Chester Dr, Madison, WI 53719
OFF MARKET

$345,100

Trulia Estimate
  • 2 Beds
  • 3 Baths
  • 1,460 sqft

Chester Dr, Madison, WI 53719

Est. Refi. Payment $2,295/mo*
Refinance Your Home

Home Value

Trulia Estimate
$345K
Since last month
Increased$2K (+0.5%)
Since last year
Decreased$38K (-10%)
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 decreased by -10% in the last 10 years
MonthEstimated value
2026
August 2026$345K
July 2026$344K
June 2026$336K
May 2026$343K
April 2026$339K
March 2026$358K
February 2026$338K
January 2026$354K
2025
2024
2023
2022
2020

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
6806 Raymond Rd #101, Madison, WI
0.30
Condo
$295,000
04/22/26
2
2
1,429
7203 Mid Town Rd #305, Madison, WI
0.32
Condo
$239,900
03/30/26
2
2
1,293
7203 Mid Town Rd #304, Madison, WI
0.32
Condo
$250,000
08/06/26
2
2
1,166
7203 Mid Town Rd #212, Madison, WI
0.32
Condo
$180,000
05/04/26
2
2
1,092
7203 Mid Town Rd #209, Madison, WI
0.32
Condo
$256,000
08/13/26
2
2
1,088
7203 Mid Town ROAD #303, Madison, WI
0.32
Condo
$240,000
06/12/26
2
2
1,078
7201 Mid Town Rd #203, Madison, WI
0.32
Condo
$233,000
10/29/25
2
2
1,061
2822 Cimarron Trl, Madison, WI
0.57
Condo
$279,800
09/16/25
2
2
1,250
7203 Mid Town Rd #301, Madison, WI
0.32
Condo
$246,000
01/16/26
2
1
1,014
2831 Cimarron Trl, Madison, WI
0.61
Condo
$245,000
04/01/26
2
2
1,250

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
2310 Whitlock Rd, Madison, WI 53719
0.04
$398,400
2
3
1,310
Off Market
2318 Whitlock Rd, Madison, WI 53719
0.06
$445,000
4
2
2,085
Recently Sold
9 Newbury Cir, Madison, WI 53711
0.06
$446,200
3
1.5
2,040
Off Market
9 Pagham Ct, Madison, WI 53719
0.09
$433,700
3
2
1,340
Off Market
6926/6930 Chester Dr, Madison, WI 53719
0.10
$567,700
5
3
2,106
Off Market
2017 Legacy Ln, Madison, WI 53719
0.10
$425,000
3
2.5
1,644
Off Market
7727 Starnova Dr, Madison, WI 53719
0.10
$449,900
3
2.5
1,526
Recently Sold
2011 Legacy Ln, Madison, WI 53719
0.10
$409,900
3
2.5
1,765
Recently Sold
7647 Stones Throw Dr, Madison, WI 53719
0.10
$497,300
3
2.5
1,649
Off Market
7717 Stones Throw Dr, Madison, WI 53719
0.10
$579,062
3
2.5
1,848
Recently Sold
2020 S High Point, Madison, WI 53719
0.10
$399,900
3
2.5
1,472
Recently Sold
18 Newbury Cir, Madison, WI 53711
0.10
$429,300
3
2
1,904
Off Market

Local Information

  • Map ViewExplore the area around Chester Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
1,460 sqft
$236/sqft

About this House

WEST! NEWER! SPARKLY CLEAN! SPACIOUS! THIS END UNIT IN THE CHESTER HILL CONDO IS ONE OF THE LARGEST FLOOR PLANS AND BACKS UP TO GREEN SPACE. FEATURES INCLUDE PRIVATE ENTRY, 2 CAR ATTACHED GARAGE, FULL BASEMENT-UNFINISHED, WOOD BURNING FIREPLACE, HICKORY FLOORING IN KITCHEN AND DINING AREAS, BREAKFAST BAR, AND MAIN LEVEL WASHER AND DRYER! BOTH BEDROOMS HAD ATTACHED FULL BATHS AND WALK-IN CLOSETS
Chester Dr, Madison, WI 53719 is a 2 bedroom, 3 bathroom, 1,460 sqft condo. More recently, it was listed as a rental in September 2012 with an asking price of $1,195 per month. That rental listing was removed on October 27, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $345,100, with a rent estimate of $2,185/month.

Home Details for Chester Dr

Property Information

Property Type / Style
Property Type: Condo

Price and Tax history

DateEventPrice
Oct 27, 2012
Source: Agent Provided
ListingRemoved
$1,125
Sep 27, 2012
Source: Agent Provided
PriceChange
$1,125
Price decreased by 6%
Sep 21, 2012
Source: Agent Provided
Listed For Rent
$1,195

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

What Locals Say about Madison

At least 1686 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 85 % Say there are sidewalks

  • 82 % Say parking is easy

  • 74 % Say car is needed

  • 71 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 70 % Say kids play outside

  • 69 % Say people would walk alone at night

  • 64 % Say it's walkable to restaurants

  • 63 % Say streets are well-lit

  • 61 % Say there's wildlife

  • 60 % Say it's quiet

  • 57 % Say neighbors are friendly

  • 54 % Say it's walkable to grocery stores

  • 54 % Say they plan to stay for at least 5 years

  • 39 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Marbledmess
    "You will love it! Can be hard to find fully enclosed yards but there are dog parks "
    0
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  • Trulia User
    "Great parks, cool restaurants"
    0
    Flag
  • Raymonroejackson
    "This community is stable, and itโ€™s important for them to remember to teach their children how to maintain its safety and strength."
    0
    Flag
  • Trulia User
    "I am newer in my neighborhood & feel welcome. Those close to me have been helpful in getting acquainted."
    0
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  • Mitchell William Beiter
    "I like all the sidewalks and restaurants nearby. I liked it a lot more than I expected, I donโ€™t see my neighbors much though"
    0
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  • Matt P
    "We absolutely love living here! There are three parks within a 10-minute walk from our house, including the multiple playground sets at the elementary school. We feel safe and secure, and we know all our neighbors. It's a great place to raise a family!"
    0
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  • Mitchell William Beiter
    "Pretty walkable I think! I donโ€™t have a pet but most roads have a sidewalk and thereโ€™s plenty of garbage cans around "
    0
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  • Lkeillorcollins
    "Have lived downtown for 10 years. Love it. So much to do, restaurants, entertainment. The lakes. Easy access to public transportation. "
    0
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  • Jlittel66
    "Friendly neighborhood community. My neighbors offer support and we have fun with neighborhood social gatherings"
    0
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  • Abdirizakmohamud05
    "The area had great park and I think itโ€™s good for families to leave there to keep kids happy. However school has also nearby as the area is been well organized for everything including bus transportation. Also you can get community guidelines if necessary"
    0
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  • Nicholas Vest
    "I donโ€™t see as many families in the new multi-level apartment buildings (the high rises). There are some families living downtown, but they might be in condos. The west and east sides outside the square and campus housing have many more families. Downtown is great for the childrenโ€™s museum, farmers market, and monona terrace has live music, etc. sometimes. Outside of the square, there are nice parks for kids and families with play sets and beaches."
    2
    Flag
  • Shirley.eckes
    "There is a pet store within walking distance as well as several parks for leashed pets and socialization"
    1
    Flag
  • Shirley.eckes
    "Friendly neighborhood, close to the lakes, restaurants and music events. The location is convenient to go downtown and bike around the lake "
    0
    Flag
  • Trulia User
    "Madisonian born and raised! Itโ€™s a beautiful city with lots of friendly faces. There are community areas and events to enjoy with family and friends year round!"
    0
    Flag
  • Shirley.eckes
    "The 5 festivals, easy bike access, great nearby bars and restaurants. Also friendly neighbors including an annual block party and round robin dinner get together "
    0
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  • Steven C. Schaefer
    "Really peaceful and serene, feels connected to nature more so than other neighborhoods in this price range"
    0
    Flag
  • Shirley.eckes
    "Festivals, lakes, biking, local restaurants, mass transportation, great neighborhoods vibe, music venues"
    0
    Flag
  • 2xb4kvtmt9
    "Age diverse neighborhood with beautiful and well maintained parks within walking distance. Homes/properties are well maintained and the proximity to all the great places and events Madison and Sun Prairie have to offer are only moments away."
    0
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  • Viajeromundo
    "Nice work man keep going man keep going hard keep going you are doing amazing things keep it coming keep going you can do what youโ€™re feeling good and you will be doing good keep "
    0
    Flag
  • Shirley.eckes
    "Convenient location with great restaurants, music venues and summer festivals. Charming houses and friendly neighbors. "
    1
    Flag
  • Msgt621
    "Walk ability, access to public transportation, close to university and downtown . Access to shopping and restaurants "
    0
    Flag
  • Xn9ymxhgrh
    "Good neighborhood but dangerious still but has been cleaned up greatly by apartment owners and the local authorities. Iโ€™ve witnessed a ton of change within the past year. "
    1
    Flag
  • Pavelec
    "Only 1 north exit and 1 south exit cuts down on traffic on the side streets. Beautiful large park in the middle of the subdivision."
    0
    Flag
  • Lindsey Ray
    "Iโ€™ve lived here for 3 years and plan to stay awhile ! Beautiful lakes, great neighborhood, friendly people, walkable and bike-able! Itโ€™s great I love it. "
    0
    Flag
  • Mm
    "Walking or biking easy access to us and hospitals and anything else you might want to do. Extra schar"
    0
    Flag
  • Simon Huang
    "I donโ€™t like about living with dog owners as my neighborhood๏ผŒbecause I am afraid of dogs๏ผŒespecially the big dogs๏ผŽI had been attacked by a dog when I was in childhood."
    0
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  • Mfzwc2snw7
    "I love living here itโ€™s home Iโ€™ve been living here for 5 years and love every second of it but right now Iโ€™m trying to move again in Fitchburg will be nice hopefully "
    0
    Flag
  • Trulia User
    "Good nice people around hear I love respect and taking care of others I love parks and school for kids all positive vibes "
    1
    Flag
  • Trulia User
    "I see lots of people walking their dogs all the time, nobody seems to have a problem with it. The area is great for walks along the bay! "
    0
    Flag
  • Trulia User
    "Very dog friendly, neighbors are always out walking their digs, and there is a popular dog park in the neighborhood "
    0
    Flag
  • Trulia User
    "I drive less than ten minutes to an industrial zone where I work. Close to downtown, belt line, Hwy 14 bike trails and Lewis nine Springs Environmental byway. "
    0
    Flag
  • Trulia User
    "Events at Olbrich are very special and often free or reasonably priced. It's overall a very kind and friendly neighborhood."
    2
    Flag
  • Trulia User
    "There is a great natural feel to living in this area. There are lots of birds, squirrels, bunnies, and chipmunks that appear outside. Mature trees exist and bring wonderful shade during the summer. "
    0
    Flag
  • Trulia User
    "Walking and bike path access to parks and trails is available. Various housing style opportunities exist in this neighborhood. A community garden is here too. Getting into downtown is very easy. Traffic is mostly off major arterial streets."
    1
    Flag
  • Trulia User
    "Its long, about to change. Still makes for a long day if you rely on public transportation. I am required to say more than my succinct sentence. "
    0
    Flag
  • Trulia User
    "Community oriented, walking distance to water, local restaurants and activities. Family friendly. "
    0
    Flag
  • Trulia User
    "I donโ€™t know much about community events, I look for decent peopleโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆโ€ฆ.decent neighborhoods. "
    0
    Flag
  • Trulia User
    "friendly neighbors, ample nature, good walking paths, safe area, walkable to downtown Middleton, accesible by the 15 busline, neighborhood pool if you want to join"
    0
    Flag
  • Trulia User
    "It is a nice commute, and most of the places around here are walkable. so you save a lot of money on gas."
    0
    Flag
  • Trulia User
    "Great access to shopping ,grocery stores, entertainment,UW campus and a UW Hospitals. Good access to bike paths and running routes. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about Chester Dr

  • What is Chester Dr estimated to be worth?
    Trulia's estimated value for Chester Dr in Madison, WI is $345,100.
  • 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 do residents say about Madison?
    Residents describe Madison, WI as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Madison, WI.

Explore by feature - Pet Friendly

495 pet-friendly rentals in Madison, WI

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

75 rentals with an outdoor space in Madison, WI

Apartments for Rent

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Off Market Homes Near Chester Dr

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Homes for sale near Chester Dr

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