21 Upland Rd, Wakefield, MA 01880
OFF MARKET

21 Upland Rd
Wakefield, MA 01880

Greenwood
  • Studio
  • 3 Baths
  • 3,928 sqft (on 0.39 acres)

$1,526,200

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $9,061/mo*
Refinance Your Home

$1,526,200

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $9,061/mo*
Refinance Your Home
Studio
3 Baths
3,928 sqft
(on 0.39 acres)

Local Information

  • Map ViewExplore the area around 21 Upland Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2003
Lot Size
0.39 acres
Living Area
3,928 sqft
Price/Sqft
$389
Parking
Garage

About this House

This single-family home is located at 21 Upland Rd, Wakefield, MA. 21 Upland Rd is in the Greenwood neighborhood in Wakefield, MA and in ZIP code 01880. This property has 3 bathrooms and approximately 3,928 sqft of floor space. This property has a lot size of 0.39 acres and was built in 2003.
21 Upland Rd, Wakefield, MA 01880 is a studio, 3 bathroom, 3,928 sqft single-family home in Greenwood, built in 2003. It last sold for $680,000 on Aug 9, 2013. It is currently off market. The Trulia Estimate is $1,526,200, with a rent estimate of $5,735/month.

Home Details for 21 Upland Rd

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Other
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price History for 21 Upland Rd

DatePriceEventSource
08/09/2013$680,000Sold
N/A

Market trends in Wakefield

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$806K
$89.83KMoM
Sale-to-List Price
—
Price per sq ft
$468
$15MoM
Available listings
54
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Property Tax and Assessment

Year2025
Tax$14,023
Assessment$1,235,500
Home facts updated by county records

Comparable Sales for 21 Upland Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
6 Salisbury Rd, Wakefield, MA
0.28
Single-Family Home
$1,195,000
12/08/25
3
2.5
2,588
762 Main St, Wakefield, MA
0.16
Single-Family Home
$1,150,000
01/30/26
6
5
4,887
4 Meriam St, Wakefield, MA
0.22
Single-Family Home
$911,000
09/18/25
3
2.5
2,306
24 Stark Ave, Wakefield, MA
0.41
Single-Family Home
$950,000
12/01/25
4
2.5
2,052
34 Stark Ave, Wakefield, MA
0.41
Single-Family Home
$725,000
04/16/26
3
2
1,702
199 Nahant St, Wakefield, MA
0.63
Single-Family Home
$1,400,000
02/13/26
4
2.5
3,500
15 Hickory Hill Rd, Wakefield, MA
0.48
Single-Family Home
$830,000
03/04/26
3
2
1,696
61 Nahant St, Wakefield, MA
0.45
Single-Family Home
$837,500
04/08/26
3
2.5
1,582
9 Lilah Cir, Wakefield, MA
0.64
Single-Family Home
$795,000
01/13/26
4
3
2,084
14 Plymouth Rd, Wakefield, MA
0.72
Single-Family Home
$700,423
10/17/25
3
2.5
2,410

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Upland Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

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

What Locals Say about Greenwood

At least 19 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 97 % Say there's holiday spirit

  • 96 % Say parking is easy

  • 96 % Say kids play outside

  • 89 % Say they plan to stay for at least 5 years

  • 88 % Say people would walk alone at night

  • 86 % Say there are sidewalks

  • 83 % Say it's walkable to restaurants

  • 83 % Say streets are well-lit

  • 80 % Say yards are well-kept

  • 75 % Say neighbors are friendly

  • 73 % Say car is needed

  • 71 % Say it's quiet

  • 56 % Say there are community events

  • 52 % Say there's wildlife

  • 29 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "been here 6 years and my neighbors and the neighborhood is the best. We all watch out for one another. It is a very peaceful area and very safe."
    0
    Flag
  • Trulia User
    "digs and walkers are always around. very friendly and secure neighborhood. everyone looks out for each other."
    0
    Flag
  • Trulia User
    "Dog owners love this neighborhood low traffic, and plenty of sidewalk space plenty of places to let the dog off the leash and run parks etc"
    0
    Flag
  • Trulia User
    "Many families in the area, with great fields, parks, and stores within walking distance. All this but still private little neighborhoods."
    0
    Flag
  • Trulia User
    "Lots of people walk their dogs around. Always friendly. Nice fields to let them loose in. Everyone is respectful"
    0
    Flag
  • Kaitlyn S.
    "Halloween is a big event . Every house is a party . My husband and I know just about everyone on our street!! We have bbq and fires with the neighbors all summer ."
    0
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  • Kaitlyn S.
    "I’ve lived in this area for 5 years now . It’s like it’s own tiny community. Everyone is very friendly and knows one another . The elementary school is excellent and the commuter rail in a walk away "
    0
    Flag
  • Sam C.
    "We are huge dog lovers and there are great places to take them for long walks."
    0
    Flag
  • Sam C.
    "The commute is very simple. There are many different ways you can use to get to the heart of Greenwood."
    0
    Flag
  • Sam C.
    "It is a small little community within a bigger town."
    0
    Flag
  • Sam C.
    "It is a GREAT place to raise kids and the school is an awesome place to learn."
    0
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  • Rebecca R.
    "We do like dogs."
    0
    Flag
  • Rebecca R.
    "It's very beautiful with nice people."
    0
    Flag
  • David S.
    "There are lots of areas to walk dogs in Greenwood, and there is access to 20 acres of town owned. Ther are woods that you can access through the playground. Veterinary services are available in Wakefield, Melrose, Stoneham, Saugus, and Reading, and most are only a few miles from Greenwood."
    0
    Flag
  • David S.
    "The rail and bus service can take you to Boston and the easy access to major highways makes commuting easy."
    0
    Flag
  • David S.
    "Quiet area, friendly neighbors, suburban bordering on rural, not crowded, lots of small businesses, but no heavy industry. Lots of trees, nice homes and scenery. Easy access to major highways, lots of places to eat or shop, no crime, fire station nearby, prompt police response if needed, & good roads. Also, local bank has a Greenwood office, and you don't have to go far to find what you need. Just a nice environment to live in. Plus, rail service to Boston, and to points North as well."
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  • David S.
    "It is NOT a rough neighborhood, nor any criminal activity here. Children are safe here. We all look out for each other. Preschool and grammar school are centrally located, and bus service is provided."
    0
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  • Huyen N.
    "Beautiful wood areas with many hiking trails. Generally quiet and pretty safe neighborhood with nice neighbors."
    0
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  • Jennifer
    "Lakes, friendly, clean, close to major highways, good schools, amazing restaurants, youth sports, lovely people "
    0
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  • Ruth J.
    "Very dog friendly and most people pick up after their dogs. There is also a dog park on Main Street and when I drive by, I always look to see if anyone is there and it puts a smile on my face."
    0
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  • Ruth J.
    "Very easy to get by through any means of transportation. There is a bus line and the commuter rail and I've been seeing a lot of bike riding."
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  • Ruth J.
    "There's Greenwood Plaza which has much to offer."
    0
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  • Ruth J.
    "The school system is very good. They also have Kumon Learning Center, which I sent my two children to for math and reading comprehension."
    0
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  • Ehlocke
    "I actually know my neighbors. Kids walk to school together. I get a text if I leave my garage door open. Very friendly area. "
    0
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  • Mj S.
    "Desirable Greenwood neighborhood is walkable and family friendly. Wonderful neighborhood community. Walking distance (5-10 minutes) to Greenwood Station commuter rail to downtown Boston. Town plows sidewalk in front of house. "
    0
    Flag

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Explore by feature - Pet Friendly

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Homes for sale near 21 Upland Rd

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Off Market Homes Near 21 Upland Rd

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