Homes for Sale in 05143

/39
$349,000
- 4 Beds
- 3 Baths
- 3,332 Sq Ft
397 River St, Chester, VT 05143

Some properties just radiate a certain warmth, charm and magic and this home is definitely one of them. Imagine sitting on the front porch and listening the soft rustle of the willow tree leaves and the babbling brook trickling by, then you step inside and feel that you have walked into a home that was truly loved. The large kitchen offers nice upgrades including tile floor, granite countertops

Lisa Kelley

Cummings & Co

(802) 392-0114

397 River St, Chester, VT 05143
/29
$329,000

$70K PRICE DROP
- 3 Beds
- 2 Baths
- 1,488 Sq Ft
447 Elm St, Chester, VT 05143

Welcome to your dream home – This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by

Lisa Kelley

Cummings & Co

(802) 200-2452

447 Elm St, Chester, VT 05143
/60
$479,000
- 4 Beds
- 3 Baths
- 2,676 Sq Ft
64 Maple St, Chester, VT 05143

Located in the village of Chester, this 4-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
/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
/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
/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
$479,000

Open Sat 12PM - 2PM $20K PRICE DROP
- 3 Beds
- 2 Baths
- 1,320 Sq Ft
547 Williams Rd, Chester, VT 05143

MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and

Terri Edgerley Edge Realty Vermont

547 Williams Rd, Chester, VT 05143
/38
$749,000

New Construction $40K 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
/53
$569,000

$26K PRICE DROP
- 3 Beds
- 2 Baths
- 2,966 Sq Ft
147 Pleasantview Ln, Chester, VT 05143

Tucked away at the end of a quiet cul-de-sac just one minute from the heart of town, this 4-bedroom retreat offers a rare blend of privacy, possibility, and connection to nature. Set on 3 mostly open acres with glimpses of the mountains and the soothing soundtrack of the nearby river, this is the kind of home that changes pace the moment you arrive. The heartbeat of the home comes from a bright

Jay Farrar Four Seasons Sotheby's Int'l Realty

147 Pleasantview Ln, Chester, VT 05143
/44
$675,000
- 4 Beds
- 2.5 Baths
- 2,600 Sq Ft
518 Baltimore Rd, Chester, VT 05143

Nestled on 10 picturesque rolling acres, just minutes from Chester Village Green and Okemo Mountain Resort, this beautiful country home offers the perfect blend of charm, comfort, and convenience. The property features established gardens, apple trees, blueberry bushes, and a stone patio—ideal for relaxing or entertaining.Inside, you’ll find two levels of well-designed living space. The

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

518 Baltimore Rd, Chester, 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
/31
$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 Realty

29 Markham Ln, Weston, VT 05161
/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
/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
/11
$149,900
- Land
- 12.7 Acres
- $11,803 per Acre
360 Dorman Rd, Andover, VT 05143

Discover the perfect blend of privacy, natural beauty, and convenience on this stunning 12.7-acre parcel nestled in the heart of the Green Mountains in Andover. This mostly wooded property offers a peaceful, secluded setting with a cleared homesite ideally positioned for southern exposure and the potential for breathtaking long-range mountain views with additional clearing.A 5-bedroom

Gary Coger Four Seasons Sotheby's Int'l Realty

360 Dorman Rd, Andover, VT 05143
/37
$1,995,000
- 4 Beds
- 2.5 Baths
- 3,839 Sq Ft
198 Piper Hill Rd, Weston, VT 05161

Uplands is a gracious 105-acre hill farm on the south-facing slope of Markham Mountain, located just outside the historic village of Weston. Anchored by an 1800s farmhouse, the main residence has been thoughtfully added on to and renovated over the years and offers over 3,839 square feet of living space, including four bedrooms, three fireplaces and an attached two bay garage. The guest house

Story Jenks LandVest, Inc/Woodstock

198 Piper Hill Rd, Weston, VT 05161
/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
/11
$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
/26
$225,000
- 3 Beds
- 1 Bath
- 1,327 Sq Ft
160 Depot St, Chester, VT 05143

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

160 Depot St, 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
/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
$129,000
- Land
- 7.95 Acres
- $16,226 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
/20
$250,000
- 3 Beds
- 1.5 Baths
- 1,140 Sq Ft
202 Mountain View, Chester, VT 05143

There’s something quietly reassuring about a home that’s stood the test of time—and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today’s lifestyle. Built circa 1945, the home offers three comfortable bedrooms—including a convenient ground-floor bedroom—and 1.5 baths, giving you flexibility for guests or single-level living. The layout is

Daire Gibney Barrett and Valley Associates Inc.

202 Mountain View, 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
/18
$74,500
- Land
- 16.24 Acres
- $4,587 per Acre
TBD Farrar Rd, Chester, VT 05143

Looking for a piece of Vermont to build a camp, cabin, ski home, full time residence, or create your own homestead? This piece is a clean slate that could be any of that! It has gentle slopes and flats for a potential building spots. Wooded and private, while being a short drive into lovely Chester, VT. This beautiful lot has so much potential, come take a look!

Erin Kendall EXP Realty

TBD Farrar Rd, Chester, VT 05143
/25
$229,000

$20K PRICE DROP
- Land
- 27.8 Acres
- $8,237 per Acre
00 Quarry Rd, Chester, VT 05143

Discover your perfect Vermont getaway on this exceptional 27.8± acre hillside parcel in picturesque Chester, Vermont. Offering sweeping mountain views, privacy, and endless possibilities, this property is ready for your vision. With an approved Vermont state wastewater permit for a 4-bedroom home, you can begin designing your dream family retreat or vacation home right away. A cleared preliminary

Geralyn Donohue Engel & Völkers Okemo

00 Quarry Rd, 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
$889,000
- 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
/28
$89,000

$6K PRICE DROP
- Land
- 10.4 Acres
- $8,558 per Acre
0 Snell Rd, Chester, VT 05143

Rolling, wooded 10.4+/- acre surveyed parcel in Chester offering 244 feet of road frontage and 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. Atop the plateau further into the lot there are nice

Geralyn Donohue Engel & Völkers Okemo

0 Snell Rd, Chester, 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
$250,000
- 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
/30
$650,000
- 3 Beds
- 3 Baths
- 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
/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

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