Windsor County, VT homes for sale & real estate

507 homes

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NEW 3 HRS AGO

$795,000

4 beds3 baths3,190 sq ft

598 E Woodstock Rd, Woodstock, VT 05091

2.94 acre lot • Garage • Built 1925

NEW 6 HRS AGOVIDEO TOUR

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Set on three peaceful acres just minutes from the historic village of Rochester, this expanded ranch offers generous living space in a lovely private setting. Amble past a historic farm along a quiet country road to the inviting homesite, perched above the White River valley. The sunny, level lot provides an ideal backdrop for gardening, recreation, and outdoor gatherings. Inside, a large open floor plan creates a perfect space for entertaining and relaxing with family and friends. The main level features a primary suite with an updated bath, a guest bedroom or office, a convenient mudroom/laundry room, and a wraparound deck for grilling, al fresco dining, or simply taking in the tranquil s

$519,000

3 beds3 baths2,736 sq ft

185 Beans Bridge Rd, Rochester, VT 05767

Wet bar • Three peaceful acres • Level lot

NEW 28 HRS AGO

ABOUT THIS HOME
Windsor County, VT Homes for Sale
1806 Brick Cape in need of new owners prepared to build equity in this wonderful treasure with 18 acres on the edge of quaint E. Bethel Village. 'AS IS' CONDITION.

$225,000

3 beds1 bath1,591 sq ft

176 Store Hill Rd, Bethel, VT 05032

18 acre lot • Built 1806

NEW 27 HRS AGO

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Almost there! This owner has taken this property to a new level. .. had the septic discovered and has a report, upgraded the electric entrance and added an EV station, laid flooring, opened up a wall for a much nicer open concept, cleaned and made into a little cottage for skiing, nature loving or just plain home. There are rain barrels for water, let nature fill them up or hire the local water company. Provision has been made for a spring in the back area. There is a seasonal stream bed next to the deck for a touch of nature. It is your turn, lift this affordable A frame to the next level. Seller has estimates for some of the upgrades. Or, use it as it is as a camp in Vermont.

$149,900

2 beds1 bath1,120 sq ft

4351 Vermont RT 11 W, Chester, VT 05143

Open concept • Ev station • Seasonal stream bed

NEW 25 HRS AGOVIDEO TOUR

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Step back in time with this charming brick Colonial home, built in 1830 and beautifully situated in the heart of Proctorsville Village. Rich in history and character, this residence offers the perfect blend of classic New England architecture and convenient village living—just steps from shops, schools, restaurants, and the village green that adds to its timeless charm. The main level welcomes you with a traditional layout featuring a spacious country kitchen, a formal dining room, and a large living room ideal for gatherings. A full bathroom on this level adds modern comfort and convenience. Upstairs, you’ll find four inviting bedrooms and a three-quarter bathroom, providing am

$249,000

4 beds2 baths2,016 sq ft

58 Depot St, Chester, VT 05153

Brick colonial home • Country kitchen • Attic space

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 27 Ash St, White River Junction, VT 05001, 4 beds, 3 baths

$499,000

4 beds3 baths2,400 sq ft

27 Ash St, White River Junction, VT 05001

Property at 51 Terrace St, Woodstock, VT 05091, 2 beds, 2 baths

$500,000

2 beds2 baths1,237 sq ft

51 Terrace St, Woodstock, VT 05091

Property at 1873 Old River Rd, White River Junction, VT 05001, 2 beds, 1 bath

$425,000

2 beds1 bath908 sq ft

1873 Old River Rd, White River Junction, VT 05001

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

$395,000

4 beds2.5 baths2,240 sq ft

215 Elm Hill St, Springfield, VT 05156

Property at 76 Colonial Dr #13, White River Junction, VT 05001, 2 beds, 1.5 baths

$239,900

2 beds1.5 baths1,072 sq ft

76 Colonial Dr #13, White River Junction, VT 05001

Property at 1928 VT. Route 131, Springfield, VT 05156, 4 beds, 1.5 baths

$825,000

4 beds1.5 baths2,200 sq ft

1928 VT. Route 131, 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 483 South St, Springfield, VT 05156, 3 beds, 1 bath

$265,000

3 beds1 bath1,716 sq ft

483 South St, Springfield, VT 05156

Property at 418 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$74,000

1 bed2 baths775 sq ft

418 Qtr. I I I Jackson Gore Inn, Ludlow, VT 05149

Property at 19 Strawberry Ln, Ludlow, VT 05149, 3 beds, 1.5 baths

$589,000

3 beds1.5 baths888 sq ft

19 Strawberry Ln, Ludlow, VT 05149

Property at 125 Redfield Proctor Rd, Hartford, VT 05059, 4 beds, 2 baths

$825,000

4 beds2 baths2,516 sq ft

125 Redfield Proctor Rd, Hartford, VT 05059

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 650 Francis Rd, Barnard, VT 05031, 2 beds, 5.5 baths

$39,000,000

2 beds5.5 baths9,950 sq ft

650 Francis Rd, Barnard, VT 05031

Property at 405 Soaring Hawk Rd, Plymouth, VT 05056, 3 beds, 2 baths

$550,000

3 beds2 baths1,728 sq ft

405 Soaring Hawk Rd, Plymouth, VT 05056

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 61 Pleasant St, Ludlow, VT 05149, 8 beds, 6 baths

$499,000

8 beds6 baths3,683 sq ft

61 Pleasant St, Ludlow, VT 05149

Property at 2769 Cloudland Rd, South Pomfret, VT 05067, 4 beds, 3.5 baths

$3,400,000

4 beds3.5 baths3,485 sq ft

2769 Cloudland Rd, South Pomfret, VT 05067

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

$599,000

5 beds3 baths2,600 sq ft

68 Passumpsic Ave, Hartford, VT 05088

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

$179,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

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

$215,000

2 beds1 bath676 sq ft

48 School St, North Springfield, VT 05150

Property at 355 Greene Rd, South Woodstock, VT 05071, 7 beds, 8.5 baths

$18,000,000

7 beds8.5 baths12,520 sq ft

355 Greene Rd, South Woodstock, VT 05071

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 184 Hazen St, White River Junction, VT 05001, 3 beds, 1.5 baths

$319,000

3 beds1.5 baths1,408 sq ft

184 Hazen St, White River Junction, VT 05001

Property at 525 Morgan Rd, Hartford, VT 05059, 2 beds, 2 baths

$390,000

2 beds2 baths1,344 sq ft

525 Morgan Rd, Hartford, VT 05059

Property at 513 Deer Brook Way Lot 16, Woodstock, VT 05091, 4 beds, 2.5 baths

$1,295,000

4 beds2.5 baths2,668 sq ft

513 Deer Brook Way Lot 16, Woodstock, VT 05091

Property at 223 Route 100 S, Ludlow, VT 05149, 5 beds, 3 baths

$295,000

5 beds3 baths3,474 sq ft

223 Route 100 S, Ludlow, VT 05149

Property at 493 Kestrell Dr, Plymouth, VT 05056, 4 beds, 3.5 baths

$657,500

4 beds3.5 baths2,126 sq ft

493 Kestrell Dr, Plymouth, VT 05056

Property at 75 Whitney Rd, Springfield, VT 05156, 3 beds, 1 bath

$239,000

3 beds1 bath1,152 sq ft

75 Whitney Rd, Springfield, VT 05156

Property at 4603 Jericho St, White River Junction, VT 05001, 4 beds, 2 baths

$499,000

4 beds2 baths1,696 sq ft

4603 Jericho St, White River Junction, VT 05001

Property at 211 Wood Rd, Hartford, VT 05059, 3 beds, 2 baths

$795,000

3 beds2 baths1,940 sq ft

211 Wood Rd, Hartford, VT 05059

Property at 77 Winding Rd, Brownsville, VT 05037, 4 beds, 2 baths

$520,000

4 beds2 baths2,380 sq ft

77 Winding Rd, Brownsville, VT 05037

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 475 Twenty Mile Stream Rd, South Reading, VT 05062, 3 beds, 3 baths

$895,000

3 beds3 baths3,920 sq ft

475 Twenty Mile Stream Rd, South Reading, VT 05062

Property at 240 Piper Hill Rd, Weston, VT 05161, 5 beds, 6.5 baths

$2,950,000

5 beds6.5 baths8,056 sq ft

240 Piper Hill Rd, Weston, VT 05161

Property at 60 Spencer Hollow Rd, Springfield, VT 05156, 2 beds, 3 baths

$899,000

2 beds3 baths2,250 sq ft

60 Spencer Hollow Rd, Springfield, VT 05156

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Average home prices near Windsor County, VT

Cities

Enfield homes for sale
$399,000
Norwich homes for sale
$639,000
Quechee homes for sale
$444,500
Hartland homes for sale
$495,000
White River Junction homes for sale
$514,500
Springfield homes for sale
$175,000
Chester homes for sale
$425,000
Lebanon homes for sale
$525,000
Rutland homes for sale
$278,000
Woodstock homes for sale
$1,195,000
Ludlow homes for sale
$564,000
Claremont homes for sale
$319,900
Randolph homes for sale
$564,000
Hanover homes for sale
$1,129,000
Windsor homes for sale
$262,750

Counties

Hillsborough County homes for sale
$560,000
Chittenden County homes for sale
$559,900
Merrimack County homes for sale
$530,000

Windsor County, VT real estate trends

All Home Types trends in Windsor County, VT

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$415,000

-7.8% YoY | Sep 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Sep 2025

Growth

% YoY

Windsor County, VT

$415,000

-7.8%

See more Windsor County, VT market insights

More to explore in Windsor County, VT

How to buy a house in Windsor County, VT

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

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Popular Markets in Vermont

Burlington homes for sale
$589,450
Stowe homes for sale
$1,175,000
Woodstock homes for sale
$1,195,000
Montpelier homes for sale
$429,500
Brattleboro homes for sale
$344,500
South Burlington homes for sale
$607,450
Shelburne homes for sale
$619,950
Waterbury homes for sale
$362,000
Rutland homes for sale
$278,000
Manchester homes for sale
$882,500
Ludlow homes for sale
$564,000
Middlebury homes for sale
$482,500
Barre homes for sale
$280,900
Bennington homes for sale
$282,000
Norwich homes for sale
$639,000

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 Oct 24 2025 on the search page

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