Does Sherman Village, Madison, WI have sidewalks?

As of early 2026, 94% of users say there are sidewalks

Is a car needed in Sherman Village, Madison, WI?

As of early 2026, 94% of users say car is needed

Is parking easy in Sherman Village, Madison, WI?

As of early 2026, 92% of users say parking is easy

Is there wildlife in Sherman Village, Madison, WI?

As of early 2026, 89% of users say there's wildlife

Is Sherman Village, Madison, WI dog-friendly?

As of early 2026, 89% of users say it's dog friendly

Is Sherman Village, Madison, WI quiet?

As of early 2026, 88% of users say it's quiet

Does Sherman Village, Madison, WI show holiday spirit?

As of early 2026, 83% of users say there's holiday spirit

Are yards well-kept in Sherman Village, Madison, WI?

As of early 2026, 83% of users say yards are well-kept

Are neighbors friendly in Sherman Village, Madison, WI?

As of early 2026, 78% of users say neighbors are friendly

Do kids play outside in Sherman Village, Madison, WI?

As of early 2026, 78% of users say kids play outside

Would people walk alone at night in Sherman Village, Madison, WI?

As of early 2026, 71% of users say people would walk alone at night

Are the streets well-lit in Sherman Village, Madison, WI?

As of early 2026, 57% of users say streets are well-lit

Is Sherman Village, Madison, WI walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

Do residents of Sherman Village, Madison, WI plan to stay at least 5 years?

As of early 2026, 50% of users say they plan to stay for at least 5 years

Is Sherman Village, Madison, WI walkable to restaurants?

As of early 2026, 38% of users say it's walkable to restaurants

Are there community events in Sherman Village, Madison, WI?

As of early 2026, 31% of users say there are community events

What is 4429 Jay Dr estimated to be worth?

Trulia's estimated value for 4429 Jay Dr in Madison, WI is $375,800 .

What is the price history for 4429 Jay Dr?

4429 Jay Dr in Madison, WI last sold for $365,000 in October 2025.

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 $427K. That is up $3.33K from the prior month.

Does 4429 Jay Dr have air conditioning?

Yes, 4429 Jay Dr in Madison, WI has air conditioning.

Does 4429 Jay Dr have laundry facilities?

Yes, 4429 Jay Dr in Madison, WI has laundry facilities.

OFF MARKET

4429 Jay Dr
Madison, WI 53704

Sherman Village

2 Beds
2 Baths
1,804 sqft (on 0.26 acres)

$375,800

Trulia Estimate

as of Aug 20, 2026

Est. Refi. Payment $2,464/mo*

Refinance Your Home

$375,800

Trulia Estimate

as of Aug 20, 2026

Est. Refi. Payment $2,464/mo*

Refinance Your Home

2 Beds

2 Baths

1,804 sqft

(on 0.26 acres)

Home Value

Trulia Estimate

$376K

Since last month

$400 (+0.1%)

Since last year

$400 (-0.1%)

Since last sale

$11K (+2.9%)

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 +125% in the last 10 years

Month	Estimated value
2026
August 2026	$376K
July 2026	$375K
June 2026	$376K
May 2026	$377K
April 2026	$382K
March 2026	$378K
February 2026	$371K
January 2026	$369K
2025
December 2025	$368K
November 2025	$366K
October 2025	$365K
September 2025	$371K
August 2025	$376K
July 2025	$369K
June 2025	$368K
May 2025	$370K
April 2025	$371K
March 2025	$360K
February 2025	$346K
January 2025	$339K
2024
December 2024	$343K
November 2024	$346K
October 2024	$349K
September 2024	$351K
August 2024	$353K
July 2024	$358K
June 2024	$362K
May 2024	$363K
April 2024	$359K
March 2024	$352K
February 2024	$342K
January 2024	$329K
2023
December 2023	$324K
November 2023	$325K
October 2023	$331K
September 2023	$334K
August 2023	$335K
July 2023	$340K
June 2023	$341K
May 2023	$332K
April 2023	$323K
March 2023	$311K
February 2023	$300K
January 2023	$298K
2022
December 2022	$297K
November 2022	$300K
October 2022	$303K
September 2022	$303K
August 2022	$302K
July 2022	$307K
June 2022	$312K
May 2022	$311K
April 2022	$307K
March 2022	$303K
February 2022	$287K
January 2022	$282K
2021
December 2021	$283K
November 2021	$281K
October 2021	$282K
September 2021	$286K
August 2021	$287K
July 2021	$294K
June 2021	$289K
May 2021	$269K
April 2021	$258K
March 2021	$243K
February 2021	$238K
January 2021	$232K
2020
December 2020	$231K
November 2020	$230K
October 2020	$229K
September 2020	$230K
August 2020	$232K
July 2020	$226K
June 2020	$233K
May 2020	$227K
April 2020	$230K
March 2020	$230K
February 2020	$216K
January 2020	$214K
2019
December 2019	$213K
November 2019	$214K
October 2019	$214K
September 2019	$213K
August 2019	$213K
July 2019	$208K
June 2019	$207K
May 2019	$208K
April 2019	$206K
March 2019	$204K
February 2019	$209K
January 2019	$199K
2018
December 2018	$194K
November 2018	$195K
October 2018	$194K
September 2018	$198K
August 2018	$198K
July 2018	$196K
June 2018	$199K
May 2018	$202K
April 2018	$197K
March 2018	$187K
February 2018	$185K
January 2018	$188K
2017
December 2017	$180K
November 2017	$183K
October 2017	$181K
September 2017	$188K
August 2017	$184K
July 2017	$185K
June 2017	$181K
May 2017	$184K
April 2017	$180K
March 2017	$179K
February 2017	$171K
January 2017	$171K
2016
December 2016	$169K
November 2016	$166K
October 2016	$168K
September 2016	$167K
August 2016	$167K

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
4406 Jay Dr, Madison, WI	0.07	Single-Family Home	$430,000	07/01/26	3	2	1,625
4417 Barby Ln, Madison, WI	0.10	Single-Family Home	$385,000	02/11/26	3	2	1,727
1121 Winn Trl, Madison, WI	0.13	Single-Family Home	$406,000	01/28/26	3	2	1,918
4609 Barby Ln, Madison, WI	0.15	Single-Family Home	$395,000	11/19/25	3	2	1,902
929 Northland Dr, Madison, WI	0.19	Single-Family Home	$349,000	11/21/25	3	2	1,594
1205 Nevada Rd, Madison, WI	0.16	Single-Family Home	$339,300	10/27/25	3	1.5	1,100
917 Monica Ln, Madison, WI	0.21	Single-Family Home	$345,000	12/05/25	3	1.5	1,496
4613 School Rd, Madison, WI	0.21	Single-Family Home	$387,500	10/08/25	3	1.5	2,103
4514 Jay Dr, Madison, WI	0.07	Single-Family Home	$378,000	06/12/26	5	2	2,084

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
4422 Jay Dr, Madison, WI 53704	0.03	$334,000	3	1	925	Off Market
4502 Jay Dr, Madison, WI 53704	0.04	$445,100	3	2	1,707	Off Market
4406 Mandrake Rd, Madison, WI 53704	0.06	$358,800	3	2	1,516	Off Market
4406 Jay Dr, Madison, WI 53704	0.07	$430,000	3	2	1,625	Recently Sold
4417 Mandrake Rd, Madison, WI 53704	0.07	$378,400	3	1	1,431	Off Market
4513 Judy Ln, Madison, WI 53704	0.07	$426,400	3	1.5	1,779	Off Market
4514 Jay Dr, Madison, WI 53704	0.07	$378,000	5	2	2,084	Recently Sold
4417 Barby Ln, Madison, WI 53704	0.10	$385,000	3	2	1,727	Recently Sold
4506 Judy Ln, Madison, WI 53704	0.10	$348,800	3	1.5	1,399	Off Market
4606 Mandrake Rd, Madison, WI 53704	0.10	$376,900	3	1.5	1,579	Off Market
4506 Northview Dr, Madison, WI 53704	0.10	$406,200	3	2	1,935	Off Market

Local Information

Map ViewExplore the area around 4429 Jay Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1959

Lot Size

0.26 acres

Living Area

1,804 sqft

Price/Sqft

$208

Parking

Garage

About this House

Discover this generously-sized home in a great North Side neighborhood filled with lots of natural light. Freshly painted & boasting updated bathrooms, kitchen, fixtures & doors, it offers modern comfort with a hint of mid-century flair. Originally a four-bedroom, the flexible layout allows you to enjoy expansive living & dining areas, or convert back to more bedrooms. Original Oak Flooring under the carpeting too! Basement Bathroom is now a half-bath, but plumbed & with plenty of room to add a tub &/or shower. Nice sized lot with a completely fenced area ready for your furry friends. Enjoy an unbeatable location within walking distance of schools, parks, sledding hill, Cherokee Marsh trails, shopping, restaurants, Willy North, farmer's market, Warner Park & the Mallards Stadium.

4429 Jay Dr, Madison, WI 53704 is a 2 bedroom, 2 bathroom, 1,804 sqft single-family home in Sherman Village, built in 1959. It last sold for $365,000 on Oct 14, 2025 (3% below the $375,000 asking price). It is currently off market. The Trulia Estimate is $375,800, with a rent estimate of $2,594/month.

Last check for updates: about 5 hours ago

Listed by Don White

First Weber Inc

Bought with: Thomas G Jennings, Stark Company, REALTORS

Source: SCWMLS, MLS#2005021

Home Details for 4429 Jay Dr

Interior Features
Interior Details Basement: Full,Partially FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 2Number of Bathrooms (main level): 2
Dimensions and Layout Living Area: 1804 Square Feet
Appliances & Utilities Appliances: Water Softener IncludedLaundry: Lower Level
Heating & Cooling Heating: Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa No Fireplace
Levels, Entrance, & Accessibility Stories: 1Levels: One

Exterior Features
Exterior Home Features Patio / Porch: PatioFencing: FencedFoundation: Poured concrete foundatn
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: 2 car,Detached
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1240 Square Feet

Property Information
Year Built Year Built: 1959
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building Construction Materials: Aluminum Siding, Brick
Property Information Not Included in Sale: Sellers' Personal Belongings.Included in Sale: Refrigerator, Stove / Oven, Dishwasher, Washer / Dryer, Water Softener, All Window Coverings. Left at convenience of seller: Shed in Backyard, Built in workbench in garage, workbench in basement, cabinet in bathroom, laundry cabinet, wall shelves, Ring Doorbells.Parcel Number: 080925219019

Price & Status
Price List Price: $375,000
Status Change & Dates Off Market Date: Tue Aug 12 2025

Active Status
MLS Status: Sold

Location
Direction & Address City: MadisonCommunity: Northland Manor
School Information Elementary School: LindberghElementary School District: MadisonJr High / Middle School: Black HawkJr High / Middle School District: MadisonHigh School: EastHigh School District: Madison

Building
Building Area Building Area: 1804 Square Feet

Lot Information
Lot Area: 0.26 acres

Offer
Listing Terms: Arms Length

Miscellaneous
BasementMls Number: 2005021Attribution Contact: HomeInfo@firstweber.comAbove Grade Unfinished Area: 1240

Price and Tax history

Date	Event	Price
Oct 14, 2025 Source: N/A	Sold	$365,000
Sep 8, 2025 Source: WIREX MLS #2005021	Pending	$375,000
Sep 6, 2025 Source: WIREX MLS #2005021	PriceChange	$375,000 Price decreased by 1%
Aug 26, 2025 Source: WIREX MLS #2005021	PriceChange	$379,900 Price decreased by 4%
Aug 12, 2025 Source: WIREX MLS #2005021	Listed For Sale	$395,000
Jun 29, 2020 Source: N/A	Sold	$224,900
May 25, 2020 Source: Agent Provided	Pending	$224,900
May 21, 2020 Source: Agent Provided	Listed For Sale	$224,900
Jan 25, 2010 Source: N/A	Sold	$140,000
Aug 30, 2008 Source: Agent Provided	ListingRemoved	$173,500
Jul 28, 2008 Source: Agent Provided	Listed For Sale	$173,500
May 12, 2008 Source: Agent Provided	ListingRemoved	$184,875
Apr 28, 2008 Source: Agent Provided	Listed For Sale	$184,875

Year	Property tax	Tax assessment
2024	$6,178	$315,600

Additional Cost

Market trends in Madison

Last updated July 2026

Avg. sale price

$427K

$3.33KMoM

Sale-to-List Price

102.4%

0.3%MoM

Price per sq ft

$266

$5MoM

Available listings

555

149MoM

Around this home

Lindbergh Elementary School
PK-5
Public
180 Students
Madison Metropolitan School District
4/10
GreatSchools Rating
Parent Rating Average
Diverse student body. Kind and qualified staff with low turnover. Strong leadership focused on results. Small classroom sizes. Despite the higher rate of poverty and higher percentage of ESL students my kids are doing well and enjoying it. This school continues to move in the right direction. Don't base your opinion entirely on standardized test scores.
Parent Review
10y ago
1 Reviews

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

Sherman Village

20 Homes For You
Buy: $255k - $550k

See Local Highlights

Neighborhood stats provided by third party data sources.

What Locals Say about Sherman Village

At least 13 Trulia users voted on each feature.

94 % Say there are sidewalks
94 % Say car is needed
92 % Say parking is easy
89 % Say there's wildlife
89 % Say it's dog friendly
88 % Say it's quiet
83 % Say there's holiday spirit
83 % Say yards are well-kept
78 % Say neighbors are friendly
78 % Say kids play outside
71 % Say people would walk alone at night
57 % Say streets are well-lit
50 % Say it's walkable to grocery stores
50 % Say they plan to stay for at least 5 years
38 % Say it's walkable to restaurants
31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

Steven C. Schaefer
Resident
1y ago
"Really peaceful and serene, feels connected to nature more so than other neighborhoods in this price range"
0
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Eva K.
Resident
6y ago
"Sherman Village is a Wonderful Neighborhood. I have lived here for 3 years and want to make it my permit home."
0
Flag
Eva K.
Resident
6y ago
"The Sherman village neighborhood is safe and friendly. The schools both elementary and middle schools are responsive and helpful."
0
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Kirstie H.
Resident
8y ago
"Quit and nice been here for years. lived here as a child and as an adult and the Northside is great."
0
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Jon B.
14y ago
"This neighborhood is near the highest elevation on the Northside of one of the USA's most livable cities.If you like the urban outdoors, the local parks and conservation areas are the best in the Capital region. Nearby Blackhawk MS recently earned another federal award for excellence. Quietest area in the City, yet easy access to downtown, airport, freeway, and MATC."
1
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LGBTQ Local Legal Protections

Frequently asked questions about 4429 Jay Dr

What is 4429 Jay Dr estimated to be worth?
Trulia's estimated value for 4429 Jay Dr in Madison, WI is $375,800.
What is the price history for 4429 Jay Dr?
4429 Jay Dr in Madison, WI last sold for $365,000 in October 2025.
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 $427K. That is up $3.33K from the prior month.
Does 4429 Jay Dr have air conditioning?
Yes, 4429 Jay Dr in Madison, WI has air conditioning.
Does 4429 Jay Dr have laundry facilities?
Yes, 4429 Jay Dr in Madison, WI has laundry facilities.