Vintage homes for sale & real estate in Windsor County, VT

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ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Newly listed antique home with space for friends and family to join you for some special Vermont time. Currently set up as a single-family home with five bedrooms & bathrooms, the flow of this house allows for privacy and socializing with the upstairs family room and lower living room. There is an attached barn with potential for finishing too as well as an attached garage for toys or cars. The back entry leads to the laundry room & the bright kitchen with a breakfast nook & into a dining room with a large built-in & a table to seat many, & then into a cozy living area with comfy furni

$369,000

5 beds5 baths2,375 sq ft

2335 Main St, Cavendish, VT 05142

Bright kitchen • Antique home • Attached barn

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Step into timeless New England charm with this historic circa 1760's expanded Cape, offering a great blend of early craftsmanship and character. The home showcases classic timber-frame construction with hand-hewn beams, beautiful plank floors, and period details that create warmth and authenticity throughout. With three bedrooms and two full bathrooms the layout includes a highly desirable first floor primary bedroom and bath, allowing for convenient single-level living while still offering flexible space for family and guests. Set on an expansive 15.55-acre parcel, the property provides mountain views, 47 blueberry bushes, and endless possibilities for agricultural, equestrian, or recreati

$749,000

3 beds1.5 baths1,938 sq ft

4205 VT Route 131, Perkinsville, VT 05151

Plank floors • Hand-hewn beams • 15.55-acre parcel

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
A circa 1734 Cape, displaying museum quality authentic detailing, in a setting worthy of a Vermont Life Magazine cover! Originally sited in N. H. , the Cape was patiently dismantled, with components meticulously cataloged, and then relocated to an idyllic Vermont hilltop setting! The interior seamlessly blends early New England architectural features with benefits of contemporary design amenities. Authentic post and beam construction, gunstock corner posts, exposed beams, extraordinary wide board floors, 4 brick fireplaces, wide board sheathing and hand planed surfaces are desirable components! The advantage of contemporary mechanical systems, a full size cement basement and whole house bac

$3,490,000

4 beds4.5 baths2,894 sq ft

1726 Skitchewaug Trl, Springfield, VT 05156

Wide board floors • Brick fireplaces • Cement basement

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Upper Farm- Circa 1799, large antique cape nestled on 12 acres with stream, multiple ponds, stunning waterfalls overlooking a large meadow. Beautiful extensive gardens for all those perennial enthusiasts with multiple stone terraces overlooking an apple orchard with a variety of types of apples. A two level barn for equipment/storage/animals. A brand new expansive 3 bay heated garage with multiple car lifts to hold a total of 8 cars. Second floor hosts a handsome 1 bedroom apt with deck. The primary residence has handsome wide pine floors throughout- exceptional craftsmanship. A vast kitchen fit for a chef- large island, stone counters with high end appliances- massive pantry with 1/2 bat

$2,895,000

5 beds7 baths8,249 sq ft

1497 Bowman Rd, South Royalton, VT 05031

Extensive gardens • Stunning waterfalls • Multiple ponds

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
* * Sales Price includes MLS#501562 & MLS#501590 Spacious 3-bedroom single-family home with an additional office/laundry room, 1.5 baths, and 1,296 sq. ft. of living space. Features include a heated enclosed porch, two-car garage, and a private backyard. Situated on a . 65± acre property with excellent Route 4 frontage and visibility, just seconds to Interstate 89. The sale also includes a 3,020 sq. ft. commercial building and a second residential home (MLS#501562 & MLS#501590), with a combined acreage of 1.3+/- acres. Offering exceptional income or mixed-use potential. Infrastructure includes two septic systems and a shared well. Ideal for owner-occupants, investors,

$899,000

3 beds1 bath1,296 sq ft

3773 woodstock Rd, White River Junction, VT 05001

Two septic systems • Private backyard • Mixed-use potential

Property at 145 Main St #212, Ludlow, VT 05149, 2 beds, 1.5 baths

$220,000

2 beds1.5 baths1,019 sq ft

145 Main St #212, Ludlow, VT 05149

Property at 79 Merrill St, Springfield, VT 05156, 4 beds, 2.5 baths

$199,000

4 beds2.5 baths2,048 sq ft

79 Merrill St, Springfield, VT 05156

Property at 4946 South Rd, South Woodstock, VT 05071, 5 beds, 3.5 baths

$1,425,000

5 beds3.5 baths3,440 sq ft

4946 South Rd, South Woodstock, VT 05071

Property at 14 Gill Ter, Ludlow, VT 05149, 4 beds, 2 baths

$799,000

4 beds2 baths2,516 sq ft

14 Gill Ter, Ludlow, VT 05149

Property at 598 E Woodstock Rd, Woodstock, VT 05091, 4 beds, 3 baths

$795,000

4 beds3 baths3,190 sq ft

598 E Woodstock Rd, Woodstock, VT 05091

Property at 1362 Barnard Rd, Woodstock, VT 05091, 4 beds, 2 baths

$2,395,000

4 beds2 baths3,000 sq ft

1362 Barnard Rd, Woodstock, VT 05091

Property at 531 Main St, Chester, VT 05143, 3 beds, 1 bath

$425,000

3 beds1 bath1,608 sq ft

531 Main St, Chester, VT 05143

Property at 89 route 12, Hartland, VT 05048, 3 beds, 1 bath

$165,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Property at 514 First Ave, Chester, VT 05143, 5 beds, 5 baths

$529,000

5 beds5 baths3,880 sq ft

514 First Ave, Chester, VT 05143

Property at 1806 Route 100 S, Rochester, VT 05767, 4 beds, 2 baths

$399,000

4 beds2 baths2,554 sq ft

1806 Route 100 S, Rochester, VT 05767

Property at 298 Jenneville Rd, Hartland, VT 05048, 4 beds, 2 baths

$635,000

4 beds2 baths2,212 sq ft

298 Jenneville Rd, Hartland, VT 05048

Property at 37 South St, Woodstock, VT 05091, 3 beds, 2 baths

$749,000

3 beds2 baths1,660 sq ft

37 South St, Woodstock, VT 05091

Property at 958 E Woodstock Rd, Woodstock, VT 05091, 3 beds, 2.5 baths

$1,100,000

3 beds2.5 baths2,220 sq ft

958 E Woodstock Rd, Woodstock, VT 05091

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

$895,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 7137 US Route 4, Bridgewater, VT 05034, 7 beds, 7 baths

$799,000

7 beds7 baths4,581 sq ft

7137 US Route 4, Bridgewater, VT 05034

Property at 3364 W Woodstock Rd, Woodstock, VT 05091, 4 beds, 3 baths

$495,000

4 beds3 baths2,470 sq ft

3364 W Woodstock Rd, Woodstock, VT 05091

Property at 1668 Hartford Ave, Hartford, VT 05001, 4 beds, 2 baths

$379,000

4 beds2 baths1,296 sq ft

1668 Hartford Ave, Hartford, VT 05001

Property at 1254 US Route 5, Springfield, VT 05156, 8 beds, 1 bath

$485,000

8 beds1 bath3,500 sq ft

1254 US Route 5, Springfield, VT 05156

Property at 46 Ledgeside Ter, White River Junction, VT 05001, 2 beds, 1 bath

$150,000

2 beds1 bath1,296 sq ft

46 Ledgeside Ter, White River Junction, VT 05001

Property at 1589 Main St, Cavendish, VT 05142, 10 beds, 10 baths

$1,500,000

10 beds10 baths7,153 sq ft

1589 Main St, Cavendish, VT 05142

Property at 1079 Fletcher Hill Rd, Woodstock, VT 05071, 2 beds, 2 baths

$425,000

2 beds2 baths1,440 sq ft

1079 Fletcher Hill Rd, Woodstock, VT 05071

Property at 454 Giddings St, North Springfield, VT 05150

$210,000

— beds— baths3,950 sq ft

454 Giddings St, North Springfield, VT 05150

Property at 109 Park Row, Rochester, VT 05767, 5 beds, 3.5 baths

$399,000

5 beds3.5 baths2,200 sq ft

109 Park Row, Rochester, VT 05767

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

$650,000

3 beds3 baths4,324 sq ft

3630 Vt Route 103 N, Chester, VT 05143

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 46 Runnals Rd, White River Junction, VT 05001, 4 beds, 4 baths

$585,000

4 beds4 baths3,934 sq ft

46 Runnals Rd, White River Junction, VT 05001

Property at 5798 W Woodstock Rd, Woodstock, VT 05091, 4 beds, 2 baths

$439,000

4 beds2 baths1,617 sq ft

5798 W Woodstock Rd, Woodstock, VT 05091

Property at 18 The Grn, Woodstock, VT 05091, 6 beds, 7 baths

$3,500,000

6 beds7 baths5,142 sq ft

18 The Grn, Woodstock, VT 05091

Property at 9 Fairview St, Springfield, VT 05156, 4 beds, 1.5 baths

$200,000

4 beds1.5 baths1,482 sq ft

9 Fairview St, Springfield, VT 05156

Property at 41 Pleasant St, Woodstock, VT 05091, 9 beds, 11 baths

$2,599,000

9 beds11 baths5,993 sq ft

41 Pleasant St, Woodstock, VT 05091

Property at 7 Slayton Ter, Woodstock, VT 05091, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,532 sq ft

7 Slayton Ter, Woodstock, VT 05091

Property at 19 Huntington Pl, Rochester, VT 05767, 6 beds, 7.5 baths

$795,000

6 beds7.5 baths4,744 sq ft

19 Huntington Pl, Rochester, VT 05767

Property at 198 Piper Hill Rd, Weston, VT 05161, 4 beds, 2.5 baths

$1,995,000

4 beds2.5 baths3,839 sq ft

198 Piper Hill Rd, Weston, VT 05161

Property at 41 VT Route 103 S, Chester, VT 05143

$299,000

— beds— baths2,702 sq ft

41 VT Route 103 S, Chester, VT 05143

Property at 85 Pallottas Hill Rd, Ludlow, VT 05149, 4 beds, 2 baths

$5,500,000

4 beds2 baths3,150 sq ft

85 Pallottas Hill Rd, Ludlow, VT 05149

Property at 3 Olney Rd, North Springfield, VT 05150

$215,000

— beds— baths2,381 sq ft

3 Olney Rd, North Springfield, VT 05150

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Vintage Homes for Sale in Windsor County

There are currently 105 vintage homes for sale in Windsor County at a median listing price of $549K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Windsor County stay on the market for 102 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 87 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 94 condos, 4 townhouses, and 27 multi-family units for sale in Windsor County last month. Find your dream home in Windsor County 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 Windsor County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Windsor County. If you're looking to sell your home in the Windsor County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Windsor County 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 Sat Jan 03 2026 on the search page

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