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$599,000
5 Beds 2 Baths 5088556 MLS
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 great light thanks to large windows, a kitchen off one side with live edge breakfast bar and stainless appliances, ample dining space open to the large front deck for outdoor enjoyment or potential future hot tub apres ski, there is a main floor bedroom and full updated bath, a second floor loft bedroom, two guest bunk rooms in the lower level, a second full updated bath with tiled showed, and a large fifth bedroom that doubles as a family room with fireplace. There is also a mudroom addition great for gear storage and getting out of the cold, a large shed for gear, ample parking, and tons of privacy. Less obvious upgrades include a standing seam metal roof, updated windows and doors, updated flooring throughout, and more, for easy turn key enjoyment or incredible rental potential thanks to the style and mountain proximity. There is direct VAST snowmobile trail access from the private level property, so you can ski half day and snowmobile the other half, without ever having to drive far.

48 Upper Highlands, Dover

$425,000
3 Beds 2 Baths 5088540 MLS
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 large windows, natural woodwork throughout, a brand new kitchen with stainless appliances and quartz counters, a spacious dining area open to the living room with gas fireplace and stone hearth, a main floor bedroom and updated full bath, 2 upstairs bedrooms including a spacious primary and a second full bath, and a main floor mudroom and laundry area great for all your seasonal gear. There is also a large owners closet or bonus room off the main bath that could serve as an office with patio door out to the deck. Less obvious upgrades include direct vent heating, all new flooring, and convenient wood shed and bear proof trash bin. This comes with all the great Chimney Hill amenities including road maintenance, community water, clubhouse with indoor and outdoor pools, hot tub, game room, theater, playground, tennis courts, basketball, gym, and more. There are also a la carte services including plowing, sanding, and trash pickup. A truly unique spot that affords Vermont charm and serenity, with easy management.

49 West Rd, Wilmington

$449,000
3 Beds 3 Baths 5088533 MLS
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 shared walls and entries, this townhome has a private entrance from the ample parking area with covered porch. Inside you are treated to a large open concept living space with vaulted ceiling and wood burning fireplace with brick hearth, updated kitchen with granite counters, stainless appliances, and breakfast bar, spacious dining area, large deck with updated composite decking ideal for entertaining, new vinyl plank flooring, a main floor updated half bath, and mudroom entry. Upstairs is a large TV loft which doubles for overflow sleeping, as well as a primary suite with private deck and updated full bath. The walkout lower level has dual large bedrooms perfect for bunks or guests, another updated full bath with laundry, and a large lockable owner closet. Energy saving MYSA thermostats throughout. Both trash and wood are conveniently located right outside. This comes with the trusted Snowtree association, outdoor pool, rec center, indoor hot tub, wood, trash, and management.

15b Snow Tree Ln Unit Clovers B, Dover

$469,000
2 Beds 3 Baths 5088530 MLS
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 stove, spacious dining area, and guest bath. There is large primary bedroom and bath on the main floor with it's own private deck. The lower level is another primary suite with a walkout access, as well as a large finishable rear room that could be ideal for media area, exercise room, or more, easily finishable. The space is a welcome surprise compared to typical ski condos and would be efficient and cost effective for a Hermitage member compared to other on site pricing. At just a 3 mile drive to the Mount Snow ski resort and even nearer the village of Wilmington and Lakes, this is a true four season getaway. Coldbrook water and sewer is $1500/year.

15 Haymaker Ln Unit 6D, Wilmington

$349,000
5 Beds 3 Baths 5088342 MLS
Historic 5 bedroom 3 bath home located in the heart of Saxtons River Village offering generous living space, classic character, and a convenient village setting. With multiple levels of living space and large rooms throughout, this home provides flexibility for a variety of living arrangements including space for guests, home offices, hobbies, or extended living needs. Original details and historic charm can be found throughout the property, giving the home warmth and personality while offering the opportunity to make it your own over time. The property features a newly drilled well, providing an important upgrade. Outside enjoy a nice fenced in yard with room for gardening, entertaining, pets, or simply relaxing outdoors. The yard offers a peaceful setting with privacy while still being conveniently located within the village. A covered porch and spacious outdoor areas add to the home’s appeal and usability throughout the seasons. Located just moments from Vermont Academy, local village amenities, and a short drive to Bellows Falls and I-91. This property offers easy access to shopping, dining, recreation, and year round outdoor activities. Whether you are looking for a full time residence or a home with room to grow, this sizable village property offers space, character, and a desirable location in one of Vermont’s most charming small town communities.

21 Main St, Rockingham

$1,100,000
4 Beds 4 Baths 5088064 MLS
Price Improvement! Escape to this beautifully updated home set on 25.9 idyllic acres of forests, meadows and stone walls, while only minutes from amenities including the local creekside farmers market, treasured food co-op and Brattleboro's vibrant downtown. A gorgeous stone floor and blown glass windows in the entry vestibule set the tone as you are drawn to the stunning great room. The home tastefully captures the historic essence of Vermont with its chestnut beams, wide plank flooring and stylish yet unpretentious design. Interior features offer the perfect balance of grandeur and intimacy with oversized windows that bathe the rooms in natural light, 3 fireplaces and authentic lighting. The kitchen is a culinary haven with state-of-the-art appliances and stunning Brazilian countertops, providing ample workspace and an eat-in area. The first floor also offers a formal dining room, a guest/primary suite with a private entrance and laundry, an office, and it's completed by a sitting room where the current owners gather around the piano. Upstairs you'll find a generous primary suite, two bedrooms, and one with a connecting room, an ideal playroom or office. The walk-out basement is partially finished with a workout room, laundry room and abundant storage. The house includes high-speed fiber internet and a whole-house generator. The attached 2-car garage is heated and a second heated detached 2-car garage with a finished loft above is perfect for playing pool and foosball with family & friends. Relaxation comes easily by the inviting in-ground pool overlooking tranquil woodlands, the stone-terraced landscape and native wildlife. This special property is nestled in a friendly community on a country road, adjacent to 367 acres of protected land with trails perfect for hiking, biking and snowshoeing. Just 2 hrs to Boston, 3.5 hrs to NYC with direct Amtrak to NYC. Easy drive to ski mountains.

390 Pleasant Valley Rd, Brattleboro

$50,000
5087971 MLS
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 getaway. The RV features multiple slide-outs that create a spacious, open feel throughout the living area. Inside, you’ll find a welcoming living room with an electric fireplace, air conditioning for warm summer days, and plenty of room to relax. The kitchen is equipped with both electric and gas refrigerator options, a gas stove, and ample storage. A dining area offers space for everyday meals or entertaining guests. The private bedroom includes a queen-size bed, while the 3/4 bath provides added convenience. An outdoor shower is also included, perfect after a day of hiking, biking, or enjoying the outdoors. The side yard offers a pleasant outdoor sitting area, ideal for morning coffee, evening gatherings, or simply taking in the peaceful surroundings. Whether you are looking for a weekend retreat, seasonal escape, or a property with existing infrastructure ready for your future plans, this unique offering combines comfort, convenience, and potential.

41 Country Club Rd, Wilmington

$550,000
5087936 MLS
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 — with infrastructure in place, income potential, and a ready-to-build house site. The Land: Spanning an elevational range from 600 to 1,200 feet, this property commands spectacular sunset views overlooking Townshend Dam Lake and the West River Valley. The forest is mature and well-stocked — last harvested in 1999 — with a professional Forest Management Plan in place prepared under the Family Forest Carbon Program (FFCP). Five distinct management stands encompass Northern Hardwood and Hemlock-Northern Hardwood Forest types, featuring Sugar Maple, Red Maple, Black Birch, American Beech, and Eastern hemlock throughout. Income-Producing Carbon Program A 5-acre parcel has been withheld from the carbon program specifically to accommodate a residential build. A 5-bedroom wastewater permit is pending. A driveway has been roughed in with culverts, extending approximately half a mile into the property — meaningful infrastructure in a town with no zoning restriction. Property features .. 20 miles to Stratton Mountain Resort (~38 minutes via VT 30/100) 30 miles to Mount Snow Resort (~45 minutes via VT 30/100) Direct VAST trail access for snowmobiling and year-round recreation 20' shipping container on site for tools, equipment, or materials storage Timber value building since 1999 harvest. Townshend's lack of zoning offers maximum flexibility for future use

188 Rattlesnake Mountain Rd, Townshend

$389,000
5087913 MLS
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 while maintaining tenant stability and occupancy. The property has been thoughtfully maintained, making it an attractive option for investors seeking both immediate cash flow and long-term upside potential. Conveniently located with easy access to local amenities, commuter routes, and the charm of Southern Vermont, this is a solid addition to any investment portfolio.

733 Rt 121, Westminster

$498,750
4 Beds 3 Baths 5087887 MLS
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 natural light, and exterior access from three sides of the home. This floor is home to the spacious primary suite including a luxurious ensuite bathroom complete with a soaking tub, dual sinks, a beautiful walk-in shower, separate toilet room, and a large walk-in closet. This level also offers a generous bonus room, laundry room, and utility room. Upstairs, enter through the back deck into a welcoming entryway leading to the expansive modern kitchen, featuring granite countertops, a large center island with pendant lighting, and plenty of space for entertaining. The open-concept kitchen, dining, and living area is centered around a striking staircase that ties the space together beautifully. This level also includes an additional bedroom and a convenient half bath. The upper floor offers two more spacious bedrooms and a full bathroom with dual sinks and a walk-in shower. Outside, relax on the deck overlooking the pool while enjoying the privacy and tranquility of the surrounding rural countryside.

1488 Hartley Hill Rd, Westminster

$799,000
4 Beds 3 Baths 5087730 MLS
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 closets and pool table. A welcoming entry with double closets provides easy access to the attached three-bay garage and wraparound porch. The adjacent mudroom includes tile flooring and practical wooden hooks, perfect for Vermont’s changing seasons. The expansive kitchen is filled with natural light from skylights and features granite countertops, abundant cabinetry, and stainless steel appliances, including a large Viking range. The formal dining room showcases softwood flooring and a sloped ceiling, while the sunken living room with cathedral ceiling centers around a stone fireplace with a propane insert and opens to a large deck and screened porch ideal for indoor-outdoor living. Two generously sized bedrooms and a shared bath complete the main level. Upstairs, the private primary suite offers patio doors to an upper deck overlooking lush gardens and the pond, along with an en suite bath and sauna for a true retreat experience. The lower level expands the home’s versatility with a second kitchen, family room, full bath, and wine room perfect for hosting guests or extended family. Located just minutes from Mount Snow and four-season recreation, this property combines natural beauty, thoughtful design, and exceptional convenience. Being offered furnished with certain exceptions.

25 Yeaw Rd, Dover

$595,000
2 Beds 3 Baths 5087641 MLS
Nestled on Historic Parker Hill, this charming residence sits on a generous 10-acre lot that blends open spaces with woodlands, offering both privacy and natural beauty. The home features classic post and beam construction, highlighted by a cathedral ceiling and hardwood floors that create a warm and welcoming atmosphere. Large windows provide captivating views of the surrounding landscape, making every room feel connected to nature. The spacious layout allows for easy flow between the open concept living and dining areas, complemented by a country kitchen with hardwood floors. A loft, complete with built-in bookcases, offers additional living space and overlooks the main area. The handsome brick chimney with a wood stove not only provides warmth but also adds a touch of rustic ambiance. On the first floor, the luxurious primary bedroom includes an ensuite bathroom and a soaking tub, as well as a bank of large windows that frame the picturesque views. Upstairs, a cozy bedroom is equipped with a half bath and built-in storage, providing comfort and functionality. Additional Spaces and Amenities: An attached 2-car garage offers convenient workshop space, along with a heated 18x13 room on the second floor that is perfect for a home office, or studio. The property also includes an equipment shed and wood storage cribs, catering to practical needs. Ideally located less than ten minutes from I-91 exit 6, the home is within easy driving distance of Okemo (30 minutes away) and the nearby towns of Chester, Springfield, and Bellows Falls. This location combines tranquility with accessibility to regional amenities and attractions.

559 Parker Hill Rd, Rockingham

$65,000
5087532 MLS
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 on the Hill at 2,000' in elevation, with indoor and outdoor heated pools, hot tub, fitness room, arcade room, community room, playroom, après ski lounge, tennis, basketball, seasonal ice skating, pickleball, tennis, fishing pond, extensive trail system on the 1,200-acre campus, with 550-acres owned in common by the members. Enjoy all that the Deerfield Valley and Southern VT offer including world class skiing and shredding, boating, golf, hiking, biking, antiques, flea markets, unique shops, artisans, crafts, music, festivals, breweries, distilleries, wineries, fine dining, and so much more!

123 High Top Rd, Wilmington

$1,800,000
4 Beds 5 Baths 5087347 MLS
One-of-a-Kind Vermont Lifestyle Property Home, 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, and designed for everyday living. Originally an inn and lovingly reimagined by its current owners, the residence offers comfortable living spaces alongside multiple options for creative use, hosting, or generating income. A separate rental ADU, classic Vermont barn, greenhouse, and expansive grounds bordered by historic stone walls create a setting that feels both private and full of possibility. Adding to the property’s versatility is the space currently home to the nationally recognized SoLo Farm & Table—an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a state-of-the-art kitchen, wood-fired masonry grill, sound-insulated dining rooms, and curated wine display, this space is ideal for a turnkey culinary venture—or could be reimagined as a studio, event venue, workshop, or expanded residential use. Outdoor living is equally compelling, featuring a beautifully designed stone patio with a custom-built whole animal cooker, a hard-wired generator, established growing spaces, and room to gather, create, and unwind. Whether you envision continuing a celebrated culinary destination, cultivating a home-based business, or simply enjoying a distinctive Vermont property with room to grow, this offering presents a rare opportunity to live, work, and thrive in one remarkable setting.

95 Middletown Rd, Londonderry

$275,000
1 Beds 1 Baths 5087298 MLS
One of a kind 1 bedroom, 1 bath condo at Snow Mountain Village near the base of the Mount Snow ski resort. This gorgeous remodeled unit has all the style you would expect in a mountain retreat, with none of the headaches. Open concept space with a vaulted living room and kitchen, a wood burning fireplace, updated kitchen with ample storage and breakfast bar, updated furnishings, paint, and flooring, great natural light from the many windows, a well sized main bedroom with full bath, mudroom entry for gear, and private sun deck overlooking the amazing ski trail views and sunsets beyond. The unit has a ski storage locker at the entry, as well as coin laundry. The HOA fee also includes direct shuttle service to and from the base area, an indoor heated pool, two hot tubs, new sauna, two tennis courts, firewood, landscaping, snow removal, building maintenance, and more.

9a Mountain Village Way Unit 141, Dover

$85,000
5087013 MLS
Fantastic double lot on top of the Hill with recent soil tests and septic design suitable for your dream home! As Chimney Hill approaches full build out, the number of remaining lots are limited. This is a brand-new cul-de-sac adjoining the National Forest. Of the 5 lots, only two remain available, including this one. Time to stop imagining and start living the dream of your own vacation home. The lot faces SW towards Bennington and is at about 2,400' in elevation. Enjoy all the amenities Chimney Hill offers and see why it has a multi-generational following and has the distinction of having the most amenities for the least dues of any HOA or COA in the Deerfield Valley. The Resort is situated on 1,200 acres with 550 owned in common by the members and has an extensive multi-purpose trail system throughout the resort campus. The exclusive members only clubhouse is located near the top of the Hill at 2,000' in elevation with fabulous seasonal ridgeline and valley views, outdoor heated pool in summer, with a small playground adjacent, and a grill for members to use. A heated indoor pool for the rest of the year, hot tub, fitness room, arcade room, small child playroom with games, and movies, a reading nook, community room which hosts member events, pickleball, tennis, basketball, snowmobiling is allowed on certain roads, biking, hiking, seasonal ice skating, fishing pond, and so much more. Plus, world class skiing and shredding is only moments away, along with fine dining, music, antiques, flea markets, theater, distilleries, breweries, wineries, local artisans, unique shops, festivals, and so much more!

402 Fox Mt Rd, Wilmington

$325,000
3 Beds 2 Baths 5086998 MLS
This affordable Dummerston home is tucked away on 11 private acres. Built with personal privacy in mind, the primary bedroom is on one end and the other 2 bedrooms and bath are at the other, eliminating hallways and adding to the living area. Warm yourself and save on fuel with the large pellet stove in the living room. Abundant light with the picture window in the front and skylight over the work area in the kitchen. Huge eat in kitchen with tons of cabinets and good baking space. School is right around the corner, minutes to the Coop! Seller must find a place to move and is actively searching. Schedule showing the house is 10 am till 130 pm Monday-Thursday. Saturday morning 9 to 1. No Sundays. 24 hours notice!

12 Autumn Gem Dr, Dummerston

$595,000
3 Beds 3 Baths 5086904 MLS
Immaculate! Lovingly reimagined over two decades, this impeccable residence blends thoughtful design with modern sustainability. The heart of the home is a chef’s kitchen with ample counter space and a spacious pantry with an integrated dining area—perfect for entertaining. Relax in the stunning living room, anchored by a gas insert fireplace crafted by a very talented local mason. Outdoor living is elevated by a light-filled sunroom overlooking a lush backyard complete with raised garden beds and blueberry bushes. Unique features include a former garage transformed into a private guest studio with a Murphy bed, and a new, oversized two-car garage with a clever "drive-through" door for garden access. There is a 40x10' attic space, perfect for tons of storage, or if more living space is needed, it may be finished. Hot water pipes are already located there. Complete with an array of solar panels,{owned}, heat pumps, a whole-house generator, and the potential for single-level living, this Brattleboro gem offers ultimate comfort and self-sufficiency.

171 Green Mdw, Brattleboro

$1,160,000
5 Beds 4 Baths 5086826 MLS
Location , Location , Location! Situated on North Brookwood just below the covered brige you'll enjoy easy access to the Wanderer ski trail as well as the resort shuttle that picks you up at your driveway! This iconic resort property features a great room with custom wood barrel cathedral ceilings, a wall of glass, wood burning fireplace and wrap around deck. Designed for the mountain enthusiast, this propery has the features you look for in a Resort Residence, 5 bedrooms (which includes a spacious and private primary suite wing), 4 updated bathrooms, a spacious media room that opens to a patio with hot tub and fire pit. The galley kitchen opens to a dining room and all with ease to entertaining and apres ski. This location is prime for winter ski and snowboarding as well as an incredible mountain biking trail system during the summer and fall. Hike, bike, golf and enjoy incredible year round activities. Very few homes become available in the North Brookwood neighborhood. Don't miss an opportunity to create your own mountain lifestyle in this great resort location.

82 N Brookwood Rd, Stratton

$135,000
5086621 MLS
2.17 acres with 199' of riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after mountain areas. Next to 16 acre Pingree Park which is minutes right down your private river trail or driveway. This park is most desirable and is at your doorstep with pickleball courts, tennis courts, playground, basketball courts, Little League baseball fields, walking trails, dog park, small pavilion and summer music. Truly an exceptional park. This secluded parcel is minutes to so many amenities, year round events, and attractions. A great, safe location for children, grandchildren and adults with outdoor recreation including the River, Nature trails, Biking, birdwatching and wildlife- plentiful on the property and surrounding areas. A conservation district on the east side of the river ensures privacy. Located only 5 minutes to the Mountain Marketplace, Flood Brook School and the Medical Center. Just 10-30 minutes to 5 major ski resorts- Stratton, Bromley, Magic, Okemo and Mount Snow. As well as cross country skiing, snowmobile trails, ice skating and more. Recreational activities abound including Lowell Lake, Gale Meadows, Hapgood Pond, Lily Pond - offering swimming, boating, tubing, fishing and fun! Quintessential Weston, Chester, Peru, and Stratton Village are just 10-20 minutes away with year-round, events and activities. As is Manchester- renowned for its historic and cultural attractions, fine dining, premier shopping and golf courses. Possible Magic Mountain Views with selective clearing. Boarders vacant property on N/E side providing unique location privacy. This is a perfect location to break ground on your country or year round retreat!

192 Pingree Park Ln, Londonderry

$122,000
5086615 MLS
2.07 acres with 140' riverfront bordering the west bank of pristine Utley Brook with headwaters flowing from the national forest. This waterfront parcel has is fully engineered with a fully permitted septic for a 4 bedroom home. Set at the end of a quiet, dead-end lane, this is a rare gem in Londonderry. Beautiful riverfront, convenient to everything in one of Vermont's most sought-after mountain areas. Next to 16 acre Pingree Park which is minutes right down your private river trail or driveway. This park is most desirable and is at your doorstep with pickleball courts, tennis courts, playground, basketball courts, Little League baseball fields, walking trails, dog park, small pavilion and summer music. Truly an exceptional park. This secluded parcel is minutes to so many amenities, year round events, and attractions. A great, safe location for children, grandchildren and adults with outdoor recreation including the River, Nature trails, Biking, birdwatching and wildlife- plentiful on the property and surrounding areas. A conservation district on the east side of the river ensures privacy. Located only 5 minutes to the Mountain Marketplace, Flood Brook School and the Medical Center. Just 10-30 minutes to 5 major ski resorts- Stratton, Bromley, Magic, Okemo and Mount Snow. As well as cross country skiing, snowmobile trails, ice skating and more. Recreational activities abound including Lowell Lake, Gale Meadows, Hapgood Pond, Lily Pond - offering swimming, boating, tubing, fishing and fun! Quintessential Weston, Chester, Peru, and Stratton Village are just 10-20 minutes away with year-round, events and activities. As is Manchester- renowned for its historic and cultural attractions, fine dining, premier shopping and golf courses. This is a perfect location to break ground on your country or year round retreat!

191 Pingree Park Ln, Londonderry

$799,000
4 Beds 5 Baths 5086432 MLS
Set on 17 private acres off Route 121, this Windham property delivers the space, flexibility, and access buyers are looking for in Southern Vermont. The open-concept main level is anchored by a grand living room with cathedral ceilings, hardwood floors, and a gas fireplace, flowing easily into a generous dining area designed to host large gatherings and a well-equipped kitchen with coffee bar. A dedicated entry drop zone keeps gear organized after long days outdoors. The layout offers strong separation of space across three levels, including an en-suite primary, additional bedrooms, and a top-floor loft ideal for overflow sleeping or a recreation zone. The lower level adds a second living area with a wood-burning stove, plus guest accommodations. Outdoor living is equally dialed in, with an upper deck featuring a brand-new hot tub, a newly built firepit, and a natural landscape that includes meadow, stream, and wooded acreage. A three-car garage adds practical year-round convenience. Located within a 20-minute drive to Stratton, Magic, and Bromley, and directly adjacent to the VAST snowmobile trail system, this property offers immediate access to Vermont’s top winter and summer activities.

1035 Vt Route 121, Windham

$475,000
5086282 MLS
This is a rare opportunity to take over a multi-family project in the heart of Brattleboro. The 0.40-acre site features a vacant three-story building that has already been gutted and fully remediated for lead paint. With town zoning already approved to expand from 8 to 13 units and full architect plans included, the heavy lifting and permitting phase is already behind you. Upon completion, the complex will offer roughly 11,183 square feet of high-demand housing. The financial incentives currently lined up for this project are significant. The sale includes access to VHIP funds : 8 original units $130,000 and the 5 new units $187,500. Additionally, there is a $125,000 Downtown State Tax Credit that can be used directly or sold to a bank at 90% face value, plus an estimated $60,000 in weatherization incentives. A recent appraisal supports a strong finished value, offering a clear path to equity for an investor. Located in a neighborhood with high rental demand and a low vacancy rate, this property is in an ideal location and could also be renovated one stage at a time so that units could go live and start generating cash flow. A lot of leg work has already been done, and the entire community wants to see this building come alive again with residents. This part of Brattleboro is thriving and this is truly the opportunity to take the worst house in the best neighborhood and turn it into affordable housing that generates a positive return. All project documents, including architect plans and both as-is and as-complete appraisals, are available in a shared Drive file. Please note that proof of funds or a commercial pre-approval is required before scheduling a showing or receiving the full data room.

33 Oak St, Brattleboro

$535,000
3 Beds 3 Baths 5086258 MLS
Section B Cul de Sac. Fabulous large house on an oversized lot! First time on the market in 20 years! 3+ bedrooms, 3 bathrooms, gas fireplace, large deck, workshop space, large driveway with plenty of level parking. Mudroom entry, laundry room, open concept living, dining and kitchen. Newer appliances, second fridge, first floor bedroom and bathroom, plus a study and two glass rooms that are connected; one was previously a hot tub room. Second level features a primary bedroom with ensuite bath, walk-in closet, and two additional bedrooms with a shared bath, and one has an oversized closet. Vaulted ceiling, natural woodwork, tons of privacy. This is it! Start living the dream of your resort getaway lifestyle. Chimney Hill is situated on 1,200 acres, with 550 owned in common by the members. Owners enjoy all the recreation amenities CHOA offers, including our exclusive member-only clubhouse located at 2,00' in elevation with an outdoor heated pool, playground, basketball and tennis, indoor heated pool and hot tub, fitness room, toddler playroom, après ski lounge, fully equipped kitchen, reading nook, community room, arcade, extensive trail system, seasonal pickleball and ice skating, and a stocked fishing pond. Plus, enjoy all that the Deerfield Valley and Southern Vermont offer including world class skiing and shredding, snowmobiling, snow shoeing, hiking, biking, boating, theater, music, breweries, distilleries, fine dining, flea markets, antiques, unique shopping, horseback riding, and so much more!

14 High Top Rd Unit B124, Wilmington

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