For Sale
Single family home for sale at 5421 Wellesley Ave, Highland Park, PA 15206 | MLS# 1776934 | Listing updated on 2026-09-30
Photo 1 of Single family home for sale at 5421 Wellesley Ave, Highland Park, PA 15206 | MLS# 1776934 | Listing updated on 2026-09-30
Photo 2 of Single family home for sale at 5421 Wellesley Ave, Highland Park, PA 15206 | MLS# 1776934 | Listing updated on 2026-09-30
Photo 3 of Single family home for sale at 5421 Wellesley Ave, Highland Park, PA 15206 | MLS# 1776934 | Listing updated on 2026-09-30
Photo 4 of Single family home for sale at 5421 Wellesley Ave, Highland Park, PA 15206 | MLS# 1776934 | Listing updated on 2026-09-30
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$400,000

Monthly Est:$1,991

  • Beds Icon2 Beds
  • Beds Icon
    1 Bath
  • Beds Icon2,033sqft

5421 Wellesley Ave, Highland Park, PA 15206

$1,991/moEst:

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  • Single Family Residence

  • Built in 1900

  • $-- HOA

  • 0.05 acre lot

  • $197/sq.ft

Description

Looking for a smart way to make homeownership work harder for you? This beautifully renovated Highland Park duplex offers the opportunity to live in one unit while generating rental income from the other. With two updated 2-bedroom, 1-bath units, separate gas and electric utilities, individual HVAC systems with central air, and extensive recent improvements, much of the heavy lifting has already been done.

Both units feature remodeled kitchens and baths, quartz countertops, stainless steel appliances, dishwashers, built-in microwaves, LVP flooring, fresh paint and approximately 90% replacement windows. A shared laundry area is located in the basement.

Unit 1 offers
a living room, kitchen, full bath and bedroom on the main level, with a second bedroom upstairs for added separation and flexibility. A private rear deck provides its own outdoor space. Unit 2 features two bedrooms plus a versatile bonus room that could serve as an office, exercise room, storage or flex space. Both units also have access to the shared backyard and patio with solar string lighting.

Major improvements include a new roof (2024), two HVAC systems with central air (2024), hot water tanks (2019 & 2020), renovated kitchens and baths, new electrical panels for each unit plus a third panel for common areas, updated flooring and paint, exterior painting and shared basement laundry.

Located in Highland Park with public transit less than two blocks away, 5421 Wellesley offers convenient access to Highland Park, the Pittsburgh Zoo & Aquarium and Bryant Street dining and shops. Bakery Square, East Liberty, Shadyside and Lawrenceville are nearby, along with Carnegie Mellon University, the University of Pittsburgh, UPMC Children’s Hospital, West Penn Hospital and UPMC Shadyside.

Whether you're considering an owner-occupied duplex or adding a well-improved property to your investment portfolio, 5421 Wellesley offers flexibility, separate utilities and two renovated units in a convenient East End location.

  • Houzeo last checked: 3 hours ago
  • Listing updated: September 30, 2026 at 8:59 pm
  • Listing Provided by: Megan Stevenson (724) 933-6300 DRE #RS348075 | RE/MAX SELECT REALTY (724) 933-6300
  • Source: West Penn MLS-PA | MLS#: 1776934 West Penn MLS-PA

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    3

  • County

    Allegheny East County

  • City

    Highland Park

  • Neighborhood

    --

  • Year Built

    1900

  • HOA Fees

    -

  • Finished Area

    2,033 sqft

  • Lot Size

    0.05 acre lot

  • Basement Area

    - sqft

  • MLS Name

    West Penn MLS

  • MLS Number

    1776934

  • MLS Status

    Active

  • Days on Market

    7

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 2

    Bathroom: 1

Interior

  • Heating

    Forced Air, Gas

  • Sewer

    Public Sewer

  • Cooling

    Central Air

Construction

  • Year Built

    Year Built: 1900

  • Home type

    Single Family Residence

  • Property Condition

    Resale

  • Roof

    Asphalt

  • Architectural Style

    Three Story

  • Construction Materials

    Brick

Utilities & Energy

  • Water Source

    Public

  • Basement

    Unfinished

  • Pool Features

    None

  • Parking Features

    On Street

Other Features

  • Community Features

    Public Transportation

Price History

DateEventPrice

09/24/2026

Source: mls_logoWest Penn MLS-PA #1775749

Listed for Sale

$400,000 +110.53%

$0/sqft

01/08/2024

Source: mls_logoWest Penn MLS-PA #1592143

Price Decreased

$190,000 -15.52%

$0/sqft

10/17/2023

Source: mls_logoWest Penn MLS-PA #1592143

Price Increased

$224,900 +2.69%

$0/sqft

04/25/2021

Source: mls_logoWest Penn MLS-PA #1495255

Sold

$219,000

$0/sqft

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Based on information from the West Penn Mutli-List, INC through Oct 08, 2026, 11:00AM. Information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 West Penn Multi-List, Inc. All Rights Reserved. 

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