Luxury homes for sale & real estate in Windsor County, VT

115 homes

Sort:

Recommended

3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Sorgenfrei, or "Carefree, " was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a testament to elegant durability. From the mahogany exterior to the hand crafted front doors and custom-wrought hardware, this spacious and meticulously considered home celebrates the skill of Vermont's most talented craftspeople. The unparalleled 180 degree views over the Woodstock valley are s

$8,000,000

3 beds3.5 baths5,384 sq ft

115 Eastman Rd, South Woodstock, VT 05071

Gourmet kitchen • Mahogany exterior • 180 degree views

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Ledgewood on Okemo, a spacious condominium located in one of the most sought-after communities on Okemo Mountain. This property offers an abundance of space, featuring two en-suites and two additional bedrooms. The expansive great room opens to a large family kitchen with two breakfast bars, providing ample seating for the whole family. You'll also appreciate the private ski-in/ski-out access and the convenience of a garage. Ledgewood on Okemo truly offers a beautiful and desirable location. Visit the Okemo real estate community today. Taxes are based on current town assessment.

$995,000

4 beds3.5 baths2,585 sq ft

117 Ledgewood Rd Unit F3 w/F4 Garage, Ludlow, VT 05149

Large family kitchen • Spacious condominium • Two breakfast bars

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
New Construction in Quechee Lakes! Introducing Mountain Stream at Quechee Lakes where modern architecture meets the natural beauty of Vermont’s premier four-season resort community. With more than 200 homesites and five distinct home styles, Mountain Stream offers thoughtfully designed residences that blend contemporary comfort with timeless surroundings. Each home features open-concept layouts, soaring ceilings, abundant natural light, and high-quality finishes that reflect a commitment to both luxury and sustainability. Energy-efficient construction ensures modern living that respects the environment without compromising style. One of the signature designs, the Thistle showcases ove

$1,495,000

3 beds4.5 baths3,120 sq ft

4070 Tichenor Rd #4070, Hartford, VT 05059

New construction • Expansive windows • Open-concept layouts

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
To be built, Mountain Stream at Quechee Lakes seamlessly integrates new construction with the natural beauty of Vermont's premier four-season resort community. Offering over 200 homesites and five distinct home styles, Mountain Stream’s residences feature modern, open layouts, abundant natural light, and soaring ceilings. The exclusive designs establish a commitment to sustainable, energy-efficient living without sacrificing luxury, evident in the high-quality finishes and features. Alder, one of Mountain Stream’s five thoughtfully crafted model homes, features a clean architectural style designed to harmonize with its surroundings. Featuring large windows, it bathes every room

$1,350,000

4 beds3 baths2,277 sq ft

4074 Tichenor Rd #4074, Hartford, VT 05059

Large windows • Mountain stream • 1 acre lot

VIDEO TOUR

ABOUT THIS HOME
Luxury Home for sale in Windsor County, VT:
Escape to Moosewalk Lane, a fully furnished and equipped luxury estate in Andover, Vermont, set on 384 acres in the iconic Green Mountains. This one of a kind property offers a rare blend of seclusion, natural beauty, and timeless craftsmanship. The custom built 10,062 square foot main house features an expansive open concept design. Crafted with post and beam timber frame construction, the soaring 2 story great room includes a dramatic stone fireplace and a chef's kitchen with double appliances, a Viking 60 inch cooktop, and a wood fired pizza oven. A cozy loft and library offer peaceful spaces to curl up with a good book. A unique main level 2 bed, 2 bath primary suite is complemented by

$6,950,000

8 beds7.5 baths10,062 sq ft

3800 Weston Andover Rd, Andover, VT 05143

Historic rock walls • 384 acre lot • 6 garage spots

Property at 1104 Main St, Cavendish, VT 05142, 3 beds, 4 baths

$895,000

3 beds4 baths3,590 sq ft

1104 Main St, Cavendish, VT 05142

Property at 699 Spear Cemetery Rd, Reading, VT 05062, 5 beds, 4 baths

$1,750,000

5 beds4 baths3,862 sq ft

699 Spear Cemetery Rd, Reading, VT 05062

Property at 49 Burton Rd, Weston, VT 05161, 6 beds, 5.5 baths

$1,250,000

6 beds5.5 baths5,790 sq ft

49 Burton Rd, Weston, VT 05161

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

$1,450,000

6 beds5.5 baths4,225 sq ft

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

Property at 37 Village Center Rd #1, Ludlow, VT 05149, 4 beds, 3 baths

$1,675,000

4 beds3 baths1,884 sq ft

37 Village Center Rd #1, Ludlow, VT 05149

Property at 1300 Mountain Rd, Ludlow, VT 05149, 4 beds, 5 baths

$2,000,000

4 beds5 baths2,887 sq ft

1300 Mountain Rd, Ludlow, VT 05149

Property at 157 Thompson Rd, Chester, VT 05143, 4 beds, 2.5 baths

$1,125,000

4 beds2.5 baths2,772 sq ft

157 Thompson Rd, Chester, VT 05143

Property at 476 Salt Ash Rd, Plymouth, VT 05056, 5 beds, 6 baths

$4,850,000

5 beds6 baths9,153 sq ft

476 Salt Ash Rd, Plymouth, VT 05056

Property at 61 Academy Cir, South Woodstock, VT 05071, 6 beds, 5 baths

$3,500,000

6 beds5 baths5,433 sq ft

61 Academy Cir, South Woodstock, VT 05071

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 51 Alpine Way Unit A4, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,499,000

4 beds3.5 baths2,184 sq ft

51 Alpine Way Unit A4, Ludlow, VT 05149

Property at 1166 Route 100, Weston, VT 05161, 5 beds, 4 baths

$859,000

5 beds4 baths4,925 sq ft

1166 Route 100, Weston, VT 05161

Property at 400 Ruusunen Rd, Springfield, VT 05156, 6 beds, 4.5 baths

$3,350,000

6 beds4.5 baths5,657 sq ft

400 Ruusunen Rd, Springfield, VT 05156

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

$2,495,000

5 beds4.5 baths4,800 sq ft

248 Gird Lot Rd, Springfield, VT 05151

Property at 228 Town Farm Rd, Ludlow, VT 05149, 4 beds, 3.5 baths

$1,200,000

4 beds3.5 baths2,530 sq ft

228 Town Farm Rd, Ludlow, VT 05149

Property at 31 Huntington Pl Unit 1,2 & 3, Rochester, VT 05767, 6 beds, 6 baths

$899,000

6 beds6 baths5,497 sq ft

31 Huntington Pl Unit 1,2 & 3, Rochester, VT 05767

Property at 657 Town Farm Rd, Ludlow, VT 05149, 4 beds, 4.5 baths

$2,600,000

4 beds4.5 baths6,548 sq ft

657 Town Farm Rd, Ludlow, VT 05149

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

$2,950,000

7 beds8.5 baths13,410 sq ft

51 E Ash Rd, Plymouth, VT 05056

Property at 399 Bentley Rd Unit 7-5440, Hartford, VT 05059, 4 beds, 3 baths

$1,490,950

4 beds3 baths2,709 sq ft

399 Bentley Rd Unit 7-5440, Hartford, VT 05059

Property at 113 N Village Rd, Ludlow, VT 05149, 5 beds, 5.5 baths

$2,650,000

5 beds5.5 baths6,188 sq ft

113 N Village Rd, Ludlow, VT 05149

Property at 320 Old Bow Rd, Springfield, VT 05156, 4 beds, 4.5 baths

$997,000

4 beds4.5 baths4,009 sq ft

320 Old Bow Rd, Springfield, VT 05156

Property at 265 Depot St, Proctorsville, VT 05153, 3 beds, 2 baths

$1,600,000

3 beds2 baths3,291 sq ft

265 Depot St, Proctorsville, VT 05153

Property at 0 Mountain Rd, Ludlow, VT 05149

$2,200,000

— beds— baths— sq ft

0 Mountain Rd, Ludlow, VT 05149

Property at 0 Newton Ln #3, White River Junction, VT 05001

$998,000

— beds— baths— sq ft

0 Newton Ln #3, White River Junction, VT 05001

Property at 00 Markham Ln, Weston, VT 05161

$875,000

— beds— baths— sq ft

00 Markham Ln, Weston, VT 05161

Property at 0 Newton Ln, White River Junction, VT 05055

$998,000

— beds— baths— sq ft

0 Newton Ln, White River Junction, VT 05055

Property at 5000 VT Route 106, Reading, VT 05062

$1,789,000

— beds— baths— sq ft

5000 VT Route 106, Reading, VT 05062

Property at 458 Woodstock Rd, Woodstock, VT 05091

$1,499,000

— beds— baths— sq ft

458 Woodstock Rd, Woodstock, VT 05091

Viewing page 3 of 3

Luxury Homes for Sale in Windsor County

There are currently 115 luxury 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 105 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.

More real estate resources for Windsor County, VT

Nearby Counties

Cities

Nearby Counties with Luxury Homes

Nearby Cities with Luxury Homes

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
$549,900
Stowe homes for sale
$1,225,000
Woodstock homes for sale
$1,195,000
Montpelier homes for sale
$365,000
Brattleboro homes for sale
$375,000
South Burlington homes for sale
$636,000
Shelburne homes for sale
$549,900
Waterbury homes for sale
$450,000
Rutland homes for sale
$269,500
Manchester homes for sale
$1,284,500
Ludlow homes for sale
$592,000
Barre homes for sale
$279,000
Middlebury homes for sale
$482,500
Bennington homes for sale
$257,450
Norwich homes for sale
$1,365,000

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 Nov 28 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

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: 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, 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

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

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.