Homes with virtual tours for Sale in Chester, VT

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VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Up a serene mountain road above the clouds in the quiet town of Andover, you’ll discover a special mountain property. This home has been distinctively renovated for carefree enjoyment. This retreat is surrounded by natural beauty with unprecedented long-range views to the west of the Green Mountain ridgeline. This highly efficient, low-maintenance home has wonderful natural light with views from nearly every window! The main level, with hickory floors, soaring cedar ceilings & spruce beams, welcomes you through a spacious atrium. It opens to a modern kitchen, dining area, and living room with a wood-burning fireplace, an ideal setting for gathering with family and friends. The m

$995,000

3 beds3 baths2,167 sq ft

979 Andover Ridge Rd, Andover, VT 05143

Long-range views • Mountain property • Hickory floors

3D WALKTHROUGH

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
If you're looking for your forever home or the perfect mountain getaway, take a peek at this locally built Green Mountain Log Home. Davidson Hill Road is home to many craftsman quality homes perched above Chester, overlooking Mt. Ascutney. The open concept first floor spills out onto the generous front deck, essentially doubling the first floor area to roam. Two nearly identical wooden clad bedrooms make up the second floor. The home has a new roof, new on-demand hot water system, fresh stain on the log exterior, updated electrical, and brand new LVL carrying beam and floor joists in the basement. Many other practical upgrades and extensive landscaping has been made and this home is in mint

$354,000

2 beds1 bath900 sq ft

302 Davidson Hill Rd, Chester, VT 05143

Updated electrical • New roof • Generous front deck

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
A rare opportunity to own a remarkable piece of Vermont and literary history. Lovingly designed and restored by the creators of the beloved Llama Llama children's book series and the accompanying Netflix animated series, this extraordinary mini-estate is offered for the first time by the family. The meticulously restored and maintained five-bedroom, five-bath, 6,100+ square foot post-and-beam home seamlessly blends a late-1700s brick home, an 1820 clapboard addition, and thoughtfully designed post-and-beam additions completed in 2012. Historic character has been carefully preserved while incorporating modern construction, insulation, systems, a built-in generator, and today's amenities. Wid

$1,600,000

5 beds5 baths6,118 sq ft

3 Eldredge Rd, Chester, VT 05143

Rooftop deck • Built in generator • Post and beam home

3D WALKTHROUGH

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Set on just over 10 picturesque acres, 3319 East Hill Road offers a rare blend of privacy, comfort, flexibility, and four season Vermont recreation. The three bedroom, three bathroom main residence is filled with natural light and features vaulted ceilings, oversized windows, warm hardwood flooring, and a open concept layout that creates an easy flow between the kitchen, dining, and living areas. At the heart of the home the spacious kitchen offers extensive cabinetry, granite countertops, generous prep space, recessed lighting, and a large breakfast bar with seating. The adjoining dining area is anchored by a brick fireplace, creating a warm and inviting gathering space after a day on the

$709,000

4 beds3.5 baths2,576 sq ft

3319 E Hill Rd, Ludlow, VT 05149

Extensive cabinetry • Large breakfast bar • Spacious kitchen

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on . 33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with butcher block counters, attractive center island with Vermont slate/stone counter, stainless steel sink and dishwasher framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom, full bath and convenient laundry area provide easy one-level living. Upstairs, two a

$479,000

3 beds2 baths1,626 sq ft

3208 Green Mountain Tpke, Chester, VT 05143

Wide-pine floors • Exposed beams • Country cabinets

Property at 81 Main St, Chester, VT 05143, 5 beds, 4 baths

$445,000

5 beds4 baths3,865 sq ft

81 Main St, Chester, VT 05143

Property at 758 Weston Andover Rd, Andover, VT 05143, 4 beds, 3.5 baths

$525,000

4 beds3.5 baths2,656 sq ft

758 Weston Andover Rd, Andover, VT 05143

Property at 168 Chandler Rd, Chester, VT 05143, 3 beds, 2 baths

$649,000

3 beds2 baths2,204 sq ft

168 Chandler Rd, Chester, VT 05143

Property at 223 Coach Rd, Chester, VT 05143, 5 beds, 3 baths

$789,000

5 beds3 baths4,388 sq ft

223 Coach Rd, Chester, VT 05143

Property at 1302 Popple Dungeon Rd, Chester, VT 05143, 5 beds, 5 baths

$1,490,000

5 beds5 baths5,400 sq ft

1302 Popple Dungeon Rd, Chester, VT 05143

Property at 3800 Weston Andover Rd, Andover, VT 05143, 8 beds, 7.5 baths

$5,150,000

8 beds7.5 baths10,062 sq ft

3800 Weston Andover Rd, Andover, VT 05143

Property at 201 Spruce Dr, Andover, VT 05143, 3 beds, 2 baths

$879,999

3 beds2 baths3,310 sq ft

201 Spruce Dr, Andover, VT 05143

Property at 250 Fenton Rd, Chester, VT 05148

$125,000

Land4.70 acres (lot)

250 Fenton Rd, Chester, VT 05148

Property at 00 Marsh Cross Rd, Andover, VT 05143

$3,150,000

Land506.00 acres (lot)

00 Marsh Cross Rd, Andover, VT 05143

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3D WALKTHROUGH

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Good news! A newly renovated, affordable, well maintained home for a reasonable price! It is expected that this home will easily meet Gov’t Loan requirements. This attractive home has easy access to downtown, shopping, parks, ski slopes, mountain hiking, river walks, interstate, and quiet living. The pleasantly comfortable yard offers reasonable privacy for outdoor gatherings, gardening, or just a place for peaceful thinking. The home has had many recent upgrades. The extensive list is available upon request. The utilities have been well maintained. The basement is partially finished, which could be added to the square footage of the home. OPEN HOUSE 8/29/26 10:00 to 2:00

$279,000

2 beds1 bath1,229 sq ft

119 Merrill St, Springfield, VT 05156

5,662 sq ft lot • Built 1940 • Listed 2 days

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Tucked along a quiet side street in Ludlow Village, 16 Smith Street is filled with warmth, character, and timeless New England charm. Beautiful wood floors, rich natural woodwork, and classic pocket doors highlight the home’s craftsmanship, while a spacious wraparound porch invites you to slow down and enjoy village life. Inside, the large country kitchen features an eat-in island and opens to an additional flexible space ideal for a breakfast nook or cozy sitting area. The inviting living room is warmed by a pellet stove, perfect for taking away the chill after a day on the slopes. With three bedrooms and three bathrooms, the home offers comfortable space for owners and guests. The p

$450,000

3 beds3 baths1,669 sq ft

16 Smith St, Ludlow, VT 05149

Country kitchen • Flexible space • Pellet stove

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Okemo Mountain Lodge B206 offers true slopeside convenience at the base of Okemo Mountain Resort. Completely remodeled and offered turnkey, this inviting one-bedroom condominium features ski-in/ski-out access just steps from the main base area, lifts, ski services, dining, and après-ski. The thoughtfully updated interior provides a comfortable, low-maintenance mountain retreat, ideal for personal getaways or a great investment property. With a proven rental history, B206 combines effortless ownership with excellent income potential. Whether you are seeking an easy ski escape or a smart Okemo investment, this beautifully renovated condominium is ready to enjoy. Taxes are based on the

$355,000

1 bed1 bath638 sq ft

350 Mountain Rd Unit B206, Ludlow, VT 05149

Remodeled • Updated interior • Turnkey

VIDEO TOUR

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Okemo Mountain Lodge Prime Location. This fabulous top-floor, one-bedroom, one-bath condominium offers true ski-in/ski-out convenience with parking and beautiful views overlooking the Okemo Base Lodge and A-B chairlifts. Located on the third level, this well-appointed retreat features a sleeper sofa and a Murphy bed for additional guests and a new electric fireplace, creating a warm and inviting space after a day on the slopes. Step outside and you’re right at the heart of Okemo’s base area, with restaurants, shops, rentals, and ski school. Walk to The Loft for a casual meal and a beverage, or take a quick 2-minute drive to the shops, restaurants, and entertainment along Main St

$375,000

1 bed1 bath599 sq ft

109 Okemo Ridge Rd Unit C-307, Ludlow, VT 05149

Beautiful views • Prime location • $986 HOA

3D WALKTHROUGH

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Set back in the woods on a quiet road, this property is within 5 minutes of Okemo Mountain Resort, golfing, shopping and dining. The open concept floor plan on the main level is inviting and warm, offering enough space for friends and family to gather. A wall of windows allows you to watch the winter snowfall, admire the summer greenery and the fall foliage, while also overlooking the back deck. The main floor also has an airlock mudroom along with two bedrooms, a full bath and a half bath. The upper floor has a nice loft, a bedroom, a bonus room/office and a 1/2 bath. There is also a 1 car garage with storage space!

$575,000

3 beds2 baths2,006 sq ft

220 Ellison Loop, Ludlow, VT 05149

Airlock mudroom • Bonus room • Wall of windows

3D WALKTHROUGH

ABOUT THIS HOME
Home with Virtual Tour for sale in Chester, VT:
Discover the quintessential Vermont mountain getaway at this inviting 3 bedroom, 2-bath South Hill home, offered fully furnished and turnkey with a proven short-term rental history. Whether you’re looking for a private retreat, an income-producing property, or the best of both, this home is ready to enjoy from day one. Set in the heart of the Okemo Valley, the location offers exceptional four-season appeal. Spend winter days skiing and snowboarding at Okemo, then return home to the warmth of a wood-burning fireplace and a relaxing soak in the 6-person hot tub. In summer and fall, enjoy hiking, biking, golf, lakes and the wonderful level and private back yard. Inside the wood two livin

$549,500

3 beds2 baths1,740 sq ft

1043 Town Farm Rd, Ludlow, VT 05149

6-person hot tub • Private retreat • Fully furnished

Property at 29 Piper Rd, North Springfield, VT 05150, 4 beds, 3 baths

$449,000

4 beds3 baths3,129 sq ft

29 Piper Rd, North Springfield, VT 05150

Property at 144 Lodge Rd #5, Ludlow, VT 05149, 1 bed, 1.5 baths

$500,000

1 bed1.5 baths1,044 sq ft

144 Lodge Rd #5, Ludlow, VT 05149

Property at 164 Pine View Ln, Cavendish, VT 05142, 4 beds, 2 baths

$600,000

4 beds2 baths2,128 sq ft

164 Pine View Ln, Cavendish, VT 05142

Property at 84 Lawrence Hill Rd, Weston, VT 05161, 3 beds, 1 bath

$475,000

3 beds1 bath1,344 sq ft

84 Lawrence Hill Rd, Weston, VT 05161

Property at 75 Upper Xrd Unit C6, Ludlow, VT 05149, 4 beds, 3 baths

$750,000

4 beds3 baths2,776 sq ft

75 Upper Xrd Unit C6, Ludlow, VT 05149

Property at 36 Okemo Trailside Ext Unit 6D, Ludlow, VT 05149, 1 bed, 1 bath

$350,000

1 bed1 bath858 sq ft

36 Okemo Trailside Ext Unit 6D, Ludlow, VT 05149

Property at 106 Upper Loop, Ludlow, VT 05149, 4 beds, 2.5 baths

$595,000

4 beds2.5 baths1,898 sq ft

106 Upper Loop, Ludlow, VT 05149

Property at 62 Okemo Trailside Ext Unit 9C, Ludlow, VT 05149, 3 beds, 2 baths

$579,000

3 beds2 baths1,470 sq ft

62 Okemo Trailside Ext Unit 9C, Ludlow, VT 05149

Property at 6 Mill St, Ludlow, VT 05149, 4 beds, 4 baths

$150,000

4 beds4 baths2,838 sq ft

6 Mill St, Ludlow, VT 05149

Property at 140 Lodge Rd #3, Ludlow, VT 05149, 2 beds, 2.5 baths

$795,000

2 beds2.5 baths1,253 sq ft

140 Lodge Rd #3, Ludlow, VT 05149

Property at 20 Church St, North Springfield, VT 05150, 3 beds, 2 baths

$299,900

3 beds2 baths2,056 sq ft

20 Church St, North Springfield, VT 05150

Property at 19 Lawridge Hts, Ludlow, VT 05149, 3 beds, 2.5 baths

$750,000

3 beds2.5 baths3,110 sq ft

19 Lawridge Hts, Ludlow, VT 05149

Property at 144 Lodge Rd Unit 1, Ludlow, VT 05149, 3 beds, 3 baths

$1,450,000

3 beds3 baths1,836 sq ft

144 Lodge Rd Unit 1, Ludlow, VT 05149

Property at 00 Markham Ln, Weston, VT 05161

$875,000

Land67.40 acres (lot)

00 Markham Ln, Weston, VT 05161

Homes with virtual tours for Sale in Chester

There are currently 14 homes with virtual tours for sale in Chester at a median listing price of $390K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chester stay on the market for 87 days. This map is refreshed with the newest listings in Chester every 15 minutes.

In the past month, 4 homes have been sold in Chester. In addition to houses in Chester, there were also 0 condos, 0 townhouses, and 1 multi-family unit for sale in Chester last month. Find your dream home in Chester using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chester are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chester. Our Chester real estate stats and trends will give you more information about home buying and selling trends in Chester. If you're looking to sell your home in the Chester area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chester with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2026 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Wed Aug 26 2026 on the search page

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