5537 Wellesley Ave, Pittsburgh, PA 15206
OFF MARKET

5537 Wellesley Ave
Pittsburgh, PA 15206

Highland Park
  • 3 Beds
  • 2 Baths
  • 2,977 sqft

$621,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $4,058/mo*
Refinance Your Home

$621,000

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $4,058/mo*
Refinance Your Home
3 Beds
2 Baths
2,977 sqft

Home Value

Trulia Estimate
$621K
Since last month
Decreased$9K (-1.4%)
Since last year
Increased$17K (+2.8%)
Since last sale
Increased$421K (+210.5%)
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 +76% in the last 10 years
MonthEstimated value
2026
August 2026$621K
July 2026$601K
June 2026$630K
May 2026$614K
April 2026$591K
March 2026$580K
February 2026$554K
January 2026$552K
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
5517 Jackson St, Pittsburgh, PA
0.12
Single-Family Home
$200,000
09/22/25
4
2.5
2,597
5201 Wellesley Ave, Pittsburgh, PA
0.29
Single-Family Home
$200,000
01/14/26
3
2
1,790
1115 N Euclid Ave, Pittsburgh, PA
0.30
Single-Family Home
$296,000
11/21/25
4
2
2,786
5512 Avondale Pl, Pittsburgh, PA
0.10
Single-Family Home
$479,000
10/24/25
4
1.5
2,668
928 Mellon St, Pittsburgh, PA
0.20
Single-Family Home
$205,000
07/07/26
3
2.5
1,990
1005 Duffield St, Pittsburgh, PA
0.32
Single-Family Home
$208,000
08/10/26
3
2
1,428
5528 Hampton St, Pittsburgh, PA
0.09
Single-Family Home
$285,000
07/08/26
4
2.5
1,998
5514 Wellesley Ave, Pittsburgh, PA
0.06
Single-Family Home
$585,000
07/14/26
5
3
2,914
631 Chislett St, Pittsburgh, PA
0.36
Single-Family Home
$285,500
11/05/25
5
2
2,622
5923 Bryant St, Pittsburgh, PA
0.40
Single-Family Home
$280,000
04/02/26
3
1.5
1,152

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
5528 Wellesley Ave, Pittsburgh, PA 15206
0.04
$550,500
4
2.5
2,108
Off Market
943 N Negley Ave #4, Pittsburgh, PA 15206
0.07
$329,000
1
1
1,008
For Sale
5563 Hampton St, Pittsburgh, PA 15206
0.10
$1,260,600
5
3.5
3,852
Off Market
5575 Hampton St, Pittsburgh, PA 15206
0.11
$799,400
6
3.5
4,870
Off Market
5577 Hampton St, Pittsburgh, PA 15206
0.11
$845,600
6
3.5
4,591
Off Market
5514 Wellesley Ave, Pittsburgh, PA 15206
0.06
$585,000
5
3
2,914
Recently Sold
5545 Avondale Pl, Pittsburgh, PA 15206
0.06
$678,600
5
3.5
-
Off Market
5528 Hampton St, Pittsburgh, PA 15206
0.09
$285,000
4
2.5
1,998
Recently Sold
1115 N Negley Ave, Pittsburgh, PA 15206
0.12
$674,900
6
7
-
Off Market
5523-5525 Avondale Pl, Pittsburgh, PA 15206
0.08
$644,900
8
5
-
Off Market
5454 Wellesley Ave, Pittsburgh, PA 15206
0.09
$775,000
6
3.5
3,081
For Sale
5528 Avondale Pl, Pittsburgh, PA 15206
0.09
$667,500
5
3.5
2,738
Off Market

Local Information

  • Map ViewExplore the area around 5537 Wellesley Ave.
  • Schools1 Preschool School1 Elementary School2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1911
Living Area
2,977 sqft
Price/Sqft
$209

About this House

This single-family home is located at 5537 Wellesley Ave, Pittsburgh, PA. 5537 Wellesley Ave is in the Highland Park neighborhood in Pittsburgh, PA and in ZIP code 15206. This property has 3 bedrooms, 2 bathrooms and approximately 2,977 sqft of floor space. This property has a lot size of 7500 sqft and was built in 1911.
5537 Wellesley Ave, Pittsburgh, PA 15206 is a 3 bedroom, 2 bathroom, 2,977 sqft single-family home in Highland Park, built in 1911. It last sold for $200,000 on Nov 4, 2020. It is currently off market. The Trulia Estimate is $621,000, with a rent estimate of $1,868/month.

Home Details for 5537 Wellesley Ave

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 10
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Brick

Property Information

Year Built
Year Built: 1911
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 7500 sqft

Price and Tax history

DateEventPrice
Nov 4, 2020
Source: N/A
Sold
$200,000

Market trends in Pittsburgh

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$265K
$11.67KMoM
Sale-to-List Price
99.6%
0.7%MoM
Price per sq ft
$188
$7MoM
Available listings
2574
110MoM
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Around this home

Neighborhood Overview

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

What Locals Say about Highland Park

At least 75 Trulia users voted on each feature.

  • 98 % Say it's dog friendly

  • 95 % Say there are sidewalks

  • 89 % Say it's walkable to restaurants

  • 82 % Say parking is easy

  • 77 % Say there's holiday spirit

  • 76 % Say kids play outside

  • 71 % Say streets are well-lit

  • 69 % Say yards are well-kept

  • 69 % Say it's walkable to grocery stores

  • 69 % Say people would walk alone at night

  • 64 % Say neighbors are friendly

  • 64 % Say they plan to stay for at least 5 years

  • 58 % Say there's wildlife

  • 55 % Say car is needed

  • 53 % Say it's quiet

  • 47 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "There is the Kingsley center where adults and children can attend, the different water parks for the summer, how close it is to Highland Park to spend time with your family, go on walks and jogs, or even use the outdoor workout stations they have. Overall you can just go for a walk and enjoy the sights! "
    0
    Flag
  • Trulia User
    "Great neighborhood I love it Nice park, restaurants and coffee shops. I love park and people around. Easily find parking every day "
    0
    Flag
  • Trulia User
    "Nearby park and playground, safe roads, quiet and neighborly. Plenty of kids around to play with. Also lots of pet owners."
    0
    Flag
  • Lance D.
    "One of the best commutes I’ve ever had; it’s Less than 30 mins on public transit or 20 mins driving myself. "
    2
    Flag
  • Billie A.
    "Everyone in Pittsburgh says their neighborhood is the best. I'd have to argue that Highland Park truly is. The neighborhood is incredibly peaceful and offers a suburban-like feel, all while being a mile away from almost everything you need. There is ample (free!) parking, and it is immediately along 2 buslines, with another 2 within walking distance that can get you to multiple corners of town. There's a wonderful mix of families, young professionals, and older folks. From what I know, the neighborhood is also largely unchanged. There's also a small "business district" with several lovely restaurants, a laundromat, a coffee shop, and even a well stocked small market. Highly walkable, supremely peaceful, and within reach to virtually everything you need, with or without a car. "
    9
    Flag
  • Lance D.
    "It’s 20-25 mins to my office using public transit; I take the bus and find it convenient compared to driving and parking. "
    0
    Flag
  • Ewatkins15
    "they would like it, the dogs that live here tend to be really well behaved, and the owners are pretty good about picking up after their animals, and we have a dog park"
    0
    Flag
  • Sam A.
    "there are great parks and playgrounds and everything u need nearby. shopping, boutiques and cafes are all in walking distance and the neighborhood schools are legitimately good schools. "
    0
    Flag
  • Ubalditocastanon
    " For me is one of the best neighbors whit good public service, like public transportation, Liberty, etc "
    0
    Flag
  • Jay H.
    "not too many kids in the neighborhood. lots of professionals and lots of dogs. very quiet. lots of park space"
    0
    Flag
  • Lynne
    "Neighborhood yard sales, musical events in Highland Park and being able to access the park easily by walking. "
    0
    Flag
  • dte s.
    "My wife and I live in Highland Park and love the community, impressive park, proximity to businesses/restaurants, and the charm of the architecture. It's a great place to live!"
    8
    Flag
  • Nathaniel G.
    "Highland Park is one of the most livable areas in and around Pittsburgh. Especially in the area nearest the park itself, the best in urban and suburban living are combined: Quiet, treelined streets with well-maintained homes are only minutes away from all the best a sophisticated urban area has to offer."
    8
    Flag

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Homes for sale near 5537 Wellesley Ave

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Off Market Homes Near 5537 Wellesley Ave

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Frequently asked questions about 5537 Wellesley Ave

  • What is 5537 Wellesley Ave estimated to be worth?
    Trulia's estimated value for 5537 Wellesley Ave in Pittsburgh, PA is $621,000.
  • What is the price history for 5537 Wellesley Ave?
    5537 Wellesley Ave in Pittsburgh, PA last sold for $200,000 in November 2020.
  • Is Pittsburgh a buyer's or seller's market?
    Pittsburgh is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Pittsburgh?
    The median sale price in Pittsburgh is $265K. That is up $11.67K from the prior month.
  • How big is the lot at 5537 Wellesley Ave?
    The lot at 5537 Wellesley Ave in Pittsburgh, PA is about 0.17 acres (7,500 sq ft).