Recently Sold Homes in Windsor County, VT

451 homes

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SOLD NOV 13, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Don’t miss this opportunity to own a move-in ready home in a peaceful neighborhood! Enjoy the ease of single-level living with laundry on the main floor, while the full basement provides excellent potential for additional finished space. The sellers have already added a fenced backyard, perfect for children, pets, and outdoor enjoyment. Conveniently located near Chester, North Springfield, Rockingham, and I-91, this home offers both comfort and accessibility. Come see if it’s the perfect fit for you!

$210,000 Last sold price

3 beds1 bath1,008 sq ft

257 Hillside Rd, Springfield, VT 05156

SOLD SEP 9, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
This charming 1900s home is ideally situated in the heart of Ludlow Village, just 0.5 miles from the Okemo Base Lodge and only 0.1 miles to restaurants and shopping. Tastefully appointed with high ceilings and large windows, the home is filled with natural light throughout. Offering 5 bedrooms and 3 baths, there’s plenty of room for family and guests. The spacious layout offers multiple areas for entertaining, including a relaxing hot tub on the porch and a private, level backyard — the perfect spot to gather around a fire and enjoy the stars. A large two-story barn adds even more value and potential. Whether you're envisioning additional living space, a guest suite, or a separ

$498,100 Last sold price

5 beds3 baths2,431 sq ft

56 Andover St, Ludlow, VT 05149

SOLD OCT 17, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Back on Market and now listed BELOW appraised value! Charming Dutch Colonial just moments from the hospital! This adorable 2-bedroom, 1-bath home is perfect for first-time buyers or those looking to downsize. Located on a quiet side street, you’ll enjoy the peaceful setting with the convenience of nearby amenities. The main level offers a cozy living room and a combined kitchen/dining area, while both bedrooms and the full bath are tucked upstairs. A heated back porch lets you enjoy the outdoors year-round—ideal for morning coffee, a reading nook, or extra flex space. A one-car garage adds convenience and additional storage, and furnishings are negotiable, making your move even

$193,000 Last sold price

2 beds1 bath942 sq ft

37 Coolidge Rd, Springfield, VT 05156

SOLD SEP 5, 2025

$340,000 Last sold price

3 beds2 baths1,500 sq ft

672 County Rd, Windsor, VT 05089

SOLD SEP 22, 2025

ABOUT THIS HOME
Recently Sold Home in Windsor County, VT:
Situated on a peaceful corner double lot, this beautifully updated home combines modern comfort with timeless charm. A bright, spacious mudroom welcomes you inside and leads to a dining area ideal for both everyday meals and holiday gatherings. The adjoining kitchen features a warm butcher-block island, custom cabinetry, under-cabinet lighting, and quality finishes that blend style with functionality. The inviting living room offers a comfortable space for relaxing or entertaining, with a sliding barn door leading to a stylish guest bath. The primary suite provides a private retreat with a generous walk-in closet, soaking tub, and convenient laundry chute. Upstairs, two additional bedrooms

$389,000 Last sold price

3 beds2 baths1,196 sq ft

62 Circle Dr, Chester, VT 05143

Property at 234 Harvard St, Springfield, VT 05156, 3 beds, 1 bath

$215,000 Last sold price

3 beds1 bath1,556 sq ft

234 Harvard St, Springfield, VT 05156

Property at 31 Maple St, Windsor, VT 05089, 3 beds, 1.5 baths

$215,000 Last sold price

3 beds1.5 baths1,900 sq ft

31 Maple St, Windsor, VT 05089

Property at 2510 E Hill Rd, Chester, VT 05143, 3 beds, 2.5 baths

$598,000 Last sold price

3 beds2.5 baths2,264 sq ft

2510 E Hill Rd, Chester, VT 05143

Property at 229 Bradley Hill Rd, Norwich, VT 05055, 5 beds, 4.5 baths

$1,400,000 Last sold price

5 beds4.5 baths4,424 sq ft

229 Bradley Hill Rd, Norwich, VT 05055

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

$427,500 Last sold price

4 beds2 baths1,700 sq ft

4 Twine Hill Rd, Ludlow, VT 05149

Property at 181 Meadow Hawk Rd, Plymouth, VT 05056, 6 beds, 5 baths

$980,000 Last sold price

6 beds5 baths4,192 sq ft

181 Meadow Hawk Rd, Plymouth, VT 05056

Property at 2110 Lynds Hill Rd, Plymouth, VT 05056, 4 beds, 2.5 baths

$503,000 Last sold price

4 beds2.5 baths1,674 sq ft

2110 Lynds Hill Rd, Plymouth, VT 05056

Property at 2579 VT Route 100, Plymouth, VT 05056, 2 beds, 1 bath

$225,000 Last sold price

2 beds1 bath864 sq ft

2579 VT Route 100, Plymouth, VT 05056

Property at 392 Gully Rd, Woodstock, VT 05091, 2 beds, 2 baths

$798,000 Last sold price

2 beds2 baths1,308 sq ft

392 Gully Rd, Woodstock, VT 05091

Property at 13 Slayton Ter, Woodstock, VT 05091, 3 beds, 2 baths

$684,000 Last sold price

3 beds2 baths1,550 sq ft

13 Slayton Ter, Woodstock, VT 05091

Property at 40 Pomfret Rd, Woodstock, VT 05091, 3 beds, 1.5 baths

$629,500 Last sold price

3 beds1.5 baths1,650 sq ft

40 Pomfret Rd, Woodstock, VT 05091

Property at 4945 South Rd, South Woodstock, VT 05071, 5 beds, 3.5 baths

$1,850,000 Last sold price

5 beds3.5 baths3,502 sq ft

4945 South Rd, South Woodstock, VT 05071

Property at 2 High St, Woodstock, VT 05091, 3 beds, 3 baths

$400,000 Last sold price

3 beds3 baths1,600 sq ft

2 High St, Woodstock, VT 05091

Property at 28 Webster Rd, Hartland, VT 05048, 3 beds, 2.5 baths

$650,000 Last sold price

3 beds2.5 baths2,230 sq ft

28 Webster Rd, Hartland, VT 05048

Property at 86 Webster Rd, Hartland, VT 05048, 3 beds, 1 bath

$243,000 Last sold price

3 beds1 bath940 sq ft

86 Webster Rd, Hartland, VT 05048

Property at 17 Route 12, Hartland, VT 05048, 3 beds, 2.5 baths

$475,000 Last sold price

3 beds2.5 baths2,152 sq ft

17 Route 12, Hartland, VT 05048

Property at 643 VT Route 12, Hartland, VT 05048, 2 beds, 1 bath

$250,000 Last sold price

2 beds1 bath1,076 sq ft

643 VT Route 12, Hartland, VT 05048

Property at 841 Farrar Rd, Chester, VT 05143, 3 beds, 1 bath

$190,000 Last sold price

3 beds1 bath1,322 sq ft

841 Farrar Rd, Chester, VT 05143

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

$350,000 Last sold price

4 beds3.5 baths2,710 sq ft

491 Farrar Rd, Chester, VT 05143

Property at 1470 Flamstead Rd, Chester, VT 05143, 2 beds, 1 bath

$359,000 Last sold price

2 beds1 bath803 sq ft

1470 Flamstead Rd, Chester, VT 05143

Property at 284 Flamstead Rd, Chester, VT 05143, 3 beds, 1.5 baths

$178,000 Last sold price

3 beds1.5 baths960 sq ft

284 Flamstead Rd, Chester, VT 05143

Property at 1937 Green Mountain Tpke, Chester, VT 05143, 2 beds, 2 baths

$550,000 Last sold price

2 beds2 baths1,812 sq ft

1937 Green Mountain Tpke, Chester, VT 05143

Property at 1502 Popple Dungeon Rd, Chester, VT 05143, 3 beds, 4 baths

$910,000 Last sold price

3 beds4 baths3,739 sq ft

1502 Popple Dungeon Rd, Chester, VT 05143

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

$210,000 Last sold price

1 bed1 bath528 sq ft

106 Hall Rd, Chester, VT 05143

Property at 1436 Route 103, Chester, VT 05143, 3 beds, 2 baths

$165,000 Last sold price

3 beds2 baths1,544 sq ft

1436 Route 103, Chester, VT 05143

Property at 230 Kevadus Cir, Chester, VT 05143, 3 beds, 1 bath

$275,000 Last sold price

3 beds1 bath894 sq ft

230 Kevadus Cir, Chester, VT 05143

Property at 87 Kevadus Cir, Chester, VT 05143, 3 beds, 1 bath

$229,000 Last sold price

3 beds1 bath840 sq ft

87 Kevadus Cir, Chester, VT 05143

Property at 643 Main St, Proctorsville, VT 05153

$355,000 Last sold price

— beds— baths5,984 sq ft

643 Main St, Proctorsville, VT 05153

Property at 110 Spaulding Rd Unit G-3, Cavendish, VT 05142, 2 beds, 2.5 baths

$430,000 Last sold price

2 beds2.5 baths1,445 sq ft

110 Spaulding Rd Unit G-3, Cavendish, VT 05142

Property at 126 Parker Ave, Proctorsville, VT 05153, 3 beds, 1 bath

$234,000 Last sold price

3 beds1 bath1,288 sq ft

126 Parker Ave, Proctorsville, VT 05153

Property at 109 High St, Cavendish, VT 05142, 3 beds, 2 baths

$330,000 Last sold price

3 beds2 baths1,798 sq ft

109 High St, Cavendish, VT 05142

Property at 2949 Route 131, Cavendish, VT 05142, 2 beds, 1 bath

$291,000 Last sold price

2 beds1 bath1,052 sq ft

2949 Route 131, Cavendish, VT 05142

Property at 996 Cavendish Gulf Rd, Cavendish, VT 05142, 2 beds, 2 baths

$299,000 Last sold price

2 beds2 baths1,526 sq ft

996 Cavendish Gulf Rd, Cavendish, VT 05142

Property at 142 Brandon Mountain Rd, Rochester, VT 05767, 3 beds, 2 baths

$356,000 Last sold price

3 beds2 baths2,092 sq ft

142 Brandon Mountain Rd, Rochester, VT 05767

Property at 199 Pine Gap Rd, Rochester, VT 05767, 2 beds

$60,100 Last sold price

2 beds— baths500 sq ft

199 Pine Gap Rd, Rochester, VT 05767

Property at 1093 Middle Hollow Rd, Rochester, VT 05767, 4 beds, 2 baths

$395,000 Last sold price

4 beds2 baths1,656 sq ft

1093 Middle Hollow Rd, Rochester, VT 05767

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Recently Sold Homes in Windsor County

There are currently 451 recently sold 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 104 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 21 2025 on the search page

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