, Dover, VT 05356

A truly unique and eclectic ski chalet. The current owner has tastefully updated this home in order to foster a tremendous rental investment, but it could also work great for anyone looking for a spacious ski home with great access off a paved town road and tremendous mountain proximity. Easily accessible off a paved road, not far from shuttle service, and only a couple miles to the Mount Snow

Adam Palmiter Berkley & Veller Greenwood/Dover

45 Blue Brook Rd, Dover, VT 05356
/10
$1,738,000
- 5 Beds
- 4.5 Baths
- 2,450 Sq Ft
34 A or B Boulder Ridge Dr, Dover, VT 05356

NEW CONSTRUCTION!! The new ownership/development team at Boulder Ridge is pleased to announce the commencement of the next phase of construction at this unique location. Just two minutes to the base of Mount Snow, awe-inspiring year-round views of the slopes of Mount Snow as well as the vast Deerfield Valley, combined with the distinct trails of the Hermitage Club in the distance (a 7 minute

John Redd Skihome Realty

34 A or B Boulder Ridge Dr, Dover, VT 05356
/35
$389,900
- 5 Beds
- 3 Baths
- 3,364 Sq Ft
21 Main St, Saxtons River, VT 05154

Welcome to history, this 1830's colonial home has so much charm and character to offer! This home is situated in the quaint village of Saxtons River just feet from the Local market store as well as the admired and prestigious Vermont Academy School. With plenty of space to host whether it be in the large grand feeling living room with the original woodwork and fireplaces or the spacious back yard

Thaddeus Abare Barrett and Valley Associates Inc.

21 Main St, Saxtons River, VT 05154
/43
$398,000
- 6 Beds
- 2 Baths
- 960 Sq Ft
247 Vt Route 100 N, Wilmington, VT 05363

Conveniently located on Route 100 between Wilmington Village and Mount Snow. Two separate 3 bedroom, totally renovated, units. This would be a wonderful multi-generational home, two family purchase, use one unit - rent one unit. Wheeler Farm view of pasture and mountain ranges. Exterior garden shed. Plenty of parking, an amazing view and waiting for you!

Janet Boyd Boyd Real Estate

247 Vt Route 100 N, Wilmington, VT 05363
/43
$1,738,000
- 5 Beds
- 4.5 Baths
- 4,100 Sq Ft
36 A or B Boulder Ridge Dr, Dover, VT 05356

Brand new luxury townhome with breathtaking Mount Snow & Hermitage Club views. Introducing a newly built, well thought out townhome spanning over 4,000 square feet, perfectly positioned just minutes from Mount Snow and The Hermitage Club. This exquisite residence combines modern mountain living with upscale comfort, offering five spacious bedrooms and five beautifully appointed bathrooms. Step

John Redd Skihome Realty

36 A or B Boulder Ridge Dr, Dover, VT 05356
/50
$339,000
- 7 Beds
- 4 Baths
- 3,000 Sq Ft
89 Gates Pond Rd, Whitingham, VT 05342

This rare multi-family home presents a unique investment opportunity, featuring four well-designed units. Nestled in the charming town of Jacksonville you're just 23 minutes from the exhilarating slopes of Mount Snow ski resort. The property offers two one-bedroom units on the first floor, alongside a spacious two-bedroom unit and a generous three-bedroom unit on the second floor. Enjoy the large

Monique White Deerfield Valley Real Estate

89 Gates Pond Rd, Whitingham, VT 05342
/51
$315,000
- 6 Beds
- 3 Baths
- 3,468 Sq Ft
31 School St, Bellows Falls, VT 05101

Attractive and well maintained 3 unit Multi-family with great in-town location. Many original features remain including wood floors, 2 marble mantles, moldings, curved walls, beautiful arches and built-ins. Unit 1 on the first floor features living room open via graceful arches to dining room, large eat-in kitchen, 2 large bedrooms,, hardwood floors, marble fireplaces. Unit 2 is on the 2nd floor

Steve Schoppmeyer BHG Masiello Brattleboro

31 School St, Bellows Falls, VT 05101
/34
$1,350,000
- 5 Beds
- 4.5 Baths
- 5,153 Sq Ft
15 Springhill Rd, Dover, VT 05356

Enjoy perfect Vermont styling in this spacious and functional home just a short drive to the Mount Snow ski resort, nearby lakes, and villages. This private location is nestled just off the Mount Snow golf course in the Deerfield Valley, and easily accessible from a paved road. The home has been fully renovated with no expense spared. Features include an open concept floor plan with expansive

Adam Palmiter Berkley & Veller Greenwood/Dover

15 Springhill Rd, Dover, VT 05356
/32
$598,000
- 5 Beds
- 2 Baths
- 2,892 Sq Ft
238 Hemlock Hill Rd, Wardsboro, VT 05355

This spacious 5 bedroom home is located on a private lot in the popular Snow Mountain Farms community. The three levels offer privacy and quiet with an outdoor fire pit, garden shed, and access to the VAST snowmobile trails. Its open floor plan with vaulted ceilings and stone hearth gas fireplace is perfect for apres ski gatherings, and the large open kitchen is ready to accommodate cooking for a

Jeffrey Sheehan Cummings & Co

238 Hemlock Hill Rd, Wardsboro, VT 05355
/9
$430,000
- 7 Beds
- 4 Baths
- 3,551 Sq Ft
1950 N Main St, Londonderry, VT 05148

PRICE REDUCTION! IT IS possible to Live rent or mortgage free!!! And HERE it is.This is a 3 unit multi-family, fully rented/money making property now..Live in one and let the other two pay your bills.. Or, use your imagination, create your vision of what this premier location could be. Zoned BOTH commercial AND residential.. this property could be a fabulous restaurant with rivers edge al fresco

Wilkie Bushby TPW Real Estate

1950 N Main St, Londonderry, VT 05148
/16
$488,875
- 5 Beds
- 4 Baths
- 3,064 Sq Ft
176 High St, Brattleboro, VT 05301

Unique opportunity to live very comfortably in the more than 1400 sq ft 1st floor apartment with private laundry, private covered porch and your own deck. The apartment has 2 plus bedrooms and 2 full bathrooms, eat in kitchen, dining room and living room. invest in your own home and have revenue from 2 apartments to help with costs. Apartment #2, on the 2nd floor, is a 1-2 bedroom unit which has

Susan Bellville Bellville Realty

176 High St, Brattleboro, VT 05301
/60
$639,000
- 5 Beds
- 2.5 Baths
- 3,000 Sq Ft
673 Route 121 E, Grafton, VT 05146

Step into a classic Vermont farmhouse from the 1830s, built by a successful mill owner and loved by its current stewards for over fifty years. Minutes from the center of charming Grafton and only thirty minutes from Okemo, this beautiful property offers wide, level lawns and sits on 45 acres of untouched woodland in the hills behind—never logged and fully unencumbered. Inside, the original

Keri Cole Williamson Group Sothebys Intl. Realty

673 Route 121 E, Grafton, VT 05146
/26
$725,000
- 18 Beds
- 8 Baths
- 4,932 Sq Ft
29 Canal St, Brattleboro, VT 05301

High cash flow 100% occupied 8 unit located in downtown Brattleboro. This property was recently renovated and is being listed at a 11% cap and an annual Net Operating Income estimated at north of ~$80K (12% cap without management fees). The property features an attractive mix of unit types and sizes including 4x rarely available oversized 3br, 2x2br and 2x1brA new owner can step into to

Michael Gilman 3GEN Real Estate Inc

29 Canal St, Brattleboro, VT 05301
/36
$499,000
- 7 Beds
- 6 Baths
- 2,178 Sq Ft
343 Haystack Rd, Wilmington, VT 05363

This spacious home is located near outdoor recreation spots like Mount Snow and Haystack Country Club. Tucked back on 3 acres with wooded surroundings offering privacy amongst the trees. The main house offers four bedrooms, four baths; including a large primary suite. The spacious basement has a kitchen, bath and living space with walkout access to the backyard. The three-car garage with a

Jessica Citera Cummings & Co

343 Haystack Rd, Wilmington, VT 05363
/41
$589,000
- 5 Beds
- 4 Baths
- 2,686 Sq Ft
23 Summit Meadows Cir, Dover, VT 05356

Spacious 5-bedroom, 4-bath home with additional designated office space, den and 2 car garage on 1.17 acres! Thoughtful floor plan includes a first-floor primary suite with wood-burning fireplace, a guest bedroom and full bath, a private office with its own full bath, and a large mudroom with laundry and storage. The open living room with vaulted ceilings, wood-burning fireplace, and abundant

Jacki Murano Southern Vermont Realty Group

23 Summit Meadows Cir, Dover, VT 05356
/28
$625,000
- 5 Beds
- 3.5 Baths
- 2,240 Sq Ft
47 Ives Rd, Wilmington, VT 05363

Unique spacious log home near the Hermitage Ski Club with easy access to the resort, direct snowmobile trail access, and tremendous privacy. Also just down the access road from the Mount Snow ski resort, nearby country village of Wilmington for shopping and dining, and gorgeous area lakes. This updated rustic retreat sits on a level lot with ample parking, winter exposure to the east, and a gear

Adam Palmiter Berkley & Veller Greenwood/Dover

47 Ives Rd, Wilmington, VT 05363
/39
$4,300,000
- 6 Beds
- 5 Baths
- 4,715 Sq Ft
141 W Ridge Rd, Stratton, VT 05360

Experience the charm of this renovated, ski-in/ski-out 6-bedroom, 5-bathroom retreat, perched as the second-highest home on Stratton’s iconic Lower Wanderer Ski Trail. Immerse yourself in the rustic elegance of this space, where expansive windows invite breathtaking outdoor views inside. This mountain sanctuary seamlessly combines modern comfort, solar technology, and nature’s serene beauty,

Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

141 W Ridge Rd, Stratton, VT 05360
/34
$374,000
- 5 Beds
- 2 Baths
- 2,736 Sq Ft
5100 Vermont Route 100, Wardsboro, VT 05355

Nestled between the renowned Mount Snow and Stratton Mountain, this completely remodeled late 19th-century Colonial offers the perfect blend of historic charm and modern comfort. Meticulously renovated, the home has been torn down to the studs and reimagined with no detail overlooked. With all new windows, insulation, electrical, and plumbing, every inch of this home has been looked after with

Mike Masters Four Seasons Sotheby's Int'l Realty

5100 Vermont Route 100, Wardsboro, VT 05355
/59
$399,000
- 5 Beds
- 3.5 Baths
- 2,800 Sq Ft
45 Dorr Fitch Rd, West Dover, VT 05356

Discover your Vermont mountain escape just 5 minutes from Mount Snow, where charm meets convenience and rental potential. This expanded chalet offers seasonal rental income, making it a smart investment for those looking to maximize returns. Step inside to find a cozy mudroom with natural stone walls, perfect for storing ski gear. The main level features an open floor plan with exposed beams, a

Richard Caplan Deerfield Valley Real Estate

45 Dorr Fitch Rd, West Dover, VT 05356
/26
$650,000
- 5 Beds
- 2 Baths
- 1,530 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
/37
$1,499,000
- 5 Beds
- 4.5 Baths
- 3,429 Sq Ft
26 Springhill Rd, Dover, VT 05301

This spectacular Post & Beam home is located just off the 13th hole of the Mount Snow Golf Course just minutes from the Mount Snow ski area. Nestled in a quiet community, with tremendous curb appeal, enjoy year round enjoyment thanks to the adjacent course, for obvious summer fun, but also snowshoeing and hiking in the winter. The interior of the home is about as good as it gets when looking for

Adam Palmiter Berkley & Veller Greenwood/Dover

26 Springhill Rd, Dover, VT 05301

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.