Andover Single-Family Homes

MLS Number 5015743

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 8
• Bathroom 8

Escape to Moosewalk Lane. A magnificent 10,062 SF family compound. Custom built, it comes fully furnished and equipped, featuring 7BR, 8BA, a separate 1BR guesthouse and office, a furnished and heated writers cabin overlooking the Connecticut River Valley, and an equipment barn, all situated on 384 acres of pristine hardwood forest, accessed by an 1800' paved driveway. Anchored by miles of woodland trails and located in Andover, Vermont, the offering includes outdoor sculpture and artwork, historic rock walls, open fields and building ruins from early settlers, along with direct access to the VAST trail system for winter trail riding. The main house features a soaring 2-story fireplace, post and beam timber frame construction, and a chef's kitchen with double appliances, Viking 60” cooktop and wood-fired interior pizza oven, while a reading loft and library add a calming vibe to the outdoor view. The primary suite has a 2BR, 2BA configuration on the main floor with 5 additional bedrooms with en suite baths. There are 6 garage bays supplied with commercial sinks, a 21' x 35' open design gym and exercise suite, and a media room with custom pool table and walkout to the ground floor. Designed for 4-season recreation, privacy and small batch maple syrup production, the hardwood forest, mountain trails, open fields, and additional access from another town road offer unlimited possibilities for the discerning buyer looking for a lifestyle in Vermont's iconic Green Mountains.

Listed by Steve Stettler and Gary Coger of Four Seasons Sotheby's Int'l Realty

MLS Number 5027492

• Land
• Address 00 Valley View Drive
• Acreage 26.99
• Area VT-Windsor
• PricePerSqFt 17969.62

A premier location abutting the Ludlow border, close to Okemo with total privacy, long range panoramic views of distant mountains and valleys at an elevation of about 2000 feet. Peace and beauty abound yet easy access to all area amenities including skiing, golf, biking, hiking and all that Southern Vermont has to offer. A State wastewater permit is in place for a 6 bedroom home and a 2 bedroom guest house. Come build your dream home in the quiet upscale community of Summit Ridge.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

MLS Number 5038811

• Residential Single Family
• Full Bath 2
• Address 847 Simonsville Road
• Construction Existing
• Bedrooms 3

Come find your own peaceful piece of the Vermont countryside in the beautiful town of Andover. Look no further than this move in ready homestead on 51.2 rolling acres with two large paddocks fenced and ready waiting for your animals, complete with two spacious sheds, and a chicken coop ready to house them. Established asparagus patch, blueberry bushes, apple trees, and even your own cranberry bog meticulously maintained by the current owners await you. Live in the updated home or build the home of your dreams up on the hill overlooking the farm. Make hay for your animals in the fields up on top of the hill, dig gravel from your own private gravel pit, or sit next to the beautiful pond! Plenty of land to hike, hunt, or just relax away from the hustle and bustle of the world. Soak up the sun in the attached sunroom or have plenty of room to have all the indoor plants you can dream of. Close to VAST snowmobile trail and within 10-45 minutes of Bromley, Okemo, Stratton, and Magic Mountains! The current owners have done so much to improve and clear the land and are ready to retire to a smaller lot. Their loss is your gain, come take a look today.

Listed by Erin Kendall of EXP Realty

MLS Number 5029533

• Residential Single Family
• Address 26 Dorman Road
• Construction Existing
• Bedrooms 4
• Bathroom 2

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.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

MLS Number 5036615

• Land
• Address 224 Arrau Road
• Acreage 8.53
• Area VT-Windsor
• PricePerSqFt 32825.32

If you're searching for a slice of paradise, look no further than this Hidden Gem. Nestled in the heart of Vermont's picturesque Green Mountains, this Andover lot offers everything you've been dreaming of. With the perfect blend of privacy and convenience, you'll find peace and quiet paired with a short drive from the charming towns of Ludlow, Weston, Chester, and Londonderry. Spanning 8.53 acres, this lot has been thoughtfully cleared and would be minimal work to create a house site. The driveway is already in place, along with a drilled well and a septic design for a 4-bedroom home, giving you a head start on turning your vision into reality. For the outdoor enthusiast, this location is a paradise. Whether you enjoy hiking, snowmobiling, mountain biking, or skiing you're in the heart of it all. With major ski resorts like Okemo, Magic Mountain, Stratton, and Bromley just a short drive away, winter adventures are at your doorstep. Create the Vermont dream home you've always imagined, and experience the beauty and tranquility this incredible property has to offer!

Listed by Thaddeus Abare of Barrett and Valley Associates Inc.

MLS Number 5001000

• Residential Single Family
• Full Bath 2
• Address 81 Trombley Road
• Construction Existing
• Bedrooms 3

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.

Listed by Erin Kendall of EXP Realty

MLS Number 5009431

• Land
• Address Valley View Drive
• Acreage 13.96
• Area VT-Windsor
• PricePerSqFt 16475.64

This piece of land offers a unique combination of privacy and expansive long-range views at an elevation of 2000+ feet, making it an ideal location for your dream home in Southern Vermont. Nestled within a serene community of fine homes, this lot is one of the few remaining opportunities to build in this desirable area. The land has a waste water permit and comes with a community leach field ready for connection. The property provides easy access to local amenities, including skiing and golf at the nearby Okemo Mountain Resort. It's the perfect spot to create your private sanctuary.

Listed by Teresa DiNapoli of Four Seasons Sotheby's Int'l Realty

MLS Number 5039076

• Land
• Address 563 Simonsville Road
• Acreage 53.94
• Area VT-Windsor
• Utilities Other

Looking for a blank canvas to make your own? Look no further than this beautiful 53+ acres in the quiet town of Andover. The property boasts several potential house seats (close to the road but also some tucked up away in the trees), a pond, high above the river, and convenient road frontages on two publicly maintained roads. Minutes from downtown Chester or Londonderry Vermont. Within 30 minutes to Bromley, Stratton, Magic, and Okemo Mountains. Close to Lowell Lake for summer hiking and kayaking. Call for your appointment today!

Listed by Erin Kendall of EXP Realty

MLS Number 5037864

• Mobile
• Area VT-Windsor
• Listing Agent Name Rebecca Seymour
• Address 501 Gates Road
• Year Built 2013

If you're looking for a smaller footprint, or tiny home living, this is a great option! One bedroom, one bath mobile home in an absolutely gorgeous setting! Sitting on it's own 2+ acres, you'll a large yard with a firepit to enjoy the summer evenings while you gaze out over stone walls to a beautiful view. This property is quiet and peaceful, but not far from several ski areas and state parks for hiking, swimming, kayaking, or whatever outdoor adventures you like! Or head into Manchester or Chester for shopping and dining! Whether you are looking for an outdoor enthusiasts weekend getaway, a quiet retreat, or a place to call come, this could be the one! *Motivated Seller!

Listed by Rebecca Seymour of Brattleboro Area Realty

MLS Number 5029048

• Land
• Address 00 Hill Top Road
• Acreage 13.34
• Area VT-Windsor
• Utilities None

If you're searching for the perfect lot to build your dream home, this 13+ acre property could be just what you've been looking for! Nestled on a peaceful road, this expansive lot offers a prime opportunity to create your ideal home while staying close to top local attractions, including the stunning mountains of Okemo, Stratton, Magic, and Bromley. With permits already in place for a four-bedroom home and an additional one-bedroom apartment, the building and approval process is streamlined to help you get started sooner. A proposed build site has already been cleared, making it easy to envision your future home. Break ground in spring 2025 as the weather warms up! This exceptional piece of land is ready for you to explore-schedule a viewing today and take the first step toward your dream build!

Listed by Flex Realty Group and Chris Williams of Flex Realty

MLS Number 5039995

• Land
• Address 00 North Hill Road
• Acreage 4.3
• Area VT-Windsor
• Utilities Cable - Available

The first step in building your Vermont Dream home is finding the perfect piece of land. Look no further! Situated on quiet country road of North Hill this parcel offers great building site, quiet location, easy access to skiing at Vail/Okemo resort (only minutes away), VAST access, close to Weston village with the Vermont Country Store and the Weston Playhouse. Soil tests were conducted years ago and were found to be suitable for septic.

Listed by Lisa Kelley of Cummings & Co

MLS Number 5036371

• Land
• Address 00 Boone Road
• Acreage 5
• Area VT-Windsor
• Utilities None

Rustic Vermont Getaway | Off-Grid Land on Snowmobile Trail Escape to the peace and quiet of rural Vermont with this unique parcel of off-grid land, perfect for a seasonal retreat or outdoor adventure basecamp. It is located off a Class 4 road, this remote property offers an authentic back-to-nature experience-accessible only in the summer months and nestled directly on a maintained snowmobile trail for winter access. Whether you dream of building a rustic summer cabin, a snowmobile hut, or an off-grid hideaway (or even a fallout shelter), this land offers the perfect blend of solitude and recreation. Surrounded by Vermont's natural beauty, this is a rare opportunity to own a piece of wild country where you can truly unplug. Key Features: - Rural location with unmatched privacy - Direct access to snowmobile trail system - Off a Class 4 seasonal road-summer access only - Ideal for off-grid living, cabin, hut, or bug-out shelter - Endless possibilities for outdoor enthusiasts, hunters, or homesteaders No power, no pavement-just you, the land, and the wide-open Vermont wilderness.

Listed by Rachael Rogala of Rachael Rogala Inc.