For Sale14d on marketHistoric · 102 yrs
5558 Aylesboro Ave
Pittsburgh, PA, 15217 • Squirrel Hill North • Allegheny County
$3,850,000
$504/sqft
Down payment assistance available
8Beds
6Baths
7,640Sqft
0.54 acLot
1924Built
Property DNA
Colonial,Three Story Style
Built 1924 · 102 years of history
10 Fireplaces
Other
Garage
Detached · Garage · Garage Door Opener
Hardwood Floors
Quality flooring throughout
This home is getting attention
Listed 14 days ago · 2,617 views · 79 saves
Market activity
Demand and pricing signals for this listing
2,617 views
People checking out this listing
79 saves
Buyers have saved this home
14 days on market
Recently listed
$504/sqft
Price per square foot
Selling Soon Prediction
ModerateThis home ranks in the top 36% of listings most likely to go under contract soon, based on market activity and demand signals.
Likelihood score
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About this home
Single Family · Built 1924 · Historic
Discover timeless elegance at 5558 Aylesboro Avenue, a grand 7500+ sq ft estate nestled in coveted Murdoch Farms enclave of Squirrel Hill. Built in 1914 to exemplify Pittsburgh's distinguished architectural heritage, the stately brick Colonial spans 3 levels with 8+ bedrooms & 5+ baths - ideal for luxurious gatherings & generational events. Original splendor of soaring ceilings, leaded glass details, custom woodwork & 10 fireplaces anchor richly appointed spaces all renovated yet instilling intended character. Underfoot, a refined blend of gleaming hardwoods, plush carpets, and designer tile guide you through the home's thoughtful layout. Amazing Primary Suite. Chef's kitchen. Netflix-featured DR. Executive office. Three season side porch. Situated on over half an acre with lush grounds and a commanding street presence. Porte cochere, detached 2-level 4 car garage, in-ground trampoline, covered patio, plus sprawling level yard with gardens.
Standout features identified
Our analysis highlights commanding street presence, custom woodwork, and in-ground trampoline as key attractions of this home.
Estimated monthly payment
Based on current rates
$24,286/month
Principal & Interest$19,153
Property Tax$3,850
Insurance$1,283
Down payment20% ($770,000)
3%50%
Est. 6.34% rate · 30yr fixed · $3,080,000 loan
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At a glance
Key facts and listing details
TypeSingle Family Residence
Year Built1924
HeatingGas, Hot Water
CoolingCentral Air
Parking4 Garage spaces
Lot0.54 Acres
Days on Zillow14 Days
Price/sqft$504
Property
Home typeSingle Family
Sub-typeSingle Family Residence
StyleColonial,Three Story
ConditionResale
Year built1924
Stories3
Systems
HeatingGas, Hot Water
CoolingCentral Air
RoofSlate
ConstructionBrick
Water / SewerPublic / Public Sewer
Parking & Outdoor
ParkingDetached, Garage, Garage Door Opener
BasementFull,Interior Entry
Fireplaces10
Lot0.54 Acres
Location & Tax
NeighborhoodSquirrel Hill North
Annual tax$39,139
Parcel0086E00220000000
Bathrooms & Fees
Full baths5
Features & details
13 categories of property features
Interior Features
Interior
Intercom
Kitchen Island
Pantry
Appliances
Some Gas Appliances
Convection Oven
Cooktop
Dishwasher
Disposal
Microwave
Refrigerator
Flooring
Hardwood
Heating
Gas
Hot Water
Cooling
Central Air
Fireplace
Other
Windows
Multi Pane
Exterior Features
Parking
Detached
Garage
Garage Door Opener
Construction
Brick
Community
Public Transportation
Security
Security System
Pool Features
None
Other Equipment
Intercom
Room details
14 rooms detailed
Master Bedroom
UpperBedroom2
UpperBedroom3
UpperBedroom4
UpperBedroom5
UpperBonus Room
UpperListing insights
Market data and value estimates
StatusFor Sale
Days on market14
Est. value$3,685,200
Est. rent$4,835/mo
Tax rate1.56%
Price/sqft$504
On marketMar 24, 2026
PostedMar 24, 2026
Last sold$2,040,500
MLS updatedMar 24, 2026
Tour days9
Views2,617
Favorites79
How are the schools in Pittsburgh?
3 schools rated nearby
Location
Pittsburgh, PA, 15217
Price history
11 events
DateEventPrice$/sqftSource
Mar 24, 2026Listed For Sale$3,850,000$504WPMLS
Dec 31, 2025Listing Removed$4,250,000$556BHHS broker feed
Aug 13, 2025Listed For Sale$4,250,000$556WPMLS
May 4, 2018Sold$2,040,500$267WPMLS
Jan 19, 2018Pending Sale$2,400,000$314Berkshire Hathaway HomeServices The Preferred Realty
Jan 18, 2018Listed For Sale$2,400,000$314Berkshire Hathaway HomeServices The Preferred Realty
Oct 26, 2012Sold$1,275,000$167WPMLS
Sep 4, 2012Price Change$1,350,000$177Howard Hanna - Seven Fields
Jun 12, 2012Listed For Sale$1,600,000$209Howard Hanna - Seven Fields
Jan 22, 2007Sold$830,000$109Public Record
Sep 22, 2003Sold$810,000$106WPMLS
Listed For Sale$3,850,000
Mar 24, 2026•$504/sqft•WPMLS
Listing Removed$4,250,000
Dec 31, 2025•$556/sqft•BHHS broker feed
Listed For Sale$4,250,000
Aug 13, 2025•$556/sqft•WPMLS
Sold$2,040,500
May 4, 2018•$267/sqft•WPMLS
Pending Sale$2,400,000
Jan 19, 2018•$314/sqft•Berkshire Hathaway HomeServices The Preferred Realty
Listed For Sale$2,400,000
Jan 18, 2018•$314/sqft•Berkshire Hathaway HomeServices The Preferred Realty
Sold$1,275,000
Oct 26, 2012•$167/sqft•WPMLS
Price Change$1,350,000
Sep 4, 2012•$177/sqft•Howard Hanna - Seven Fields
Listed For Sale$1,600,000
Jun 12, 2012•$209/sqft•Howard Hanna - Seven Fields
Sold$830,000
Jan 22, 2007•$109/sqft•Public Record
Sold$810,000
Sep 22, 2003•$106/sqft•WPMLS
Tax history
24 years of records
YearTax paidAssessed value
Apr 7, 2025$38,935$1,582,000
Apr 7, 2024$36,449$1,582,000
Apr 7, 2023$7,483$1,582,000
Apr 7, 2022$7,483$1,582,000
Apr 7, 2021$8,350$1,765,400
Apr 7, 2020$8,183$1,765,400
Apr 7, 2019$5,946$1,257,000
Apr 7, 2018$28,446$1,257,000
Apr 7, 2017$28,446$1,257,000
Apr 7, 2016$5,946$1,257,000
Apr 7, 2015$27,817$1,257,000
Apr 7, 2014$3,306$1,275,000
Apr 7, 2013—$958,300
Apr 7, 2012—$705,000
Apr 7, 2011—$705,000
Apr 7, 2010—$705,000
Apr 7, 2009—$585,600
Apr 7, 2008—$585,600
Apr 7, 2007—$585,600
Apr 7, 2006—$755,000
Apr 7, 2005—$770,000
Apr 7, 2004—$755,000
Apr 7, 2003—$770,000
Apr 7, 2002—$882,300
Nearby homes
Neighborhood details
Local context around this listing
Pittsburgh, PA • Allegheny County
Nearby neighborhoods
BloomfieldBrooklineCarrickCastle ShannonMount LebanonNorth OaklandOaklandShadysideSquirrel Hill NorthSquirrel Hill South
Nearby cities
Allison ParkBethel ParkCoraopolisGibsoniaMcKees RocksMcKeesportMonroevilleNew Kensington
Nearby zip codes
15206152101521215213152171522115227152351523615237
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