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88 Windward South Road, 
Dorset, VT 05251

$1,175,000


3

Beds


3

Baths


3,094

Sq Ft


Single Family

Active

Listed by

David Halligan

Four Seasons Sotheby'S Int'L Realty

802-362-4551

Last updated:

September 17, 2026, 04:49 AM

MLS#

5108534

Source:

PrimeMLS

About This Home

88 Windward South Road

Beautifully maintained contemporary home on 3.62 private acres with elevated westerly views of Mt. Equinox and spectacular sunsets. Designed by renown architect Deborah Berke, Dean of the Yale School of Architecture, this light-filled home offers the ease of main-level living with a first-floor primary suite, laundry, bright office, den with custom built-ins, and spacious living room with vaulted ceiling, wood-burning fireplace, and oak floors. The kitchen features a center island and Aga stove, opening to dining and living areas ideal for everyday comfort and entertaining. Upstairs are two generous guest bedrooms, abundant closets - including a cedar-lined walk-in - and a full bath. Enjoy the seasons from the screened porch or custom fieldstone patio with sitting wall and awnings. Quality features include central air, whole-house generator, security system, water filtration, standing-seam metal roof, Andersen windows, attached two-car garage, and excellent dry basement storage. Minutes to Manchester and Dorset, this private, move-in-ready property offers convenience, comfort, and enduring Vermont charm.

Home Facts

Single Family

3 Baths

3 Bedrooms

Built in 1981

Subdivision & Development:

Windward South

Price Summary

1,175,000

$379 per Sq. Ft.

MLS #:

5108534

Last Updated:

September 17, 2026, 04:49 AM

Added:

10 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

3

Bathrooms

Total Bathrooms:

3

Full Bathrooms:

2

Interior

Living Area:

3,094 Sq. Ft.


Structure

Structure

Building Area:

4,367 Sq. Ft.

Year Built:

1981


Lot

Lot Size (Sq. Ft):

157,687


Finances & Disclosures

Finances

Price:

$1,175,000

Price per Sq. Ft:

$379 per Sq. Ft.

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Copyright 2026 Prime MLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of Prime MLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated September 17, 2026

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.