Is Greendale, WI dog-friendly?

As of early 2026, 94% of users say it's dog friendly

Is parking easy in Greendale, WI?

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

Do kids play outside in Greendale, WI?

As of early 2026, 86% of users say kids play outside

Would people walk alone at night in Greendale, WI?

As of early 2026, 84% of users say people would walk alone at night

Are yards well-kept in Greendale, WI?

As of early 2026, 84% of users say yards are well-kept

Is a car needed in Greendale, WI?

As of early 2026, 82% of users say car is needed

Is Greendale, WI quiet?

As of early 2026, 79% of users say it's quiet

Does Greendale, WI show holiday spirit?

As of early 2026, 79% of users say there's holiday spirit

Is there wildlife in Greendale, WI?

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

Does Greendale, WI have sidewalks?

As of early 2026, 71% of users say there are sidewalks

Are neighbors friendly in Greendale, WI?

As of early 2026, 63% of users say neighbors are friendly

Is Greendale, WI walkable to restaurants?

As of early 2026, 57% of users say it's walkable to restaurants

Are the streets well-lit in Greendale, WI?

As of early 2026, 54% of users say streets are well-lit

Is Greendale, WI walkable to grocery stores?

As of early 2026, 53% of users say it's walkable to grocery stores

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

As of early 2026, 52% of users say they plan to stay for at least 5 years

Are there community events in Greendale, WI?

As of early 2026, 47% of users say there are community events

CONTINGENT

5249 Lakeside DRIVE
Greendale, WI 53129

3 Beds
1.5 Baths
1,482 sqft

$369,900

Est. Mortgage $2,461/mo*

Get Pre-Qualified

$369,900

Est. Mortgage $2,461/mo*

Get Pre-Qualified

3 Beds

1.5 Baths

1,482 sqft

We estimate this home will sell faster than 100% nearby.

Local Information

-- mins to

Commute Destination

Description

Pride of ownership is evident in this meticulously maintained home nestled on a quiet street just steps from the walking path to Scout Lake. Enjoy an updated kitchen, newer appliances/flooring/siding/roof/mechanicals. Spacious living room with an add'l family room leading to the deck-great for summer gatherings or quiet evenings. Both bathrooms are tastefully updated. Ideal location close to freeway, Whitnall Park and Historic Downtown Greendale which is known for its numerous community events such as Village Days, Dicken's Christmas and 4th of July Parade/Festivities to name a few. Don't miss out on an opportunity where you can experience all that Greendale has to offer.

We estimate this home will sell faster than 100% nearby.

Home Highlights

Parking

2 Car Garage

Outdoor

Patio

A/C

Heating & Cooling

HOA

None

Price/Sqft

$250

Listed

9 days ago

Home Details for 5249 Lakeside DRIVE

Active Status
MLS Status: Contingent

Interior Features
Interior Details Basement: Block,Crawl Space,FullNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bathroom, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths Number of Bedrooms: 3Main Level Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout Living Area: 1482 Square Feet
Appliances & Utilities Appliances: Dishwasher, Dryer, Microwave, Oven, Range, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling Heating: Natural Gas,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Natural Gas
Levels, Entrance, & Accessibility Stories: 1Levels: One

Exterior Features
Exterior Home Features Patio / Porch: Patio
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Door Opener,Attached,2 Car
Frontage Not on Waterfront
Water & Sewer Sewer: Public Sewer
Finished Area Finished Area (above surface): 1482 Square Feet

Days on Market
Days on Market: 9

Property Information
Year Built Year Built: 1964
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building Construction Materials: Aluminum Siding, Aluminum/Steel, Brick, Brick/Stone, Wood SidingNot a New Construction
Property Information Condition: 21+ YearsIncluded in Sale: Refrigerator, Oven/Range, Microwave, Dishwasher, Washer, Dryer, Freezer, DisposalParcel Number: 6650073000

Price & Status
Price List Price: $369,900Price Per Sqft: $250

Location
Direction & Address City: Greendale
School Information Elementary School: Highland ViewElementary School District: GreendaleJr High / Middle School: GreendaleJr High / Middle School District: GreendaleHigh School: GreendaleHigh School District: Greendale

Agent Information
Listing Agent Listing ID: 1967023

Building
Building Area Building Area: 1483 Square Feet

HOA
Association for this Listing: Metro MLS

Lot Information
Lot Area: 7840.8 sqft

Miscellaneous
BasementMls Number: 1967023Living Area Range: 1251-1500Living Area Range Units: Square FeetMunicipality: GreendaleZillow Contingency Status: ContingentAttribution Contact: brookfieldfrontdesk@realtyexecutives.comAbove Grade Unfinished Area: 1482

Additional Information
Source Internet Entire Listing Display

Last check for updates: about 7 hours ago

Listing courtesy of Julie Johnson

Realty Executives Integrity Brookfield

Originating MLS: Metro MLS

Source: WIREX MLS, MLS#1967023

Also Listed on WIREX MLS.

Market trends in Greendale

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

11MoM

Price History for 5249 Lakeside DRIVE

Date	Price	Event	Source
06/21/2026	$369,900	Contingent	WIREX MLS #1967023

06/18/2026	$369,900	Listed For Sale	WIREX MLS #1967023

05/15/2001	$155,900	Sold	N/A
Recording Date 05/15/2001 Contract Date 04/30/2001 County Transfer Tax N/A Total Transfer Tax $468
01/18/2001	$102,000	Sold	N/A
Recording Date 01/18/2001 Contract Date 01/02/2001 County Transfer Tax N/A Total Transfer Tax $306

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Property Tax and Assessment

Year	2024
Tax	$5,302
Assessment	$322,100

Home facts updated by county records

Comparable Sales for 5249 Lakeside DRIVE

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
5154 Maplewood DRIVE, Greendale, WI	0.20	Single-Family Home	$369,000	08/13/25	3	1.5	1,554
5389 S 51st STREET, Greendale, WI	0.31	Single-Family Home	$432,000	04/03/26	3	1.5	1,593
5400 Laura LANE, Greendale, WI	0.36	Single-Family Home	$379,000	03/26/26	3	1.5	1,404
5623 Bentwood LANE, Greendale, WI	0.32	Single-Family Home	$327,000	04/27/26	3	1	1,056
5590 Leroy LANE, Greendale, WI	0.27	Single-Family Home	$420,000	07/21/25	3	1.5	1,549
5309 Mansfield DRIVE, Greendale, WI	0.52	Single-Family Home	$330,000	08/07/25	3	1	1,266
5619 Badger COURT, Greendale, WI	0.49	Single-Family Home	$314,000	08/29/25	3	1.5	1,525
5302 Lakeview DRIVE, Greendale, WI	0.31	Single-Family Home	$350,000	06/18/26	3	1.5	1,144
6310 Schoolway, Greendale, WI	0.56	Single-Family Home	$385,000	08/27/25	3	1.5	1,482

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
Est. $409,300
3 bd
1.5 ba
1,500 sqft
5229 Lakeside DRIVE,
Greendale, WI 53129
Closed
OFF MARKET
Est. $429,000
3 bd
2 ba
1,854 sqft
5407 Lory DRIVE,
Greendale, WI 53129
Closed
OFF MARKET
Est. $465,200
4 bd
2.5 ba
2,235 sqft
5378 Lilac LANE,
Greendale, WI 53129
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OFF MARKET
Est. $435,400
3 bd
1.5 ba
1,672 sqft
5040 Steeple DRIVE,
Greendale, WI 53129
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OFF MARKET
Est. $417,300
3 bd
1.5 ba
1,500 sqft
5175 Maplewood DRIVE,
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OFF MARKET
Est. $404,100
3 bd
1.5 ba
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4995 Steeple DRIVE,
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OFF MARKET
Est. $428,600
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5154 Maplewood DRIVE,
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OFF MARKET
Est. $446,900
3 bd
2 ba
1,695 sqft
5333 Lilac LANE,
Greendale, WI 53129
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OFF MARKET
Est. $410,900
3 bd
1.5 ba
1,903 sqft
5151 Maplewood DRIVE,
Greendale, WI 53129
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OFF MARKET
Est. $408,700
3 bd
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5422 Meadow DRIVE,
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OFF MARKET
Est. $441,700
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5590 Leroy LANE,
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OFF MARKET
Est. $449,600
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 5249 Lakeside DRIVE.

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 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
Resident
6mo ago
"Great community, and very friendly people. A lot of fun events every month. Has everything you need close: shopping, doctors, restaurants, etc. my"
0
Flag
Lindalee
Resident
7mo ago
"It’s a friendly community for dogs. Everyone is very respectful and careful to keep the community clean."
0
Flag
6zs94dtn7m
Resident
1y ago
"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
Resident
5y ago
"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
Resident
6y ago
"Good area, great location btw downtown Milwaukee and the airport. Quick 20 min commute to common areas in the metro. "
0
Flag
Lsr30green
Resident
6y ago
"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.
Resident
6y ago
"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
Flag
Zoey
Resident
6y ago
"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
Resident
6y ago
"Great schools, safe neighborhood, great for walking . Close to south ridge mall and movie theaters. family friendly "
1
Flag
Jennifer.nappe
Resident
7y ago
"My neighborhood has some access to public transportation but you'd have to walk a few miles to get to the bus stop. "
0
Flag
Annalisepm
Resident
7y ago
"Everyone knows every dog in the neighborhood by name, and watches out for them. Very welcoming neighborhood!"
0
Flag
Megoniglek
Resident
8y ago
"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
Flag

LGBTQ Local Legal Protections

Julie Johnson, Realty Executives Integrity Brookfield

5249 Lakeside DRIVE, Greendale, WI 53129 is a 3 bedroom, 2 bathroom, 1,482 sqft single-family home built in 1964. This property is currently available for sale and was listed by WIREX MLS on Jun 12, 2026. The MLS # for this home is MLS# 1967023.

5249 Lakeside DRIVE
Greendale, WI 53129

$369,900

$369,900

Local Information