Windsor County, VT homes for sale & real estate

410 homes

Sort:

Recommended

1471 County Rd, Windsor, VT 05086
1471 County Rd, Windsor, VT 05086
1471 County Rd, Windsor, VT 05086
ABOUT THIS HOME
Windsor County, VT Homes for Sale
Nestled in a peaceful rural setting, this roomy 4-bedroom, 3-bathroom home offers incredible potential for those looking to create their dream country home. While the property is in need of some work, it features a generous layout and sits on a little over an acre, which allows for plenty of space to enjoy the beautiful setting. The home features hardwood floors, vinyl windows, a pellet stove, as well as nicely appointed kitchen and granite countertops. Whether you're an investor or a homeowner with a vision, this fixer upper is a rare opportunity to craft a customized living space in a serene countryside location. Showing requires 24-hour notice due to tenants, property is being sold &quot

$289,900

4 beds2.5 baths2,196 sq ft

1471 County Rd, Windsor, VT 05086

1.14 acre lot • 2 garage spots • Car-dependent

350 Lyman Batcheller Rd Unit 1C, Hartford, VT 05059
350 Lyman Batcheller Rd Unit 1C, Hartford, VT 05059
350 Lyman Batcheller Rd Unit 1C, Hartford, VT 05059
ABOUT THIS HOME
Windsor County, VT Homes for Sale
Welcome to this nicely updated 3-bedroom condo in the Salt Box village of Quechee Lakes. Ideally located within walking distance to the heart of the village, you'll enjoy easy access to the Village Green, library, and the renowned Simon Pearce restaurant and glassblowing studio. Inside, the condo features warm, beautiful wood floors and a tastefully updated kitchen, blending comfort and style. Offered fully furnished, it’s ready for you to move in and start enjoying the Quechee lifestyle immediately. A rare walk-out lower level adds valuable living space with a cozy family room and a private bedroom—perfect for guests or a quiet retreat. As part of Quechee Lakes, you’ll ha

$405,000

3 beds2 baths2,092 sq ft

350 Lyman Batcheller Rd Unit 1C, Hartford, VT 05059

$1,815 HOA • Community pool • Car-dependent

186 Mountain Vw, Chester, VT 25143
186 Mountain Vw, Chester, VT 25143
186 Mountain Vw, Chester, VT 25143
ABOUT THIS HOME
Windsor County, VT Homes for Sale
This Charming, well appointed home has much to offer! This turn key home is tucked away in a great location and neighborhood in walking distance to shops, food options and schools. The home itself has been updated and features many positives like almost all double pane windows, a recently redone paved driveway, an updated mudroom area, a metal standing seam roof, and much more. With a good size back yard and deck it is a perfect place to have family and friends over and enjoy!

$249,900

3 beds1 bath966 sq ft

186 Mountain Vw, Chester, VT 25143

0.25 acre lot • Car-dependent

358 US Route 5, Windsor, VT 05089
358 US Route 5, Windsor, VT 05089
358 US Route 5, Windsor, VT 05089
ABOUT THIS HOME
Windsor County, VT Homes for Sale
Charming Duplex in the Heart of Windsor – Ideal for Owner-Occupants or Investors! Discover a fantastic opportunity to own a versatile, income-producing duplex in the vibrant and historic town of Windsor. Perfectly suited for an owner-occupant looking to offset their mortgage with rental income—or a savvy investor seeking solid returns—this well-maintained property offers both comfort and cash flow. Each unit features 2 spacious bedrooms, 1 full bathroom, a bright living area, and a spacious kitchen, making it ideal for tenants or personal use. Separate utilities ensure ease of management and straightforward billing, while continued thoughtful maintenance enhances long-term

$325,000

4 beds2 baths2,452 sq ft

358 US Route 5, Windsor, VT 05089

0.75 acre lot • Car-dependent

3630 Vt Route 103 N, Chester, VT 05143
3630 Vt Route 103 N, Chester, VT 05143
3630 Vt Route 103 N, Chester, VT 05143
ABOUT THIS HOME
Windsor County, VT Homes for Sale
Exceptional Investment Opportunity in Chester, VT Discover this stunning, completely renovated property that beautifully combines modern amenities with unique character. Featuring two residential units. This home showcases high-quality upgrades throughout. Enjoy peace of mind with new electrical, plumbing, insulation, and energy-efficient windows. The kitchens and bathrooms have been meticulously designed, incorporating reclaimed materials that add warmth and charm to the contemporary aesthetic. In addition to the inviting residential spaces, this property includes a versatile two-story commercial area currently occupied by a successful, established business making it ideal for investors o

$650,000

3 beds3 baths4,324 sq ft

3630 Vt Route 103 N, Chester, VT 05143

2 acre lot • Car-dependent

Property at 509 Church Hl, Woodstock, VT 05091, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,150 sq ft

509 Church Hl, Woodstock, VT 05091

Property at 761 Main St, Cavendish, VT 05142, 6 beds, 2 baths

$325,000

6 beds2 baths2,518 sq ft

761 Main St, Cavendish, VT 05142

Property at 515 Shattuck Hill Rd Unit 515, 513 & 511, West Windsor, VT 05037, 6 beds, 5.5 baths

$1,597,000

6 beds5.5 baths4,225 sq ft

515 Shattuck Hill Rd Unit 515, 513 & 511, West Windsor, VT 05037

Property at 687 S Perry Rd, Barnard, VT 05091, 5 beds, 4.5 baths

$1,749,000

5 beds4.5 baths4,617 sq ft

687 S Perry Rd, Barnard, VT 05091

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

$1,485,000

5 beds4.5 baths4,424 sq ft

229 Bradley Hill Rd, Norwich, VT 05055

Property at 412 Skyland Ln, Woodstock, VT 05091, 4 beds, 4.5 baths

$7,250,000

4 beds4.5 baths5,087 sq ft

412 Skyland Ln, Woodstock, VT 05091

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

$399,000

4 beds3.5 baths2,710 sq ft

491 Farrar Rd, Chester, VT 05143

Property at 13 Overlook Dr, Springfield, VT 05156, 4 beds, 2 baths

$420,000

4 beds2 baths1,917 sq ft

13 Overlook Dr, Springfield, VT 05156

Property at 952 Scout Camp Rd, Plymouth, VT 05056, 3 beds, 2 baths

$650,000

3 beds2 baths1,200 sq ft

952 Scout Camp Rd, Plymouth, VT 05056

Property at 241 North Rd, Barnard, VT 05031, 4 beds, 2 baths

$599,000

4 beds2 baths2,306 sq ft

241 North Rd, Barnard, VT 05031

Property at 168 Thorn Apple Ln, Hartford, VT 05001, 4 beds, 4 baths

$779,000

4 beds4 baths2,912 sq ft

168 Thorn Apple Ln, Hartford, VT 05001

Property at 248 Gird Lot Rd, Weathersfield, VT 05151, 5 beds, 4.5 baths

$2,695,000

5 beds4.5 baths3,090 sq ft

248 Gird Lot Rd, Weathersfield, VT 05151

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

$640,000

3 beds2.5 baths1,835 sq ft

2475 Little Hollow Rd, Rochester, VT 05060

Property at 775 E Lake Rd, Ludlow, VT 05149, 4 beds, 3 baths

$1,700,000

4 beds3 baths4,351 sq ft

775 E Lake Rd, Ludlow, VT 05149

Property at 100 Pomfret Rd, Woodstock, VT 05091, 4 beds, 2.5 baths

$945,000

4 beds2.5 baths2,044 sq ft

100 Pomfret Rd, Woodstock, VT 05091

Property at 643 Main St, Cavendish, VT 05153

$419,000

— beds— baths5,984 sq ft

643 Main St, Cavendish, VT 05153

Property at 7511 Woodstock Rd, Hartford, VT 05059, 4 beds, 3 baths

$1,595,000

4 beds3 baths3,311 sq ft

7511 Woodstock Rd, Hartford, VT 05059

Property at 240 QII Jackson Gore Inn Unit 240 QII, Ludlow, VT 05149, 1 bath

$57,000

0 beds1 bath390 sq ft

240 QII Jackson Gore Inn Unit 240 QII, Ludlow, VT 05149

Property at 15 Hathorn Hill Ext, Woodstock, VT 05091, 4 beds, 3.5 baths

$2,199,000

4 beds3.5 baths3,564 sq ft

15 Hathorn Hill Ext, Woodstock, VT 05091

Property at 1497 Bowman Rd, Barnard, VT 05031, 5 beds, 7 baths

$3,275,000

5 beds7 baths8,249 sq ft

1497 Bowman Rd, Barnard, VT 05031

Property at 7 North St, Woodstock, VT 05091, 2 beds, 3 baths

$1,850,000

2 beds3 baths2,106 sq ft

7 North St, Woodstock, VT 05091

Property at 291 Tall Timbers Dr, Hartford, VT 05001, 2 beds, 2 baths

$119,500

2 beds2 baths924 sq ft

291 Tall Timbers Dr, Hartford, VT 05001

Property at 107 Winding Brook Ln, Hartford, VT 05001, 3 beds, 2 baths

$450,000

3 beds2 baths1,989 sq ft

107 Winding Brook Ln, Hartford, VT 05001

Property at 1140 Murphy Rd Unit 10B, Hartford, VT 05059, 3 beds, 3 baths

$615,000

3 beds3 baths2,439 sq ft

1140 Murphy Rd Unit 10B, Hartford, VT 05059

Property at 276 Connecticut River Rd, Springfield, VT 05156, 1 bed, 1 bath

$130,000

1 bed1 bath829 sq ft

276 Connecticut River Rd, Springfield, VT 05156

Property at 2334 South Rd, Woodstock, VT 05091, 3 beds, 2.5 baths

$2,200,000

3 beds2.5 baths5,422 sq ft

2334 South Rd, Woodstock, VT 05091

Property at 17 Golf Ave, Woodstock, VT 05091, 3 beds, 2.5 baths

$775,000

3 beds2.5 baths1,850 sq ft

17 Golf Ave, Woodstock, VT 05091

Property at 9671 VT Route 12, Barnard, VT 05031, 3 beds, 3 baths

$2,195,000

3 beds3 baths2,997 sq ft

9671 VT Route 12, Barnard, VT 05031

Property at 222 Park View Rd, Springfield, VT 05156, 3 beds, 2.5 baths

$535,000

3 beds2.5 baths1,933 sq ft

222 Park View Rd, Springfield, VT 05156

Property at 62 Highland Vws N, Ludlow, VT 05149, 3 beds, 3 baths

$765,000

3 beds3 baths2,247 sq ft

62 Highland Vws N, Ludlow, VT 05149

Property at 938 Stigers Rd, Andover, VT 05143, 3 beds, 3.5 baths

$1,650,000

3 beds3.5 baths2,614 sq ft

938 Stigers Rd, Andover, VT 05143

Property at 44 Watershed Rd, Bethel, VT 05032, 4 beds, 2 baths

$375,000

4 beds2 baths2,425 sq ft

44 Watershed Rd, Bethel, VT 05032

Property at 35 Depot St, Hartford, VT 05088, 4 beds, 2 baths

$435,000

4 beds2 baths2,352 sq ft

35 Depot St, Hartford, VT 05088

Property at 840 Sugar Hill Rd, Bethel, VT 05032, 3 beds, 2 baths

$829,000

3 beds2 baths2,868 sq ft

840 Sugar Hill Rd, Bethel, VT 05032

Property at 66 Union St, Windsor, VT 05089, 3 beds, 2 baths

$255,000

3 beds2 baths1,743 sq ft

66 Union St, Windsor, VT 05089

Property at 5685 VT Route 12, Barnard, VT 05031, 5 beds, 5.5 baths

$4,490,000

5 beds5.5 baths8,122 sq ft

5685 VT Route 12, Barnard, VT 05031

Viewing page 2 of 9

Average home prices near Windsor County, VT

Cities

Enfield homes for sale
$660,950
Norwich homes for sale
$1,095,000
Quechee homes for sale
$429,000
Hartland homes for sale
$589,000
White River Junction homes for sale
$423,000
Springfield homes for sale
$199,000
Chester homes for sale
$364,500
Lebanon homes for sale
$509,450
Rutland homes for sale
$286,000
Woodstock homes for sale
$1,150,000
Ludlow homes for sale
$547,000
Claremont homes for sale
$380,000
Randolph homes for sale
$427,063
Hanover homes for sale
$1,235,000
Windsor homes for sale
$255,000

Counties

Hillsborough County homes for sale
$599,900
Chittenden County homes for sale
$619,000
Merrimack County homes for sale
$549,900

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)

$455,000

+27.8% YoY | May 2025

1 year
3 year
5 year

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

Location

Data

May 2025

Growth

% YoY

Windsor County, VT

$455,000

+27.8%

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

See more home buying guides

Popular Markets in Vermont

Burlington homes for sale
$560,000
Stowe homes for sale
$1,050,000
Woodstock homes for sale
$1,150,000
Montpelier homes for sale
$481,000
Brattleboro homes for sale
$339,000
South Burlington homes for sale
$677,000
Shelburne homes for sale
$774,900
Waterbury homes for sale
$400,000
Manchester homes for sale
$1,195,000
Rutland homes for sale
$286,000
Ludlow homes for sale
$547,000
Bennington homes for sale
$284,000
Barre homes for sale
$285,000
Middlebury homes for sale
$614,000
Norwich homes for sale
$1,095,000

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 Sun Jun 15 2025 on the search page

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Become a Lender Partner

Subsidiaries

Rent.

ApartmentGuide

Bay Equity Home Loans

Title Forward

Countries

United States

Canada

Updated January 2023: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, TITLE FORWARD, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.