Properties Near 1749 Middletown Road Andover, VT

*MOTIVATED SELLERS* Down a quiet country road, where pavement yields to gravel and the air carries the scent of pine and possibility, this 3-bedroom, 3-bathroom home is nestled into 2.8 acres of Vermont woodland. Private and peaceful, yet just a short drive to both Weston Village and Londonderry Village, with ski resorts close enough for spontaneous powder days, yet far enough to keep the traffic at bay. The home is the perfect balance of seclusion and accessibility. The home is designed with space and flow in mind, and radiates natural light throughout its generous layout. The first floor features an open-concept kitchen and dining area, while the living room stands apart as its own spacious retreat—anchored by a stunning stone fireplace that sets the tone for cozy evenings and mountain memories. A half bath, mudroom, and access to the back deck complete this level. Upstairs, the primary bedroom features a full en-suite bath, accompanied by two additional bedrooms and a second full bathroom. Below, an expansive unfinished basement is ready for whatever you imagine: game room, studio, and so on. The outside deck is ideal for grilling, reading, and simply listening to the birds in your own forested sanctuary. Off the deck in the winter, the ridge line reveals itself through the trees, which could be further expanded with selected clearing. This home is a place to breathe deep, live simply, and feel the seasons shift around you.

Welcome to this attractive Andover Contemporary home, perfectly suited for year-round living or as a Vermont vacation retreat. Built in 2005, this 3 bedroom, 2 bath residence offers modern comfort in a peaceful country setting on 2.1 acres while being just minutes from Okemo Mountain Resort and close to scenic snowmobile trails—ideal for outdoor enthusiasts in every season. The inviting open-concept main level features a spacious living area with vaulted ceiling and is filled with natural light, seamlessly blending kitchen with breakfast bar, dining, and living room. Two bedrooms and a full bath complete this level, offering convenience and functionality for family and guests. The finished, walkout lower level provides flexible living options with an additional room—perfect for a home office, study, or media space—alongside a cozy woodstove that adds charm while keeping heating costs low. The newly upgraded large, front deck is the perfect place to sip morning coffee and take in the view. Step outside to the beautifully landscaped yard with plenty of room for gardening, plus a firepit designed for gatherings. Two detached sheds offer storage and workshop potential for waxing your skis or wood/snowmobile/lawnmower storage. Whether you love skiing, hiking, or simply relaxing in Vermont’s natural beauty, this property delivers the perfect balance of comfort, location, and lifestyle.

Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a town-maintained road and plowed right to your door, is ready for a complete restoration. Its form and orientation make it an ideal candidate for renovation, preserving the rural character that defines this part of Vermont. Several original outbuildings remain, including a tall silo, classic barns, and a sugarhouse—all reminders of the land’s agricultural roots. Power and utilities are in place, and the road frontage provides easy access in all seasons. This is a solid opportunity for someone looking to rebuild, reimagine, or create a homestead with scale and history. Located between Chester, Weston, Londonderry, and the Okemo Valley, it offers both privacy and proximity to year-round recreation.

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.

This wonderful home has so much to offer! This property has many great features including a brand new roof just put on this summer, great large windows allowing nature light into the living space, a very large oversized Two car garage which also has a magnificent workshop with 220 electric already hooked up, wonderful garden areas with flowers and bushes and so much more! The property also features a newly built timber frame sugar style shack perfect for many different uses. There is the possibility for single level living with the downstairs bedroom being right across from the full bathroom as well as the laundry hook up's being on the first floor. In a great location just a few minutes from the quaint town of Chester 13 minutes from Magic Mountain and just 25 minutes from Okemo Mountain where there are shops, restaurants, Skiing and so much more!

Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the mostly wooded acreage. The long driveway approach gives you a true sense of a cabin in the woods retreat. A recently done septic Design and Wastewater permit make this a year round home possibility. Fantastic location on Middletown Rd. Just minutes to center of Weston where you'll find the Vermont Country Store, excellent dining and the historic Weston Playhouse. Near several major ski resorts, Okemo, Magic, Stratton and Bromley Mountain. This is truly a find that offers the best of the Vermont experience. State approved WW permit available

This charming saltbox cape contains four bedrooms and two bathrooms. Situated high above and overlooking the West River, this house has a level yard and year-round possibilities. An open concept main level with a wood stove, a bedroom, and a full bath. Upstairs, you'll find three additional bedrooms and a second bathroom. The unfinished full basement is your blank canvas! The backyard is fenced for your furry friends and there is the perfect perch for chairs to glance down on the river and watch the day slip away. Flat level driveway for easy access. This house is close to Londonderry for shopping and 20 minutes to Okemo, Magic and Bromley!

Prepare for an exhilarating mountain getaway at this enchanting four-bedroom chalet, nestled on a lush 2.1-acre estate in the heart of Andover. 2025 Ski season has been epic so far! Envision yourself minutes away from four renowned ski resorts, making this the perfect launchpad for your winter adventures. Immerse yourself in the local charm with easy access to the VAST trail network, offering a plethora of entry points nearby. This alpine retreat has been a cherished sanctuary for over 40 years, lovingly maintained by its owners and their dedicated local caretakers. Offering a seamless blend of comfort and convenience, this home is sold fully furnished, ready for you to step in and relish its homely charm "as is." The layout features two cozy bedrooms on each floor, ensuring ample space for family and guests alike. Step inside to discover a welcoming front porch at the entry level, and ascend to the top floor to unwind on the deck with south-eastern views. The heart of the chalet hosts the kitchen and dining areas on the first floor, while the main living and family rooms upstairs provide a spacious haven for relaxation and entertainment. Enhanced by high-speed fiber optics internet from VTel, stay connected and productive in your serene mountain escape. Positioned ideally for those passionate about skiing and outdoor activities, choose from Magic, Stratton, Okemo, and Bromley ski areas, or indulge in hiking, fishing, biking, golfing, and swimming in the vibrant surroundings.

This beautiful privately located 3 bedroom, 2 bathroom manufactured home is move in ready and just waiting for your finishing touches! It has a wonderful level yard with plenty of space for gardens, room to play, or put in a camp fire to sit around on a lovely Vermont evening. There is an additional gravel pad in place that you could put a tiny home as a rental opportunity or a guest house when company comes to visit. You can use the drilled well for both house and the tiny house you add. There is also an approved septic design in place if you choose to add a tiny house there. Other great features are a 30 x 60 hoop building with lots of storage space and another shed with even more storage potential! Would make a great first home, family home, home for someone looking to downsize, or so many other options! Call to schedule your appointment today! Agent is a relative of seller.