5429 Chestnut Dr, Racine, WI 53402
OFF MARKET

5429 Chestnut Dr
Racine, WI 53402

  • 4 Beds
  • 3 Baths

$432,800

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $2,732/mo*
Refinance Your Home

$432,800

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $2,732/mo*
Refinance Your Home
4 Beds
3 Baths

Local Information

  • Map ViewExplore the area around 5429 Chestnut Dr.
  • Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautifully maintained inside and out! This four bedroom Colonial gives you the space you've been looking for. New neutral color carpet in formal living and dining rooms. Family room with stone fireplace. Kitchen with appliances, pantry and dinette. Master suite has cathedral ceiling, walk-in closet and private bath with Whirlpool. Lots of rec room potential. Newer windows, soffits, fascia, furnace, central air, roof and deck with charming trellis. Fenced yard with fountain.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 5429 Chestnut Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 2

Property Information

Year Built
Year Built: 1991
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 5429 Chestnut Dr

DatePriceEventSource
05/19/2015$197,000Sold
N/A
02/15/2015$195,000PriceChange
Agent Provided
01/17/2015$205,000PriceChange
Agent Provided
03/07/2014$209,900PriceChange
Agent Provided
03/06/2014$214,900Listed For SaleAgent Provided
03/04/2014$21,000Sold
N/A
10/17/2013$214,900ListingRemovedAgent Provided
08/21/2013$214,900Listed For SaleAgent Provided

Market trends in Caledonia

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
67
24MoM
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Property Tax and Assessment

Year2024
Tax$5,776
Assessment$379,300
Home facts updated by county records

Comparable Sales for 5429 Chestnut Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5450 Charles STREET, Racine, WI
0.04
Single-Family Home
$460,000
11/26/25
4
2.5
2,745
1615 Palamino DRIVE, Racine, WI
0.09
Single-Family Home
$410,000
07/25/25
3
2.5
2,045
5536 Whirlaway LANE, Racine, WI
0.24
Single-Family Home
$351,000
11/17/25
4
2.5
2,659
1709 Tiffany DRIVE, Racine, WI
0.19
Single-Family Home
$320,600
08/22/25
4
2.5
2,750
1519 Tiffany DRIVE, Racine, WI
0.16
Single-Family Home
$275,000
11/17/25
3
2.5
1,864
1212 Palamino DRIVE, Racine, WI
0.15
Single-Family Home
$410,000
08/15/25
3
2.5
1,716
1507 Tiffany DRIVE, Racine, WI
0.16
Single-Family Home
$400,000
07/08/25
4
3.5
2,300
1123 Palamino DRIVE, Racine, WI
0.20
Single-Family Home
$385,000
05/29/26
4
1.5
1,989
5427 Sunshine Ln, Racine, WI
0.19
Single-Family Home
$410,000
07/25/25
3
3
-
5443 Heidi DRIVE, Racine, WI
0.25
Single-Family Home
$448,000
02/02/26
3
2.5
2,020

Nearby homes

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Assigned Schools

These are the assigned schools for 5429 Chestnut Dr.
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 Caledonia

At least 65 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 91 % Say parking is easy

  • 90 % Say yards are well-kept

  • 90 % Say kids play outside

  • 88 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 80 % Say people would walk alone at night

  • 78 % Say it's quiet

  • 75 % Say there's wildlife

  • 65 % Say neighbors are friendly

  • 51 % Say they plan to stay for at least 5 years

  • 35 % Say there are community events

  • 26 % Say streets are well-lit

  • 22 % Say it's walkable to grocery stores

  • 19 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "People are generally friendly here. A lot of younger people are moving in making it quite the variety of ages. Great place to live!"
    0
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  • Carlabrowning
    "I don’t have a commute. I work from home. But every thing you could possibly need is between 2-5 miles from my home. It’s fantastic. Love it here. "
    0
    Flag
  • Hyltonbrownmaria
    "Once a year our neighbors come together, all who’s in attendance cook something so that our neighbors can enjoy. "
    1
    Flag
  • Steward338
    "We have lived in the community for a couple years, people are responsible and friendly. Neighbors look out for each other."
    0
    Flag
  • Elle W
    "Very safe, dog-friendly area! Just be sure to watch for coyotes at night. They come into my back yard often & once were less than two feet away from my small dachshund puppy. If I hadn’t come outside in that second, the coyote would’ve ran off with my pup for sure!"
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  • Amosno
    "We live in a quiet neighborhood and everyone is very friendly. Not a lot of restaurants or things to do in the village of Caledonia. However it is a safe community to raise children."
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  • Allison V.
    "Really nice, quiet community. Friendly people. Great place to raise a family. Very well kept houses and yards "
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    Flag
  • Lisanlesrvs
    "In our neighborhood. All the dogs that I see are on leashes. All the pet owners pick up after their pets if they go potty in front of your house."
    0
    Flag
  • Lisanlesrvs
    "I live in a condo in the woods. Just love it!! Our condos are on a very quiet cul-de-sac. Most of us are retirees. Everyone here is very friendly. A lot of good walking areas. Grocery stores and clothing shops, hospital and Lake Michigan is about 15 minutes away from here......everything is very convenient. "
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  • Amosno
    "I love walking my dogs and being outside in my neighborhood. The neighbors are friendly and everybody watches out for each other. I would like to see more shopping in the area."
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    Flag
  • Kristina S.
    "I see and talk with people walking their dogs up and down the street. they even go the park in the other neighborhood across the street..by a little school. it's a quiet area. "
    0
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  • Kristina S.
    "My Commute is not at all hard to get to grocery store for I am less than mile away, and including the access to buses.; even the Wis. Coach Bus u can catch. "
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  • Cindy Skovsted
    "Raising our children in this peaceful friendly neighborhood in a home we built w/ extreme detail, care & customized extras was the best decision we have ever made & we are excited to sell it to someone who we are sure will enjoy all of it's wonderfulness also. Entertaining friends in the home & on the fabulous deck in the back yard brought us so much joy, along w/ the sun room, fire pit & hot tub family together times."
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  • Mr.andMrs.Gibas
    "we have lived here since 2006. The neighbors are friendly. There is a big to do when it comes to Trick or Treat. Many neighbors go way out to decorate their front yards for this day. The kids were where kids are now grown, so this neighborhood needs new families to liven it up again. It is safe to walk, many people do, or ride bikes and walk their dogs. We are a neighborhood with in a neighborhood. What I mean is there is a pond with houses around it and then there is a houses around those homes. It is nice in the summer time, fall and winter. Many decorate for Christmas too. I love this area and would recommend it for sure."
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  • Emerald S.
    "it's quiet not much traffic. there's not much community events in neighborhood but River Bend Nature Reserve is close by there's trails and events at that location that benefits the Reserve. there's couple near by and food shopping center. here's no community guidelines, it's all apt. building on my street. "
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  • Amosno
    "Hon my neighborhood is great and has lots of fun stuff to do and as beautiful and highly decorated and accessible to a lot of convenient stores in a lot of gas stations and a meat market and I love one love me enough but up"
    0
    Flag
  • Amosno
    "We have friendly neighbors and we all watch out for each other. Lots of block parties and close to shopping and schools."
    0
    Flag
  • Amosno
    "Great place to raise a family. Close to interstate and downtown restaurants and activities. Safe and friendly area with a lot of new growth and jobs in the area."
    0
    Flag
  • Guenther j.
    "No events, but each cul-de-sac in the Crestview Park neighborhood connects to a little playground. It’s really nice and there are tons of fun (and safe) shortcuts for kids to get to their friends’ house."
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  • Lanita B.
    "Many kids in the neighborhood. They make their way around and all like to play basketball, soccer etc in the street. Fun safe neighborhood!"
    0
    Flag
  • ljcexpress0818
    "Family friendly neighborhood with nice park nearby. Small town atmosphere."
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  • Don
    "Love Caledonia's less expensive Racine taxes while you live next door to Milwaukee. My kids are able to go to Racine,Oak Creek or Franklin schools due to the "bordering districts". Safe, clean, country living. Miles of horse, walking, biking, ATV, snowmobile, fishing, boating..etc... a recreational dream all within this small charming town."
    0
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  • Jeff
    "Excellent neighborhood and its location makes it a quick commute to Milwaukee."
    0
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Homes for sale near 5429 Chestnut Dr

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Off Market Homes Near 5429 Chestnut Dr

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5429 Chestnut Dr, Racine, WI 53402 is a 4 bedroom, 3 bathroom single-family home built in 1991. This property is not currently available for sale. 5429 Chestnut Dr was last sold on May 19, 2015 for $197,000. The current Trulia Estimate for 5429 Chestnut Dr is $432,800.