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.
For sale
$2,380,000
14 Hillside Ave, Winchester, MA 01890
4beds
3,881sqft
Single Family Residence
Built in 1870
0.28 Acres Lot
$2,305,000 Zestimate®
$613/sqft
$-- HOA
What's special
- 16 days |
- 1,364 |
- 77 |
Zillow last checked:
Listing updated:
Listed by:
Rebecca Huang 617-888-0018,
William Raveis R.E. & Home Services 617-322-3933
Source: MLS PIN,MLS#: 73541163
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Level: Second
Bedroom 2
- Level: Second
Bedroom 3
- Level: Second
Bedroom 4
- Level: Basement
Bedroom 5
- Level: First
Primary bathroom
- Features: Yes
Bathroom 1
- Level: Second
Bathroom 2
- Level: Second
Bathroom 3
- Level: Second
Dining room
- Level: First
Family room
- Level: First
Kitchen
- Level: First
Living room
- Level: First
Heating
- Central, Electric
Cooling
- Central Air, Heat Pump
Appliances
- Included: Electric Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator
- Laundry: First Floor, Electric Dryer Hookup, Washer Hookup
Features
- Bonus Room, Wine Cellar
- Flooring: Vinyl, Hardwood
- Basement: Full,Finished
- Number of fireplaces: 2
Interior area
- Total structure area: 3,881
- Total interior livable area: 3,881 sqft
- Finished area above ground: 2,615
- Finished area below ground: 1,266
Property
Parking
- Total spaces: 10
- Parking features: Detached, Paved Drive, Off Street
- Garage spaces: 1
- Uncovered spaces: 9
Features
- Patio & porch: Deck
- Exterior features: Deck
Lot
- Size: 0.28 Acres
Details
- Parcel number: M:005 B:0269 L:0,895722
- Zoning: RDB
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Victorian,Italianate
- Property subtype: Single Family Residence
Materials
- Foundation: Stone
Condition
- Year built: 1870
Utilities & green energy
- Electric: Circuit Breakers
- Sewer: Public Sewer
- Water: Public
- Utilities for property: for Electric Range, for Electric Oven, for Electric Dryer, Washer Hookup
Community & HOA
Community
- Features: Park, Public School
HOA
- Has HOA: No
Location
- Region: Winchester
Financial & listing details
- Price per square foot: $613/sqft
- Tax assessed value: $1,500,400
- Annual tax amount: $16,639
- Date on market: 6/24/2026
Estimated market value
$2,305,000
$2.19M - $2.42M
$6,275/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/24/2026 | Listed for sale | $2,380,000+78.9%$613/sqft |
Source: MLS PIN #73541163 Report a problem | ||
| 8/21/2025 | Sold | $1,330,000-11.3%$343/sqft |
Source: MLS PIN #73362145 Report a problem | ||
| 5/19/2025 | Price change | $1,499,000-6.3%$386/sqft |
Source: MLS PIN #73362145 Report a problem | ||
| 5/7/2025 | Price change | $1,599,000-3.1%$412/sqft |
Source: MLS PIN #73362145 Report a problem | ||
| 4/21/2025 | Listed for sale | $1,650,000$425/sqft |
Source: MLS PIN #73362145 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $16,639 +5.8% | $1,500,400 +8% |
| 2024 | $15,734 +1.9% | $1,388,700 +6.2% |
| 2023 | $15,437 +4.7% | $1,308,200 +11% |
| 2022 | $14,741 +2.8% | $1,178,300 +5.4% |
| 2021 | $14,344 +3.6% | $1,118,000 |
| 2020 | $13,852 +10.9% | $1,118,000 +8.3% |
| 2019 | $12,496 +3.4% | $1,031,900 +4.1% |
| 2018 | $12,080 +2% | $991,000 +2.8% |
| 2017 | $11,843 +7.3% | $964,400 +2.1% |
| 2016 | $11,033 +3.3% | $944,600 +7.4% |
| 2015 | $10,678 +7.5% | $879,600 +12.1% |
| 2014 | $9,932 +0.5% | $784,500 +1.4% |
| 2013 | $9,880 +1.8% | $773,700 |
| 2012 | $9,710 +3.7% | $773,700 |
| 2011 | $9,362 +4.1% | $773,700 -1% |
| 2010 | $8,994 +2.1% | $781,400 |
| 2009 | $8,806 +3.6% | $781,400 -2.8% |
| 2008 | $8,496 +4.6% | $803,800 +2.3% |
| 2007 | $8,120 +2.3% | $786,100 +2.7% |
| 2006 | $7,940 +4.1% | $765,700 +4.6% |
| 2005 | $7,630 +0.6% | $732,200 +9.9% |
| 2004 | $7,582 +2.7% | $666,300 +2.7% |
| 2003 | $7,381 +6.4% | $648,600 +3.4% |
| 2002 | $6,936 +48.5% | $627,100 +65.4% |
| 2000 | $4,671 -5.6% | $379,200 +12.2% |
| 1999 | $4,948 | $338,000 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
See how much you could borrow to make a competitive offer.
Climate risks
Neighborhood: 01890
Nearby schools
GreatSchools rating
- 9/10Lincoln Elementary SchoolGrades: K-5Distance: 0.2 mi
- 8/10McCall Middle SchoolGrades: 6-8Distance: 0.2 mi
- 10/10Winchester High SchoolGrades: 9-12Distance: 0.5 mi
Schools provided by the listing agent
- Elementary: Lincoln
- Middle: Mccall Middle
- High: Winchester Hs
Source: MLS PIN. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Massachusetts
- Middlesex County
- Winchester
- 01890
- 14 Hillside Ave
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