2533 Gregory St, Madison, WI 53711
OFF MARKET

$784,200

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,092 sqft

2533 Gregory St, Madison, WI 53711

Dudgeon-Monroe
Est. Refi. Payment $5,119/mo*
Refinance Your Home

Home Value

Trulia Estimate
$784K
Since last month
Decreased$11K (-1.4%)
Since last year
Increased$34K (+4.5%)
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 +104% in the last 10 years
MonthEstimated value
2026
August 2026$784K
August 2026$784K
July 2026$795K
June 2026$802K
May 2026$810K
April 2026$806K
March 2026$796K
February 2026$748K
January 2026$731K
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
2529 Gregory St, Madison, WI
0.01
Single-Family Home
$750,000
05/05/26
4
1.5
2,127
610 Leonard St, Madison, WI
0.28
Single-Family Home
$900,000
07/13/26
4
2.5
2,211
636 Crandall St, Madison, WI
0.15
Single-Family Home
$840,000
06/03/26
3
2
1,817
2510 Commonwealth Ave, Madison, WI
0.10
Single-Family Home
$775,000
08/21/26
3
1.5
1,767
414 Virginia Ter, Madison, WI
0.33
Single-Family Home
$750,000
12/19/25
4
3
2,364
434 Virginia Ter, Madison, WI
0.29
Single-Family Home
$1,111,000
07/02/26
3
2.5
2,212
2929 Monroe St, Madison, WI
0.29
Single-Family Home
$475,000
03/04/26
4
2
2,322
2428 Fox Ave, Madison, WI
0.17
Single-Family Home
$718,000
06/23/26
3
2
1,543
2221 Keyes Ave, Madison, WI
0.40
Single-Family Home
$957,500
09/08/26
4
2.5
2,000
453 Virginia Ter, Madison, WI
0.24
Single-Family Home
$635,000
06/15/26
3
1.5
1,427

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
2605 Gregory St, Madison, WI 53711
0.04
$846,600
4
1.5
1,580
Off Market
616 Sprague St, Madison, WI 53711
0.03
$817,100
3
1.5
1,288
Off Market
628 Sprague St, Madison, WI 53711
0.04
$822,300
3
1.5
1,568
Off Market
2529 Gregory St, Madison, WI 53711
0.01
$750,000
4
1.5
2,127
Recently Sold
639 Knickerbocker St, Madison, WI 53711
0.08
$935,300
3
2.5
1,946
Off Market
640 Sprague St, Madison, WI 53711
0.07
$657,000
3
1
1,975
Off Market
639/643 Crandall St, Madison, WI 53711
0.12
$996,600
4
2.5
3,082
Off Market
653 Sheldon St, Madison, WI 53711
0.10
$638,000
2
2
1,364
Recently Sold
605 Sheldon St, Madison, WI 53711
0.07
$893,100
3
2
2,745
Off Market
664 Sprague St, Madison, WI 53711
0.11
$773,500
4
3
2,663
Off Market
2421 Gregory St, Madison, WI 53711
0.07
$650,000
3
1
1,564
For Sale
660 Knickerbocker St, Madison, WI 53711
0.13
$766,600
3
1.5
1,587
Off Market

Local Information

  • Map ViewExplore the area around 2533 Gregory St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1924
2,092 sqft
$375/sqft

About this House

This single-family home is located at 2533 Gregory St, Madison, WI. 2533 Gregory St is in the Dudgeon-Monroe neighborhood in Madison, WI and in ZIP code 53711. This property has 4 bedrooms, 3 bathrooms and approximately 2,092 sqft of floor space. This property has a lot size of 3106 sqft and was built in 1924.
2533 Gregory St, Madison, WI 53711 is a 4 bedroom, 3 bathroom, 2,092 sqft single-family home in Dudgeon-Monroe, built in 1924. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $784,200, with a rent estimate of $3,910/month.

Home Details for 2533 Gregory St

Interior Features

Interior Details
BasementTypes of Rooms: Family Room
Levels, Entrance, & Accessibility
Stories: 2.5
Heating & Cooling
Cooling System: Central
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1924Year Updated: 1960
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 3106 sqft

Price and Tax history

YearProperty taxTax assessment
2024
$12,947
$661,400
Home facts updated by county records

Market trends in Madison

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$429K
$2.5KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$259
$7MoM
Available listings
551
5MoM

Around this home

Neighborhood Overview

Dudgeon-Monroe
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Dudgeon-Monroe

At least 2 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say yards are well-kept

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say people would walk alone at night

  • 100 % Say there are sidewalks

  • 100 % Say kids play outside

  • 86 % Say there are community events

  • 82 % Say neighbors are friendly

  • 75 % Say car is needed

  • 71 % Say there's holiday spirit

  • 67 % Say it's quiet

  • 60 % Say they plan to stay for at least 5 years

  • 50 % Say there's wildlife

  • 50 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Some people have dogs off leash and insist their dog is friendly even when you ask them to not approach. Not everyone respects what you ask for your dogs needs."
    5
    Flag
  • Waltergrote
    "Awesome neighborhood. Very walkable to great restaurants, parks, zoo, bike trail, arboretum, and Camp Randall. "
    0
    Flag
  • Pjcashman
    "Great family neighbourhood. Fantastic location. Close to fine restaurants and nice shops. Enjoyed living there for a number of years. Highly recommended. Very safe. Trader Joes is a big plus. "
    2
    Flag
  • Kira
    "Lovely serene and safe. Great for families, kids, dogs and folks who want peace and quiet while still being in the city mix. Very natural zen setting with cool low key neighbors. Who could ask for more?! Wish we still lived there but since we cannot, hopefully you will get to:) "
    0
    Flag
  • pmcichan
    "A very friendly and active neighborhood with a number of excellent restaurants. Easy access to campus, downtown and the beltline. A little oasis in the middle of Madison!"
    2
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2533 Gregory St

  • What is 2533 Gregory St estimated to be worth?
    Trulia's estimated value for 2533 Gregory St in Madison, WI is $784,200.
  • Is Madison a buyer's or seller's market?
    Madison is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $429K. That is up $2.5K from the prior month.
  • What are the closest schools to 2533 Gregory St?
    The closest schools to 2533 Gregory St in Madison, WI are Franklin Elementary School (Pre-K), Hamilton Middle School (rated 8/10), Randall Elementary School (rated 9/10).
  • Does 2533 Gregory St have air conditioning?
    Yes, 2533 Gregory St in Madison, WI has air conditioning.
  • How big is the lot at 2533 Gregory St?
    The lot at 2533 Gregory St in Madison, WI is about 0.07 acres (3,106 sq ft).

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Apartments for Rent

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