Windsor County, VT homes for sale & real estate

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ABOUT THIS HOME
Windsor County, VT Homes for Sale
Imagine living in an 1806 home on a Vermont green. Located in the heart of the Green Mountains in the quaint town of Rochester, along the scenic Route 100 corridor. The property is currently a classic Vermont Inn with a chef-owned restaurant and tavern with lovely accommodations. Easily refurnished for private use. The home sits atop the Rochester Green. The village features galleries, shops, and seasonal recreation venues all within walking distance. Prominently featured in the town is the Ridgeline Outdoor Collective which provides backcountry trail opportunities for skiers, hikers, and mountain bikers. As you walk out the front door of the home the first thing you see is the picturesque

$795,000

6 beds7.5 baths4,744 sq ft

19 Huntington Pl, Rochester, VT 05767

Green mountains • Rochester green • In-law quarters

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Welcome to your Woodstock affordable retreat! This inviting, end-unit, two-level townhouse in the sought-after Heritage Condominium community is nestled on a dead-end road just minutes west of the historic village of Woodstock. This bright 856 sq/ft two-level home offers an open-concept first floor with a carpeted living/dining area warmed by Empire gas heat (plus electric backup). From this space, step through a newer sliding door to a private deck overlooking landscaped, level grounds on 7 acres of shared land. The kitchen is light-filled and efficient, ideal for everyday living. Hardwood hallway and stairs with dual handrails lead to the second-floor loft, a versatile space with a newer

$230,000

1 bed1 bath856 sq ft

42 Heritage Condo Way Unit 14D, Woodstock, VT 05091

Private deck • Landscaped grounds • Attic storage

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Light, bright one bedroom unit on the 1st floor of the Georgian building at Silver Brook Common. 801 sq ft! Recent improvements include new refrigerator, a/c unit, ceiling fan, and window blinds. Condo dues include your heat, hot water, water, sewer, trash service, landscaping, and snow plowing! Laundry room in lower level of the building. Walking distance to Advance Transit bus stop. Just 3 miles to the Dartmouth campus, Hanover shopping, etc! Subject to Silver Brook Common Association rules. Buyers charged $1000 transfer fee at closing. There is a $1100 special assessment scheduled for 2026 for exterior painting of the building.

$225,000

1 bed1 bath801 sq ft

46A Barrister Dr #205, Hartford, VT 05001

One bedroom unit • Window blinds • New refrigerator

VIDEO TOUR

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Welcome to this Okemo Mountain home located just a short walk to the slopes! Thoughtfully designed and lovingly maintained by its original owners, this 5-bedroom home offers space, comfort, and the perfect location for year-round enjoyment. Step inside to an open foyer with a convenient half bath and office area, leading into a bright main living space. The open-concept kitchen, dining, and living room is ideal for entertaining. The kitchen features a large island, a walk-in pantry, and access to the attached garage. Two glass sliders allow natural light and open to an expansive south-facing deck. Upstairs, the primary bedroom features a vaulted ceiling and a private 3/4 bath with a custom-

$1,250,000

5 beds3.5 baths3,652 sq ft

53 Ponus Rd, Ludlow, VT 05149

Open-concept kitchen • Okemo mountain home • Open foyer

ABOUT THIS HOME
Windsor County, VT Homes for Sale
This nicely laid out Two family plus carriage house has great potential! With key updates like updated roofing and double paned vinyl windows in the second floor unit. The carriage house boasts much potential with new siding materials on sight and currently the interior is being worked on for a renter that is already in place.

$126,000

6 beds3 baths2,377 sq ft

6-8 Crescent St, Springfield, VT 05156

Updated roofing • New siding materials • 0.33 acre lot

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 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 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 143 Spoonerville Rd, Springfield, VT 05150, 3 beds, 2 baths

$369,000

3 beds2 baths1,320 sq ft

143 Spoonerville Rd, Springfield, VT 05150

Property at 333 Music Mountain Rd, Stockbridge, VT 05772, 3 beds, 2 baths

$715,000

3 beds2 baths2,542 sq ft

333 Music Mountain Rd, Stockbridge, VT 05772

Property at 7 Common St, Springfield, VT 05156, 8 beds, 15 baths

$379,000

8 beds15 baths4,936 sq ft

7 Common St, Springfield, VT 05156

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 3019 Popple Dungeon Rd, Chester, VT 05143, 1 bed, 1 bath

$169,000

1 bed1 bath200 sq ft

3019 Popple Dungeon Rd, Chester, VT 05143

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 760 E Ash Rd, Plymouth, VT 05056, 4 beds, 3.5 baths

$715,000

4 beds3.5 baths2,654 sq ft

760 E Ash Rd, Plymouth, VT 05056

Property at 254/256 Qtr. I Jackson Gore Inn, Ludlow, VT 05149, 1 bed, 2 baths

$72,000

1 bed2 baths775 sq ft

254/256 Qtr. I Jackson Gore Inn, Ludlow, VT 05149

Property at 33 Mountain Ave, Woodstock, VT 05091, 2 beds, 3.5 baths

$1,295,000

2 beds3.5 baths2,280 sq ft

33 Mountain Ave, Woodstock, VT 05091

Property at 402 Marsh Family Rd, Hartford, VT 05047, 2 beds, 2.5 baths

$399,000

2 beds2.5 baths2,332 sq ft

402 Marsh Family Rd, Hartford, VT 05047

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 1011 Quechee Hartland Rd, Hartford, VT 05059, 3 beds, 1.5 baths

$440,000

3 beds1.5 baths1,460 sq ft

1011 Quechee Hartland Rd, Hartford, VT 05059

Property at 115 Prior Rd, Cavendish, VT 05142, 3 beds, 2.5 baths

$795,000

3 beds2.5 baths2,128 sq ft

115 Prior Rd, Cavendish, VT 05142

Property at 3914 South Rd, Woodstock, VT 05071, 4 beds, 3 baths

$725,000

4 beds3 baths3,584 sq ft

3914 South Rd, Woodstock, VT 05071

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 185 Beans Bridge Rd, Rochester, VT 05767, 3 beds, 3 baths

$519,000

3 beds3 baths2,736 sq ft

185 Beans Bridge Rd, 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 4351 Vermont RT 11 W, Chester, VT 05143, 2 beds, 1 bath

$149,900

2 beds1 bath1,120 sq ft

4351 Vermont RT 11 W, Chester, VT 05143

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

$859,000

2 beds3 baths2,250 sq ft

60 Spencer Hollow Rd, Springfield, VT 05156

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 238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149, 2 beds, 2 baths

$95,000

2 beds2 baths1,025 sq ft

238 Q1 Jackson Gore Inn Unit 238 Q1, Ludlow, VT 05149

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

$995,000

4 beds2 baths4,144 sq ft

1607 Massey Rd, Springfield, VT 05156

Property at 26 Mt Peg Rd Unit B, Woodstock, VT 05091, 3 beds, 3.5 baths

$995,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit B, Woodstock, VT 05091

Property at 26 Mt Peg Rd Unit C, Woodstock, VT 05091, 3 beds, 3.5 baths

$995,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit C, Woodstock, VT 05091

Property at 26 Mt Peg Rd Unit A, Woodstock, VT 05091, 3 beds, 3.5 baths

$1,195,000

3 beds3.5 baths2,592 sq ft

26 Mt Peg Rd Unit A, Woodstock, VT 05091

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Average home prices near Windsor County, VT

Cities

Enfield homes for sale
$415,000
Norwich homes for sale
Quechee homes for sale
$499,000
Hartland homes for sale
$882,500
White River Junction homes for sale
$485,000
Killington Village homes for sale
$345,000
Chester homes for sale
$477,000
Lebanon homes for sale
$539,000
Rutland homes for sale
$269,000
Woodstock homes for sale
$1,095,000
Ludlow homes for sale
$585,000
Claremont homes for sale
$320,000
Randolph homes for sale
$529,000
Hanover homes for sale
$699,500
Windsor homes for sale
$180,000

Counties

Hillsborough County homes for sale
$549,900
Chittenden County homes for sale
$550,000
Merrimack County homes for sale
$499,450

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)

$435,000

+10.4% YoY | Oct 2025

1 year
3 year
5 year

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

Location

Data

Oct 2025

Growth

% YoY

Windsor County, VT

$435,000

+10.4%

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

See more home buying guides

Popular Markets in Vermont

Burlington homes for sale
$549,450
Stowe homes for sale
$1,150,000
Woodstock homes for sale
$1,095,000
Montpelier homes for sale
$350,000
Brattleboro homes for sale
$360,000
South Burlington homes for sale
$666,130
Shelburne homes for sale
$549,900
Waterbury homes for sale
$424,500
Rutland homes for sale
$269,000
Manchester homes for sale
$1,269,000
Ludlow homes for sale
$585,000
Barre homes for sale
$279,000
Middlebury homes for sale
$482,500
Bennington homes for sale
$272,000
Norwich homes for sale
$0

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 Wed Dec 10 2025 on the search page

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