Andover Homes with Two Rivers Supervisory Union School district

Welcome to Andover, Vermont – a hidden gem nestled in the heart of Windsor County! This charming town is steeped in natural beauty and offers a serene lifestyle that many dream of. With its picturesque landscapes, rolling hills, and lush forests, Andover is the perfect retreat for those seeking tranquility and outdoor adventure.

Andover is known for its close-knit community and friendly atmosphere, making it an ideal place for families and individuals alike. The town is part of the Two Rivers Supervisory Union School District, which is dedicated to providing quality education and fostering a supportive learning environment for students. Families will appreciate the commitment to academic excellence and the diverse extracurricular activities available to students, ensuring a well-rounded education.

In addition to its strong educational foundation, Andover boasts a variety of recreational opportunities. Residents can explore the scenic hiking trails, enjoy fishing in the nearby rivers, or simply take in the stunning views of the Green Mountains. The town’s rich history is also reflected in its charming architecture and local landmarks, providing a sense of nostalgia and community pride.

Whether you’re looking for a cozy cottage or a spacious family home, Andover offers a range of real estate options to suit your needs. With its idyllic setting and welcoming community, Andover is not just a place to live – it's a place to call home. Come discover the magic of Andover, Vermont, and find your perfect slice of paradise in this enchanting town!

Newest Andover Homes with Two Rivers Supervisory Union School district

$589,000

3 Beds ⋅ 2 Baths ⋅ 5099361 MLS

Silence is the first thing you notice. Set on 10+/- peaceful acres in Andover, this comfortable and well-maintained three-bedroom, two-bath home offers the kind of Vermont setting that is getting harder to find. No traffic noise, no bustle, just woods, privacy and room to breathe. Inside, the home is warm and inviting, with an easy layout equally suited to full-time living or weekends in the mountains. The eat-in kitchen opens to its own private deck, while a second expansive deck offers plenty of room for outdoor dining, relaxing and enjoying the surrounding landscape. A large three-bay garage provides excellent space for vehicles, outdoor gear, snowmobiles, bikes or a workshop. Adventure is close at hand, with the Okemo State Forest and more than 13,000 acres of conserved land nearby. Okemo Mountain Resort, the charming village of Weston and the quiet community of Andover are all within easy reach. Offered fully furnished and ready to enjoy, this is a true Vermont retreat without the work of starting from scratch. Arrive, settle in and let the quiet take over.

314 Dorman Rd, Andover

$650,000

5097693 MLS

Located in the town of Andover, VT, this 10.4 acre parcel, showcasing an amazing long range mountain view, awaits the home of your dreams. The approach to the property is gorgeous with dramatic views and large neighboring parcels. The house site is tucked in the forest, with a roughed-in driveway already in place. This property has been thoughtfully composed, setting the stage for your custom home project. The open meadow has been stumped, seeded and defines one of the most protected and secluded, untouched areas in Southern Vermont. All pre-construction permits are approved, including a 6 bedroom, state approved septic permit, taking the preliminary stress of site work out of your project. It’s literally shovel ready for you to design your Vermont retreat and obtain your construction permit at the charmingly laid back Andover Town Hall within two weeks. The owners have taken care of all the necessary environmental protections, ensuring minimal impact on the natural beauty of the land. The premier ski areas of Stratton, Bromley, Okemo Mountains are 20-30 min away. Magic Mountain, favored by the locals for its steep terrain, is at your doorstep. For theater buffs, the Weston Playhouse is nearby and Manchester shopping/dining is a 30 min drive away. Lowell Lake State Park, a favorite spot for picnics, kayaking and fishing, is just around the corner. Enjoy one of the most protected and secluded, untouched areas in Southern Vermont, a short drive away from down country points: Tappen zee Bridge - 3.5 hrs, Boston- I495 2.5 hrs and 2 hrs to Bradley Int’l and Albany Airports. The hard work is done, now it’s time to make your dream of building a home in Vermont come true!

00 Little Pond Rd, Andover

$575,000

4 Beds ⋅ 4 Baths ⋅ 5097485 MLS

A rare opportunity to own two well-maintained homes on one beautiful country property! The main residence offers 3 bedrooms and 3 baths with a warm, inviting interior featuring hardwood floors, abundant built-ins, and thoughtfully designed living spaces that blend character with everyday comfort. Step outside to the back deck overlooking beautifully landscaped gardens and a spacious lawn, an ideal setting for entertaining, relaxing, or simply enjoying the peaceful surroundings. The separate 1-bedroom, 1-bath cottage provides outstanding flexibility as a guest house, private retreat, home office, or income-producing rental. Whether you're seeking supplemental rental revenue or accommodations for extended family and friends, this charming cottage offers endless possibilities. A two-car garage, mature landscaping, and meticulous maintenance complete this exceptional property. Conveniently located just a short drive from Okemo Ski Resort, Magic Mountain Ski Area, the renowned Weston Playhouse, and the shops and restaurants of Chester, you'll enjoy easy access to year-round recreation, cultural attractions, and quintessential Vermont charm. This unique property is ideal as a primary residence, vacation home, or investment opportunity with built-in rental income potential. Visit the Okemo real estate community today. Taxes are based on town assessment.

758 Weston Andover Rd, Andover

$85,000

5094515 MLS

ANDOVER 3.99 Acres on the Williams River that was once a part of the Historic Jaquith Homestead. Walk the old mowing road that winds through the property, leading to three meadow areas along the river. The central meadow has a designated home site for a 4 bedroom state approved septic. The owners have just had the house location resighted to make sure it is out of the flood zone. A great spot for a camper or tiny home! The sleepy hamlet of Andover is around the corner and is a reminder of days gone by. There is a clay shooting range for hunting practice just up the road and a historic tavern to enjoy at day's end. Close to Magic Mountain, 20 min. to Okemo, Bromley and 40 min. to Stratton.

00 Simonsville Rd, Andover

$5,150,000

8 Beds ⋅ 8 Baths ⋅ 5089880 MLS

Bringing generations together in a place that inspires connection, adventure, celebration, work and stewardship, Moosewalk Lane is a purpose built multigenerational family compound. Created over two decades and set on 384 private acres in Vermont's Green Mountains, Moosewalk Lane is offered fully furnished and equipped. Anchored by a 10,062 square foot timber frame home, guest house, writer's cabin, equipment barn, and miles of private trails, Moosewalk provides a true sense of place where comfort, privacy, and recreation exist in equal measure. Designed for year round living and entertaining, the compound comfortably accommodates extended family, friends, and guests with eight bedrooms, seven full baths, a dramatic two story great room, a chef's kitchen with Viking appliances and an Italian wood fired pizza oven, a library, media and game room, fitness space, six garage bays, and thoughtfully designed gathering places both inside and out. Just beyond the backyard, Broadway, the property's original logging road turned trailhead, provides direct access to the balance of the 384 acre property and four season recreation. Ride horses through open meadows, hike, snowshoe, or explore miles of private woodland trails, produce maple syrup from your own gravity fed sugarbush, enjoy direct access to Vermont's VAST trail system, or retreat to the writer's cabin overlooking the Connecticut River Valley. Historic stone walls, managed hardwood forests, abundant wildlife, and protected Current Use acreage reflect more than ownership, they reflect stewardship. Thoughtfully created for extended family, private retreats, entertaining, or simply escaping the pace of everyday life, Moosewalk offers something increasingly rare: a place where time slows, memories are made, meals are shared, and life is measured by moments well spent.

3800 Weston Andover Rd, Andover

$595,000

5077135 MLS

Discover 220± acres of pristine woodland offering the ultimate blend of privacy, recreation, and opportunity. With a mix of gently level terrain and elevated ridgelines that may offer sweeping mountain views, this remarkable parcel provides endless possibilities — from a private estate setting to potential subdivision. The VAST snowmobile trail runs directly through a portion of the property, offering immediate access to Vermont’s extensive trail system for year-round adventure right from your doorstep. Whether you envision an off-grid cabin tucked deep in the woods or a custom-built retreat with unmatched seclusion, this land delivers the space and serenity to bring your vision to life. Ideally located just minutes from the charming villages of Weston and Ludlow for dining and shopping, and a short drive to premier ski destinations including Okemo Mountain Resort, Magic Mountain Ski Area, Bromley Mountain, and Stratton Mountain Resort — this is a rare opportunity to own substantial acreage in one of Southern Vermont’s most sought-after recreational areas. Privacy. Potential. Adventure. All in one extraordinary property. Taxes are based on the current town assessment.

Markham Mountain Rd, Andover

$879,999

3 Beds ⋅ 2 Baths ⋅ 5074216 MLS

Set on over five acres of rolling Vermont hillside, this three-bedroom, two-bath home is perfectly positioned for year-round enjoyment with a special focus on summer living and seamless access to some of southern Vermont’s top mountain destinations, including Okemo Mountain Resort, Stratton Mountain Resort, Bromley Mountain, and Magic Mountain Ski Area. Offered turnkey, it’s an ideal basecamp for making the most of every season while staying ready for ski season ahead. Inside, an attached two-car garage leads into a practical mudroomideal for stashing summer gear now and ski equipment later. The light-filled great room and open-concept kitchen form a welcoming space for gathering year-round. Two comfortable bedrooms and a full bath are located on the main level, while upstairs, a private primary suite features a loft overlooking the living area, a spacious bath, walk-in closet, and a dedicated home office. The finished walkout lower level enhances the home’s versatility, offering a game room, TV lounge, additional finished space, and laundry area, with direct access to a hot tub perfect after a summer hike or a winter day on the slopes. A detached one-car garage and additional outbuilding provide extra storage for all your seasonal gear. Warmer months take center stage here, with long days spent hiking and biking nearby trails, exploring local lakes and farmers markets, or relaxing on the expansive wraparound deck overlooking peaceful countryside views. The property’s partially open land and privacy create a true summer retreat atmosphere perfect for entertaining, unwinding, and reconnecting with nature. As fall arrives, the landscape transforms with classic Vermont foliage, while winter brings easy access to premier skiing and VAST snowmobile trails just a short drive away. Blending laid back summer living with effortless winter readiness, this property captures the essence of Vermont in every season inviting, adaptable, and ready for whatever the year brings.

201 Spruce Dr, Andover

$449,000

5 Beds ⋅ 1 Baths ⋅ 5064459 MLS

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.

127 Trombley Rd, Andover

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .