Homes for Sale in 05143

/17
$75,000
- 2 Beds
- 1 Bath
- 620 Sq Ft
1144 Potash Brook Rd, Chester, VT 05143

Nice country spot with older mobile home on it. Property is located in a flood zone so if removed could not be replaced with a permanent structure. Power, septic and electric on sight along with a 1 car garage. Home could be repaired, would also make a great spot for a snowbird wanting a spot in Vermont or anyone looking to park an RV. Property is sold AS IS CASH ONLY

Julie Buffum

Buffum Realty

1144 Potash Brook Rd, Chester, VT 05143
/37
$399,000

New Construction
- 4 Beds
- 2.5 Baths
- 2,148 Sq Ft
40 Fenton Rd, Chester, VT 05143

This property is a handy man's dream for someone who has a vision of finishing a house and turning it into their own sanctuary. The bones of the house are in place, furnace and piping for heat are in, rough plumping and wiring are done, and most sheet rock is completed. Gas fireplace is mounted and vented to outside and kitchen cabinets are on site. It boasts a little over 2000 square feet of

John Napier

TPW Real Estate

40 Fenton Rd, Chester, VT 05143
/60
$479,000
- 3 Beds
- 3 Baths
- 2,676 Sq Ft
64 Maple St, Chester, VT 05143

Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You’ll enter through the heated attached two-car garage into a layout that’s both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area

Betsy Adamovich Real Broker LLC

64 Maple St, Chester, VT 05143
/58
$475,000
- 5 Beds
- 4 Baths
- 3,865 Sq Ft
81 Main St, Chester, VT 05143

Step into a piece of Chester's history with this sprawling Folk Victorian offering over 3,800 square feet of living space, five bedrooms, and four bathrooms. Rich in character and architectural detail, this home offers the space and flexibility to accommodate a variety of lifestyles. Inside, you'll find generously sized rooms throughout, including a spacious living room anchored by a wood-burning

Betsy Adamovich Real Broker LLC

81 Main St, Chester, VT 05143
/16
$3,150,000
- Land
- 506 Acres
- $6,225 per Acre
Markham Mountain, Andover, VT 05143

Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence.This land's historical roots run deep, originally belonging to the Marsh

Story Jenks LANDVEST

Markham Mountain, Andover, VT 05143
/39
$1,200,000
- 4 Beds
- 3 Baths
- 3,308 Sq Ft
76 Goldthwaite Rd, Chester, VT 05143

Experience the Vermont lifestyle in this beautifully renovated 1864 Brick Federal-style farmhouse set on 7.8 private acres just minutes from town. Rich in historic character and thoughtfully updated for modern living, this exceptional property offers the perfect blend of comfort, charm, and year-round recreation.Inside, you’ll find four spacious bedrooms, wide plank wood floors, and inviting

Gary Coger Four Seasons Sotheby's Int'l Realty

76 Goldthwaite Rd, Chester, VT 05143
/3
$175,000
- Land
- 12.51 Acres
- $13,989 per Acre
377 Coach Rd, Chester, VT 05143

Minutes to the Village Green, yet peaceful and private, this rare parcel offers the perfect balance of convenience and Vermont tranquility. The property features beautiful long-range views and a small pond with potential for expansion, creating a picturesque setting for your future home.Located in an area identified for development, it offers both a wonderful building site and long-term

Elissa Scully Mary W. Davis Realtor & Assoc., Inc.

377 Coach Rd, Chester, VT 05143
/36
$299,000
- 2 Beds
- 1 Bath
- 750 Sq Ft
29 Markham Ln, Weston, VT 05161

This delightful 2-bedroom, 1-bath cottage located in the heart of the picturesque village of Weston is waiting for a new owner that is looking for a sweet little Vermont retreat. Built in 1947, this home offers timeless character with cozy living spaces and classic Vermont charm. Perfectly situated within walking distance to the Weston Playhouse, the iconic Vermont Country Store, and locally

Catherine Cairns Maple Leaf Real Estate

29 Markham Ln, Weston, VT 05161
/20
$85,000
- Land
- 3.99 Acres
- $21,303 per Acre
00 Simonsville Rd, Andover, VT 05143

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

Geralyn Donohue Four Seasons Sotheby's Int'l Realty

00 Simonsville Rd, Andover, VT 05143
/22
$85,000
- Land
- 5 Acres
- $17,000 per Acre
0 Linden Way Unit 5093908, Chester, VT 05143

Privacy doesn't have to mean isolation!!Wooded acreage, village convenience, and modern connectivity are rarely found in the same package. This newly approved 5 acre parcel in Chester, Vermont offers a private setting surrounded by mature forest while remaining just minutes from the historic village center. Accessed via a private right-of-way, the property provides a peaceful location for a

Daire Gibney Barrett and Valley Associates Inc.

0 Linden Way Unit 5093908, Chester, VT 05143
/16
$3,150,000
- Land
- 506 Acres
- $6,225 per Acre
00 Marsh Cross Rd, Andover, VT 05143

Red Top is a breathtaking 506 +/- acre parcel in the town of Andover and on the border of Weston. Here, the rugged grandeur of the Green Mountains unfolds, offering extraordinary views to the South, where the mountain silhouettes stretch across the skyline and the imposing profile of Glebe Mountain asserts its presence. This land's historical roots run deep, originally belonging to the Marsh

Story Jenks LandVest, Inc/Woodstock

00 Marsh Cross Rd, Andover, VT 05143
/44
$849,000
- 5 Beds
- 3 Baths
- 4,388 Sq Ft
223 Coach Rd, Chester, VT 05143

Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to

Daire Gibney Barrett and Valley Associates Inc.

223 Coach Rd, Chester, VT 05143
/14
$289,000
- 2 Beds
- 2.5 Baths
- 1,475 Sq Ft
106 Contro Rd, Chester, VT 05143

Sweet! An just in time for the holidays. This cabin has been lived in year round and has a drilled well, septic and electric. The basement has been partially finished with the fixtures of a 3/4 bath but no wall coverings, so the square footage is not counted here. The tenant does not have internet so it is best to check on phone/tv and internet from the providers. The property is being divided

Christine Lewis Brattleboro Area Realty

106 Contro Rd, Chester, VT 05143
/51
$390,000
- 3 Beds
- 2 Baths
- 1,304 Sq Ft
663 Depot St, Chester, VT 05143

Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that’s hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates.

Betsy Adamovich Real Broker LLC

663 Depot St, Chester, VT 05143
/60
$649,000
- 3 Beds
- 2 Baths
- 2,205 Sq Ft
688 Hidden Heights Rd, Chester, VT 05143

Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the

Joseph Karl William Raveis Real Estate Vermont Properties

688 Hidden Heights Rd, Chester, VT 05143
/17
$225,000
- Land
- 27.2 Acres
- $8,272 per Acre
0 E Hill Rd, Andover, VT 05143

Nestled in the heart of Vermont’s scenic countryside, this beautiful 27.2-acre parcel offers the perfect setting to build your dream home or mountain retreat. Mostly wooded with over 800 feet of road frontage, the property combines privacy, natural beauty, and easy access to some of Southern Vermont’s most desirable destinations.Enjoy mountain and scenic views that provide ideal building

Gary Coger Four Seasons Sotheby's Int'l Realty

0 E Hill Rd, Andover, VT 05143
/60
$549,000

$50K PRICE DROP
- 2 Beds
- 2 Baths
- 850 Sq Ft
794 White Rd, Windham, VT 05359

Enjoy the best of Vermont living in this thoughtfully renovated home on a paved country road in Windham. Renovated down to the studs, this property offers upgrades inside and out—new standing seam roof, new siding, new windows, full-house generator, new central air and heating systems, plus new electrical and plumbing systems upgraded to 200 amps. The home is insulated with rockwool and foam

Erica Reynolds Southern Vermont Realty Group

794 White Rd, Windham, VT 05359
/60
$625,000
- 4 Beds
- 3.5 Baths
- 2,656 Sq Ft
758 Weston-Andover Rd, Chester, VT 05143

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

Kevin Barnes William Raveis Real Estate Vermont Properties

758 Weston-Andover Rd, Chester, VT 05143
/60
$750,000
- 3 Beds
- 2 Baths
- 1,695 Sq Ft
955 Smokeshire Rd, Chester, VT 05143

Tucked away on a quiet country road in one of Chester’s most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle—just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside,

Katherine Burns William Raveis Real Estate Vermont Properties

955 Smokeshire Rd, Chester, VT 05143
/19
$595,000
- Land
- 220.11 Acres
- $2,703 per Acre
0 Markham Mountain Rd, Andover, VT 05143

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,

Kevin Barnes William Raveis Real Estate Vermont Properties

0 Markham Mountain Rd, Andover, VT 05143
/58
$880,000
- 3 Beds
- 3 Baths
- 3,000 Sq Ft
330 Spruce Dr, Chester, VT 05143

Mountain View Timber Frame Retreat on 25+ Acres in Andover – This exceptional timber-frame home is true perfection and offers long-range mountain views, sunny southeastern exposure, and complete privacy and access to everything that makes you want to call Vermont home. The authentic post-and-beam retreat blends timeless craftsmanship with modern comfort and is offered fully furnished, making it

Claudia Harris Mary Mitchell Miller Real Estate

330 Spruce Dr, Chester, VT 05143
/60
$200,000
- Land
- 6.63 Acres
- $30,166 per Acre
00 Vermont 103, Andover, VT 05143

Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With aproposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offersample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

Rachael Lange Lange & Lange

00 Vermont 103, Andover, VT 05143
/9
$119,000

$10K PRICE DROP
- Land
- 7.95 Acres
- $14,969 per Acre
0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143

Nestled in the picturesque hills of Chester, this inviting 7.95+/- acre property offers the perfect blend of privacy, beauty, and potential. Wander through a peaceful forest where moss covered stones, classic Vermont stone walls, and soft woodland light create a truly serene setting. With some thoughtful clearing, this parcel could open up to stunning views overlooking the charming fields and

Thaddeus Abare Barrett and Valley Associates Inc.

0 Green Mountain Turnpike Unit 5081034, Chester, VT 05143
/20
$169,000
- 1 Bed
- 1 Bath
- 200 Sq Ft
3019 Popple Dungeon Rd, Chester, VT 05143

Discover serene beauty in this charming 200 Sq Ft Tiny House, nestled on a picturesque 1-acre lot alongside the South Branch of the Williams River. A unique opportunity awaits as the tiny house is conveniently adjacent to a 2-bedroom cottage in need of renovation. Waiting for its new owner to continue the transformation. This property offers numerous options, allowing you to live in the cozy tiny

Gary Coger Four Seasons Sotheby's Int'l Realty

3019 Popple Dungeon Rd, Chester, VT 05143
/60
$115,000
- Land
- 3.28 Acres
- $35,061 per Acre
00 Vt Route 103 N, Chester, VT 05143

Tucked just off scenic Route 103 in charming Chester, this parcel offers a prime opportunity to create your own Vermont retreat. With a proposed well and septic design already in place, much of the groundwork has been done—now it's your turn to bring the vision to life. The lot offers ample space for parking and potential for mountain or woodland views with some strategic tree clearing. Whether

Rachael Lange Lange & Lange

00 Vt Route 103 N, Chester, VT 05143
/38
$695,000

New Construction $94K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
717 Horsenail Hill Rd, Chester, VT 05143

Welcome to your brand-new, 2,400 sq ft dream home! This modern, open-concept residence shines with high ceilings and abundant natural light. The gourmet kitchen is a showstopper, boasting custom cabinetry, stone countertops, a large island, and state-of-the-art appliances.The luxurious primary suite features a double vanity, custom shower, and walk-in closet. Upstairs, find three spacious

Robin Apps Four Seasons Sotheby's Int'l Realty

717 Horsenail Hill Rd, Chester, VT 05143
/38
$249,000
- 1,922 Sq Ft
3668 Vt Route 103 N, Chester, VT 05143

Entrepreneurs and investors take note! This commercially zoned property offers exceptional potential for a home-based business, investment opportunity, or live/work lifestyle. The property features an oversized barn, multiple outbuildings, and ample space to support a wide variety of business ventures, workshops, storage, or hobby pursuits.The home is currently configured as two charming

Daniel Vigeant Mary W. Davis Realtor & Assoc., Inc.

3668 Vt Route 103 N, Chester, VT 05143
/3
$159,000
- Land
- 5 Acres
- $31,800 per Acre
00 Contro Rd, Chester, VT 05143

There are many ways to love Vermont and many ways to live here. This 5 acre parcel has a great open meadow perfect for a homestead farm, little get away cottage or a lovely lodge! Just build the lifestyle you want and forget the rest! A few minutes to Main Street Chester and the Common, A few more to the interstate, and nestled close to skiing, hiking and boating. The WWW permit is issued, town

Christine Lewis Brattleboro Area Realty

00 Contro Rd, Chester, VT 05143
/60
$879,999

$9K PRICE DROP
- 3 Beds
- 2 Baths
- 3,310 Sq Ft
201 Spruce Dr, Chester, VT 05143

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

Mendi Michael Engel & Völkers Okemo

201 Spruce Dr, Chester, VT 05143
/9
$195,000
- Land
- 1.2 Acres
- $162,500 per Acre
4769 Pikes Falls Rd, Jamaica, VT 05143

This 1.2-acre parcel offers what few properties in Southern Vermont can—a front-row seat to one of the region’s most breathtaking natural landscapes. Abutting the renowned Pikes Falls swimming hole and waterfall, this land enjoys immediate proximity to a setting protected by the Conservation Society of Southern Vermont. Glamping has become one of Vermont’s most sought-after experiences, and this

Rachel Febbie EXP Realty

4769 Pikes Falls Rd, Jamaica, VT 05143
/19
$650,000
- Land
- 10.03 Acres
- $64,806 per Acre
00 Little Pond Rd, Andover, VT 05143

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

Geralyn Donohue Four Seasons Sotheby's Int'l Realty

00 Little Pond Rd, Andover, VT 05143
/14
$74,000
- Land
- 15.5 Acres
- $4,774 per Acre
00 Remington Rd, Chester, VT 05143

Bring your ideas for building your own home on this 15.5 acre parcel of land in the quintessential town of Chester. Located minutes to the 91 FWY. Vermont Academy nearby along with several hiking and snowmobile trails. Seller has included the cost for clearing the building site and a driveway to house site. Come look at this property and enjoy all it has to offer.

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

00 Remington Rd, Chester, VT 05143
/21
$135,000

$130K PRICE DROP
- Land
- 13.96 Acres
- $9,670 per Acre
0 Valley View Dr Unit 5009431, Andover, VT 05143

UNBELIEVABLE VALUE in a great setting ! Bordering the Ludlow line and set at an elevation of 2,000+ feet, this exceptional parcel offers privacy, expansive long-range views, and an ideal setting for your Southern Vermont dream home. Located within a peaceful community of fine homes, this is one of the few remaining opportunities to build in this highly desirable area. The property includes a

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

0 Valley View Dr Unit 5009431, Andover, VT 05143
/22
$249,000

$50K PRICE DROP
- Land
- 84 Acres
- $2,964 per Acre
000 Green Mountain Turnpike, Andover, VT 05143

84+/- Acres with Stunning Mountain Views in Chester, Vermont Discover a breathtaking 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.

000 Green Mountain Turnpike, Andover, VT 05143
/17
$485,000
- Land
- 26.99 Acres
- $17,970 per Acre
00 Valley View Dr, Andover, VT 05143

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

Teresa DiNapoli Four Seasons Sotheby's Int'l Realty

00 Valley View Dr, Andover, VT 05143
/36
$235,000

$15K PRICE DROP
- 3 Beds
- 1 Bath
- 980 Sq Ft
64 County Rd, North Springfield, VT 05150

Enjoy the ease of single-level living in this 2008 single-wide home set on 2.5 peaceful Vermont acres. The open-concept kitchen and living area is filled with natural light, creating a warm and inviting atmosphere. Offering three bedrooms, one full bath, and a convenient laundry area. Recent improvements include new carpeting and fresh interior paint, making this home truly move-in ready. The

Carol Slocum Keller Williams Realty Metro-Keene

64 County Rd, North Springfield, VT 05150
/31
$349,000

$100K PRICE DROP
- 3 Beds
- 2 Baths
- 1,788 Sq Ft
1397 Popple Dungeon Rd, Chester, VT 05143

Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for—flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved

Daire Gibney Barrett and Valley Associates Inc.

1397 Popple Dungeon Rd, Chester, VT 05143
/14
$87,500
- Land
- 10.4 Acres
- $8,413 per Acre
00 Snell Rd, Chester, VT 05143

CHESTER 10.4+/- acre parcel of land offers offers 180 degree ridgeline views with clearing from an elevated plateau for either a house site or a camp site with a home closer to the town maintained road. A nice stream meanders through the property which is dotted with large rocks and stone walls. There is 245 ft. of frontage on Snell Road and utility pole at the road. Close to Okemo and Magic

Geralyn Donohue Four Seasons Sotheby's Int'l Realty

00 Snell Rd, Chester, VT 05143
/30
$650,000
- 4,324 Sq Ft
3630 Vt Route 103 N, Chester, VT 05143

Exceptional Investment Opportunity in Chester, VT Discover 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

3630 Vt Route 103 N, Chester, VT 05143
/32
$153,000
- Land
- 4.7 Acres
- $32,553 per Acre
250 Fenton Rd, Chester, VT 05143

Welcome to a place where the sound of the river becomes part of your daily rhythm. This 4.7-acre parcel with an end-of-road location offers an extraordinary 1,400 feet of frontage on the Williams River, creating a private and tranquil retreat just five minutes from the quintessential Vermont charm of Chester Village. The land unfolds beautifully: wide, flat, sun-filled fields stretch toward the

Rachel Febbie EXP Realty

250 Fenton Rd, Chester, VT 05143

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