Custom-built ~6,000 sq ft Colonial estate offering 5 bedrooms, 4.5 bathrooms, and panoramic hilltop views on over an acre of beautifully landscaped grounds. Ideally located on the desirable West Side of Winchester, just minutes from Vinson-Owen Elementary School. This impeccably maintained residence features a gourmet chef's kitchen with high-end appliances, oversized center island, walk-in pantry, and dining area that opens to a spacious family room with a gas fireplace and custom millwork. The main level also includes formal living and dining rooms, a private study, and an oversized mudroom with direct access to the attached three-car garage. The second level offers a luxurious primary suite with a spa-like ensuite bath, three additional bedrooms, a laundry room, and multiple well-appointed bathrooms. The finished walk-up third level serves as an ideal guest retreat or bonus living space, complete with a bedroom, full bathroom, and additional lounge area. The home offers multiple living and dining areas, a fully equipped laundry room, and abundant natural light throughout. Outside, enjoy a private patio overlooking the expansive backyard - perfect for outdoor dining, entertaining, or relaxing. Short- and long-term rentals available. Offered fully furnished or unfurnished.
Amenities
In-unit amenities
These amenities may not be available for every unit
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Internet
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Property details
Interior
Basement Information
Basement Sq. Ft: 2,005
Bathroom Information
# of Full Baths: 4
# of 1/2 Baths: 1
Heating & Cooling
Heating Type: Forced Air
Fireplace Information
# of Fireplaces: 1
Has Fireplace
Room Information
# of Rooms: 12
Exterior
Exterior Information
Physical Condition: Average
Building Style Type: Greek Revival
Construction Type: Frame
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable
Property Information
Living Sq. Ft: 5,357
Gross Sq. Ft: 9,519
# of Units: 1
# of Stories: 3
Lot Information
# of Buildings: 1
Land Sq. Ft: 47,045
Municipality Name: WINCHESTER
Acres: 1.08
Zoning Code: RDA
State Use Description: 1-FAMILY RESIDENCE
Financial
Assessor Information
Assessment Year: 2025
Public facts
Beds: 5
Baths: 4.5
Sq. Ft.: 5,357
Stories: 3.0
Lot Size: 1.08 acres
Style: Single Family Residential
Year Built: 2019
Year Renovated: —
County: Middlesex County
APN: 821337S
Home facts updated by county records on Jul 29, 2026
Sale and tax history for 186 Ridge St
Sale History
Tax History
Date
Event
Price
MLS PIN #72536934
Jun 24, 2020
Sold
$2,499,000
$466/sq ft
Aug 13, 2019
Pending
—
Jul 30, 2019
Contingent
—
Jul 18, 2019
Listed
$2,499,000
$466/sq ft
To Be Built - Beautiful new construction home located on the West Side of Town and proudly situated on over an acre lot with gorgeous views! 5 bedroom 4.5 bath, 5,820SF custom built colonial with three-car attached garage with side entrance into oversized mudroom. Main level features gourmet kitchen with high-end appliances, oversized island, dining area, adjacent family room with gas FP, custom woodwork, walk-in pantry, study, dining room & formal LR. Second level features a grand master suite, three additional beds, laundry room & finished walk-up 3rd level with guest bedroom & full bath. To be completed for Spring 2020 occupancy, option to customize today! Minutes from Vinson Owen Elementary!
Year
Property tax
Land + Additions
Assessment*
2025
$33,765 (+21.2%)
$817,100 + $2,227,500
$3,044,600
2023
$27,852 (+1.6%)
$777,100 + $2,135,200
$2,912,300
2022
$27,426 (+1.2%)
$615,500 + $1,576,800
$2,192,300
2021
$27,101 (+316.2%)
$535,500 + $1,576,800
$2,112,300
2020
$6,511 (+13.1%)
$525,500
2019
$5,758 (+4.2%)
$475,500
2018
$5,528 (−0.7%)
$453,500
2017
$5,569 (+7.0%)
$453,500
2016
$5,203 (+3.2%)
$445,500
2015
$5,044
$415,500
Around this home
Schools
Places
Transit
9/10
Vinson-Owen Elementary School
Public, PreK-5 • Assigned • 0.1mi
9/10
McCall Middle School
Public, 6-8 • Assigned • 2.1mi
10/10
Winchester High School
Public, 9-12 • Assigned • 2.2mi
Provided by GreatSchools
About West
Side
West Side, located between the Aberjona River and the Middlesex Fells Reservation, is a residential and commuter-friendly Winchester neighborhood with leafy side streets and trail-forward green space. The neighborhood’s character concentrates around the Winchester Center area at Main Street and Church Street, where independent cafes, small shops, and the commuter rhythm of the station set the pace. Community pillars include the Winchester Community Music School, the Winchester Unitarian Society’s historic campus, and the Jenks Center. Housing reads as classic New England—Colonial Revivals, Victorians, and well-kept mid-century homes—on walkable blocks with stone walls and mature trees. The Fells’ trailheads and reservoirs shape daily routines, while the river corridor adds a quieter, tucked-away geography. A short ride to the station keeps Boston-bound schedules in view without turning the streetscape into a thoroughfare.
Provided by Walk Score and Local Logic
Public facts and zoning for 186 Ridge St
Beds
5
Baths
4.5
Sq. Ft.
5,357
Stories
3
Lot Size
1.08 Acres
Style
Single Family Residential
Year Built
2019
Year Renovated
—
County
Middlesex County
APN
821337S
Home facts updated by county records on Jul 29, 2026.
Additional resources
Zoning
Working on getting current and accurate zoning information for this home.Learn more
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 98° expected this year, 15 days in 30 years
6/10 Wind Factor
50% chance of strong winds in next 30 years
3/10 Air Factor
2 unhealthy days expected this year, 3 days in 30 years
Provided by First Street
Thinking of selling?
Estimated sale price
$3.09M – $3.75M
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Listing agent: Anzor Sidamonidze (6175999109)
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.
In-unit amenities
These amenities may not be available for every unit