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:
Charming Lake Cottage with Over 113 +/-Feet of Waterfront on Lake Pauline. Lovingly maintained by the same family since the 1940s, this delightful lakefront cottage is a rare find. Step inside to discover original touches like tongue-and-groove paneling and vintage details that evoke a simpler time, all thoughtfully preserved. Modern updates blend seamlessly with its nostalgic charm and include a spacious eat-in kitchen, full bathroom, partial concrete basement, replacement windows, and a recently installed oil tank. The detached one-car garage provides convenient storage for your kayaks, paddleboards, and other lake toys. This property offers a spectacular location less than two miles from

$425,000

3 beds1 bath895 sq ft

121 E Lake Rd, Ludlow, VT 05149

Vintage details • Replacement windows • 0.49 acre lot

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
A rare opportunity to own a piece of Vermont history - The North Pomfret Store & Post Office, c. 1830. This 3-story New Englander offers charm, character, and a solid income stream on 3.25 picturesque acres. With 5 total units, the property includes 3 residential apartments (one 2-bedroom, one 1-bedroom, and an Efficiency), a ground-floor commercial office space, and the historic U. S. Post Office - anchored by a new 5-year lease. Most tenants pay their own electrical bills, and the owner provides baseboard FHW heat to most units with a newly upgraded boiler in 2023. The spacious 3,500+ sq/ft building features classic post-and-beam construction, wood frame, and a walkout basement idea

$495,000

4 beds3 baths3,350 sq ft

7868 Pomfret Rd, North Pomfret, VT 05053

5 total units • 3.25 acre lot • Built 1830

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Asa Greene traveled to Vermont in 1783 to establish a farm in the high hills in Bridgewater after serving in the American Revolution. 242 Years later the farmhouse still stands at the end of Old Bridgewater Hill Road after nearly 50 years of careful restoration and renovations made to accommodate an active, growing family. Creatively blending old & new the farmhouse takes advantage of an inspired site overlooking the Ottauquechee (Abnaki translated Bright Water) River with views sweeping from west & Killington Peak to the valley leading to Woodstock a few miles east. Surrounded by 47 acres of fields & forest and sheltered from nor'easter storms the farm is the gateway to e

$3,300,000

4 beds4 baths5,000 sq ft

1279 Old Bridgewater Hill Rd, Bridgewater Corners, VT 05035

Splendid views • 47 acres • 47.24 acre lot

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
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

$389,000

3 beds2 baths1,488 sq ft

447 Elm St, Chester, VT 05143

Attached garage • Barn • Natural light

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Windsor County, VT:
Nestled on 102 acres in Bethel, Vermont, this property offers the perfect blend of privacy, natural beauty, and functionality. Rolling pastures, wooded trails, and breathtaking Green Mountain views create a serene backdrop for everyday living or a weekend retreat. The land is well-suited for equestrian or hobby farming pursuits, featuring multiple open fields, a four-stall run-in barn, and a larger barn for storage, equipment, or livestock. With trails weaving through the acreage, it is ideal for horseback riding, hiking, skiing, or simply exploring your own private sanctuary. At the heart of the estate is a welcoming home that combines rustic Vermont character with modern comfort. A vaulte

$949,000

5 beds3 baths2,807 sq ft

157 Dartt Hill Rd, Bethel, VT 05032

Green mountain views • 102 acre lot • 4 garage spots

Property at 18 Elm St, Norwich, VT 05055, 5 beds, 3.5 baths

$1,365,000

5 beds3.5 baths3,925 sq ft

18 Elm St, Norwich, VT 05055

Property at 5518 VT Route 12, Barnard, VT 05031, 6 beds, 4.5 baths

$1,999,000

6 beds4.5 baths7,619 sq ft

5518 VT Route 12, Barnard, VT 05031

Property at 78 Division St, Hartford, VT 05088, 2 beds, 2 baths

$339,000

2 beds2 baths1,451 sq ft

78 Division St, Hartford, VT 05088

Property at 7873 Pomfret Rd, North Pomfret, VT 05053, 3 beds, 1.5 baths

$434,500

3 beds1.5 baths1,582 sq ft

7873 Pomfret Rd, North Pomfret, VT 05053

Property at 2475 Little Hollow Rd, Randolph, VT 05060, 3 beds, 2.5 baths

$599,900

3 beds2.5 baths1,835 sq ft

2475 Little Hollow Rd, Randolph, VT 05060

Property at 2706 E Woodstock Rd, Woodstock, VT 05091, 4 beds, 3.5 baths

$1,750,000

4 beds3.5 baths5,000 sq ft

2706 E Woodstock Rd, Woodstock, VT 05091

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 86 Main St, Ludlow, VT 05149, 11 beds, 10 baths

$1,350,000

11 beds10 baths6,069 sq ft

86 Main St, Ludlow, VT 05149

Property at 303 Woodbury Rd Unit 6/3/59, Springfield, VT 05156, 3 beds, 2 baths

$847,000

3 beds2 baths2,034 sq ft

303 Woodbury Rd Unit 6/3/59, Springfield, VT 05156

Property at 513 Giddings St, North Springfield, VT 05150, 5 beds, 3 baths

$325,000

5 beds3 baths2,963 sq ft

513 Giddings St, North Springfield, VT 05150

Property at 222 River St, Bethel, VT 05032, 3 beds, 2 baths

$215,000

3 beds2 baths2,121 sq ft

222 River St, Bethel, VT 05032

Property at 158 Macintosh Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$399,000

3 beds2 baths2,446 sq ft

158 Macintosh Hill Rd, Bethel, VT 05032

Property at 1134 Route 106, Reading, VT 05062, 5 beds, 2.5 baths

$745,000

5 beds2.5 baths2,717 sq ft

1134 Route 106, Reading, VT 05062

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 2 Pond St, Ludlow, VT 05149, 4 beds, 1 bath

$299,000

4 beds1 bath1,554 sq ft

2 Pond St, Ludlow, VT 05149

Property at 6852 US Route 4, Bridgewater, VT 05034, 3 beds, 2 baths

$449,000

3 beds2 baths1,489 sq ft

6852 US Route 4, Bridgewater, VT 05034

Property at 35 Stevens Rd, Cavendish, VT 05142, 4 beds, 3 baths

$695,000

4 beds3 baths3,100 sq ft

35 Stevens Rd, Cavendish, VT 05142

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 454 Gidding St, North Springfield, VT 05150

$410,000

— beds— baths3,950 sq ft

454 Gidding St, North Springfield, VT 05150

Property at 3 Mace Hill Rd, Hartland, VT 05048, 6 beds, 3 baths

$425,000

6 beds3 baths2,243 sq ft

3 Mace Hill Rd, Hartland, VT 05048

Property at 32 Reed St, Springfield, VT 05156

$169,000

— beds— baths1,662 sq ft

32 Reed St, Springfield, VT 05156

Property at 61 Academy Cir, South Woodstock, VT 05071, 6 beds, 5 baths

$3,500,000

6 beds5 baths5,433 sq ft

61 Academy Cir, South Woodstock, VT 05071

Property at 29-31 High St, Ludlow, VT 05149, 6 beds, 3 baths

$595,000

6 beds3 baths3,325 sq ft

29-31 High St, Ludlow, VT 05149

Property at 325 Cemetery Rd, West Windsor, VT 05089, 4 beds, 2 baths

$1,325,000

4 beds2 baths2,554 sq ft

325 Cemetery Rd, West Windsor, VT 05089

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 101 Mount Vernon St, Springfield, VT 05156, 5 beds, 2 baths

$250,000

5 beds2 baths1,728 sq ft

101 Mount Vernon St, Springfield, VT 05156

Property at 31 Huntington Pl Unit 1,2 & 3, Rochester, VT 05767, 6 beds, 6 baths

$899,000

6 beds6 baths5,497 sq ft

31 Huntington Pl Unit 1,2 & 3, Rochester, VT 05767

Property at 13 Hawthorn St, Hartford, VT 05001, 8 beds, 4 baths

$489,000

8 beds4 baths3,483 sq ft

13 Hawthorn St, Hartford, VT 05001

Property at 85 Main St #101, Ludlow, VT 05149, 2 beds, 2 baths

$375,000

2 beds2 baths900 sq ft

85 Main St #101, Ludlow, VT 05149

Property at 165 N Main St, Rochester, VT 05767, 3 beds, 2 baths

$339,000

3 beds2 baths2,224 sq ft

165 N Main St, Rochester, VT 05767

Property at 41 Lawrence Hill Rd, Weston, VT 05161, 7 beds, 6 baths

$799,000

7 beds6 baths4,642 sq ft

41 Lawrence Hill Rd, Weston, VT 05161

Property at 18 Oak Chapel Rd, Bridgewater Corners, VT 05035, 3 beds

$239,000

3 beds— baths1,984 sq ft

18 Oak Chapel Rd, Bridgewater Corners, VT 05035

Property at 3 Olney St, North Springfield, VT 05150

$410,000

— beds— baths2,381 sq ft

3 Olney St, North Springfield, VT 05150

Property at 55 Horseshoe Ave, Hartford, VT 05001, 2 beds, 2 baths

$419,000

2 beds2 baths1,832 sq ft

55 Horseshoe Ave, Hartford, VT 05001

Property at 108 Main St, Ludlow, VT 05149, 5 beds, 2 baths

$650,000

5 beds2 baths2,947 sq ft

108 Main St, Ludlow, VT 05149

Property at 52 Upper Rd, Bridgewater, VT 05035, 7 beds, 6 baths

$799,000

7 beds6 baths5,028 sq ft

52 Upper Rd, Bridgewater, VT 05035

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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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