2 Hillside Ave, Winchester, MA 01890
Property image
Property image
OFF MARKET

$1,829,600

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,672 sqft (on 0.25 acres)

2 Hillside Ave, Winchester, MA 01890

Est. Refi. Payment $10,895/mo*
Refinance Your Home
Currently Off Market - Sold Jan 10, 2024 for $1,600,000

Home Value

Trulia Estimate
$1.83M
Since last month
Decreased$19K (-1%)
Since last year
Increased$39K (+2.2%)
Since last sale
Increased$230K (+14.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +52% in the last 10 years
MonthEstimated value
2026
August 2026$1.83M
August 2026$1.83M
July 2026$1.85M
June 2026$1.86M
May 2026$1.88M
April 2026$1.87M
March 2026$1.88M
February 2026$1.82M
January 2026$1.78M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
178 Mystic Valley Pkwy, Winchester, MA
0.11
Single-Family Home
$1,770,000
09/12/25
3
2.5
2,850
77 Washington St, Winchester, MA
0.14
Single-Family Home
$1,700,000
10/16/25
5
3.5
2,718
263 Highland Ave, Winchester, MA
0.13
Single-Family Home
$1,574,500
03/30/26
4
3
3,343
8 Felsdale Close, Winchester, MA
0.44
Single-Family Home
$1,930,000
01/09/26
4
2.5
3,658
30 Prospect St, Winchester, MA
0.27
Single-Family Home
$2,450,000
12/16/25
4
3
2,519
6 Davey Ln, Winchester, MA
0.22
Single-Family Home
$2,250,000
09/02/26
4
3
4,210
14 Rangeley Rdg, Winchester, MA
0.43
Single-Family Home
$1,500,000
08/14/26
3
2
2,387
32 Oak St, Winchester, MA
0.50
Single-Family Home
$1,375,000
01/23/26
4
3
2,652
46 Church St, Winchester, MA
0.44
Single-Family Home
$1,965,000
01/27/26
4
3.5
3,475
4 Sargent Rd, Winchester, MA
0.68
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
10-10 Winthrop St #A, Winchester, MA 01890
0.04
-
4
1.5
2,057
Off Market
189 Mystic Valley Pkwy, Winchester, MA 01890
0.05
$2,432,700
6
2.5
3,543
Off Market
13 Winthrop St, Winchester, MA 01890
0.02
$1,269,600
4
2
3,443
Off Market
195 Mystic Valley Pkwy, Winchester, MA 01890
0.05
$1,493,700
4
2
2,897
Off Market
6 Francis Circuit #6, Winchester, MA 01890
0.07
-
2
2
1,540
Off Market
178 Mystic Valley Pkwy, Winchester, MA 01890
0.11
$1,815,100
3
2.5
2,850
Off Market
26 Crescent Rd, Winchester, MA 01890
0.07
$1,503,300
3
2.5
1,680
Off Market
77 Washington St, Winchester, MA 01890
0.14
$1,749,500
5
3.5
2,718
Off Market
18 Myrtle St #18, Winchester, MA 01890
0.12
$914,400
2
1
1,420
Off Market
117 Mount Vernon St, Winchester, MA 01890
0.14
$1,370,300
3
2.5
2,141
Off Market
263 Highland Ave, Winchester, MA 01890
0.13
$1,574,500
4
3
3,343
Recently Sold

Local Information

  • Map ViewExplore the area around 2 Hillside Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1875
0.25 acre lot
2,672 sqft
$685/sqft
Garage

About this House

Lovely Colonial Revival in pristine condition, located in one of Winchester's most desirable neighborhoods. Close to schools, library, train, downtown and Middlesex Fells. Enter the home through a charming arched porch offering sunset views. Extensively updated, this home features high ceilings, abundant light and classic period details-stained glass window, bullseye moldings, decorative trim and HW floors. The 1st floor open concept floor plan includes a living room with gas fireplace, dining room, kitchen and half bath. Three light filled bedrooms, an office and full bath complete the 2nd floor. The 3rd floor features a private ensuite bedroom with sitting area. The lower-level offers a family room, 2nd office, half bath, laundry and exterior door. The spacious corner lot features a partially fenced yard, mature perennial plantings, majestic beech tree, 2-car garage, paved driveway for 6 cars and rear deck. Enjoy this beautiful home so close to all that Winchester has to offer.
2 Hillside Ave, Winchester, MA 01890 is a 4 bedroom, 4 bathroom, 2,672 sqft single-family home built in 1875. It last sold for $1,600,000 on Jan 10, 2024 (7% above the $1,495,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,829,600, with a rent estimate of $7,131/month.
Last check for updates: about 15 hours ago
Listed by Ann Basmaji, (617) 957-5878
Barrett Sotheby's International Realty, (781) 729-7900
Anne Spry, (781) 405-4730
Bought with: Karen S. Garrett, (732) 995-9482, Better Homes and Gardens Real Estate - The Shanahan Group, (781) 729-9030
Source: MLS PIN, MLS#73155199

Home Details for 2 Hillside Ave

Interior Features

Interior Details
Basement: Full,Finished,Walk-Out Access,Interior Entry,Sump PumpNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Bathroom 1, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 2672 Square Feet
Appliances & Utilities
Utilities: for Gas Range, for Gas Oven, for Gas Dryer, Washer HookupAppliances: Gas Water Heater, Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, ENERGY STAR Qualified Dryer, ENERGY STAR Qualified Washer, Range HoodDishwasherDisposalLaundry: Flooring - Stone/Ceramic Tile,In Basement,Gas Dryer Hookup,Washer HookupMicrowaveRefrigerator
Heating & Cooling
Heating: Central,Baseboard,Electric Baseboard,Hot Water,Natural Gas,OtherHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living RoomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers, 200+ Amp Service
Windows, Doors, Floors & Walls
Window: Insulated Windows, Storm Window(s), ScreensDoor: Insulated Doors, Storm Door(s), French DoorsFlooring: Wood, Tile, Hardwood, Pine, Flooring - Stone/Ceramic Tile, Flooring - Hardwood
Levels, Entrance, & Accessibility
Accessibility: NoFloors: Wood, Tile, Hardwood, Pine, Flooring Stone Ceramic Tile, Flooring Hardwood

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, Deck - WoodFencing: FencedExterior: Porch, Deck - Wood, Rain Gutters, Professional Landscaping, Sprinkler System, Decorative Lighting, Screens, Fenced Yard, Stone WallFoundation: Stone, Brick/MortarSprinkler System
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 6No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 8Parking: Detached,Garage Door Opener,Storage,Garage Faces Side,Paved Drive,Off Street,Driveway,Paved
Frontage
Waterfront: Lake/Pond, Walk to, 1/2 to 1 Mile To Beach, Beach Ownership(Public)Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: 81.00

Property Information

Year Built
Year Built: 1875
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial Revival
Building
Construction Materials: FrameNot Attached PropertyDoes Not Include Home Warranty
Property Information
Parcel Number: 895246

Price & Status

Price
List Price: $1,495,000
Status Change & Dates
Off Market Date: Thu Sep 21 2023

Active Status

MLS Status: Sold

Location

Direction & Address
City: Winchester
School Information
Elementary School: LincolnJr High / Middle School: MccallHigh School: Whs

Building

Building Area
Building Area: 2672 Square Feet

Community

Community Features: Public Transportation, Shopping, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Private School, Public School, T-Station, SidewalksNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.25 acres

Offer

Contingencies: Pending P&S

Energy

Energy Efficiency Features: Thermostat

Miscellaneous

BasementMls Number: 73155199

Additional Information

Public TransportationShoppingTennis Court(s)ParkWalk/Jog TrailsGolfMedical FacilityBike PathConservation AreaHighway AccessHouse of WorshipPrivate SchoolPublic SchoolT-StationSidewalks

Price and Tax history

DateEventPrice
Jan 10, 2024
Source: MLS PIN #73155199
Sold
$1,600,000
Sep 17, 2023
Source: MLS PIN #73155199
Contingent
$1,495,000
Sep 13, 2023
Source: MLS PIN #73155199
Listed For Sale
$1,495,000
Mar 24, 2021
Source: N/A
ListingRemoved
Apr 30, 2013
Source: N/A
Sold
$880,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.47M
$62.83KMoM
Sale-to-List Price
101.9%
0.2%MoM
Price per sq ft
$574
$3MoM
Available listings
64
13MoM

Around this home

What Locals Say about Winchester

At least 93 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say yards are well-kept

  • 87 % Say people would walk alone at night

  • 85 % Say parking is easy

  • 79 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say it's walkable to restaurants

  • 77 % Say kids play outside

  • 75 % Say streets are well-lit

  • 74 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say there's wildlife

  • 66 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 64 % Say it's quiet

  • 54 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diana P.
    "Winchester is the cutest town, perfect for families. There is Town Say, and Enka, and everything is very family oriented. We even have great pubs/restaurants as well as sub shops, Greek food, nail salons, anything you could want in a home town!"
    7
    Flag
  • Dominic
    "Phenomenal public school system beginning from Kindergarten and extremely welcoming to new residents transferring in."
    0
    Flag
  • Stacie
    "Very family oriented. Not a great neighborhood if you don’t have children. Great, easy commute into the city. Not enough good restaurants that aren’t overpriced though. "
    0
    Flag
  • Yjchoi7
    "Very safe neighborhood.there are often summer events on the common. Teenagers can take train into Boston area fairly easily as there are two stops within Winchester. Fells is a great place for summer walks. "
    2
    Flag
  • Luis B.
    "perfect for my family It is livable stores Closer to me Barbershop computer store Restaurants I will love to buy a house in this area "
    2
    Flag
  • Yjchoiyjchoi
    "It’s very quiet and safe generally. Yet it’s close to Boston and Cambridge city life within a few stops of the commuter from Winchester. "
    0
    Flag
  • Tara
    "I have lived in this neighborhood for 25 years. I love it. Everybody is friendly and kind. The crime is minimal and it’s very quiet. "
    2
    Flag
  • Katie41287
    "I’m not afraid to walk home at 11pm, the town is clean and has plenty of events around town, the people are friendly and it is near public transportation. "
    1
    Flag
  • Anna S.
    "Excellent school Easy commute to Boston Downtown Great parks and pond nearby"
    0
    Flag
  • tod g.
    "Lovely town with easy access to Boston and easy getaway to northern New England."
    0
    Flag
  • jfrancis6
    "Family community built around three streets that form a circle that only has traffic of residents. The area borders the Town of Winchester forest that is great for walks and snow shoeing in winter. All homes are large and attract families were children can safely play and bike in the neighborhood. Many homes have residents who grow up in the neighborhood as children and returned to raise their families. A short walk 4/10 of a mile to train station for those who work in Boston a trip that takes 12 minutes with only one stop. Schools in Winchester are among the best in Massachusetts, a primary attraction to the Town. The Town center is only one mile away and has an addition train station there as well. The Mystic lakes are just beyond the train station with a Town beach and boating opportunities. The Town also borders a 2500 acre forest known as the Fells consisting of the Town water supply and miles of hiking or mountain biking."
    0
    Flag
  • marta3467
    "Can see kids playing ball in street; people walking their dog and Horn Pond and several nice restaurants all within walking distance"
    1
    Flag

LGBTQ Local Legal Protections

The property listing data and information 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 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 set forth herein.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

Frequently asked questions about 2 Hillside Ave

  • What is 2 Hillside Ave estimated to be worth?
    Trulia's estimated value for 2 Hillside Ave in Winchester, MA is $1,829,600.
  • What is the price history for 2 Hillside Ave?
    2 Hillside Ave in Winchester, MA last sold for $1,600,000 in January 2024.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $1.47M. That is up $62.83K from the prior month.
  • Does 2 Hillside Ave have air conditioning?
    Yes, 2 Hillside Ave in Winchester, MA has air conditioning.
  • Does 2 Hillside Ave have laundry facilities?
    Yes, 2 Hillside Ave in Winchester, MA has laundry facilities.

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