OFFER DEADLINE TUESDAY JUNE 9, 12PM. Beautifully appointed 5BR, 2 full/2 half bath home with 3,136 sq ft of thoughtfully designed living space on a flat, fully fenced .34 acre lot. Renovated kitchen with quartz countertops and luxury appliances. Expansive and bright living room with custom built-ins, window seating, and gas fireplace. The main living level also offers 3 spacious bedrooms and a serene primary suite with a walk-in closet and private en suite bath. Fully refreshed entry-level offers another bedroom, includes a custom mudroom off the 2-car attached garage, half bath, and laundry room. Completed with an oversized media room with walkout access. Generous, manicured yard with expanded patio--perfect for everyday living and entertaining outdoors. New systems, flexible layout, abundant natural light, and thoughtful updates throughout. Extra outdoor storage with included shed. Minutes from the Middlesex Fells Reservation, top-rated schools, and vibrant downtown Winchester.
Est. $5,420 per month, based on comparable rentals
Sale and tax history for 22 Hollywood Rd
Sale History
Tax History
Date
Event
Price
MLS PIN #73527768
Jul 13, 2026
Sold
$2,150,000
$686/sq ft
Jun 17, 2026
Pending
—
Jun 10, 2026
Contingent
—
Jun 1, 2026
Listed
$1,999,000
$637/sq ft
MLS PIN #72053194
Nov 3, 2016
Sold
$1,200,000
$383/sq ft
Aug 23, 2016
Pending
—
Aug 15, 2016
Listed
$1,150,000
$367/sq ft
+17
Love living near the city but want a yard? This spacious 5 bedroom, 2 full, 2 half bath home in Winchester, is a must see! Located perfectly in a quiet neighborhood with a beautiful fenced in backyard, this home offers plenty of space and privacy. The spacious living room and beautifully renovated kitchen are ideal for intimate gatherings for all your friends and family. This house showcases immaculate hardwood floors, 2 fireplaces, granite countertops, an island in the kitchen and stainless steel appliances. Upstairs you will find 4 generously sized bedrooms, inclusive of the master bedroom and bath. Just steps down to the lower level, you will find another bedroom and a fully finished basement, inclusive of an entertainment room with convenient access to the large backyard. You will be able to enjoy a cookout on the patio with friends and family, while the kids have plenty of room to play. This house also contains a 2 car garage and a large paved driveway.
Public Records
May 23, 2008
Sold
$940,000
$300/sq ft
MLS PIN #70716614
May 23, 2008
Listing Removed
—
May 22, 2008
Sold
$940,000
$300/sq ft
Apr 29, 2008
Contingent
—
Mar 18, 2008
Listing Removed
—
Feb 25, 2008
Listed
$969,000
$309/sq ft
Extravagant traditional 4 level/multi-level located in one of the most desirable neighborhoods in Winchester, the East Hills.This home has been fully renovatd & features a 25x16 two floor addition,custom Brookhaven cherry kit w/3 pendant lights over island,tanbrown granite counter tops & full back splash, stainless appliances & cherry Bosch dishwasher,recessed lightg,lower level media/billiard rm w/surround sound,new baths,systms,roof,gutters,pella windows,stylish entry foyer & great yard!
Public Records
Dec 31, 1991
Sold
$296,500
$95/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$18,886 (+11.7%)
$1,022,000 + $681,000
$1,703,000
2023
$16,902 (−0.6%)
$949,000 + $655,000
$1,604,000
2022
$17,006 (+8.4%)
$766,500 + $592,900
$1,359,400
2021
$15,694 (+6.7%)
$638,800 + $584,400
$1,223,200
2020
$14,703 (+9.0%)
$602,300 + $584,400
$1,186,700
2019
$13,487 (+2.1%)
$529,300 + $584,400
$1,113,700
2018
$13,208 (+9.2%)
$499,100 + $584,400
$1,083,500
2017
$12,098 (+10.6%)
$469,900 + $515,300
$985,200
2016
$10,935 (+4.2%)
$469,900 + $466,300
$936,200
2015
$10,490 (+6.4%)
$427,100 + $437,000
$864,100
2014
$9,855 (−0.9%)
$355,900 + $422,500
$778,400
2013
$9,940 (+10.2%)
$355,900 + $422,500
$778,400
2012
$9,018 (+3.7%)
$355,900 + $362,700
$718,600
2011
$8,695
$355,900 + $362,700
$718,600
2010
$8,687 (+2.1%)
$381,400 + $373,300
$754,700
2009
$8,505
$381,400 + $373,300
$754,700
Public record
Beds
3
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
0.34 Acres
Year renovated
—
Sq. Ft.
3,136
Year built
1962
Style
Single Family Residential
County
Middlesex County
APN
3789630S
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 20, 2026.
Property details
Parking
Parking Information
Has Garage
Has Open Parking
# of Garage Spaces: 2
# of Covered Spaces: 2
Open Parking Spaces: 4
Parking Spaces: 6
AttachedGarageYN: Yes
Parking Features: Attached, Garage Door Opener, Paved Drive, Paved
Laundry Features: Exterior Access, Electric Dryer Hookup, Washer Hookup
Fireplace Information
Has Fireplace
# of Fireplaces (Total): 2
Fireplace Features: Living Room
Appliances
Appliances: Gas Water Heater, Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Plumbed For Ice Maker
Utilities: for Gas Range, for Gas Oven, for Electric Dryer, Washer Hookup, Icemaker Connection, Outdoor Gas Grill Hookup
Sewer: Public Sewer
Water Source: Public
Electric: 200+ Amp Service
Heating & Cooling
Has Heating
Has Cooling
Heating: Forced Air, Baseboard, Heat Pump, Natural Gas
Cooling: Central Air, Heat Pump
Location
School Information
Elementary School: Lincoln
Middle Or Junior School: Mccall
High School: Winchester
Location Information
Directions: Highland Ave to Pierrepont Rd, left onto Hollywood Rd
UnparsedAddress: 22 Hollywood Rd, Winchester MA 01890
Community Information
Senior CommunityYN: No
Community Features: Public Transportation, Pool, Tennis Court(s), Park, Golf, Medical Facility, Bike Path, Conservation Area, House of Worship, Public School
Public facts
Beds: 3
Baths: 3.0
Sq. Ft.: 3,136
Stories: 2.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1962
Year Renovated: —
County: Middlesex County
APN: 3789630S
Home facts updated by county records on Aug 20, 2026
Other
Miscellaneous Information
Heat Zones: 3
Listing Information
Exclusions: Wine And Wine Fridge Garage Excluded
StandardStatus: Closed
Around this home
Schools
Lincoln Elementary School
Public K-5 • Assigned • 0.8mi
9/10
McCall Middle School
Public 6-8 • Assigned • 0.8mi
9/10
Winchester High School
Public 9-12 • Assigned • 1.1mi
10/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
2/10 Fire Factor
0.15% chance of being in a wildfire in next 30 years
5/10 Heat Factor
7 hot days expected this year, 14 days in 30 years
Wind Factor
We're working on getting current and accurate wind risk information for this home.
Air Factor
We're working on getting current and accurate air risk information for this home.
Provided by First Street
Historical weather
Winchester, MA • 01890
Average low and high temperatures (°F)
34
20
36
21
51
32
60
40
69
51
80
61
85
67
80
60
75
57
64
46
53
36
39
24
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
87/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in Winchester. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.7 hrs
5.8 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.86M – $2.25M
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