Londonderry, VT | 135 Overlook Drive

Quintessential 1880s Vermont farmhouse in bucolic Weston. Nestled on 7 private acres, this 4 bedroom, 3 bath retreat offers authentic pine floors, historical charm throughout with a tranquil pond greeting you upon arrival. It is the perfect blend or timeless character and rural serenity. BRAND NEW DRILLED WELL & MOUND SEPTIC SYSTEM just installed in August 2026. Updated electric makes this house ready for the next steward. The kitchen is authentic and you may choose to update. Situated in the picturesque town of Weston, one of Southern Vermont's most coveted historic villages. The village is home to the iconic Vermont Country Store and the renowned Weston Theater Company. The large swimming pond is spring fed from the babbling brook that boarders the back of the property. A quick drive away find skiing at Okemo Mountain Resort, Bromley, Magic and Stratton, while Summer days can be spent swimming at Hapgood Pond or exploring the West River. Grades 9-12 Have School Choice including Burr and Burton Acadamy. Your piece of Vermont history starts here. Come see this charming Vermont home being sold furnished. Call today!

Tucked into the peaceful woods of Windham, Vermont, this cherished Timber Ridge residence offers a rare opportunity to own a piece of true Vermont legacy. Custom built and lovingly held by the same family across three generations, this home is filled with decades of storied memories, seasonal celebrations, and effortless mountain living. Set on a picturesque one acre wooded parcel, the home’s expansive wrapping decks elevate you straight into the canopy, creating an immersive, treehouse like atmosphere. Whether you are sipping morning coffee surrounded by autumn foliage or relaxing after a day on the slopes, the setting offers complete tranquility and privacy. Inside, the layout balances comfort, versatility, and classic rustic charm. Enjoy seamless single level living with a spacious primary suite located right on the main floor. The home features three dedicated bedrooms (currently designated as four on the town lister card), offering ample space for a crowd. A finished bonus room, previously used as a home office , adapts easily to a bunk room, play area, or secondary media lounge. The pellet stove keeps it warm and the separate entrance allows for privacy. A dedicated workshop provides the ideal footprint for tuning skis, maintaining gear, or tackling creative hands on projects. Located in the heart of the Green Mountains, Timber Ridge serves as an exceptional four season basecamp. Winter enthusiasts will appreciate having five major ski areas within a 30-minute drive, while summer brings endless outdoor recreation, from nearby lakes, ponds, and hidden waterfalls to vibrant local farmers markets, hiking trails, and artisanal shops. This special home stands ready to welcome its next chapter and a new generation of mountain memories.

Discover this charming Vermont log cabin, built by Richard Ragone, one of the pre-eminent log home builders in the northeast. 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 just 15-20 minutes to Stratton, Bromley, Okemo, and Mt. Snow. In the warmer weather enjoy easy access to local hiking, biking, swimming and golf courses.

Imagine turning off the main road as the canopy thickens, the drone of highway traffic fading into the quiet rustle of wind through northern hardwoods. Up on a gentle knoll surrounded by over two wooded acres, 292 Forest Mountain Road feels less like a house and more like a breath of fresh air. Morning here starts slowly. Coffee brews while sunlight filters through the trees, casting soft shadows across comfortable living spaces designed for easy, unpretentious living. Spring and summer bring lush green privacy, with plenty of room on the knoll to tuck in a vegetable garden, sip evening drinks outdoors, or simply listen to the forest. Autumn transforms the acreage into a front-row seat for southern Vermont's foliage, while winter brings that distinct, quiet magic, unloading ski gear after a day on the slopes at nearby Bromley or Stratton, stepping inside, and letting the day’s chill melt away. It’s the kind of retreat where Fridays mean shedding city schedules, picking up morning pastries at the local general store down the road, and letting days stretch out naturally. Whether you’re tinkering with projects in the detached garage with workshop, hosting friends for a long weekend, or spending a quiet afternoon with a good book, the home offers a warm, low maintenance haven that lets you focus on being here, not maintaining it. Property Details Setting: 2.25 private, wooded acres situated on a peaceful knoll Interior: 2,000 sq. ft. contemporary layout featuring 3 bedrooms and 2 baths Outbuildings: Detached workshop/garage with room for standard vehicles, hobby space, and mountain gear storage Location: Peru, VT, minutes to Bromley Mountain, Stratton Resort, Magic Mountain, and the shops and dining of Manchester

What do you get when two pioneers buy a beautiful colonial farmstead with the intention of sticking around quite a while, rehabilitate it for their long-term use, and then find out work will require them to relocate?  You get this gorgeously renovated 4-bath-4-bed 1890 construction on over 2.5 lovely acres back on the market!  Sellers are motivated due to having already relocated for work!  Historical authenticity has not been sacrificed in their successful pursuit of modern comfort:  the tasteful remodeling of the kitchen, bathrooms, floors, ceilings, and more won't distract from your delight in the rustic touches left intact or even improved upon.  Luxuriate in central AC, a true Vermont rarity, when you come in from your work in the expansive 2-floor garage/barn, chicken coop, or on the grounds graced by a lovingly cared for orchard beside a scenic private pond.  Did we mention the orchard?  Apples, peaches, pears and cherries dot the landscape, an arborist's dream, with gorgeous mountain views in the distance!  Nestled in the desirable town of Londonderry, you have access to year-round amenities at a level not found in every ski town: it's home to Magic Mountain, and a short drive away from Bromley, Stratton, and Okemo.  In the warmer months, enjoy gorgeous 102-acre Lowell Lake, its state park and its islands just minutes away!  While newly-planted arbor vitae promise to shoot up quickly and reduce the highway noise, the house sits comfortably above Vermont Route 11, a road offering pleasant drives between ski towns.  Once you're inside or in your backyard, you may be surprised how quickly you forget about the world going by and remember to be glad you bought this diamond-out-of-the-rough.  Sold largely furnished!  Inquire today while it's still available!

This spacious Londonderry contemporary house sits on a sunny, level one-acre lot and is conveniently located at the base of Glebe Mountain and mere minutes from Magic Mountain for snow sports and Lowell Lake for summer hikes, kayaking and keeping an eye on the native loons that nest there. The layout offers three levels of bright and roomy living spaces with a comfortable floorplan and lots of room for gathering or finding private quiet time. The main level features a large kitchen and dining area, living room with fireplace and vaulted ceilings, and two bedrooms including an expansive primary suite with a fireplace, walk-in closet and private bathroom. Above is large loft, partially open to the area below and suitable for almost any use (home office, library, play space) with lots of attic space for storage. A partially finished lower level (above grade at the rear of the house with full walk-out and regular windows) has a large rec room with woodstove and hearth, two additional bedrooms, laundry, full bathroom, bonus room, and a large workshop in the mechanical and utility area. The two-car garage with workshop and upper level, and a garden shed complete the offering. Renovations were in progress but incomplete, and the house needs work (mostly cosmetic) and updating, and it is priced to reflect that need. Londonderry is a dynamic community with a good mix of primary and vacation homes with access to great schools, shopping and dining, four-season recreation in any direction, arts and music through the year, and a fantastic farmers market in the summer and fall. The location and community will support your investment, so come take a look!

Lucky for the next Buyer that this home is back on market because last buyer could not secure financing! This comfortable home is situated in a peaceful and open sunny meadow surrounded by mature trees and 10 acres of Vermont woods offering total privacy. A view of Magic Mountain is a bonus as is the close proximity to shopping and dining. An important feature of the home is the newly added Lochinvar high efficiency propane boiler with on demand hot water installed in November of 2025. The 4 bedroom, 2 bath home has been lovingly cared for by the owners of it for over 25 years. The house has had many updates including cedar shake siding and the first floor windows replaced in 2008. In addition, the two baths were updated and a heated mudroom/sunroom was added. One of the baths features a shower for two with dual shower heads. The living area features a Hearthstone propane stove that turns on with the flip of a switch and looks and heats like a wood-burning stove without the effort. The separate two-car garage also has a loft area. The walk-out basement is huge and offers a regulation slate pool table and ping pong table as well as the laundry area. The West River Trail that is so popular for walking/jogging/biking, and cross country skiing is just a short walk away. Stratton, Bromley and Magic are all within a 20 minute drive.

Investment opportunity! This beautiful ski country compound offers 3 potential streams of rental income, or a home where you can enjoy sweeping views of the West River Valley just minutes away from Magic Mountain skiing and a surprising array of amenities in Londonderry’s town center. A barn apartment over a garage with a 3/4 bath, and an upstairs and downstairs unit with a full bath each, are all equipped with their own kitchen and come with paying tenants. Keep the property in its current configuration, or combine the main house into one living area, with the barn as an in-law suite. A septic design exists for a subdivision of the property which, if the subdivision is obtained and a septic permit approved, would enable further development. Property to be sold as-is. Owner financing available.

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 family room 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, Bromley, and Magic Mountain ski areas, this property is well suited as a primary residence, vacation home, or investment opportunity. Offered with appliances included, including washer and dryer, and being sold as is.

Escape to Vermont living in this bright and inviting 3 bedroom, 2 bathroom home set on a generous 0.64-acre corner lot along a quiet country road. Offering 1,150 sq. ft. of comfortable space, this property perfectly balances peaceful rural charm with exceptional convenience. The main level features a functional galley kitchen flowing into an open-concept living and dining area ideal for hosting after a day outdoors. Upstairs, you’ll find 3 bright bedrooms and a full bathroom complete with a soaking tub for ultimate relaxation, as well as a private balcony off one bedroom to enjoy morning coffee and crisp mountain air. Outside, the spacious yard includes a handy storage shed and plenty of room to garden or unwind. Unbeatable location just minutes to skiing at Bromley and Magic Mountains, local shops in downtown Londonderry, and a quick summer dip in Utley Brook. Whether you are seeking a full-time residence or a low-maintenance getaway, this home offers the best of Southern Vermont in every season.

Charming Farmhouse Gem in the Heart of Londonderry Welcome home to this inviting 2-bedroom, bonus room and 2-bathroom residence centrally located in Londonderry, VT a dream location for outdoor enthusiasts with quick, convenient access to world-class skiing at Magic, Bromley, Stratton, and Okemo Mountains in the winter. Summer and fall you are close to hiking the multitude of trails, kayaking, swimming or fishing at a one of the nearby state parks. The local coffee shop is within walking distance as well as the Londonderry Farmers Market! Inside, the home features classic farmhouse-style decor and warm, bright natural light throughout its comfortable living spaces. Step outside into a private backyard oasis designed for year-round fun and relaxation, complete with a cozy fire pit, a classic tree swing, and a custom treehouse. Whether you are looking for a primary residence or the ultimate Vermont ski getaway, this property seamlessly blends cozy style, outdoor adventure, and quintessential New England charm.

PRICE REDUCTION-- to Sell! It is possible to live rent or mortgage free and here’s your opportunity. This fully rented, three unit multi family property is already generating income. Live in one unit and let the other two cover your expenses, or bring your own vision to life in this premier location. Zoned for both commercial and residential use, the possibilities are extensive. Imagine a riverfront restaurant with al fresco dining, a new retail shop, an exercise or hot yoga studio, an art gallery, or continue with office and wellness services the property currently includes office space and a massage therapy business. The offering includes two houses, one apartment unit, an office space unit, and four garages along the Utley Brook branch of the West River. You’ll enjoy 365 feet of beautiful waterfront and 435 feet of frontage on Londonderry Marketplace, with ample parking to support your business or development plans. All three residential units are fully rented and generating strong income. There are many properties on the market but only one with this unique combination of location, flexibility, and potential. An exceptional opportunity to create the lifestyle or business you envision.

Opportunity awaits in this three-bedroom, two-bath home set in a peaceful Vermont location near Bromley Mountain, Hapgood Pond, and the Catamount Trail. The single-level floor plan offers a comfortable living room with a brick fireplace, a separate dining area, and plenty of natural light. A new roof provides an important recent improvement, while the interior is ready for updates and a new owner’s personal vision. With some TLC, this property could become a welcoming primary residence, weekend getaway, or four-season Vermont retreat. Enjoy easy access to skiing, hiking, swimming, cross-country skiing, and the many year-round recreational opportunities the area has to offer.

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 embark on your next business adventure, this property is a rare find in picturesque Southern Vermont. Don’t miss your chance to own a slice of Vermont. Schedule a showing today and explore the possibilities! There are 4 pictures that are virtual renovations of rooms in the house.