Kayla Brown
REALTOR®
BEDS3
BATHS2 full 1 partial
SQUARE FEET3,094
MLS#5108534
STATUSActive
PROPERTY TYPEResidential - Single Family
SUBDIVISIONWindward South
SCHOOLTaconic and Green Regional
Listing Courtesy of:
Four Seasons Sothebys Intl Realty
Agency Phone: 802-362-4551
Associate Name: David Halligan
Property Description
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.
Property Features
Property Type: Residential - Single Family
Basement: Concrete, Concrete Floor, Crawl Space, Full, Insulated, Interior Stairs, Storage Space, Unfinished
Basement: Yes
Cooling: Central AC
Fenced: Yes
Garage: 2 car attached
Heating: Oil, Forced Air, Hot Air, In Floor
Home Style: Contemporary
Lot Size: 3.62 Acres
Roof Type: Standing Seam
Stories: 2.0
Taxes: $14,045
Year Built: 1981
Amenities
Blinds
Cedar Closet
Dining Area
Wood Fireplace
1 Fireplace
Kitchen Island
Primary BR w/ BA
Natural Light
Security
Soaking Tub
Vaulted Ceiling
Walk-in Closet
Programmable Thermostat
1st Floor Laundry
Partial Fence
Garden Space
Patio
Screened Porch
Double Pane Window(s)
Feature Descriptions
Accessibility: 1st Floor 1/2 Bathroom, 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor Hrd Surfce Flr, Grab Bars in Bathroom, Hard Surface Flooring, 1st Floor Laundry
Appliances: Dishwasher, Dryer, Microwave, Wall Oven, Gas Range, Refrigerator, Washer, Domestic Water Heater, Owned Water Heater
Baths 1/2: 1
Baths Full: 2
Color: grey
Construction: Wood Siding
Days on Site: 6
Driveway: Gravel
Electric: 200+ Amp Service, Circuit Breaker(s), Generator
Equipment: Air Conditioner, CO Detector, Security System, Smoke Detector, Standby Generator
Exterior: Wood Siding
Flood Zone: No
Flooring: Carpet, Hardwood
Foundation: Poured Concrete
Lot: Country Setting, Landscaped, Mountain View, Sloping, Subdivision, View, Wooded, Neighborhood, Rural, Private
Number of Rooms: 7
Parking: Auto Open, Driveway, Garage, Parking Spaces 6+, Unpaved, Attached
Restrictions: None
Road Frontage: 386
Roads: Dead End, Gravel, Private Road, Privately Maintained
Sewer: Septic
Sq. Ft. Above Grade Finished: 3094
Sq. Ft. Total Finished: 3094
Total Stories: 2
Water: Drilled Well
Water Access: No
Water View: No
Zoning: residential
Room Sizes
Kitchen: 15 x 11 Level - 1
Dining Room: 14 x 11 Level - 1
Living Room: 25 x 16 Level - 1
Den: 15 x 9 Level - 1
Primary Bedroom: 15 x 15 Level - 1
Bedroom: 19 x 11 Level - 2
Bedroom: 15 x 14 Level - 2
Local Schools
High School: Burr and Burton Academy
Middle School: Manchester Elementary& Middle
Elementary School: Dorset Elementary School
School District: Taconic and Green Regional
Listed By / Shown By
Listed By
Agency Name: Four Seasons Sothebys Intl Realty
Agent Name: David Halligan
Agency Phone: 802-362-4551
Shown By
Agent Name: Kayla Brown
Agent Phone: (207) 692-6175
Agency Title: Better Homes and Gardens Real Estate The Masiello Group
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Estimated Payment
$ 4,128.17 per month $2,615.04 Principal & Interest $1,170.42 Property Tax $342.71 Homeowner's Insurance
Listing data compilation and photo(s) copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data Last Updated 2026-09-13 23:33:22 
88 Windward South Road | MLS# 5108534
This single family home located at 88 Windward South Road, Dorset, VT 05251 is currently listed for sale with an asking price of $1,175,000. This property was built in 1981 and has 3 bedrooms and 2 full and 1 partial baths with 3094 sq. ft. Windward South Road is located in the Windward South subdivision within the Taconic and Green Regional school district. Search Windward South real estate on kaylabrown.masiellogrouprealestate.com today.