Windsor County, VT homes for sale & real estate

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ABOUT THIS HOME
Windsor County, VT Homes for Sale
Fully furnished condo nestled in a small quiet community just 5 minutes from "Historic Woodstock". Super location! This unit is in very good condition- first floor comprised of a den//bedroom with pocket doors for added privacy and an adjacent 3/4 bath. Spacious living room anchored by a newer propane fireplace to curl up with a book on a cold winter day. A couple of steps down takes you into a renovated kitchen with small eating area overlooking the back deck. Tall ceilings allow this space to feel spacious with an abundance of natural light. Second floor consisted of a very large primary bedroom with ample closets and sitting area. A full bathroom and the second bedroom is a p

$450,000

2 beds3 baths2,091 sq ft

85 Townhouse Way #14, Woodstock, VT 05091

Walk out patio • Renovated kitchen • New slider doors

FOR SALE BY OWNER

ABOUT THIS HOME
Windsor County, VT Homes for Sale
All BRAND NEW APPLIANCES including the furnace and washer dryer, attic as well for storage, close to the school district and down town Springfield! Pets allowed max 2- dogs must weigh under 35 and below unless it is a therapy dog.

$275,000

3 beds2 baths1,234 sq ft

4 Pine Brook Ln Apt B6, North Springfield, VT 05150

Brand new appliances • Attic for storage • Built 1998

ABOUT THIS HOME
Windsor County, VT Homes for Sale
The ideal property for a SKI CLUB! 7 bedrooms! 6 bathrooms! An immaculate, professionally appointed commercial kitchen! Spacious common rooms and dining areas! A classic and inviting bar/lounge area! An interior with the true Vermont style appeal of exposed beams, wood floors and a stone faced fireplace! This inviting New England style building is perfectly situated midway between world class skiing at Killington and the numerous year round amenities of shopping, dining and cultural events of historic Woodstock Village! The highly visible and well known property is easily accessed year round off a well maintained paved road. Conveniently separated within this highly versatile complex is a c

$749,000

7 beds8 baths7,428 sq ft

52 Upper Rd, Bridgewater, VT 05035

Commercial kitchen • Year round amenities • Bar lounge area

ABOUT THIS HOME
Windsor County, VT Homes for Sale
The Dewey House joins timeless elegance with contemporary convenience. Situated on a quiet road adjacent to the Quechee Gorge waterfall in the charming town of Quechee, this property offers easy access to I-89, I-91, and Route 4. Nearby walking trails and direct water access lend themselves to outdoor pursuits, while the views from the house and its decks over the mill pond and hills create the perfect place to visit with friends, relax to the soothing sounds of the waterfall, or watch for eagles and hot air balloons. Whether you intend to run this as a private home, a short-term rental, or a B & B, you'll love being on this gracious property. Enter through the front door to an expansiv

$1,275,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Expansive foyer • Views over the hills • Walking trails

ABOUT THIS HOME
Windsor County, VT Homes for Sale
Looking for a Summer Project? Put your ambition and skills to work in this unfinished, single-story 30' x 24'+ wood framed shell constructed with beefy rough-cut lumber. Electric service provided by Green Mountain Power (meter on building). Public water service to, and public sewage disposal from, are available on site. Currently, there is no electrical wiring, plumbing pipes, nor fixtures, but materials on site included. Built on top of an existing 1942-vintage foundation where a previous dwelling burned back in 1982. Basement has a concrete floor with higher-than-typical height clearance, with rear exterior door. There is an opening from main floor into basement, but NO STAIRS in place

$50,000

Studio1 bath— sq ft

178 Church St, Bethel, VT 05032

Public water service • Composite siding • Level lot

Property at 1787 Route 100 N, Ludlow, VT 05149, 3 beds, 4 baths

$535,000

3 beds4 baths2,727 sq ft

1787 Route 100 N, Ludlow, VT 05149

Property at 919 VT Route 100 S, Rochester, VT 05767, 3 beds, 1 bath

$339,000

3 beds1 bath1,144 sq ft

919 VT Route 100 S, Rochester, VT 05767

Property at 924 Okemo Ridge Rd Unit S 11, Ludlow, VT 05149, 7 beds, 6.5 baths

$4,775,000

7 beds6.5 baths6,624 sq ft

924 Okemo Ridge Rd Unit S 11, 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 136 Store Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$130,000

3 beds2 baths1,359 sq ft

136 Store Hill Rd, Bethel, VT 05032

Property at 320 Okemo Trailside Ext Unit 36E, Ludlow, VT 05149, 3 beds, 3.5 baths

$1,100,000

3 beds3.5 baths1,796 sq ft

320 Okemo Trailside Ext Unit 36E, Ludlow, VT 05149

Property at 281 Okemo Trailside Ext Unit 30C, Ludlow, VT 05149, 4 beds, 2.5 baths

$795,000

4 beds2.5 baths1,842 sq ft

281 Okemo Trailside Ext Unit 30C, Ludlow, VT 05149

Property at 1354 Vermont Route 100, Stockbridge, VT 05772, 3 beds, 2.5 baths

$850,000

3 beds2.5 baths4,088 sq ft

1354 Vermont Route 100, Stockbridge, VT 05772

Property at 66 Duttonsville School Dr, Cavendish, VT 05142, 2.5 baths

$499,000

Studio2.5 baths7,445 sq ft

66 Duttonsville School Dr, Cavendish, VT 05142

Property at 133 Stagecoach Rd, Norwich, VT 05055, 2 beds, 1 bath

$470,000

2 beds1 bath1,144 sq ft

133 Stagecoach Rd, Norwich, VT 05055

Property at 879 E Ash Rd #5, Plymouth, VT 05056, 4 beds, 3.5 baths

$499,000

4 beds3.5 baths2,436 sq ft

879 E Ash Rd #5, Plymouth, VT 05056

Property at 39 Wallis View Ln, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,250,000

4 beds3.5 baths4,111 sq ft

39 Wallis View Ln, Ludlow, VT 05149

Property at 101 Okemo Trailside Ext Unit 41C, Ludlow, VT 05149, 3 beds, 2.5 baths

$669,000

3 beds2.5 baths1,842 sq ft

101 Okemo Trailside Ext Unit 41C, Ludlow, VT 05149

Property at 726 E Ash Rd, Plymouth, VT 05056, 6 beds, 7.5 baths

$850,000

6 beds7.5 baths5,588 sq ft

726 E Ash Rd, Plymouth, VT 05056

Property at 51 E Ash Rd, Plymouth, VT 05056, 7 beds, 8.5 baths

$2,650,000

7 beds8.5 baths13,410 sq ft

51 E Ash Rd, Plymouth, VT 05056

Property at 224 Quent Phelan Rd, Ludlow, VT 05149, 4 beds, 2 baths

$800,000

4 beds2 baths2,228 sq ft

224 Quent Phelan Rd, Ludlow, VT 05149

Property at 40 Union St, White River Junction, VT 05001, 4 beds, 2 baths

$329,000

4 beds2 baths1,373 sq ft

40 Union St, White River Junction, VT 05001

Property at 41 Parkhurst Rd Unit L-4, Proctorsville, VT 05153, 3 beds, 3.5 baths

$599,000

3 beds3.5 baths2,023 sq ft

41 Parkhurst Rd Unit L-4, Proctorsville, VT 05153

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

$875,000

3 beds3.5 baths2,584 sq ft

26 Mt Peg Rd Unit B, Woodstock, VT 05091

Property at 196 Cowdrey Outlook, Bethel, VT 05032, 3 beds, 1 bath

$1,595,000

3 beds1 bath1,708 sq ft

196 Cowdrey Outlook, Bethel, VT 05032

Property at 1589 Main St, Cavendish, VT 05142, 10 beds, 10 baths

$1,400,000

10 beds10 baths7,153 sq ft

1589 Main St, Cavendish, VT 05142

Property at 292 Okemo Trailside Ext Unit 34E, Ludlow, VT 05149, 4 beds, 2.5 baths

$1,100,000

4 beds2.5 baths1,842 sq ft

292 Okemo Trailside Ext Unit 34E, Ludlow, VT 05149

Property at 51 High St, Ludlow, VT 05149, 5 beds, 2.5 baths

$729,000

5 beds2.5 baths2,018 sq ft

51 High St, Ludlow, VT 05149

Property at 191 Moon Shadow Dr Unit M19, Ludlow, VT 05149, 5 beds, 6.5 baths

$3,250,000

5 beds6.5 baths5,728 sq ft

191 Moon Shadow Dr Unit M19, Ludlow, VT 05149

Property at 3341 Trebo Rd, Chester, VT 05143, 4 beds, 2.5 baths

$535,000

4 beds2.5 baths2,464 sq ft

3341 Trebo Rd, Chester, VT 05143

Property at 299 Latham Works Ln, White River Junction, VT 05001, 3 beds, 1 bath

$369,440

3 beds1 bath1,569 sq ft

299 Latham Works Ln, White River Junction, VT 05001

Property at 257 Solitude Rd Unit N-102, Ludlow, VT 05149, 2 beds, 2.5 baths

$675,000

2 beds2.5 baths1,166 sq ft

257 Solitude Rd Unit N-102, 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 76 Goldthwaite Rd, Chester, VT 05143, 4 beds, 3 baths

$1,200,000

4 beds3 baths3,308 sq ft

76 Goldthwaite Rd, Chester, VT 05143

Property at 109 Park Row, Rochester, VT 05767, 5 beds, 3.5 baths

$319,000

5 beds3.5 baths2,200 sq ft

109 Park Row, Rochester, VT 05767

Property at 46 Fowler Rd Unit O205, Ludlow, VT 05149, 3 beds, 2 baths

$730,000

3 beds2 baths1,296 sq ft

46 Fowler Rd Unit O205, Ludlow, VT 05149

Property at 122 Quechee Hollow Ln Unit 4A, Quechee, VT 05059, 1 bed, 1 bath

$225,000

1 bed1 bath720 sq ft

122 Quechee Hollow Ln Unit 4A, Quechee, VT 05059

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

$294,000

2 beds1 bath750 sq ft

29 Markham Ln, Weston, VT 05161

Property at 4 Pine Brook Ln, North Springfield, VT 05150, 3 beds, 2 baths

$275,000

3 beds2 baths1,234 sq ft

4 Pine Brook Ln, North Springfield, VT 05150

Property at 35 White Loop Unit B101, Ludlow, VT 05149, 2 beds, 2 baths

$645,000

2 beds2 baths1,044 sq ft

35 White Loop Unit B101, Ludlow, VT 05149

Property at 65 Giddings St, North Springfield, VT 05150, 8 beds, 7 baths

$699,000

8 beds7 baths5,003 sq ft

65 Giddings St, North Springfield, VT 05150

Viewing page 11 of 13

Average home prices near Windsor County, VT

Cities

Enfield homes for sale
$374,900
Norwich homes for sale
$1,165,000
Quechee homes for sale
$375,000
White River Junction homes for sale
$429,500
Springfield homes for sale
$259,000
Chester homes for sale
$390,000
Lebanon homes for sale
$486,500
Rutland homes for sale
$299,000
Plainfield homes for sale
$549,999
Woodstock homes for sale
$975,000
Ludlow homes for sale
$599,000
Claremont homes for sale
$349,900
Randolph homes for sale
$335,000
Hanover homes for sale
$1,045,000
Windsor homes for sale
$335,000

Counties

Grafton County homes for sale
$499,000
Hillsborough County homes for sale
$529,950
Merrimack County homes for sale
$532,000

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)

$518,839

+29.7% YoY | Sep 2026

1 year
3 year
5 year

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

Location

Data

Sep 2026

Growth

% YoY

Windsor County, VT

$518,839

+29.7%

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
$525,000
Stowe homes for sale
$1,061,950
Woodstock homes for sale
$975,000
Montpelier homes for sale
$430,000
South Burlington homes for sale
$683,500
Brattleboro homes for sale
$289,000
Waterbury homes for sale
$442,500
Rutland homes for sale
$299,000
Ludlow homes for sale
$599,000
Shelburne homes for sale
$594,500
Waitsfield homes for sale
$515,000
Middlebury homes for sale
$499,000
Manchester homes for sale
$995,000
Bennington homes for sale
$257,000
Norwich homes for sale
$1,165,000

Copyright 2026 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 Sat Oct 24 2026 on the search page

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