Is Dudgeon-Monroe, Madison, WI dog-friendly?

As of early 2026, 100% of users say it's dog friendly

Are yards well-kept in Dudgeon-Monroe, Madison, WI?

As of early 2026, 100% of users say yards are well-kept

Is Dudgeon-Monroe, Madison, WI walkable to grocery stores?

As of early 2026, 100% of users say it's walkable to grocery stores

Is Dudgeon-Monroe, Madison, WI walkable to restaurants?

As of early 2026, 100% of users say it's walkable to restaurants

Is parking easy in Dudgeon-Monroe, Madison, WI?

As of early 2026, 100% of users say parking is easy

Would people walk alone at night in Dudgeon-Monroe, Madison, WI?

As of early 2026, 100% of users say people would walk alone at night

Does Dudgeon-Monroe, Madison, WI have sidewalks?

As of early 2026, 100% of users say there are sidewalks

Do kids play outside in Dudgeon-Monroe, Madison, WI?

As of early 2026, 100% of users say kids play outside

Are there community events in Dudgeon-Monroe, Madison, WI?

As of early 2026, 86% of users say there are community events

Are neighbors friendly in Dudgeon-Monroe, Madison, WI?

As of early 2026, 82% of users say neighbors are friendly

Is a car needed in Dudgeon-Monroe, Madison, WI?

As of early 2026, 75% of users say car is needed

Does Dudgeon-Monroe, Madison, WI show holiday spirit?

As of early 2026, 71% of users say there's holiday spirit

Is Dudgeon-Monroe, Madison, WI quiet?

As of early 2026, 67% of users say it's quiet

Do residents of Dudgeon-Monroe, Madison, WI plan to stay at least 5 years?

As of early 2026, 60% of users say they plan to stay for at least 5 years

Is there wildlife in Dudgeon-Monroe, Madison, WI?

As of early 2026, 50% of users say there's wildlife

Are the streets well-lit in Dudgeon-Monroe, Madison, WI?

As of early 2026, 50% of users say streets are well-lit

OFF MARKET

2916 Gregory St
Madison, WI 53711

Dudgeon-Monroe

2 Beds
2 Baths
1,270 sqft

$589,300

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $3,677/mo*

Refinance Your Home

$589,300

Trulia Estimate

as of Jul 4, 2026

Est. Refi. Payment $3,677/mo*

Refinance Your Home

2 Beds

2 Baths

1,270 sqft

Local Information

Map ViewExplore the area around 2916 Gregory St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This single-family home is located at 2916 Gregory St, Madison, WI. 2916 Gregory St is in the Dudgeon-Monroe neighborhood in Madison, WI and in ZIP code 53711. This property has 2 bedrooms, 2 bathrooms and approximately 1,270 sqft of floor space. This property has a lot size of 5117 sqft and was built in 1918.

2916 Gregory St, Madison, WI 53711 is a 2 bedroom, 2 bathroom, 1,270 sqft single-family home in Dudgeon-Monroe, built in 1918. It last sold for $237,000 on Apr 5, 2010. It is currently off market. The Trulia Estimate is $589,300, with a rent estimate of $2,933/month.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Cooling only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 2916 Gregory St

Interior Features
Interior Details BasementTypes of Rooms: Family Room
Levels, Entrance, & Accessibility Stories: 1.5
Heating & Cooling Cooling System: Central
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: Asphalt
Parking & Garage GarageParking Space: 1Parking: Garage Detached

Property Information
Year Built Year Built: 1918Year Updated: 1965
Property Type / Style Property Type: Single Family HomeArchitecture: Bungalow

Community
Units in Building: 1

Lot Information
Lot Area: 5117 sqft

Price History for 2916 Gregory St

Date	Price	Event	Source
04/05/2010	$237,000	Sold	N/A
Recording Date 04/05/2010 Contract Date 03/31/2010 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Madison

Last updated May 2026

Avg. sale price

$415K

$8.83KMoM

Sale-to-List Price

101.7%

1.3%MoM

Price per sq ft

$250

$8MoM

Available listings

661

102MoM

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Property Tax and Assessment

Year	2024
Tax	$9,179
Assessment	$468,900

Home facts updated by county records

Comparable Sales for 2916 Gregory St

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
3116 Gregory St, Madison, WI	0.12	Single-Family Home	$600,000	12/01/25	2	1.5	1,122
653 Sheldon St, Madison, WI	0.26	Single-Family Home	$638,000	05/28/26	2	2	1,364
3222 Gregory St, Madison, WI	0.19	Single-Family Home	$410,000	06/04/26	2	1	830
636 Crandall St, Madison, WI	0.12	Single-Family Home	$840,000	06/03/26	3	2	1,817
3314 Gregory St, Madison, WI	0.23	Single-Family Home	$550,000	10/02/25	4	2	1,405
706 Briar Hill Rd, Madison, WI	0.48	Single-Family Home	$285,000	04/06/26	2	1.5	720
714 Baltzell St, Madison, WI	0.10	Single-Family Home	$720,000	10/15/25	3	1.5	2,319
3901 Meyer Ave, Madison, WI	0.37	Single-Family Home	$370,000	11/10/25	3	2	1,276
628 Sprague St, Madison, WI	0.20	Single-Family Home	$797,500	07/24/25	3	1.5	1,568
2314 Keyes Ave, Madison, WI	0.46	Single-Family Home	$575,000	02/02/26	2	1.5	1,333

Nearby homes

Get a sense of prices in the area by checking nearby homes.

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OFF MARKET
Est. $973,400
4 bd
3 ba
2,565 sqft
2906 Gregory St,
Madison, WI 53711
OFF MARKET
Est. $688,400
3 bd
2 ba
1,328 sqft
610 Pickford St,
Madison, WI 53711
OFF MARKET
Est. $906,300
3 bd
2 ba
1,705 sqft
2804 Gregory St,
Madison, WI 53711
SOLD
OCT 15, 2025
$720,000
3 bd
1.5 ba
2,319 sqft
714 Baltzell St,
Madison, WI 53711
OFF MARKET
Est. $623,200
3 bd
1.5 ba
1,410 sqft
644 Crandall St,
Madison, WI 53711
OFF MARKET
Est. $1,006,600
4 bd
2.5 ba
3,082 sqft
639/643 Crandall St,
Madison, WI 53711
SOLD
DEC 1, 2025
$600,000
2 bd
1.5 ba
1,122 sqft
3116 Gregory St,
Madison, WI 53711
OFF MARKET
Est. $860,200
4 bd
1.5 ba
1,580 sqft
2605 Gregory St,
Madison, WI 53711
OFF MARKET
Est. $722,000
3 bd
1 ba
1,292 sqft
664 Crandall St,
Madison, WI 53711
OFF MARKET
Est. $942,900
3 bd
2.5 ba
1,946 sqft
639 Knickerbocker St,
Madison, WI 53711
OFF MARKET
Est. $945,900
3 bd
2.5 ba
1,768 sqft
701 Gilmore St,
Madison, WI 53711
SOLD
MAR 2, 2026
$605,000
3 bd
1 ba
1,192 sqft
742 Baltzell St,
Madison, WI 53711

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Additional Cost

Assigned Schools

These are the assigned schools for 2916 Gregory St.

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Dudgeon-Monroe

8 Homes For You
Buy: $625k - $5m

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
Resident
3y ago
"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."
4
Flag
Waltergrote
Resident
5y ago
"Awesome neighborhood. Very walkable to great restaurants, parks, zoo, bike trail, arboretum, and Camp Randall. "
0
Flag
Pjcashman
Resident
6y ago
"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
13y ago
"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
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pmcichan
13y ago
"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
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