5237 Roberts Dr, Greendale, WI 53129
OFF MARKET

5237 Roberts Dr
Greendale, WI 53129

  • 3 Beds
  • 1.5 Baths
  • 1,478 sqft (on 0.28 acres)

$402,900

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,714/mo*
Refinance Your Home

$402,900

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,714/mo*
Refinance Your Home
3 Beds
1.5 Baths
1,478 sqft
(on 0.28 acres)

Home Value

Trulia Estimate
$403K
Since last month
Decreased$5K (-1.3%)
Since last year
Increased$21K (+5.6%)
Since last sale
Increased$132K (+48.8%)
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 +85% in the last 10 years
MonthEstimated value
2026
August 2026$402K
July 2026$407K
June 2026$413K
May 2026$408K
April 2026$402K
March 2026$398K
February 2026$384K
January 2026$376K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
5107 Russell COURT EAST East, Greendale, WI
0.17
Single-Family Home
$375,000
01/12/26
3
1.5
1,478
5316 Robin DRIVE, Greendale, WI
0.14
Single-Family Home
$381,300
04/24/26
3
1.5
1,898
5126 Russell DRIVE, Greendale, WI
0.07
Single-Family Home
$425,000
01/09/26
3
2
3,023
5115 Russell COURT EAST East, Greendale, WI
0.12
Single-Family Home
$475,000
09/05/25
4
2
1,960
4748 Sycamore STREET, Greendale, WI
0.38
Single-Family Home
$340,000
11/26/25
3
1.5
1,876
5207 Oakton LANE, Greendale, WI
0.41
Single-Family Home
$400,000
05/15/26
3
2
1,945
5527 Oakwood STREET, Greendale, WI
0.42
Single-Family Home
$385,000
10/24/25
3
1.5
1,976
5782 Rustic LANE, Greendale, WI
0.29
Single-Family Home
$425,000
06/17/26
4
2
1,101
5826 Sugarbush LANE, Greendale, WI
0.53
Single-Family Home
$435,000
05/22/26
3
1.5
1,566
5544 Oakwood STREET, Greendale, WI
0.40
Single-Family Home
$359,900
06/25/26
3
1.5
1,236

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
5233 Roberts DRIVE, Greendale, WI 53129
0.03
$434,800
3
1.5
1,404
Off Market
5233 Roberts DRIVE, Milwaukee, WI 53213
0.03
$431,300
3
1.5
1,404
Off Market
5202 Roberts DRIVE, Greendale, WI 53129
0.07
$420,400
3
1.5
1,974
Off Market
5238 Roberts DRIVE, Greendale, WI 53129
0.03
$412,700
3
1.5
1,360
Off Market
5230 Raven DRIVE, Greendale, WI 53129
0.09
$417,800
3
1.5
1,474
Off Market
5126 Russell DRIVE, Greendale, WI 53129
0.07
$425,000
3
2
3,023
Recently Sold
5317 Radcliff DRIVE, Greendale, WI 53129
0.10
$399,400
3
1
2,193
Off Market
5318 Radcliff DRIVE, Greendale, WI 53129
0.12
$497,100
4
2.5
2,142
Off Market
5115 Russell COURT EAST East, Greendale, WI 53129
0.12
$501,900
4
2
1,960
Off Market
5316 Robin DRIVE, Greendale, WI 53129
0.14
$381,300
3
1.5
1,898
Recently Sold
5312 Robin DRIVE, Greendale, WI 53129
0.16
$419,800
4
2
1,917
Off Market
5208 Raven DRIVE, Greendale, WI 53129
0.19
$381,900
3
1.5
1,394
Off Market

Local Information

  • Map ViewExplore the area around 5237 Roberts Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1965
Lot Size
0.28 acres
Living Area
1,478 sqft
Price/Sqft
$273
Parking
Garage

About this House

Welcome home to this beautiful and spacious move-in ready Ranch home nestled on a corner lot that is walking distance to local parks and an elementary school. Impeccably maintained with tons of NEW updates. Huge Eat in Kit opens to LR and DR area, 3 Bedrooms with brand new HWFs. Relax in the family room with NFP which opens to a private patio surrounded by gardens. Clean and dry full basement is ready for your Rec Room ideas. Make your home dreams come true!
5237 Roberts Dr, Greendale, WI 53129 is a 3 bedroom, 2 bathroom, 1,478 sqft single-family home built in 1965. It last sold for $270,000 on Feb 24, 2021. It is currently off market. The Trulia Estimate is $402,900, with a rent estimate of $2,207/month.

Home Details for 5237 Roberts Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family Home

Building

Levels, Entrance, & Accessibility
Disabled Access

Exterior Features

Exterior Home Features
Exterior: BrickPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Lot Information

Lot Area: 0.28 acres

Price and Tax history

DateEventPrice
Feb 24, 2021
Source: N/A
Sold
$270,000
Dec 29, 2020
Source: Agent Provided
Listed For Sale
$274,900

Market trends in Greendale

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
21
5MoM

Around this home

What Locals Say about Greendale

At least 64 Trulia users voted on each feature.

  • 94 % Say it's dog friendly

  • 92 % Say parking is easy

  • 86 % Say kids play outside

  • 84 % Say people would walk alone at night

  • 84 % Say yards are well-kept

  • 82 % Say car is needed

  • 79 % Say it's quiet

  • 79 % Say there's holiday spirit

  • 72 % Say there's wildlife

  • 71 % Say there are sidewalks

  • 63 % Say neighbors are friendly

  • 57 % Say it's walkable to restaurants

  • 54 % Say streets are well-lit

  • 53 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 47 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Lindalhudig
    "Great community, and very friendly people. A lot of fun events every month. Has everything you need close: shopping, doctors, restaurants, etc. my"
    0
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  • Lindalee
    "It’s a friendly community for dogs. Everyone is very respectful and careful to keep the community clean."
    0
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  • 6zs94dtn7m
    "There is always something happening in the greendale village, from farmers markets to village days and even cool holiday themed events for kids "
    0
    Flag
  • Adelaecker0820
    "Everyone lives their dogs. Everyone is kind and has them. There are great places to take your dog and there are great side walks."
    0
    Flag
  • Daniella_maloney
    "Good area, great location btw downtown Milwaukee and the airport. Quick 20 min commute to common areas in the metro. "
    0
    Flag
  • Lsr30green
    "We have festivals, parades, and school events in the area. You can also see the fire works in the summer time at a local park, which is always beautiful."
    1
    Flag
  • Jana M.
    "I just moved back to the area. Absolutely love this neighborhood and all it has to offer. The community is close knit and there are lots of activities as well as places to walk and for kids to play. "
    0
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  • Zoey
    "There is a nature preserve that is like walking into the woods up north, amazing little hiking spot to walk dogs in. "
    0
    Flag
  • T_reiter
    "Great schools, safe neighborhood, great for walking . Close to south ridge mall and movie theaters. family friendly "
    1
    Flag
  • Jennifer.nappe
    "My neighborhood has some access to public transportation but you'd have to walk a few miles to get to the bus stop. "
    0
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  • Annalisepm
    "Everyone knows every dog in the neighborhood by name, and watches out for them. Very welcoming neighborhood!"
    0
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  • Megoniglek
    "I’ve lived here for most of my life and it’s a great place to grow up or raise a family. Very safe and nice place. "
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 5237 Roberts Dr

  • What is 5237 Roberts Dr estimated to be worth?
    Trulia's estimated value for 5237 Roberts Dr in Greendale, WI is $402,900.
  • What is the price history for 5237 Roberts Dr?
    5237 Roberts Dr in Greendale, WI last sold for $270,000 in February 2021.
  • Is Greendale a buyer's or seller's market?
    Greendale is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Greendale?
    Residents describe Greendale, WI as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Greendale, WI.
  • Does 5237 Roberts Dr have air conditioning?
    Yes, 5237 Roberts Dr in Greendale, WI has air conditioning.
  • Does 5237 Roberts Dr have laundry facilities?
    Yes, 5237 Roberts Dr in Greendale, WI has in-unit laundry.

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