Is Shorewood Hills, WI walkable to grocery stores?

As of early 2026, 95% of users say it's walkable to grocery stores

Is Shorewood Hills, WI walkable to restaurants?

As of early 2026, 89% of users say it's walkable to restaurants

Do kids play outside in Shorewood Hills, WI?

As of early 2026, 88% of users say kids play outside

Is parking easy in Shorewood Hills, WI?

As of early 2026, 86% of users say parking is easy

Is Shorewood Hills, WI dog-friendly?

As of early 2026, 85% of users say it's dog friendly

Is there wildlife in Shorewood Hills, WI?

As of early 2026, 84% of users say there's wildlife

Would people walk alone at night in Shorewood Hills, WI?

As of early 2026, 79% of users say people would walk alone at night

Does Shorewood Hills, WI have sidewalks?

As of early 2026, 75% of users say there are sidewalks

Does Shorewood Hills, WI show holiday spirit?

As of early 2026, 72% of users say there's holiday spirit

Is Shorewood Hills, WI quiet?

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

Are there community events in Shorewood Hills, WI?

As of early 2026, 63% of users say there are community events

Are neighbors friendly in Shorewood Hills, WI?

As of early 2026, 57% of users say neighbors are friendly

Is a car needed in Shorewood Hills, WI?

As of early 2026, 53% of users say car is needed

Are yards well-kept in Shorewood Hills, WI?

As of early 2026, 47% of users say yards are well-kept

Do residents of Shorewood Hills, WI plan to stay at least 5 years?

As of early 2026, 33% of users say they plan to stay for at least 5 years

Are the streets well-lit in Shorewood Hills, WI?

As of early 2026, 29% of users say streets are well-lit

What is 1244 Wellesley Rd estimated to be worth?

Trulia's estimated value for 1244 Wellesley Rd in Madison, WI is $1,131,300 .

Is Madison a buyer's or seller's market?

Madison is currently a seller's market, based on recent for-sale activity.

What do residents say about Madison?

Residents describe Madison, WI as walkable to grocery stores, walkable to restaurants, and easy to park in. See recently sold homes in Madison, WI .

What are the closest schools to 1244 Wellesley Rd?

The closest schools to 1244 Wellesley Rd in Madison, WI are Hamilton Middle School (rated 8/10), Shorewood Hills Elementary School (Pre-K, rated 10/10), West High School (rated 9/10).

Does 1244 Wellesley Rd have air conditioning?

Yes, 1244 Wellesley Rd in Madison, WI has air conditioning.

Does 1244 Wellesley Rd have laundry facilities?

Yes, 1244 Wellesley Rd in Madison, WI has in-unit laundry.

OFF MARKET

$1,131,300

Trulia Estimate

6 Beds
3.5 Baths
3,695 sqft (on 2.90 acres)

1244 Wellesley Rd, Madison, WI 53705

Est. Refi. Payment $7,352/mo*

Refinance Your Home

Home Value

Trulia Estimate

$1.13M

Since last month

$11K (-1%)

Since last year

$48K (+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 +64% in the last 10 years

Month	Estimated value
2026
August 2026	$1.13M
August 2026	$1.13M
July 2026	$1.14M
June 2026	$1.14M
May 2026	$1.16M
April 2026	$1.17M
March 2026	$1.14M
February 2026	$1.07M
January 2026	$1.06M
2025
December 2025	$1.07M
November 2025	$1.07M
October 2025	$1.06M
September 2025	$1.08M
August 2025	$1.08M
July 2025	$1.09M
June 2025	$1.06M
May 2025	$1.06M
April 2025	$1.03M
March 2025	$1.01M
February 2025	$961K
January 2025	$933K
2024
December 2024	$922K
November 2024	$958K
October 2024	$1M
September 2024	$1.02M
August 2024	$1.03M
July 2024	$1.03M
June 2024	$1.02M
May 2024	$1.02M
April 2024	$1.02M
March 2024	$985K
February 2024	$956K
January 2024	$898K
2023
December 2023	$904K
November 2023	$912K
October 2023	$944K
September 2023	$951K
August 2023	$939K
July 2023	$953K
June 2023	$972K
May 2023	$927K
April 2023	$896K
March 2023	$867K
February 2023	$853K
January 2023	$854K
2022
December 2022	$854K
November 2022	$880K
October 2022	$894K
September 2022	$904K
August 2022	$902K
July 2022	$925K
June 2022	$943K
May 2022	$935K
April 2022	$913K
March 2022	$896K
February 2022	$850K
January 2022	$828K
2021
December 2021	$826K
November 2021	$830K
October 2021	$831K
September 2021	$829K
August 2021	$836K
July 2021	$849K
June 2021	$876K
May 2021	$875K
April 2021	$839K
March 2021	$803K
February 2021	$797K
January 2021	$788K
2020
December 2020	$790K
November 2020	$787K
October 2020	$783K
September 2020	$776K
August 2020	$763K
July 2020	$750K
June 2020	$751K
May 2020	$749K
April 2020	$747K
March 2020	$740K
February 2020	$748K
January 2020	$754K
2019
December 2019	$756K
November 2019	$733K
October 2019	$875K
September 2019	$876K
August 2019	$884K
July 2019	$886K
June 2019	$939K
May 2019	$950K
April 2019	$705K
March 2019	$718K
February 2019	$691K
January 2019	$742K
2018
December 2018	$739K
November 2018	$720K
October 2018	$724K
September 2018	$718K
August 2018	$729K
July 2018	$718K
June 2018	$706K
May 2018	$710K
April 2018	$694K
March 2018	$693K
February 2018	$689K
January 2018	$686K
2017
December 2017	$679K
November 2017	$696K
October 2017	$688K
September 2017	$688K
August 2017	$695K
July 2017	$697K
June 2017	$701K
May 2017	$691K
April 2017	$705K
March 2017	$694K
February 2017	$693K
January 2017	$687K
2016
December 2016	$688K
November 2016	$681K
October 2016	$687K
September 2016	$691K

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
1015 Yale Rd, Madison, WI	0.26	Single-Family Home	$1,500,000	07/31/26	4	2.5	4,350
1219 Wellesley Rd, Madison, WI	0.07	Single-Family Home	$1,100,000	12/30/25	4	2	2,891
2933 Colgate Rd, Madison, WI	0.29	Single-Family Home	$1,950,000	07/22/26	4	3.5	3,453
1226 Sweetbriar Rd, Madison, WI	0.08	Single-Family Home	$1,175,000	08/03/26	3	2.5	2,000
1234 Sweetbriar Rd, Madison, WI	0.06	Single-Family Home	$885,000	08/03/26	3	1.5	2,054
3316 Blackhawk Dr, Madison, WI	0.42	Single-Family Home	$1,690,000	06/18/26	4	2.5	2,989
1007 Edgehill Dr, Madison, WI	0.35	Single-Family Home	$1,380,000	07/01/26	4	3	2,576
3309 Tally Ho Ln, Madison, WI	0.52	Single-Family Home	$1,400,000	07/03/26	5	4	4,100
3440 Topping Rd, Madison, WI	0.54	Single-Family Home	$1,050,000	09/30/25	4	2.5	4,336
3425 Crestwood Dr, Madison, WI	0.52	Single-Family Home	$1,495,000	11/17/25	4	3.5	3,201

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
1234 Wellesley Rd, Madison, WI 53705	0.03	$1,625,000	5	3.5	3,473	For Sale
1234 Sweetbriar Rd, Madison, WI 53705	0.06	$885,000	3	1.5	2,054	Recently Sold
1226 Wellesley Rd, Madison, WI 53705	0.05	$845,300	3	2.5	1,989	Off Market
1226 Sweetbriar Rd, Madison, WI 53705	0.08	$1,175,000	3	2.5	2,000	Recently Sold
1219 Wellesley Rd, Madison, WI 53705	0.07	$1,100,000	4	2	2,891	Recently Sold
1213 Sweetbriar Rd, Madison, WI 53705	0.09	$2,088,700	4	3.5	3,300	Off Market
1210 Sweetbriar Rd, Madison, WI 53705	0.11	$1,469,000	5	3	2,973	For Sale
2809 Columbia Rd, Madison, WI 53705	0.16	$1,847,000	5	3	3,380	Off Market
3110 Oxford Rd, Madison, WI 53705	0.19	$1,555,500	4	2.5	3,102	Off Market
3113 Oxford Rd, Madison, WI 53705	0.20	$1,590,000	4	3.5	3,551	Off Market
3112 Oxford Rd, Madison, WI 53705	0.20	$1,006,800	3	2.5	2,345	Off Market
1107 Wellesley Rd, Madison, WI 53705	0.18	$1,740,100	4	3.5	3,712	Off Market

Local Information

Map ViewExplore the area around 1244 Wellesley Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1935

2.9 acre lot

3,695 sqft

$306/sqft

Garage

About this House

Lovingly maintained w/ old style charm. Flexible home offers up to 6 bedrms including a "guest suite" that could serve as master bedrm or au pair suite w/ private entrance. Features include refinished hardwds, new carpet & paint. LL partially finished to include rec rm. Large paver patio, perennial gardens w/ paver path & fenced, gated area for pets or children. Rare 2-car attached garage. Easy access to UW, pool, parks, schools. Assessment does not reflect all living area.

1244 Wellesley Rd, Madison, WI 53705 is a 6 bedroom, 4 bathroom, 3,695 sqft single-family home built in 1935. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,131,300, with a rent estimate of $5,852/month.

Home Details for 1244 Wellesley Rd

Interior Features
Interior Details BasementIn-law unitNumber of Rooms: 14Types of Rooms: Dining Room, Laundry Room, Office, Recreation Room, Sun Room
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood
Appliances & Utilities DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: AsphaltExterior: Stone, VinylLawn
Parking & Garage GarageParking Spaces: 4Parking: Garage Attached, Off Street

Property Information
Year Built Year Built: 1935
Property Type / Style Property Type: Single Family HomeArchitecture: Tudor

Building
Levels, Entrance, & Accessibility Disabled Access

Community
Units in Building: 1

Lot Information
Lot Area: 2.90 acres

Price and Tax history

Date	Event	Price
Oct 14, 2019 Source: Agent Provided	ListingRemoved	$899,900
Jul 5, 2019 Source: Agent Provided	PriceChange	$899,900 Price decreased by 5%
May 30, 2019 Source: Agent Provided	Listed For Sale	$949,900

Year	Property tax	Tax assessment
2024	$14,285	$947,700

Additional Cost

Market trends in Shorewood Hills

Last updated July 2026

Avg. sale price

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Sale-to-List Price

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Price per sq ft

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Available listings

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Around this home

Shorewood Hills Elementary School
PK-5
Public
368 Students
Madison Metropolitan School District
10/10
GreatSchools Rating
Parent Rating Average
I am a mother of three school-aged children. We came from another country because my husband is pursuing his PhD studies here. When we arrived, my children didn’t speak English, and I was very worried about how they would adapt to a new culture, language, and school environment.From the very first day, we felt truly welcomed and cared for by everyone at the school. We experienced genuine kindness and support from every person we met. Last year, my eldest son faced some challenges, and the school staff responded with incredible understanding and professionalism.I want to sincerely thank Principal Gillespie and all the wonderful teachers who supported us and helped create such a warm, inclusive, and encouraging atmosphere.
Parent Review
1y ago
4 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.

What Locals Say about Shorewood Hills

At least 14 Trulia users voted on each feature.

95 % Say it's walkable to grocery stores
89 % Say it's walkable to restaurants
88 % Say kids play outside
86 % Say parking is easy
85 % Say it's dog friendly
84 % Say there's wildlife
79 % Say people would walk alone at night
75 % Say there are sidewalks
72 % Say there's holiday spirit
67 % Say it's quiet
63 % Say there are community events
57 % Say neighbors are friendly
53 % Say car is needed
47 % Say yards are well-kept
33 % Say they plan to stay for at least 5 years
29 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Shannon Riley
Resident
2y ago
"I work on the west side so everyone is heading in when I am going out and heading out when I am heading in. Easy to get almost anywhere from here."
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Trulia User
Prev. Resident
5y ago
"Spring harbor is a nice and quiet little neighborhood with good parks and a beach. Good for walking and jogging. "
0
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Trulia User
Visitor
5y ago
"I live in Shorewood Hills, but we walk the Spring Harbor neighborhood and use the public boat ramp. It is a great location and has a good public school."
0
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Designerardis
Resident
5y ago
"My neighborhood does not have good mass transit. Most people use Uber OT Taxis when they need transportation other than their own vehicles."
0
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Designerardis
Resident
6y ago
"4th of July parade and fireworks. Numerous community clubs. Neighborhood pool. Neighborhood grade school. "
0
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Jeffgun61
Resident
8y ago
"I have lived here for 10 years and have always enjoyed the relaxed small town feel and unique neighborhoods. Ease of access to shopping and other amenities, as well as downtown Madison are a plus."
0
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Cfree22508
12y ago
"Close to shopping malls, groceries, restaurants - all within walking distance. "
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Frequently asked questions about 1244 Wellesley Rd

What is 1244 Wellesley Rd estimated to be worth?
Trulia's estimated value for 1244 Wellesley Rd in Madison, WI is $1,131,300.
Is Madison a buyer's or seller's market?
Madison is currently a seller's market, based on recent for-sale activity.
What do residents say about Madison?
Residents describe Madison, WI as walkable to grocery stores, walkable to restaurants, and easy to park in. See recently sold homes in Madison, WI.
What are the closest schools to 1244 Wellesley Rd?
The closest schools to 1244 Wellesley Rd in Madison, WI are Hamilton Middle School (rated 8/10), Shorewood Hills Elementary School (Pre-K, rated 10/10), West High School (rated 9/10).
Does 1244 Wellesley Rd have air conditioning?
Yes, 1244 Wellesley Rd in Madison, WI has air conditioning.
Does 1244 Wellesley Rd have laundry facilities?
Yes, 1244 Wellesley Rd in Madison, WI has in-unit laundry.