Homes for Sale near Green Mountain Union High School

/46
$825,000
- 3 Beds
- 3 Baths
- 1,432 Sq Ft
58 Greenbush Rd, Cavendish, VT 05142

Charming Cape Cod Home in a Serene Country Setting – 10.10 AcresWelcome to this beautifully transformed Cape Cod-style home, nestled on just over 10 acres of picturesque countryside. Offering a perfect blend of classic charm and modern convenience, this inviting property is ideal for those seeking tranquility and space. Step onto the welcoming front porch, where you can relax and

Katie Ladue Gilbert KW Vermont Woodstock

58 Greenbush Rd, Cavendish, VT 05142
/34
$895,000
- 3 Beds
- 5 Baths
- 3,590 Sq Ft
1104 Main St, Cavendish, VT 05142

Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuite, 5 bath log home. The Great Room boasts a floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is

Frank Provance Diamond Realty

1104 Main St, Cavendish, VT 05142
/40
$950,000
- 4 Beds
- 4 Baths
- 3,278 Sq Ft
2904 E Hill Rd, Andover, VT 05143

Perched on 60 acres with views of Okemo Mountain from its second floor, this custom designed contemporary is hitting the market for the first time. Built by an international journalist and his writer wife as a retreat for their family and high profile friends, it now awaits its next lucky stewards. Filled with natural light, the rambling home was inspired by a friend's classic Vermont

Steve Stettler Four Seasons Sotheby's Int'l Realty

2904 E Hill Rd, Andover, VT 05143
/58
$995,000
- 3 Beds
- 3.5 Baths
- 2,544 Sq Ft
725 Flamstead Rd, Chester, VT 05143

Immaculately maintained 2,700+ sq ft home offers privacy, peace, and mountain views—just 15 minutes to Okemo Mountain and 4 minutes to the village of Chester. Step inside to find an open, flowing layout with timeless and gorgeous Brazilian rosewood floors, a wood burning fireplace in the living room, and walls of windows that frame the landscape. The family chef will happily welcome opportunities

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

725 Flamstead Rd, Chester, VT 05143
/49
$1,175,000
- 4 Beds
- 4 Baths
- 3,920 Sq Ft
1847 Trebo Rd, Chester, VT 05143

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

Gary Coger Four Seasons Sotheby's Int'l Realty

1847 Trebo Rd, Chester, VT 05143
/47
$549,000
- 4 Beds
- 2 Baths
- 2,300 Sq Ft
127 Pleasant St, Cavendish, VT 05142

This lovingly restored Arts and Crafts style home is located just 10 minutes from Okemo Mountain. Built in 1928, this home sits on a peaceful, elevated street in Cavendish, just steps from the town’s sledding hill. Owned by the same family for 20 years, the memories made here are priceless. The children learned to ski at Okemo and with everyone grown, the family is ready to pass along this

Tyleen Murray Kelley Real Estate, Inc.

127 Pleasant St, Cavendish, VT 05142
/59
$1,225,000
- 4 Beds
- 4.5 Baths
- 4,420 Sq Ft
2941 Twenty Mile Stream Rd, Cavendish, VT 05142

Experience timeless elegance and modern luxury in this exquisitely renovated 1834 farmhouse, gracefully sited on one of Cavendish’s most sought-after country roads. Thoughtfully updated while preserving its historic charm, this extraordinary residence features a state-of-the-art chef’s kitchen, whole house a/c and an expansive open-concept main level adorned with original hand-hewn beams and

Joseph Karl William Raveis Real Estate Vermont Properties

2941 Twenty Mile Stream Rd, Cavendish, VT 05142
/55
$649,000
- 3 Beds
- 2.5 Baths
- 3,040 Sq Ft
656 Main St, Chester, VT 05143

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

656 Main St, Chester, VT 05143
/60
$595,000
- 6 Beds
- 1 Bath
- 2,308 Sq Ft
525 Route 103 N, Chester, VT 05143

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.

525 Route 103 N, Chester, VT 05143
/56
$599,999
- 5 Beds
- 3.5 Baths
- 2,443 Sq Ft
1057 Quarry Rd, Chester, VT 05143

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.

1057 Quarry Rd, Chester, VT 05143
/52
$627,500
- 3 Beds
- 2.5 Baths
- 1,868 Sq Ft
2510 E Hill Rd, Chester, VT 05143

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

2510 E Hill Rd, Chester, VT 05143
/51
$695,000
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
35 Stevens Rd, Cavendish, VT 05142

This is a dream come true for someone who is seeking a Vermont nature retreat in every season. Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The views of Mother Nature

Betty McEnaney Diamond Realty

35 Stevens Rd, Cavendish, VT 05142
/27
$539,000
- 6 Beds
- 2 Baths
- 2,304 Sq Ft
81 High St, Cavendish, VT 05142

Do you love antique homes? Come and take a look and decide how that you would like to use this property. This renovated 1850's home is currently set up as two income-producing units (a three-bedroom unit upstairs and a two-bedroom (could be three) unit on the main level). There is even additional space on the third floor that could be finished too. By simply removing a piece of sheetrock in the

Tyleen Murray Kelley Real Estate, Inc.

81 High St, Cavendish, VT 05142
/34
$299,000
- 2 Beds
- 1 Bath
- 1,052 Sq Ft
2949 Vermont 131, Cavendish, VT 05142

This private mountain home, on 15+/- acres, is right across the street from a popular fly-fishing river, is only 11 miles from Okemo Mountain and only 10 miles from I-91. There’s plenty of garden space, a small stream, and room to homestead! Entering upstairs, brings you into a bright, open kitchen/dining area, with some additional winter warmth provided by the wood stove. The cozy living

Sue Starr-Adams EXP Realty

2949 Vermont 131, Cavendish, VT 05142
/19
$250,000
- 1 Bed
- 1 Bath
- 617 Sq Ft
413 Hidden Heights Rd, Chester, VT 05143

Until this last winter this was a really sweet 16 x 24 log cabin. Then it became fire damaged and now the owner would love to have someone bring it back to its former glory. Nice, private area on a town-maintained country road. All utilities are underground, including a 330-gallon propane tank, electric power from the street, and water from the 230' drilled well. The cabin has 1 bath, a

Glenn Olney Barrett and Valley Associates Inc.

413 Hidden Heights Rd, Chester, VT 05143
/15
$55,000
- Land
- 0.35 Acre
- $157,143 per Acre
150 Parker Ave, Proctorsville, VT 05153

Tucked among mature maples and just a short drive from Ludlow and Chester,this classic New England barn offers a rare opportunity to own a piece of Vermont history. With its weathered wood siding, original beams, and classic gable roofline, the structure stands as a testament to traditional craftsmanship. Inside, exposed timber framing and a partial stone foundation highlight its old-world

Frank Provance Diamond Realty

150 Parker Ave, Proctorsville, VT 05153
/60
$240,000
- 3 Beds
- 1 Bath
- 1,024 Sq Ft
442 Vermont 103, Chester, VT 05143

Adorable Village Home in the Heart of Chester, VermontThis charming 3-bedroom, 1-bath home is packed with personality and Vermont village charm! Set on a sunny quarter-acre lot, this sweet property features an oversized deck perfect for summer barbecues, a great yard for play or gardening, and a convenient attached garage.Inside, you’ll love the warm, inviting living space with

Rachael Rogala Rachael Rogala Inc.

442 Vermont 103, Chester, VT 05143
/19
$389,900
- 2 Beds
- 1 Bath
- 900 Sq Ft
302 Davidson Hill Rd, Chester, VT 05143

This Cozy cabin tucked away along the outskirts of Chester is sure to impress. With a brand new roof, heating system and more this is the perfect turn key retreat. The property features both open lawn and forest to explore, just up the road from snowmobiling and hiking trails this property has the ability to be your home base for all your favorite activities year around. Including close proximity

Thaddeus Abare Barrett and Valley Associates Inc.

302 Davidson Hill Rd, Chester, VT 05143
/21
$150,000
- Land
- 3.60 Acres
- $41,667 per Acre
263 High Ridge Rd, Cavendish, VT 05142

Good land has been hard to find lately. Good land with a view of Okemo even more so. This double lot has huge westerly views towards Okemo. The driveway is roughed in and the septic is designed and permitted for parcel #71. This lot has a septic design for a 3br home plus an additional allocation for a 1br apartment over the garage. You can combine the two and build a 4 bedroom home should you

Joseph Karl William Raveis Real Estate Vermont Properties

263 High Ridge Rd, Cavendish, VT 05142
/29
$299,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
842 Main St, Proctorsville, VT 05153

Cared for by one owner for many years, this two-story home on .26 +/- acres was rebuilt in 1977 and would make a very cute ski house, vacation or full-time home. Enter through the enclosed breezeway which is a great space for entertaining or relaxing. The eat-in kitchen includes a breakfast/dining nook and excellent counter space. The living room is spacious and has plenty of natural light. A

Geralyn Donohue Engel & Völkers Okemo

842 Main St, Proctorsville, VT 05153
/25
$359,000
- 3 Beds
- 1,504 Sq Ft
1749 Middletown Rd, Andover, VT 05143

Tucked away on 31 beautiful acres in Andover is this lovely camp, cottage ready to be finished and enjoyed. The current owners have provided a great start with electric service, forced hot air heat and a finished living room to relax in. The land is a nature lover's dream with a year round stream in back of the camp, open area with a firepit and surrounded by a vast variety of trees on the

Gary Coger Four Seasons Sotheby's Int'l Realty

1749 Middletown Rd, Andover, VT 05143
/43
$420,000
- 2 Beds
- 2.5 Baths
- 1,445 Sq Ft
60 Spaulding Rd Unit J1, Cavendish, VT 05153

Nestled on a quaint hillside in the Okemo Valley, the Castle Hill Resort offers an abundance of amenities with ownership in the resort community. This rare two-bedroom condominium provides ample space for everyone with extra windows for light and views. This is rare as most buildings are Quad-plexes and this building is a top and bottom Duplex, sharing no walls with neighbors! Enjoy an on-suite

Joseph Karl William Raveis Real Estate Vermont Properties

60 Spaulding Rd Unit J1, Cavendish, VT 05153
/15
$94,500
- Land
- 4.05 Acres
- $23,333 per Acre
00 Hillcrest Dr, Andover, VT 05143

Ready to Build in Southern Vermont!Dreaming of a serene mountain getaway or your forever home in Vermont? This 4.± acre gem on a quiet dead-end road offers peace, privacy, and convenience. With a State-issued wastewater permit already in hand for a 5-bedroom home, you can hit the ground running on your build. Power is right at the road and fiber-optic internet is available—ideal for

Daire Gibney Barrett and Valley Associates Inc.

00 Hillcrest Dr, Andover, VT 05143
/21
$55,000
- Land
- 1.52 Acres
- $36,184 per Acre
0 Remington Rd Unit 5049900, Chester, VT 05143

If you're dreaming of open skies, peaceful surroundings, and your own slice of Vermont, this property delivers. Just minutes from the charming Chester village green, this land offers the best of both worlds—seclusion and convenience. Step onto the property and take in the wide-open space surrounded by mature trees, offering privacy and natural beauty in every season. Whether you're envisioning

Frank Provance Diamond Realty

0 Remington Rd Unit 5049900, Chester, VT 05143
/20
$85,000
- Land
- 1.82 Acres
- $46,703 per Acre
0 Remington Rd Unit 5049898, Chester, VT 05143

Bring your plans and build your own piece of paradise! Just minutes from the iconic Chester town green, this scenic parcel offers the perfect blend of privacy, mountain views, and convenience. With a cleared, gently sloping build site already in place, this lot is ready for your imagination. Underground power is on site, and a well-crafted stone retaining wall, drilled well and septic components

Frank Provance Diamond Realty

0 Remington Rd Unit 5049898, Chester, VT 05143
/32
$2,250,000
- 2 Beds
- 4 Baths
- 2,410 Sq Ft
611 Simmons Rd, Chester, VT 05143

Skygate Farm is a historic Vermont farmstead first settled in the 1800s, which today spans over 300 acres of meadows, forests, trails, and weathered stone walls. The setting speaks of an early farmer’s wisdom — sited along a gentle hill to shield against the northwest winds, while opening to the first light of day and the vast mountain views to the east. Found at the end of a winding gravel road,

Dia Jenks LandVest, Inc/Woodstock

611 Simmons Rd, Chester, VT 05143
/56
$1,249,000
- 4 Beds
- 2.5 Baths
- 2,772 Sq Ft
157 Thompson Rd, Chester, VT 05143

Step back in time and experience the timeless charm of this beautifully preserved historic farm, originally known as Thompson Farm and later operated as Jersey Girl Farm. Dating back to 1830, this remarkable property blends 19th-century character with modern sustainability and comfort. The main house retains its original doors and slate roof, while recent upgrades include a new heating system,

Joe Castaluccio Winhall Real Estate

157 Thompson Rd, Chester, VT 05143
/60
$1,500,000
- 10 Beds
- 12 Baths
- 5,500 Sq Ft
1589 Main St, Cavendish, VT 05142

Glimmerstone Mansion—an extraordinary legacy estate where timeless elegance meets modern sophistication. Set on 2.4± beautifully landscaped acres, this iconic property—listed on the National Historic Register—has been meticulously restored, thoughtfully upgraded, and exquisitely furnished. At the heart of the estate is the grand 10-bedroom mansion, where nearly every bedroom and gathering space

Kevin Barnes William Raveis Real Estate Vermont Properties

1589 Main St, Cavendish, VT 05142
/12
$249,000
- 3 Beds
- 1 Bath
- 1,440 Sq Ft
419 Coach Rd, Chester, VT 05143

Price Reduction! Come see this private 2-acre lot, off a side street close to the picturesque Chester village. This well maintained 1968 mobile home has a bright open concept addition. Close to ski mountains and other snowmobile trails. Make this a Vermont getaway or a permanent home joining a wonderful community.

Amy Carson Lowe's Real Estate, LLC

419 Coach Rd, Chester, VT 05143
/23
$80,000
- Land
- 3.99 Acres
- $20,050 per Acre
00 Simonsville Rd, Andover, VT 05143

3.99 +/- acres in Andover close to year round recreation of surrounding towns. This lot was approved by Vt ww dept. in 2008 for a 4 bedroom home and has being updated with a new survey and a revised engineered plan with relocation of the proposed leach field is in process. Located along almost 1000' of the Williams River, after two major storm events, this lot has not lost much ground. A driveway

Geralyn Donohue Engel & Völkers Okemo

00 Simonsville Rd, Andover, VT 05143
/32
$344,900
- 3 Beds
- 2 Baths
- 1,798 Sq Ft
109 High St, Cavendish, VT 05142

Discover the perfect blend of small-town charm and four-season adventure in the heart of Cavendish. Perched on a sunny corner lot with views of Hawks Mountain, this classic Vermont home offers easy access to everything from skiing at Okemo to hiking, biking, and swimming nearby. Step inside through the thoughtfully planned mudroom and enter a warm, updated eat-in kitchen—complete with

Dana Haley Diamond Realty

109 High St, Cavendish, VT 05142
/29
$275,000
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
81 Trombley Rd, Andover, VT 05143

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

81 Trombley Rd, Andover, VT 05143
/13
$129,000
- Land
- 3.24 Acres
- $39,815 per Acre
Lot 3 Mattson Rd, Chester, VT 05143

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

Jessica Citera Cummings & Co

Lot 3 Mattson 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, 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

Gary Coger Four Seasons Sotheby's Int'l Realty

3630 Vt Route 103 N, Chester, VT 05143
/32
$325,000
- 6 Beds
- 2 Baths
- 2,518 Sq Ft
761 Main St, Cavendish, VT 05153

Location, Location, Location...Large families and investors take note. This classic colonial located on the corner of Main Street and Twenty Mile Stream Road is ready for the next family to enjoy or use for rental income. This was the family's gathering house for 55 years, and now it could be yours. There are 6 bedrooms, a woodstove/fireplace, mudroom, 1 car garage/workshop, and bonus space on

Kevin Barnes William Raveis Real Estate Vermont Properties

761 Main St, Cavendish, VT 05153
/29
$399,000
- 4 Beds
- 3.5 Baths
- 2,710 Sq Ft
491 Farrar Rd, Chester, VT 05143

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

Daire Gibney Barrett and Valley Associates Inc.

491 Farrar Rd, Chester, VT 05143
/52
$419,000
- 5,984 Sq Ft
643 Main St, Cavendish, VT 05153

After owning this property for more than 50 years, the Seller is ready to relocate and pass along this classic brick home with lots of square footage and potential. Once having 4 apartments in the main house and an attached barn, the Seller made the upper level of the barn into her own unit. The kitchen was removed from one of the house units and made into a laundry room, so there are currently

Tyleen Murray Kelley Real Estate, Inc.

643 Main St, Cavendish, VT 05153
/58
$635,000
- 3 Beds
- 3.5 Baths
- 2,203 Sq Ft
44 Freeman Rd Unit B2, Cavendish, VT 05153

The Castle Hill Resort & Spa is an award winning destination located just minutes from Okemo Mountain Resort. This ground floor 3br +loft & den features 3.5 baths. This townhouse condo has floor to ceiling windows that provide natural light throughout. The open living room, dining room, and kitchen offer an inviting atmosphere for gatherings. The ground floor patio offers outdoor seating and has

Joseph Karl William Raveis Real Estate Vermont Properties

44 Freeman Rd Unit B2, Cavendish, VT 05153
/35
$199,000
- 3 Beds
- 1 Bath
- 1,322 Sq Ft
841 Farrar Rd, Chester, VT 05143

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

841 Farrar Rd, Chester, VT 05143
/11
$119,000
- Land
- 16 Acres
- $7,589 per Acre
00 E Hill Rd, Andover, VT 05143

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.

00 E Hill Rd, Andover, VT 05143

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Copyright 2025 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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.