38 Winchester St #2, Brookline, MA 02446
Property image
Property image
OFF MARKET

$407,500

Trulia Estimate
as of Sep 9, 2026
  • 1 Bed
  • 1 Bath
  • 500 sqft

38 Winchester St #2, Brookline, MA 02446

Corey Hill

Home Highlights

Apartment
500 sqft
$815/sqft

Local Information

  • Map ViewExplore the area around 38 Winchester St #2.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Available June 1st: Charming raised first-floor condo in a professionally managed building in the heart of Coolidge Corner. This beautifully maintained unit features high ceilings, tall windows, and gorgeous hardwood floors throughout. The renovated kitchen boasts granite counters and stainless steel appliances. Enjoy excellent afternoon sun on your private rear porch with western exposure. The unit offers fantastic storage space and a stylishly updated bathroom. Unbeatable location, situated half a block from the T (Green Line), shops and restaurants. Amenities: common laundry in the building, bicycle storage and heat & hot water are included in the rent. No undergraduates and no pets.

Owner pays for heat, hot water and water. Tenant is responsible for electricity and renters insurance. No fee is due to the listing agent.
38 Winchester St #2, Brookline, MA 02446 is a 1 bedroom, 1 bathroom, 500 sqft apartment in Corey Hill. It last sold for $224,000 on May 10, 2011 (9,233% above the $2,400 asking price). More recently, it was listed as a rental in April 2026 with an asking price of $2,400 per month. That rental listing was removed on May 2, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $407,500, with a rent estimate of $2,551/month.

Home Details for 38 Winchester St #2

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
Refrigerator
Heating & Cooling
Air ConditioningCooling System: Window Unit
Levels, Entrance, & Accessibility
Floors: Hardwood, Tile

Comparable Sales for 38 Winchester St #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
97 Sewall Ave #5, Brookline, MA
0.48
Apartment
$542,500
06/30/26
1
1
650 sqft
20 Saint Paul St #2, Brookline, MA
0.48
Apartment
$400,000
10/14/25
2
1
703 sqft
56 Park Vale Ave #4, Allston, MA
0.82
Apartment
$345,000
03/31/26
1
1
470 sqft
369 Tappan St #12, Brookline, MA
0.69
Apartment
$500,000
10/17/25
1
1
678 sqft
1404 Commonwealth Ave #8, Brighton, MA
0.74
Apartment
$432,000
10/31/25
1
1
653 sqft
1564 Commonwealth Ave #6, Brighton, MA
0.83
Apartment
$350,000
07/30/26
1
1
650 sqft
21 Westbourne Ter #3, Brookline, MA
0.46
Apartment
$580,000
10/30/25
2
1
876 sqft
100 Washington St #2, Brighton, MA
0.94
Apartment
$415,000
04/03/26
1
1
600 sqft
10 Jamaicaway #28, Boston, MA
1.03
Apartment
$305,000
06/16/26
1
1
390 sqft
15 N Beacon St #910, Allston, MA
1.00
Apartment
$395,000
08/31/26
1
1
573 sqft
Home facts updated by county records

Nearby homes

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Rental Market Trends in Corey Hill

Last updated Sep 2026
Trulia Rent Estimate$2,551/mo
Average rent
$3.4K
$1.45KMoM
Available listings
141
View rental market trends in Brookline, MA

Around this home

Neighborhood Overview

Corey Hill
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Corey Hill

At least 48 Trulia users voted on each feature.

  • 100 % Say there are sidewalks

  • 97 % Say it's walkable to grocery stores

  • 96 % Say it's walkable to restaurants

  • 95 % Say it's dog friendly

  • 88 % Say people would walk alone at night

  • 84 % Say streets are well-lit

  • 77 % Say there's wildlife

  • 71 % Say kids play outside

  • 67 % Say there's holiday spirit

  • 62 % Say neighbors are friendly

  • 58 % Say parking is easy

  • 48 % Say they plan to stay for at least 5 years

  • 45 % Say there are community events

  • 45 % Say it's quiet

  • 28 % Say yards are well-kept

  • 22 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Very dog friendly "
    0
    Flag
  • Trulia User
    "I’v stayed in a hotel in this neighborhood. It is a beautiful area with many shops to explore. Hope to move to this area. "
    0
    Flag
  • Pat B.
    "It's dog friendly...there's lots of parks around to take pets."
    0
    Flag
  • Pat B.
    "The commute is pretty easy. The train is pretty reliable around here so it makes getting to and from the area pretty simple. I wish there were more buses though."
    0
    Flag
  • Pat B.
    "The closeness of the transportation is great. All of the major green lines are very close to Corey Hill and it makes getting around very easy."
    3
    Flag
  • Pat B.
    "There's some strange people who are around, but they're harmless. There's lots of daycare places, so if someone has a young kid there's lots of options nearby."
    1
    Flag
  • Tkesav
    "corey hill is near coolidge corner. yoy can see skyline of Boston..close to Trader Joes, Wholefoods, Fenway,."
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
May 2, 2026
Source: Zillow Rentals
ListingRemoved
$2,400
Apr 16, 2026
Source: Zillow Rentals
Listed For Rent
$2,400
Apr 14, 2016
Source: Agent Provided
ListingRemoved
$1,875
Apr 8, 2014
Source: Agent Provided
ListingRemoved
$1,750
Mar 5, 2014
Source: Agent Provided
PriceChange
$1,750
Price decreased by 5%

Frequently asked questions about 38 Winchester St #2

  • What is 38 Winchester St #2 estimated to be worth?
    Trulia's estimated value for 38 Winchester St #2 in Brookline, MA is $407,500.
  • What is the price history for 38 Winchester St #2?
    38 Winchester St #2 in Brookline, MA last sold for $224,000 in May 2011.
  • Is Brookline a buyer's or seller's market?
    Brookline is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Brookline?
    The median sale price in Brookline is $1.22M. That is down $182K from the prior month.
  • Does 38 Winchester St #2 have air conditioning?
    Yes, 38 Winchester St #2 in Brookline, MA has air conditioning.

Homes for rent near 38 Winchester St #2

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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