49 Lorena Rd, Winchester, MA 01890
Property image
71996490_4
OFF MARKET

$2,040,800

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,391 sqft (on 0.43 acres)

49 Lorena Rd, Winchester, MA 01890

Est. Refi. Payment $12,177/mo*
Refinance Your Home
Currently Off Market - Sold May 24, 2016 for $1,100,000

Home Value

Trulia Estimate
$2.04M
Since last month
Decreased$39K (-1.8%)
Since last year
Increased$21K (+1%)
Since last sale
Increased$958K (+87.1%)
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 +85% in the last 10 years
MonthEstimated value
2026
August 2026$2.06M
July 2026$2.1M
June 2026$2.12M
May 2026$2.1M
April 2026$2.08M
March 2026$2.03M
February 2026$1.94M
January 2026$1.91M
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
58 Jefferson Rd, Winchester, MA
0.19
Single-Family Home
$1,850,000
04/23/26
4
2.5
2,910
30 Prospect St, Winchester, MA
0.25
Single-Family Home
$2,450,000
12/16/25
4
3
2,519
17 Dennett Rd, Winchester, MA
0.35
Single-Family Home
$1,500,000
10/09/25
3
2.5
2,283
4 Leslie Rd, Winchester, MA
0.13
Single-Family Home
$2,120,000
04/28/26
5
3.5
2,860
8 Felsdale Close, Winchester, MA
0.20
Single-Family Home
$1,930,000
01/09/26
4
2.5
3,658
4 Sargent Rd, Winchester, MA
0.41
Single-Family Home
$1,355,000
11/20/25
4
2.5
2,865
17 Cranston Rd, Winchester, MA
0.34
Single-Family Home
$1,560,000
04/30/26
4
2.5
2,578
22 Hollywood Rd, Winchester, MA
0.26
Single-Family Home
$2,150,000
07/13/26
5
3
3,136
446 Highland Ave, Winchester, MA
0.46
Single-Family Home
$940,000
12/23/25
2
1.5
2,033
6 Alden Ln, Winchester, MA
0.50
Single-Family Home
$1,275,000
06/25/26
3
2
1,511

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
50 Lorena Rd, Winchester, MA 01890
0.03
$3,377,700
5
4.5
7,242
Off Market
12 Ledgewood Rd, Winchester, MA 01890
0.12
$3,350,100
5
4.5
5,069
Off Market
4 Leslie Rd, Winchester, MA 01890
0.13
$2,120,000
5
3.5
2,860
Recently Sold
8 Felsdale Close, Winchester, MA 01890
0.20
$1,930,000
4
2.5
3,658
Recently Sold
94 Lawson Rd, Winchester, MA 01890
0.19
$2,293,000
5
4
5,484
Off Market
58 Jefferson Rd, Winchester, MA 01890
0.19
$1,850,000
4
2.5
2,910
Recently Sold
57 Jefferson Rd, Winchester, MA 01890
0.20
$2,382,100
4
3.5
3,274
Off Market
25 Ledgewood Rd, Winchester, MA 01890
0.25
$3,705,900
5
4.5
5,500
Off Market
30 Prospect St, Winchester, MA 01890
0.25
$2,450,000
4
3
2,519
Recently Sold
382 S Border Rd, Winchester, MA 01890
0.23
$2,450,000
6
5.5
4,563
Recently Sold
35 Lawson Rd, Winchester, MA 01890
0.26
$2,747,600
6
5
5,263
Off Market
22 Hollywood Rd, Winchester, MA 01890
0.26
$2,150,000
5
3
3,136
Recently Sold

Local Information

  • Map ViewExplore the area around 49 Lorena Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1948
Lot Size
0.43 acres
Living Area
2,391 sqft
Price/Sqft
$854

About this House

Located in one of Winchesters most sought after neighborhoods, this 1948 Cape in need of updating, is being sold "as is". Surrounded by multi-million dollar homes this is a fantastic rehab opportunity or design and build your custom home on this 19,000sf lot well suited for a walk-out basement. With a 2 car attached garage this could also be a perfect home for the ambitious "downsizers" looking to customize their next home. Showings start at the open house Sunday May 1st 12:00-2:00pm. Seller to review offers Wednesday after 12:00pm. Please allow 24 hours for reply
49 Lorena Rd, Winchester, MA 01890 is a 4 bedroom, 2 bathroom, 2,391 sqft single-family home built in 1948. It last sold for $1,100,000 on May 24, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,040,800, with a rent estimate of $5,570/month.

Home Details for 49 Lorena Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1948
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.43 acres

Price and Tax history

DateEventPrice
May 24, 2016
Source: N/A
Sold
$1,100,000
May 7, 2016
Source: Agent Provided
Pending
$949,900
Apr 29, 2016
Source: Agent Provided
Listed For Sale
$949,900

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

Frequently asked questions about 49 Lorena Rd

  • What is 49 Lorena Rd estimated to be worth?
    Trulia's estimated value for 49 Lorena Rd in Winchester, MA is $2,040,800.
  • What is the price history for 49 Lorena Rd?
    49 Lorena Rd in Winchester, MA last sold for $1,100,000 in May 2016.
  • 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.
  • How big is the lot at 49 Lorena Rd?
    The lot at 49 Lorena Rd in Winchester, MA is about 0.43 acres (18,730 sq ft).

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