14 Hillside Ave Winchester, MA 01890
Winchester AreaEstimated payment $14,018/month
Highlights
- Wine Cellar
- Colonial Architecture
- Wood Flooring
- Lincoln Elementary School Rated A
- Deck
- 4-minute walk to Manchester Field
About This Home
Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester's highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester's most sought-after neighborhoods.
Open House Schedule
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Sunday, July 19, 202612:00 to 1:30 pm7/19/2026 12:00:00 PM +00:007/19/2026 1:30:00 PM +00:00Add to Calendar
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $16,639
Year Built
- Built in 1870
Lot Details
- 12,057 Sq Ft Lot
- Property is zoned RDB
Parking
- 1 Car Detached Garage
- Driveway
- 9 Open Parking Spaces
- Off-Street Parking
Home Design
- Colonial Architecture
- Italianate Architecture
- Victorian Architecture
- Stone Foundation
Interior Spaces
- 2 Fireplaces
- Wine Cellar
- Bonus Room
- Finished Basement
- Basement Fills Entire Space Under The House
Kitchen
- Oven
- Range
- Dishwasher
- Disposal
Flooring
- Wood
- Vinyl
Bedrooms and Bathrooms
- 4 Bedrooms
- Primary bedroom located on second floor
Laundry
- Laundry on main level
- Washer and Electric Dryer Hookup
Schools
- Lincoln Elementary School
- Mccall Middle School
- Winchester High School
Utilities
- Central Heating and Cooling System
- 2 Cooling Zones
- 2 Heating Zones
- Heat Pump System
- Electric Water Heater
Additional Features
- Deck
- Property is near schools
Listing and Financial Details
- Assessor Parcel Number M:005 B:0269 L:0,895722
Community Details
Overview
- No Home Owners Association
Recreation
- Park
Map
Tax History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $16,639 | $1,500,400 | $964,300 | $536,100 |
| 2024 | $15,734 | $1,388,700 | $895,500 | $493,200 |
| 2023 | $15,437 | $1,308,200 | $826,600 | $481,600 |
| 2022 | $14,741 | $1,178,300 | $723,300 | $455,000 |
| 2021 | $14,344 | $1,118,000 | $663,000 | $455,000 |
| 2020 | $13,852 | $1,118,000 | $663,000 | $455,000 |
| 2019 | $12,496 | $1,031,900 | $576,900 | $455,000 |
| 2018 | $12,080 | $991,000 | $549,300 | $441,700 |
| 2017 | $11,843 | $964,400 | $549,300 | $415,100 |
| 2016 | $11,033 | $944,600 | $549,300 | $395,300 |
| 2015 | $10,678 | $879,600 | $499,400 | $380,200 |
| 2014 | $9,932 | $784,500 | $417,600 | $366,900 |
Property History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 06/24/2026 06/24/26 | For Sale | $2,380,000 | +78.9% | $613 / Sq Ft | |
| 08/21/2025 08/21/25 | Sold | $1,330,000 | -11.3% | $511 / Sq Ft | View Prior Sale |
| 07/03/2025 07/03/25 | Pending | -- | -- | -- | |
| 05/19/2025 05/19/25 | Price Changed | $1,499,000 | -6.3% | $575 / Sq Ft | |
| 05/07/2025 05/07/25 | Price Changed | $1,599,000 | -3.1% | $614 / Sq Ft | |
| 04/21/2025 04/21/25 | For Sale | $1,650,000 | -- | $633 / Sq Ft |
Purchase History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Quit Claim Deed | $1,330,000 | -- | |
| Personal Reps Deed | -- | None Available |
Mortgage History
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $931,000 | New Conventional | |
| Closed | $1,633,950 | Adjustable Rate Mortgage/ARM | |
| Previous Owner | $1,633,950 | Adjustable Rate Mortgage/ARM |
Source: MLS Property Information Network (MLS PIN)
MLS Number: 73541163
APN: WINC-000005-000269
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
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.
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