2529 Gregory St, Madison, WI 53711
Property image
Property image
SOLD
MAY 5, 2026

$736,600

Trulia Estimate
  • 4 Beds
  • 1.5 Baths
  • 2,127 sqft

2529 Gregory St, Madison, WI 53711

Dudgeon-Monroe
Est. Refi. Payment $4,959/mo*
Refinance Your Home
Currently Off Market - Sold May 5, 2026 for $750,000

Home Value

Trulia Estimate
$737K
Since last month
Decreased$5K (-0.6%)
Since last year
Increased$27K (+3.8%)
Since last sale
Decreased$16K (-2.1%)
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 +88% in the last 10 years
MonthEstimated value
2026
September 2026$735K
August 2026$737K
July 2026$739K
June 2026$745K
May 2026$751K
April 2026$756K
March 2026$793K
February 2026$777K
January 2026$705K
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
2510 Commonwealth Ave, Madison, WI
0.09
Single-Family Home
$775,000
08/21/26
3
1.5
1,767
2428 Fox Ave, Madison, WI
0.16
Single-Family Home
$718,000
06/23/26
3
2
1,543
610 Leonard St, Madison, WI
0.27
Single-Family Home
$900,000
07/13/26
4
2.5
2,211
714 Baltzell St, Madison, WI
0.27
Single-Family Home
$720,000
10/15/25
3
1.5
2,319
453 Virginia Ter, Madison, WI
0.23
Single-Family Home
$635,000
06/15/26
3
1.5
1,427
653 Sheldon St, Madison, WI
0.09
Single-Family Home
$638,000
05/28/26
2
2
1,364
2314 Keyes Ave, Madison, WI
0.23
Single-Family Home
$575,000
02/02/26
3
2
1,769

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
628 Sprague St, Madison, WI 53711
0.04
$815,400
3
1.5
1,568
Off Market
616 Sprague St, Madison, WI 53711
0.04
$817,100
3
1.5
1,288
Off Market
640 Sprague St, Madison, WI 53711
0.07
$649,400
3
1
1,975
Off Market
2605 Gregory St, Madison, WI 53711
0.05
$835,600
4
1.5
1,580
Off Market
653 Sheldon St, Madison, WI 53711
0.09
$638,000
2
2
1,364
Recently Sold
639 Knickerbocker St, Madison, WI 53711
0.08
$926,700
3
2.5
1,946
Off Market
605 Sheldon St, Madison, WI 53711
0.06
$909,900
3
2
2,745
Off Market
2530 Commonwealth Ave, Madison, WI 53711
0.09
$819,900
3
2
1,848
Off Market
2421 Gregory St, Madison, WI 53711
0.06
$650,000
3
1
1,564
For Sale
2538 Commonwealth Ave, Madison, WI 53711
0.10
$717,800
3
1.5
1,587
Off Market
664 Sprague St, Madison, WI 53711
0.11
$840,000
4
3
2,663
For Sale

Local Information

  • Map ViewExplore the area around 2529 Gregory St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1933
2,127 sqft
$353/sqft
Open Parking

About this House

Classic 4-bedroom Colonial in the heart of Dudgeon-Monroe, The main level offers a bright, inviting dining space and a beautifully remodeled kitchen (TDS, 2013) featuring stainless appliances, heated Marmoleum floors, solid surface countertops, and custom Woodhaven cabinetry. A warm, welcoming living room with wood-burning fireplace and hardwood floors throughout completes the space, along with a convenient half bath. Upstairs, you’ll find four bedrooms with refurbished hardwood floors and a full bath, one bedroom opens to a spacious composite deck, perfect for morning coffee or evening unwinding. The finished lower level adds flexible living space for work or play. Ideally located near Lake Wingra, the Southwest Commuter Path, and the vibrant shops, cafés, and parks along Monroe Street.
2529 Gregory St, Madison, WI 53711 is a 4 bedroom, 2 bathroom, 2,127 sqft single-family home in Dudgeon-Monroe, built in 1933. It last sold for the $750,000 asking price on May 5, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $736,600, with a rent estimate of $3,501/month.
Last check for updates: about 3 hours ago
Listed by Carlos Alvarado
Compass Real Estate Wisconsin
Bought with: Mary Whitcomb, Compass Real Estate Wisconsin
Source: SCWMLS, MLS#2019753

Home Details for 2529 Gregory St

Active Status

MLS Status: Sold

Interior Features

Interior Details
Basement: Full,Walk-Out Access,Finished,Sump PumpNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2127 Square Feet
Appliances & Utilities
Utilities: Internet - CableAppliances: Washer, Dryer, Water Softener IncludedDryerLaundry: Lower LevelWasher
Heating & Cooling
Heating: Radiant Floor,None,RadiantHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Radiant Floor
Fireplace & Spa
Number of Fireplaces: 1Fireplace: 1 fireplace, Wood BurningHas a Fireplace
Levels, Entrance, & Accessibility
Stories: 2Levels: Two

Exterior Features

Exterior Home Features
Patio / Porch: DeckFencing: FencedVegetation: WoodedFoundation: Poured concrete foundatn
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: No Garage
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1753 Square Feet

Property Information

Year Built
Year Built: 1933
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Aluminum Siding, Brick, Vinyl Siding
Property Information
Not Included in Sale: Seller's personal propertyIncluded in Sale: Range/oven, refrigerator, dishwasher, disposal, water softener, washer and dryerParcel Number: 070928104193

Price & Status

Price
List Price: $750,000Price Per Sqft: $353/sqft

Location

Direction & Address
City: Madison
School Information
Elementary School: Franklin/RandallElementary School District: MadisonJr High / Middle School: HamiltonJr High / Middle School District: MadisonHigh School: WestHigh School District: Madison

Building

Building Area
Building Area: 2127 Square Feet

Lot Information

Lot Area: 3484.8 sqft

Offer

Listing Terms: Arms Length

Miscellaneous

BasementMls Number: 2019753Above Grade Unfinished Area: 1753

Price and Tax history

DateEventPrice
May 5, 2026
Source: N/A
Sold
$750,000
Apr 8, 2026
Source: WIREX MLS #2019753
Contingent
$750,000
Apr 2, 2026
Source: WIREX MLS #2019753
Listed For Sale
$750,000
Mar 14, 2026
Source: WIREX MLS #2017210
ListingRemoved
$775,000
Mar 4, 2026
Source: WIREX MLS #2017210
Listed For Sale
$775,000

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 2529 Gregory St

  • What is 2529 Gregory St estimated to be worth?
    Trulia's estimated value for 2529 Gregory St in Madison, WI is $736,600.
  • What is the price history for 2529 Gregory St?
    2529 Gregory St in Madison, WI last sold for $750,000 in May 2026.
  • 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.
  • Does 2529 Gregory St have air conditioning?
    Yes, 2529 Gregory St in Madison, WI has air conditioning.
  • Does 2529 Gregory St have laundry facilities?
    Yes, 2529 Gregory St in Madison, WI has in-unit laundry.

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