Homes for Sale near Chester-Andover Elementary School

Magnificent Queen Ann Style Victorian with 3 bedrooms, 2.5 baths on .37 acres in Chester Village. The remarkable front porch has a beautiful archway and intricate, colorful ornamentation. A tiled entryway/coatroom leads to the elegant foyer with dramatic stairway and beautiful glass Art Nouveau Newel post light. The living room features a marble fireplace, pocket doors and original stained glass

Geralyn Donohue Engel & Völkers Okemo

Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal

Tyleen Murray Kelley Real Estate, Inc.

The possibilities are endless with this beautiful property that has been in the same family since 1964! You will not find a nicer piece of Vermont land than this, with approx. 34 acres of open pastureland bordered by hundreds of feet of the Williams River. This stream offers some great summertime activities such as swimming and fishing! The house and attached barns can be a showplace with some

Glenn Olney Barrett and Valley Associates Inc.

Chester Haven on a Quiet Dead-End Road. Tucked away in a serene neighborhood, this spacious 5-bedroom, 4-bath home offers over 3,400 sq ft of beautifully designed living space—perfect for both everyday comfort and grand entertaining. Located on a peaceful dead-end street, yet just minutes from the charm and convenience of Main Street, this property offers the best of both worlds. Inside,

Suzanne Garvey Mary W. Davis Realtor & Assoc., Inc.

With only 50 stone homes in all of Vermont, this one stands out as possibly the most beautiful and uniquely situated on 20 acres of gorgeous green lawn, fields, forest, extensive stone walls; a mere 2 miles to Chester. Since 2020 the house has been transformed and restored w/improvements such as interior & exterior paint, new windows & French Doors, stone steps & walkways, 50 panel Solar Array,

David White OwnerEntry.com

This home on East Hill Road commands one of the area's best views all the way to Stratton! It is one of those spots where the view is different every day & spectacular! The home sits on 14 acres & it overlooks land protected by the Vermont Land Trust and mountains beyond. From the moment you enter, you won't want to leave. It is immaculate and ready to go. A large mudroom with a slate floor &

Betty McEnaney Diamond Realty

Rivers Edge Farm is an absolutely diverse agricultural property which serves bovine, equine and many other farm animals currently and in its past history. 22+ organic acres of rich river bottom land yields a robust crop of haylage, corn or hay or whatever suits your needs. The buildings are mixed use for the owners. Some are animal occupied and feed storage and one is a large garage/workshop

Leila Tarantelli KW Coastal and Lakes & Mountains Realty/Hanover

Discover a truly exceptional, custom-built contemporary home nestled on approximately 79 breathtaking acres with panoramic views, offering the ultimate Vermont lifestyle. This versatile 4-bedroom residence features a flexible floor plan that includes a private in-law suite, perfect for extended family, guests, or additional living options.The setting is nothing short of spectacular. Enjoy two

Gary Coger Four Seasons Sotheby's Int'l Realty

Don’t miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer,

Joshua Lemieux Remax Summit

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

Erin Kendall EXP Realty

Nestled on a quiet dirt road in scenic Chester just 10 mile from Okemo, this 3.24-acre parcel offers the perfect blend of open space and wooded privacy. The front of the lot features a sunny, open field with a pole barn—ideal for storage, hobbies, or future expansion.As you move toward the back of the property, the land gently slopes up to a wooded hillside that levels out beautifully—creating a

Jessica Citera Cummings & Co

Exceptional Investment Opportunity in Chester, VTDiscover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously

Gary Coger Four Seasons Sotheby's Int'l Realty

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.

Daire Gibney Barrett and Valley Associates Inc.

Welcome to 938 Stigers Road, a masterpiece in the mountains! Discover a stunning fusion of artistry and craftsmanship in this exquisite timber frame home, tucked away in the serene beauty of the mountains.This residence is the inspired creation of a visionary artist and a skilled builder, resulting in a one-of-a-kind retreat where design and nature are in perfect harmony.Fall in love with the

Liz Moore Four Seasons Sotheby's Int'l Realty

The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room

Geralyn Donohue Engel & Völkers Okemo

Looking for an opportunity in an ideal location? This property offers unbeatable potential in the sought-after town of Chester. Located on a quiet country road, but still just a couple miles from downtown shopping and dining you get the best of both worlds. This property offers both open and wooded acreage with fruit trees to enjoy! Featuring two generously sized garages, this home is ideal for

Taylor Medeiros-Batey KW Coastal and Lakes & Mountains Realty/Hanover

Rooted in along scenic East Hill Road in the bucolic town of Andover, this 16-acre parcel offers a rare opportunity to create your own private haven in one of Southern Vermont’s most peaceful and charming settings. Just minutes from Ludlow and the slopes of Okemo Mountain, this location strikes the perfect balance between quiet countryside and convenient access to skiing, shopping, dining, and

Daire Gibney Barrett and Valley Associates Inc.

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

Lisa Kelley Cummings & Co

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

Erin Kendall EXP Realty

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

Erin Kendall EXP Realty

Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today’s updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to

Betsy Adamovich Real Broker LLC

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

Thaddeus Abare Barrett and Valley Associates Inc.

Rustic Vermont Getaway | Off-Grid Land on Snowmobile TrailEscape 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

Rachael Rogala Rachael Rogala Inc.

Absolutely stunning architecture located just steps from the village green and across the road from the historic Congregational Church. This property has five apartments. The kitchen appliances are included in each and there is a shared washer and dryer available for tenant use. Each of the five units has its own 100-amp electric panel box. The heat is a central, oil fired boiler providing

Betty McEnaney Diamond Realty

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

Daire Gibney Barrett and Valley Associates Inc.

91± Acres with Stunning Mountain Views in Chester, VermontDiscover a breathtaking 91± acre property just minutes from the charming village of Chester, Vermont. This expansive parcel features stunning alpine views of Fox Chair Mountain, over 3,000 feet of road frontage, and power and internet access along more than half the frontage. Located on the historic Green Mountain Turnpike, this property

Daire Gibney Barrett and Valley Associates Inc.

Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame construction, the

Steve Stettler Four Seasons Sotheby's Int'l Realty

Chester Vt 1377 VTRT 103. , Multi Family , Many good uses for property. One and two-family residential and professional office, retail store if it were a home occupation or home business. There are 2 separate buildings. One needs to be finished, main building 3 floor could be finished for more living space.

Mike England Michael England Real Estate

Looking to live near the Chester Green? This may be the home for you! Currently used as a four-unit apartment building with one 2 bedroom apartment, one 1 bedroom apartment and two studio apartments. The house is in need of renovation however, the style and location would lend well to that investment.

John Tolosky Barrett and Valley Associates Inc.

Just minutes from the Chester Green. The largest available lot in the subdivision with end of the road privacy. This almost 10 acre parcel will afford long distance mountain views with clearing. Underground power is at the lot and the permitted septic is an inground system. All of the heavy lifting is done. Bring your plans and your builder or have the seller build your dream home! PLEASE

Frank Provance Diamond Realty

This rolling, wooded 10.4+/- acre surveyed parcel in Chester offers 244 feet of road frontage and gently rolling land with a mix of hardwoods and pine. A lovely stream meanders through the property which is also dotted with interesting large boulders and old stone walls. If you are looking for privacy, there is potential for a secluded home site set back from the road. Utility pole is at the road

Geralyn Donohue Engel & Völkers Okemo

Tucked along the scenic curves of Route 103 & surrounded by the rolling beauty of Chester, Vermont, this unique French Provincial–meets–Vermont cabin is more than just a house—it’s an invitation to breathe deeper, slow down, & reconnect with the rhythm of nature. Wake each morning to the soothing sound of a nearby creek & the scent of fresh mountain air drifting through the trees. Step outside

Erin Kendall EXP Realty

Explore this 27.8 acre+/- hillside parcel with mountain views and an approved VT state permit for a 4 bedroom family residence, close to the Village of Chester and adjoining Chester Town land. An easily accessed preliminary site has already been cleared. At the top of the ridge, a nice cleared plateau would be a fabulous spot for an off-the-grid bonus cabin retreat with amazing views! This parcel

Geralyn Donohue Engel & Völkers Okemo

This is a one-of-a-kind legacy property, off the beaten path and accessible to everything that makes Southern Vermont an incredible place to call home. The 57.2 acres offer the perfect mix with hardwoods (maples and more), pine groves, open meadows, a pond spanning apprx 1/4-acre, and spectacular southern views and all-day sunlight. Come build your Vermont dream house and be assured of total

Claudia Harris Mary Mitchell Miller Real Estate

Newly subdivided parcel in Chester just North of the Stone Village and on the way to Okemo Mountain! Lot 4 is a 3.35 +/- surveyed lot with proposed shared driveway and a private building site set back and elevated from the road. Just across from the Williams River and near a town wildlife sanctuary, this property is ready for your construction project with approved subdivision and State

Geralyn Donohue Engel & Völkers Okemo

Just North of the Stone Village in Chester on the way to Okemo Mountain, one of two building lots within easy access of of 91 and Chester Village! Lot 3 is a 3.28 +/- surveyed lot with proposed shared driveway and private building site set back and elevated from the road. Across from the Williams River and near a town wildlife sanctuary, this property is ready for your construction project with

Geralyn Donohue Engel & Völkers Okemo