Vintage homes for sale & real estate in 05143, VT

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3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
Here's a great opportunity to own a property on Chester's busy Main Street, Route 103 and Route 11. Situated between the Jiffy Mart and the General Dollar Store, there are many possibilities here for a commercial enterprise. Or you can use one unit for a nice business office and continue to rent the other two existing apartments. Presently, all three units are vacant. Easy to show! There is good road frontage for plenty of parking. Consider the options here and take a look today!

$299,000

— beds— baths2,702 sq ft

41 VT Route 103 S, Chester, VT 05143

Main street location • Plenty of parking • Good road frontage

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
Built in 1803, this home has lived many lives and still stands with purpose. Set within one of Chester’s historic districts, it sits naturally among period homes and the steady pace of village life. The lot is larger than what is typical in town, room for garden , 2 horse stalls and even a horse paddock near the river. It’s a property that allows you to live outwardly—work the land, keep animals, or simply enjoy open, private space. Inside, the home is warm and inviting, with a layout that supports both daily living and gathering. The large living room, anchored by two fireplaces, is a natural place to slow down. A formal dining room is ideal for hosting, and a generous ro

$529,000

5 beds5 baths3,880 sq ft

514 First Ave, Chester, VT 05143

Garden • Separate rental unit • Horse stalls

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a town-maintained road and plowed right to your door, is ready for a complete restoration. Its form and orientation make it an ideal candidate for renovation, preserving the rural character that defines this part of Vermont. Several original outbuildings remain, including a tall silo, classic barns, and a sugarh

$449,000

5 beds1 bath2,856 sq ft

127 Trombley Rd, Chester, VT 05143

Original farmhouse • Distant ridgelines • Mixed forest

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
A beautiful property needing someone to either do a barn to house conversion or build new on a scenic spot toward the back of the field which overlooks the barns, field, and hills beyond. This was a dairy farm years ago, and the barn still has some stanchions in place. Not a property for anyone to move right into since it needs finishing. This is more suited to a cash sale or special financing. Brockway Mills is a lightly traveled paved road just a half mile or so from Route 103. About equal distance between the scenic towns of Chester and Bellows Falls, and Springfield hospital and shopping is minutes away. Skiing is not far away at Okemo, and it's only 10 minutes from I-91 exit 6! This pr

$249,900

2 beds1 bath— sq ft

2137 Brockway Mills Rd, Chester, VT 05101

Brockway mills gorge • Overlooks the barns • 13 acre lot

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
Have you been waiting to buy just the right property? An impressive home in a special town in an amazing state might be perfect. This well-loved Victorian has 4 bedrooms in the main house and another 3 bedrooms in the carriage house unit. There is a storage room in between the two spaces with doors to open to easily connect the units. The beautiful main house has a farmhouse-style kitchen, formal dining room for holiday dinners, 2 connecting living spaces with fireplace, a bedroom and a full bath. Upstairs are 3 more bedrooms and a full and half bath. The character and antique doors and trim make this house a home. The carriage house unit has 3 bedrooms, a kitchen and full bath and a large

$599,000

7 beds3.5 baths3,850 sq ft

534 Elm St, Chester, VT 05143

Formal dining room • Victorian home • Carriage house unit

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

$625,000

4 beds3 baths2,794 sq ft

95 Church St, Chester, VT 05143

Property at 447 Elm St, Chester, VT 05143, 3 beds, 2 baths

$389,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

Property at 1057 Quarry Rd, Chester, VT 05143, 5 beds, 3.5 baths

$594,000

5 beds3.5 baths3,470 sq ft

1057 Quarry Rd, 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 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 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 918 Lovers Lane Rd, Chester, VT 05143

$145,000

— beds— baths— sq ft

918 Lovers Lane Rd, Chester, VT 05143

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ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
Effortless Style Meets Vermont Village Living Sweeping arches, sun-soaked spaces, and vintage charm, this Ludlow Village home is the perfect blend of character and modern comfort. Lovingly cared for over 33 years, it's been thoughtfully renovated to keep the history intact while adding all the upgrades you want. Wake up to southern light streaming into your sunroom, sip coffee on the elevated deck with mountain views, or gather friends around the patio's hot tub and gas fire pit after a day on the slopes. With Okemo Mountain Resort just minutes away, you can ski in winter, golf in summer, and explore pristine lakes all year long. Inside, high-speed internet keeps you connected while heated

$799,000

4 beds2 baths2,516 sq ft

14 Gill Ter, Ludlow, VT 05149

Hot tub • High-speed internet • Elevated deck

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
Brand new custom renovated 3bedroom/2bath home in the charming and desirable town of Cavendish, close to Okemo and four-season recreation. From the outside, this home exudes classic New England charm, but step inside through the mudroom to witness a breathtaking, top-to-bottom modern renovation. Inside, discover a bright, open floor plan with gleaming variegated hardwood floors, and recessed lighting throughout. Stunning kitchen has been thoughtfully designed with white shaker cabinets, black concrete countertops, stylish backsplash and new stainless-steel appliances The "wow-factor" continues with modern fixtures, recessed lighting, custom trim and two-tone pain. Upstairs you wil

$395,000

3 beds2 baths1,312 sq ft

228 Cavendish Gulf Rd, Cavendish, VT 05495

Open floor plan • Modern renovation • Recessed lighting

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
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 owned shops. Enjoy easy access to nearby ski areas, including Bromley, Magic, Okemo and Stratton as well as the scenic town green, and all that this vibrant village has to offer. Weston is a short drive to Manchester Center for outlet shopping and dining as well as other outdoor activities including

$299,000

2 beds1 bath750 sq ft

29 Markham Ln, Weston, VT 05161

New flooring • Scenic town green • New electrical panel

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
This nicely laid out Two family plus carriage house has great potential! With key updates like updated roofing and double paned vinyl windows in the second floor unit. The carriage house boasts much potential with new siding materials on sight and currently the interior is being worked on for a renter that is already in place.

$126,000

6 beds3 baths2,377 sq ft

6-8 Crescent St, Springfield, VT 05156

Updated roofing • New siding materials • 0.33 acre lot

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
This Unique property features a large 3 unit building all featuring 2 bedrooms and 1 bathroom, with an additional carriage house with 2 bedrooms and 1 bathroom aswell. With a new heating system replaced in 2023 and many other key updates.

$249,000

8 beds4 baths3,312 sq ft

715-717 Giddings St, North Springfield, VT 05150

0.5 acre lot • Built 1820 • Listed 23 days

ABOUT THIS HOME
Vintage Home for sale in 05143, VT:
This great property has a great central location in walking distance to downtown Springfield featuring all of the local amenities. The property overlooks the Black River and with good maintenance history on all systems this has the potential to be a great investment.

$249,000

7 beds4 baths3,294 sq ft

57 River St, Springfield, VT 05156

Walking distance • Central location • 5,662 sq ft lot

Property at 51 Merrill St, Springfield, VT 05156, 6 beds, 4 baths

$186,000

6 beds4 baths2,304 sq ft

51 Merrill St, Springfield, VT 05156

Property at 7 Common St, Springfield, VT 05156, 8 beds, 15 baths

$379,000

8 beds15 baths4,936 sq ft

7 Common St, Springfield, VT 05156

Property at 3 Wall St, Springfield, VT 05156, 4 beds, 4 baths

$249,000

4 beds4 baths2,767 sq ft

3 Wall St, Springfield, VT 05156

Property at 1909 Davidson Hill Rd, Westminster, VT 05158, 3 beds, 2 baths

$429,900

3 beds2 baths2,140 sq ft

1909 Davidson Hill Rd, Westminster, VT 05158

Property at 226 Fellows Hill Rd, Springfield, VT 05156, 3 beds

$79,900

3 beds— baths1,075 sq ft

226 Fellows Hill Rd, Springfield, VT 05156

Property at 270 Quarry Rd, Perkinsville, VT 05151, 2 beds, 1 bath

$169,000

2 beds1 bath884 sq ft

270 Quarry Rd, Perkinsville, VT 05151

Property at 58 Depot St, Chester, VT 05153, 4 beds, 2 baths

$249,000

4 beds2 baths2,016 sq ft

58 Depot St, Chester, VT 05153

Property at 50 Bates Rd, Cavendish, VT 05142, 3 beds, 1 bath

$299,000

3 beds1 bath1,800 sq ft

50 Bates Rd, Cavendish, VT 05142

Property at 215 Elm Hill St, Springfield, VT 05156, 4 beds, 2.5 baths

$379,000

4 beds2.5 baths2,240 sq ft

215 Elm Hill St, Springfield, VT 05156

Property at 198 Depot St, Proctorsville, VT 05153, 5 beds, 3 baths

$415,000

5 beds3 baths1,976 sq ft

198 Depot St, Proctorsville, VT 05153

Property at 11 Fornuto Rd, Wardsboro, VT 05355, 3 beds, 1.5 baths

$285,000

3 beds1.5 baths3,096 sq ft

11 Fornuto Rd, Wardsboro, VT 05355

Property at 48 School St, North Springfield, VT 05150, 2 beds, 1 bath

$205,000

2 beds1 bath676 sq ft

48 School St, North Springfield, VT 05150

Property at 1607 Massey Rd, Springfield, VT 05156, 4 beds, 2 baths

$995,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 15 Frederic St, Springfield, VT 05156, 2 beds, 1 bath

$229,000

2 beds1 bath1,228 sq ft

15 Frederic St, Springfield, VT 05156

Vintage Homes for Sale in 05143

There are currently 12 vintage homes for sale in 05143 at a median listing price of $467K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 05143 stay on the market for 87 days. This map is refreshed with the newest listings in 05143 every 15 minutes.

In the past month, 8 homes have been sold in 05143. In addition to houses in 05143, there was also 1 condo, 0 townhouses, and 1 multi-family unit for sale in 05143 last month. Find your dream home in 05143 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 05143 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 05143. If you're looking to sell your home in the 05143 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 05143 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 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 Tue Nov 25 2025 on the search page

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