Chester, VT homes for sale & real estate

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3D WALKTHROUGH

ABOUT THIS HOME
Chester, VT Homes for Sale
Beautifully set in total privacy, this cozy cabin is the perfect retreat! Nestled on a secluded, level lot, this charming home offers a peaceful escape surrounded by nature. Inside, you’ll find wide pine floors, granite countertops, and a freshly painted interior and exterior that give the space an updated feel. The spacious layout includes large rooms and a versatile loft ideal for guests, a small home office, or extra storage. Unwind in the large Jacuzzi jet tub after a long day, or step outside to enjoy the beautifully landscaped grounds. A serene, oversized pond adds to the tranquil setting, while a fenced-in garden area is perfect for growing your own vegetables or flowers. Relax

$349,000

2 beds1 bath803 sq ft

1470 Flamstead Rd, Chester, VT 05143

Wide pine floors • Granite countertops • Secluded level lot

ABOUT THIS HOME
Chester, VT Homes for Sale
Welcome to your dream home – This meticulously maintained New England-style gem is bursting with charm and modern convenience. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the beautiful hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine bei

$399,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

Attached garage • Barn • Natural light

ABOUT THIS HOME
Chester, VT Homes for Sale
Tucked back from the paved road and surrounded by woods, this charming 3-bedroom, 1.5-bath home offers both privacy and convenience. With a little updating and personal touch, it has all the makings of a wonderful starter home or the perfect Vermont getaway. Ideally located near several major ski areas and the lakes region, you’ll enjoy year-round recreation — from winter skiing to summer days on the water. A true four-season retreat waiting for its next chapter! Best suited as cash or conventional purchase.

$189,900

3 beds1.5 baths960 sq ft

284 Flamstead Rd, Chester, VT 05143

Four season retreat • Lakes region • 1 acre lot

ABOUT THIS HOME
Chester, VT Homes for Sale
You have got to see this stunning, fully renovated home, rebuilt from the studs up with meticulous attention to detail while maintaining its classic New England charm! Perfectly perched on the picturesque rolling hills of desirable Chester, this 4bdrm, 3bath beauty offers the ideal balance of comfort, elegance, and modern functionality. Set on 6 private acres overlooking open fields and peaceful pastures, this home is designed to take full advantage of its breathtaking surroundings. Step inside and you’re greeted by a spacious, sun-filled kitchen and dining area where large windows frame panoramic views of the countryside. The easy flow and layout blends seamlessly, perfect for entert

$599,900

4 beds3 baths2,689 sq ft

1573 Flamstead Rd, Chester, VT 05143

Private acres • Fully renovated home • Spacious kitchen

ABOUT THIS HOME
Chester, VT Homes for Sale
Enjoy the best of Vermont living in this thoughtfully renovated home on a 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 board, and the foundation is sealed with full drainage installed around the perimeter. Step inside to a light-filled interior with new flooring, walls, and fixtures throughout. The spacious kitchen features Big Chill appliances and opens to a lovely front porch overlooking the old stone walls that borde

$599,000

2 beds2 baths850 sq ft

794 White Rd, Chester, VT 05359

Renovated home • New siding • Full-house generator

Property at 2651 Twenty Mile Stream Rd, Cavendish, VT 05143, 4 beds, 3.5 baths

$2,250,000

4 beds3.5 baths3,000 sq ft

2651 Twenty Mile Stream Rd, Cavendish, VT 05143

Property at 106 Hall Rd, Chester, VT 05143, 1 bed, 1 bath

$249,000

1 bed1 bath528 sq ft

106 Hall Rd, Chester, VT 05143

Property at 26 Main St, Chester, VT 05143, 4 beds, 1.5 baths

$425,000

4 beds1.5 baths2,562 sq ft

26 Main St, Chester, VT 05143

Property at 3619 Baltimore Rd, Chester, VT 05143, 3 beds, 2 baths

$335,000

3 beds2 baths1,584 sq ft

3619 Baltimore Rd, Chester, VT 05143

Property at 717 Horsenail Hill Rd, Chester, VT 05143, 4 beds, 2.5 baths

$789,000

4 beds2.5 baths2,400 sq ft

717 Horsenail Hill Rd, Chester, VT 05143

Property at 1342 Old Stage Rd, Chester, VT 05143, 2 beds, 2 baths

$895,745

2 beds2 baths1,576 sq ft

1342 Old Stage Rd, Chester, VT 05143

Property at 231 Richardson Rd, Chester, VT 05143, 3 beds, 1.5 baths

$375,000

3 beds1.5 baths1,304 sq ft

231 Richardson Rd, Chester, VT 05143

Property at 688 Hidden Heights Rd, Chester, VT 05143, 3 beds, 2 baths

$685,000

3 beds2 baths2,205 sq ft

688 Hidden Heights Rd, Chester, VT 05143

Property at 95 Church St, Chester, VT 05143, 4 beds, 3 baths

$667,500

4 beds3 baths2,794 sq ft

95 Church St, Chester, VT 05143

Property at 663 Depot St, Chester, VT 05143, 3 beds, 2 baths

$410,000

3 beds2 baths1,304 sq ft

663 Depot St, Chester, VT 05143

Property at 302 Davidson Hill Rd, Chester, VT 05143, 2 beds, 1 bath

$359,900

2 beds1 bath900 sq ft

302 Davidson Hill Rd, Chester, VT 05143

Property at 1749 Middletown Rd, Andover, VT 05143, 3 beds

$359,000

3 beds— baths1,504 sq ft

1749 Middletown Rd, Andover, VT 05143

Property at 611 Simmons Rd, Chester, VT 05143, 2 beds, 4 baths

$2,250,000

2 beds4 baths3,514 sq ft

611 Simmons Rd, Chester, VT 05143

Property at 2904 E Hill Rd, Andover, VT 05143, 4 beds, 4 baths

$855,000

4 beds4 baths3,278 sq ft

2904 E Hill Rd, Andover, VT 05143

Property at 157 Thompson Rd, Chester, VT 05143, 4 beds, 2.5 baths

$1,125,000

4 beds2.5 baths2,772 sq ft

157 Thompson Rd, Chester, VT 05143

Property at 419 Coach Rd, Chester, VT 05143, 3 beds, 1 bath

$239,000

3 beds1 bath1,440 sq ft

419 Coach Rd, Chester, VT 05143

Property at 1847 Trebo Rd, Chester, VT 05143, 4 beds, 4 baths

$998,000

4 beds4 baths3,920 sq ft

1847 Trebo Rd, Chester, VT 05143

Property at 525 Route 103 N, Chester, VT 05143, 6 beds, 1 bath

$495,000

6 beds1 bath2,308 sq ft

525 Route 103 N, Chester, VT 05143

Property at 160 Depot St, Chester, VT 05143, 3 beds, 1 bath

$225,000

3 beds1 bath1,327 sq ft

160 Depot St, Chester, VT 05143

Property at 81 Trombley Rd, Andover, VT 05143, 3 beds, 2 baths

$275,000

3 beds2 baths1,232 sq ft

81 Trombley Rd, Andover, VT 05143

Property at 3630 Vt Route 103 N, Chester, VT 05143, 3 beds, 3 baths

$625,000

3 beds3 baths4,324 sq ft

3630 Vt Route 103 N, Chester, VT 05143

Property at 491 Farrar Rd, Chester, VT 05143, 4 beds, 3.5 baths

$399,000

4 beds3.5 baths2,710 sq ft

491 Farrar Rd, Chester, VT 05143

Property at 515 Main St, Chester, VT 05143, 4 beds, 4 baths

$169,000

4 beds4 baths3,024 sq ft

515 Main St, Chester, VT 05143

Property at 423 Main St, Chester, VT 05142, 6 beds, 5 baths

$575,000

6 beds5 baths3,217 sq ft

423 Main St, Chester, VT 05142

Property at 26 Dorman Rd, Chester, VT 05143, 4 beds, 2 baths

$325,000

4 beds2 baths1,248 sq ft

26 Dorman Rd, Chester, VT 05143

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

$6,950,000

8 beds7.5 baths10,062 sq ft

3800 Weston Andover Rd, Andover, VT 05143

Property at 00 Remington Rd, Chester, VT 05143

$74,000

— beds— baths— sq ft

00 Remington Rd, Chester, VT 05143

Property at 2137 Brockway Mills Rd, Chester, VT 05143

$295,000

— beds— baths— sq ft

2137 Brockway Mills Rd, Chester, VT 05143

Property at 918 Lovers Lane Rd, Chester, VT 05143

$145,000

— beds— baths— sq ft

918 Lovers Lane Rd, Chester, VT 05143

Property at 1175 Quarry Rd, Chester, VT 05143

$300,000

— beds— baths— sq ft

1175 Quarry Rd, Chester, VT 05143

Property at 2 Old Stage Rd Lot 2, Chester, VT 05143

$75,000

— beds— baths— sq ft

2 Old Stage Rd Lot 2, Chester, VT 05143

Property at 00 Vermont Route 103, Chester, VT 05143

$200,000

— beds— baths— sq ft

00 Vermont Route 103, Chester, VT 05143

Property at 00 VT Route 103 N Lot 4, Chester, VT 05143

$115,000

— beds— baths— sq ft

00 VT Route 103 N Lot 4, Chester, VT 05143

Property at 00 VT Route 103 N Lot 3, Chester, VT 05143

$115,000

— beds— baths— sq ft

00 VT Route 103 N Lot 3, Chester, VT 05143

Property at 00 Hillcrest Rd, Andover, VT 05143

$94,500

— beds— baths— sq ft

00 Hillcrest Rd, Andover, VT 05143

Property at 0 Remington Rd #11, Chester, VT 05143

$55,000

— beds— baths— sq ft

0 Remington Rd #11, Chester, VT 05143

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Average home prices near Chester, VT

Cities

Zip Codes
Minor Civil Divisions

05143 homes for sale
$485,000

Chester, VT real estate trends

$352K

Sale price

$178

Sale $/sq ft

Over list price

0.1%

Days on market

Down payment

—

Total homes sold

See more Chester, VT market insights

More to explore in Chester, VT

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Copyright 2025 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 Thu Sep 18 2025 on the search page

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