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

129 homes

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ABOUT THIS HOME
Vintage Home for sale in Windsor County, 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

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Welcome to this delightful 3-bedroom, 1-bath home nestled in the picturesque village of Chester, Vermont. Perfectly situated within walking distance to local shops, schools, and restaurants, this property offers the ideal blend of convenience and small-town charm. Step inside to find a spacious mudroom and laundry area — a practical entryway for Vermont living. The open kitchen and dining area provide plenty of room for gatherings, while the cozy living room invites relaxation after a long day. A full bathroom completes the main level for easy accessibility. Upstairs, you’ll find three comfortable bedrooms filled with natural light. The attached back barn offers exciting potenti

$425,000

3 beds1 bath1,608 sq ft

531 Main St, Chester, VT 05143

Attached back barn • Spacious mudroom • Fire pit

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The main home is inviting and well-appointed, offering two covered porches, a large eat-in kitchen, a cozy living room with a gas fireplace, and two dedicated game rooms for guest entertainment. Recent updates include new furniture, paint, flooring, and mini splits for year-round comfort. Attache

$799,000

7 beds7 baths4,581 sq ft

7137 US Route 4, Bridgewater, VT 05034

Large eat-in kitchen • Cozy living room • Gas fireplace

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Welcome to "Valley Brook Farm", a Historic Cape in the middle of Horse country on 12.92 acres with Barns, rolling & level Pasture, a swimming Pond, and Brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 Cape offers the warmth of wide pine floors, post-and-beam character, and sun-filled spaces. The 1.75-story home (2,212+ sq ft) includes 4 bedrooms and 2 full baths. The charming country kitchen features an expansive Family Room area and breakfast nook with a view of the rear meadows. The adjoining pantry, pellet stove, and coat closet make for practical Vermont

$635,000

4 beds2 baths2,212 sq ft

298 Jenneville Rd, Hartland, VT 05048

Swimming pond • 12.92 acres • Barns

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Much more here than meets the eye. This home had heating efficiency completed with SEVCA, new siding, new hot water heater, chimney and furnace inspected and some new exterior paint. Nice level yard, attached two car garage PLUS detached barn! Close to downtown Chester and 15 minutes to Ludlow and Okemo/Vail resort. There is a large 3-season porch, two spacious bedrooms and large country kitchen. This little gem is just waiting for a little polish and it will make a wonderful home. Easy to view, improvements are listed in documents.

$239,000

2 beds1 bath1,222 sq ft

1374 VT Route 103 N, Chester, VT 05143

New siding • New exterior paint • Chimney inspected

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 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 29 Markham Ln, Weston, VT 05161, 2 beds, 1 bath

$299,000

2 beds1 bath750 sq ft

29 Markham Ln, Weston, VT 05161

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 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 228 Cavendish Gulf Rd, Cavendish, VT 05495, 3 beds, 2 baths

$395,000

3 beds2 baths1,312 sq ft

228 Cavendish Gulf Rd, Cavendish, VT 05495

Property at 68 Jarvis St, Windsor, VT 05089, 3 beds, 1 bath

$165,000

3 beds1 bath1,602 sq ft

68 Jarvis St, Windsor, VT 05089

Property at 57 River St, Springfield, VT 05156, 7 beds, 4 baths

$249,000

7 beds4 baths3,294 sq ft

57 River St, Springfield, VT 05156

Property at 226 Fellows Hill Rd, Springfield, VT 05156, 3 beds, 1 bath

$79,900

3 beds1 bath1,075 sq ft

226 Fellows Hill Rd, Springfield, VT 05156

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

$175,000

2 beds1 bath1,296 sq ft

46 Ledgeside Ter, White River Junction, VT 05001

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 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 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 6-8 Crescent St, Springfield, VT 05156, 6 beds, 3 baths

$126,000

6 beds3 baths2,377 sq ft

6-8 Crescent St, Springfield, VT 05156

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

$2,600,000

4 beds2 baths3,000 sq ft

1362 Barnard Rd, Woodstock, VT 05091

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 31 Lakota Rd, Barnard, VT 05031, 3 beds, 2 baths

$424,900

3 beds2 baths1,288 sq ft

31 Lakota Rd, Barnard, VT 05031

Property at 221 Grout Rd, Perkinsville, VT 05151, 6 beds, 4 baths

$728,500

6 beds4 baths3,000 sq ft

221 Grout Rd, Perkinsville, VT 05151

Property at 17 Linden Hl, Woodstock, VT 05091, 4 beds, 3 baths

$1,200,000

4 beds3 baths2,736 sq ft

17 Linden Hl, Woodstock, VT 05091

Property at 715-717 Giddings St, North Springfield, VT 05150, 8 beds, 4 baths

$249,000

8 beds4 baths3,312 sq ft

715-717 Giddings St, North Springfield, VT 05150

Property at 282 Skunk Hollow Rd, Hartland, VT 05048, 3 baths

$452,600

— beds3 baths2,915 sq ft

282 Skunk Hollow Rd, Hartland, VT 05048

Property at 127 Trombley Rd, Chester, VT 05143, 5 beds, 1 bath

$449,000

5 beds1 bath2,856 sq ft

127 Trombley Rd, Chester, VT 05143

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 68 Passumpsic Ave, Hartford, VT 05088, 5 beds, 3 baths

$599,000

5 beds3 baths2,400 sq ft

68 Passumpsic Ave, Hartford, VT 05088

Property at 1 Depot St, Wilder, VT 05088

$999,500

— beds— baths3,218 sq ft

1 Depot St, Wilder, VT 05088

Property at 3 Chester Rd, Springfield, VT 05156, 3 beds, 1 bath

$165,000

3 beds1 bath1,704 sq ft

3 Chester Rd, Springfield, VT 05156

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

$1,150,000

3 beds2.5 baths2,220 sq ft

958 E Woodstock Rd, Woodstock, VT 05091

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

$399,900

4 beds2 baths1,296 sq ft

1668 Hartford Ave, Hartford, VT 05001

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

Property at 815 Route 100, Weston, VT 05161, 6 beds, 7 baths

$695,000

6 beds7 baths3,880 sq ft

815 Route 100, Weston, VT 05161

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Vintage Homes for Sale in Windsor County

There are currently 129 vintage homes for sale in Windsor County at a median listing price of $550K. 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 89 days. This map is refreshed with the newest listings in Windsor County every 15 minutes.

In the past month, 103 homes have been sold in Windsor County. In addition to houses in Windsor County, there were also 105 condos, 4 townhouses, and 26 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 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 Fri Nov 28 2025 on the search page

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