31 properties for sale in Sherwood Forest, Londonderry town Windham County Vermont

Discover this charming Vermont log cabin, situated on a quiet, secluded lot just 5 minutes from downtown Londonderry, and 15 minutes to downtown Manchester's restaurants and shopping. This home offers the perfect balance of peaceful mountain living and easy access to local amenities. The first level welcomes you into a large, open-concept living room, dining room, and kitchen area, perfect for entertaining. This level also includes two bedrooms, full bathroom, and a dedicated storage room. Upstairs, you will find two additional large bedrooms, a full bathroom, and a spacious open loft area, offering versatile space for family, guests, or home office. Outdoors there's a brand new deck-the perfect place to enjoy a quiet cup of coffee, or glass of wine. Ideally situated for year-round adventure located less than 10 minutes to Magic Mountain, and just15-20 minutes to Stratton, Bromley, Okemo, and Mt. Snow. In the warmer weather enjoy easy access to local hiking, biking, swimming and golf c

Perched on the top floor, this beautifully maintained 3-bedroom, 2-bath ski-on/ski-off Arlington House condo offers exceptional comfort, natural light, and breathtaking views of Stratton Mountain and the surrounding peaks. Cathedral ceilings and a dramatic wall of glass fill the living space with sunshine while framing the stunning mountain vistas. Enjoy cozy winter evenings by the wood-burning fireplace or relax on the spacious deck after a day of hiking and outdoor adventure in the warmer months. Ideally located just steps from the clubhouse, pool, and tennis courts, this residence combines convenience with a true mountain retreat feel. Lovingly owned by the same family since it was built, the property has been impeccably cared for and remains in pristine condition. A rare opportunity to own a light-filled Bromley getaway in an unbeatable slopeside location!

Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratton Mountain, this property is more than just a home-it is a private outdoor sanctuary meticulously designed by The Wadsworth Company for the modern adventurer. The centerpiece of the property is a striking, contemporary dwelling that masterfully blends industrial strength with warm, natural aesthetics. Its bold, dark-bronze standing seam metal exterior provides a sleek, low-maintenance finish that stands out against the lush Vermont landscape. The upper-level living space features a massive wall of glass that opens onto a spacious deck, offering a one-of-a-kind vantage point to enjoy your morning coffee while scouting the ski conditions across the valley. Complementing the living quarters, the ground floor offers high-clearance multi-functional space, perfect for a professional-grade workshop, gear room, or housing a f

Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk to/from Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous 2-story Deck with outdoor shower. This property is the ultimate vacation or year-round residence with no detail overlooked. A Fabulous, grand Main Living area with high ceilings features a wood-burning Fireplace in the Living room which is open to the large Dining room w/ sitting area, wet bar and sliders to the expansive, 2-level Deck with lovely mountain views. The chef's Kitchen has professional appliances (Thermador gas cooktop and dual ovens, Sub-Zero refrigerator, and Bosch dishwasher), custom cabinetry, and gorgeous soapstone counters. The two En-suites are located off the main living area,

Tucked into the Old Farm community in Winhall, this inviting condominium offers classic Vermont character with the ease of association living. The main building has pre-1900 roots, with later additions that help create a warm and practical mountain-town retreat. A hydronic electric baseboard heating system, replaced when the current owners purchased the property, is complemented by a pellet stove for added warmth and comfort. A heat pump water heater, 200 amp electrical service, Xfinity availability, private basement storage, and an exterior NEMA 14-50 plug add everyday convenience. The seller reports that appliances including washer, dryer, dishwasher, refrigerator, electric range, and microwave are included, with all appliances new except the range. Pets are allowed through the association, offering flexibility for owners looking to enjoy Vermont with four-legged companions. Association maintenance includes snow removal, trash pickup, and year-round maintenance through Homestead. Con

Welcome home to this spectacular, multi-level property in Bromley Village, a private slopeside community in Peru. Conveniently located just a short walk tou002Ffrom Bromley Mountain's ski slopes, the Village Clubhouse, and across from the Village pond. A well designed layout which features 5 Bedrooms (including two En-suites), a total of 5 Bathrooms, multiple spacious Living areas, and a fabulous 2-story Deck with outdoor shower. This property is the ultimate vacation or year-round residence with no detail overlooked. A Fabulous, grand Main Living area with high ceilings features a wood-burning Fireplace in the Living room which is open to the large Dining room wu002F sitting area, wet bar and sliders to the expansive, 2-level Deck with lovely mountain views. The chef's Kitchen has professional appliances (Thermador gas cooktop and dual ovens, Sub-Zero refrigerator, and Bosch dishwasher), custom cabinetry, and gorgeous soapstone counters. The two En-suites are located off the main livi

Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and a full basement providing additional storage and utility space. Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational Generac whole-house generator. While some cosmetic updates would enhance the home, it is move-in ready and offers an excellent opportunity to personalize over time. The open, usable lot provides space for outdoor recreation, gardening, or simply enjoying the surrounding natural setting. Bordering more than 100 acres of town-owned, non-developable land, the property enjoys exceptional privacy and direct access to the beauty of Vermont's landscape. Conveniently located near Londonderry's shops and restaurants, with easy access to Stratton, Bromle

Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a bathroom, providing an ideal layout for family or guests. The finished basement offers a family room and bar area, perfect for entertaining, relaxing or additional living space. The main property has an attached two car garage. The property includes a spacious barn with a full 1 bedroom apartment above- perfect for guests, extended family, or rental opportunity. With abundant storage throughout both the home and barn, this property is perfectly suited for those seeking peaceful country living with modern amenities and room to grow

Imagine your own private Vermont resort getaway just a short drive from Bromley Mountain! Nestled on 12 peaceful acres, this property offers the perfect blend of relaxation, recreation, and convenience. Spend summer days swimming or paddling on your private pond, relaxing on the sandy beach, soaking in the hot tub, or unwinding in the sauna after a workout in your home gym. Evenings can be enjoyed fireside under the stars. The main residence boasts a flowing floor plan designed for entertaining, with large windows filling the home with natural light and framing water views from nearly every room. A brand-new septic system, built for seven bedrooms, ensures comfort and space for all. The oversized two-car garage provides ample storage for all your outdoor gear. Set apart among the trees, the guest cottage offers its own sense of retreat with vaulted ceilings, an open living space, two en-suite bedrooms, and an additional two-car garage. A short walking path leads directly to the water's

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi

Perfectly positioned in the heart of Vermont's sought-after Golden Triangle, this charming two-bedroom plus loft home offers the ideal balance of year-round recreation and cozy mountain living. Just minutes from Magic Mountain, Bromley Mountain, and Stratton Mountain, you'll enjoy easy access to skiing, hiking, golf, shopping, dining, and all the outdoor adventures Southern Vermont has to offer. Lovingly cared for, the home has been thoughtfully enhanced with tasteful touches that add warmth and character while preserving its inviting charm. Recent improvements include a new roof and new oil tank, providing added peace of mind for the next owner. The versatile floor plan features two comfortable bedrooms plus a loft. Whether you're looking for a full-time residence or a weekend escape, this home offers the flexibility to fit your lifestyle. Enjoy relaxing after a day on the slopes or simply unwinding in the peaceful surroundings that make this area so special. With its unbeatable locat

Perfectly positioned in the heart of Vermont's sought-after Golden Triangle, this charming two-bedroom plus loft home offers the ideal balance of year-round recreation and cozy mountain living. Just minutes from Magic Mountain, Bromley Mountain, and Stratton Mountain, you'll enjoy easy access to skiing, hiking, golf, shopping, dining, and all the outdoor adventures Southern Vermont has to offer. Lovingly cared for, the home has been thoughtfully enhanced with tasteful touches that add warmth and character while preserving its inviting charm. Recent improvements include a new roof and new oil tank, providing added peace of mind for the next owner. The versatile floor plan features two comfortable bedrooms plus a loft. Whether you're looking for a full-time residence or a weekend escape, this home offers the flexibility to fit your lifestyle. Enjoy relaxing after a day on the slopes or simply unwinding in the peaceful surroundings that make this area so special. With its unbeatable locat

Set on 3.9 level acres in a quiet neighborhood just minutes from the village of Londonderry, this four-bedroom, two-bath chalet offers comfortable year-round living or an ideal Vermont getaway. The home features a functional floor plan with four bedrooms, generous living space, and a full basement providing additional storage and utility space. Recent improvements include a brand-new roof (2026) and the added peace of mind of a fully operational Generac whole-house generator. While some cosmetic updates would enhance the home, it is move-in ready and offers an excellent opportunity to personalize over time. The open, usable lot provides space for outdoor recreation, gardening, or simply enjoying the surrounding natural setting. Bordering more than 100 acres of town-owned, non-developable land, the property enjoys exceptional privacy and direct access to the beauty of Vermont's landscape. Conveniently located near Londonderry's shops and restaurants, with easy access to Stratton, Bromle

One-of-a-Kind Vermont Lifestyle Property Home, Income and 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 and Table-an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a

One-of-a-Kind Vermont Lifestyle Property Home, Income and 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 and Table-an award-winning farm-to-table restaurant with a loyal following. Fully equipped with a

Set on nine acres, this inviting three bedroom brick home offers a rare blend of comfort, space, and rural charm. The main level features a large primary bedroom, with a beautiful full bathroom and walk in closet. Each room on the main level you'll find bright and comfortable living spaces and a beautiful sunroom that overlooks the surrounding fields. Upstairs, two spacious bedrooms share a bathroom, providing an ideal layout for family or guests. The finished basement offers a family room and bar area, perfect for entertaining, relaxing or additional living space. The main property has an attached two car garage. The property includes a spacious barn with a full 1 bedroom apartment above- perfect for guests, extended family, or rental opportunity. With abundant storage throughout both the home and barn, this property is perfectly suited for those seeking peaceful country living with modern amenities and room to grow

Encompassing over 200 acres of pasture and forest, Timberland Farm is anchored by an early 1800s farmhouse that feels at once timeless and lived-in, a place shaped by centuries of stories, music, and shared meals. The living spaces feel both intimate and generous, framed by hand-hewn beams and original wide pine floors. From the dining room to the music room, wood-burning fireplaces crowned with antique mantels add warmth and character, while the expansive kitchen hearth draws one in for easy conversation and board games. Built-in bookcases, plaster walls, wood paneling, and windows overlooking the land lend the house a quiet, grounded grace. The farmhouse also includes a lower-level guest apartment with a private entrance. Nearby, a charming guest cabin, once the town's blacksmith shop, provides a private haven for visitors. The barn has been thoughtfully reimagined and now houses a commercial kitchen, gym, and offices, offering flexibility for creative enterprise and agricultural ven

Set on seven private fenced acres with stone walls and dual gated entrances, this custom Vermont property offers privacy, flexibility, and year-round access to Southern Vermont's premier recreational destinations. Perched on scenic Cobble Ridge in Londonderry, the property enjoys southwest exposure and seasonal Green Mountain views. Natural light fills the great room, where a brick fireplace anchors the living space. The kitchen with premium appliances flows into the dining and living areas, creating an inviting setting for entertaining and everyday living. The main residence features three ensuite bedrooms, including a lower-level suite and an upper-level suite that could each serve as a primary bedroom, depending on how the home is used. Additional living spaces provide flexibility for guests, recreation, remote work, or additional sleeping accommodations. A separate one-bedroom guest cottage offers added privacy and versatility. Designed for both gathering and retreat, the property

Motivated sellers! Charming Property with Endless Possibilities in Southern Vermont Nestled on 5 acres in the heart of Southern Vermont, this unique property offers the perfect blend of history, versatility, and potential. Currently operating as a successful business with fabrics, sewing machines, notions and more. This property presents an exceptional opportunity for a variety of uses -whether you're looking to return it to a spacious home with 4-bedrooms, or start your own thriving business venture. The building's furnace keeps the winters warm and the summers with central air conditioning ensure year-round comfort. This property features plenty of parking, making it ideal for commercial use or family gatherings. A true highlight is the large, historic waterwheel barn, providing a space with endless potential for creative projects or storage. If you're a handy person, the barn is a perfect opportunity for a workshop. Whether you're looking to settle into a quiet country home or embar

Escape to the heart of Southern Vermont in this recently renovated chalet-style mountain home, where timeless charm meets four-season recreation. Being sold fully furnished. Ideally located under 25 minutes from four premier ski resorts - Bromley, Stratton, Magic, and Okemo - this inviting retreat offers the perfect balance of adventure and relaxation. Set against a backdrop of breathtaking mountain views and abutting protected lands, the home offers a peaceful setting that invites you to slow down and enjoy the beauty of every season. The one-car garage offers plenty of storage. Whether you're sipping your morning coffee on the deck as the sun rises over the mountains or gathering with friends after a day on the slopes, this fully furnished property embodies the classic Vermont lifestyle. Inside, the home features three comfortable bedrooms - each with its own well-appointed ensuite bath with radiant flooring heat - and a spacious family room designed for entertaining, game nights, an

Beautifully renovated 4-bedroom home with a stylish 2-bedroom accessory dwelling, offering the perfect blend of modern comfort, flexibility, and Vermont charm. Whether you're looking for space for extended family, guests, or the potential for rental income, this thoughtfully designed property offers endless possibilities. Step inside to discover contemporary upgrades throughout, where every detail has been carefully considered. Filled with natural light, the home's inviting floor plan creates a bright and airy feel from room to room. The beautifully updated kitchen, refreshed finishes, and modern touches make this home truly move-in ready while maintaining its warm and welcoming character. The dining room is highlighted by a beautiful propane fireplace, creating the perfect ambiance for dinners, holiday gatherings, and entertaining friends year-round. Outside, you'll find a peaceful yard designed for relaxing and enjoying Vermont's natural beauty. Two spacious decks provide plenty of r

This is the ultimate modern Alpine chalet, fully renovated yet boasting the classic flat-sawn balusters characteristic of mountain homes in the Alps. Three expansive floors offer sunny, well-appointed space, beginning with a roomy mudroom, three bedrooms and two bathrooms (one en-suite). Head upstairs to join your friends and family in the open-concept European kitchen/living/dining room with expanded island optimal for entertaining - grill and wraparound deck just outside the kitchen. The fourth bedroom - a primary suite with en-suite bathroom - is on this level. On the walk-out lower level, a game room with pool table and a separate TV room with gas stove offer a getaway before soaking in the hot tub, within earshot of the babbling brook down the hill. Nestled in the coveted community of Strattonwald, this 4-bedroom home offers Stratton shuttle access right from the driveway. Strattonwald's rare swimming pond, sandy beach, tennis/pickleball courts, picnic area, and space to fish and

Nestled in the heart of Vermont's scenic countryside, this beautifully maintained log cabin offers the perfect blend of rustic charm and cozy comfort. Surrounded by nature and timeless New England beauty, the home welcomes you with warm wood interiors, exposed beams, and an inviting atmosphere ideal for year-round living or a peaceful getaway. Thoughtfully cared for and full of character, the cabin features comfortable living spaces, a charming country feel, and the tranquility only Vermont can offer. Whether relaxing by the fire, enjoying crisp mountain air from the porch, or taking in the picturesque surroundings, this enchanting retreat captures the essence of cozy Vermont living. Powder Mill is a unique community designed for the outdoor enthusiast.Offering direct access to trails, snowmobile routes, scenic ponds, and a welcoming neighborhood feel. Outdoor recreation can be enjoyed year-round. In the winter, residents and visitors are just a short drive from the renowned ski slopes

Historic Jack's Hill House, masterfully designed by Vermont Vernacular Designs. Nestled on approximately 21 private acres along a winding country road and bordered by National Forest, Still Meadows Farm offers a rare blend of timeless New England character, modern comfort, and unparalleled access to Vermont's outdoor lifestyle. Outdoor enthusiasts will appreciate the property's proximity to the Catamount Trail and endless opportunities for hiking, skiing, snowshoeing, mountain biking, and exploring the surrounding forests. Gardeners will fall in love with the established perennial gardens, peaceful woodland paths, and open meadows that create a true Vermont sanctuary. Spectacular mountain views stretch across the landscape, including captivating vistas toward Stratton Mountain and seasonal views of Bromley Mountain. Whether enjoying a quiet morning coffee overlooking the mountains or relaxing beside one of three Rumford fireplaces, you'll experience a sense of stepping back in time whi