Date
Details
Price
Change
Source
2/13/2026
Listed
$1,075,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/50
$1,075,000 Just Listed
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Property Description
Gracious colonial offers an exceptional blend of location, charm, and thoughtful updates. Enjoy walkable access to Whitefish Bay favorites including Sendik's, Stone Creek, the library, and cherished traditions like 4th of July parade. Elementary, middle, and high schools are conveniently close. The fenced yard feels like a private, serene retreat--lushly framed by mature landscaping and perfect for quiet mornings, relaxed entertaining, inspired gardening, or a future addition. Classic character meets modern sensibility with 2 GFPs, serene primary suite with a beautiful bath, a refreshed hall bath, and 3 more upstairs bedrooms. The main level offers a private office and flexible den or 5th bedroom with nearby full bath. Loved by the same owner for 25 years and ready for its next chapter.
Full Property Details
Full Property Details for 5550 N Hollywood Ave
General
- Price: $1,075,000
- Taxes: $14,087 (2025)
- Status: Active
- Type: Single Family
- Source: MetroMLS_Milwaukee_Wirex
- MLS ID: 1949605
- Updated: 2/13/2026
- Added to Site: 1 day(s) ago
Interior
- Number of Rooms: 9
- Interior Features: 2 or more Fireplaces, Gas Fireplace, High Speed Internet, Skylight, Walk-In Closet(s), Wood Floors
- Appliances: Dishwasher, Dryer, Freezer, Microwave, Oven, Range, Refrigerator, Washer
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
- Bathroom: At least one Bathtub, Ceramic Tile, MBR Bath Separate Tub, MBR Bath Walk-in Shower, Off Master Bedroom, Shower over Tub, Shower Stall
Bedrooms
- Total Bedrooms: 4
- Bedroom 2: 12 x 11, Upper Level
- Bedroom 3: 12 x 10, Upper Level
- Bedroom 4: 11 x 10, Upper Level
Other Rooms
- Living Room: 21 x 13, Main Level
- Kitchen: 12 x 10, Main Level
- Dining Room: 13 x 12, Main Level
- Den: 13 x 10, Main Level
- Other Room 1: 10 x 9, Main Level
Exterior
- Exterior Features: Patio
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Garage Description: Electric Door Opener, Electric Vehicle Charging Station(s)
Location
- County: Milwaukee
- Driving Directions: South of Silver Spring on Hollywood Avenue.
School Information
- School District: Whitefish Bay
- Elementary School: Richards
- Middle School: Whitefish Bay
- High School: Whitefish Bay
Heating & Cooling
- Heating/Cooling: Natural Gas, Central Air Conditioning, Forced Air
Utilities
- Water/Sewer: Municipal Sewer, Municipal Water
Structural Information
- Architectural Style: Two Story, Colonial
- Exterior Const.: Brick, Wood
- Basement Desc.: Block, Crawl Space, Full
- Square Feet: 2,774
- Year Built: 1937
Additional Structures
- Other Structures: Storage Shed
Lot Features
- Lot Size (Acres): 0.3
- Zoning: res
Financial Considerations
- Tax Amount: $14,087
- Tax Year: 2025
Listed by Keller Williams Realty-Milwaukee North Shore
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— 5550 N Hollywood Ave —
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NMLS#: 1598647
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Schools
Schools serving 5550 N Hollywood Ave
School District:Whitefish Bay School District
| Name | Grades | Distance |
|---|---|---|
Richards Elementary School 5812 North Santa Monica Boulevard, Whitefish Bay, WI 53217 | PK-5 | 0.5 mi |
Whitefish Bay Middle School 1144 East Henry Clay Street, Whitefish Bay, WI 53217 | 6-8 | 0.5 mi |
Whitefish Bay High School 1200 East Fairmount Avenue, Whitefish Bay, WI 53217 | 9-12 | 0.4 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5550 N Hollywood Ave
Tax History
Tax History for 5550 N Hollywood Ave
Year
Property Taxes
Change
Tax Assessment
Change
2024
-100%
$962,900
35%
2023
$10,753
-2%
$713,600
22%
2022
$10,944
-10%
$582,700
—
2021
$12,173
-3%
$582,700
—
2020
$12,614
-2%
$582,700
—
2019
$12,885
11%
$582,700
14%
2018
$11,623
-3%
$512,200
—
2017
$11,925
1%
$512,200
—
2016
$11,854
1%
$512,200
—
2015
$11,777
1%
$512,200
—
2014
$11,612
17%
$512,200
17%
2013
$9,894
—
$438,800
—
2012
$9,871
—
$438,800
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 5550 N Hollywood Ave
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- Single Family
- Active
- Updated 9 days ago
- 5Beds
- 4Total Baths
- 4,075Sq. Ft.
- Single Family
- Active
- Updated 9 days ago
- 5Beds
- 4Total Baths
- 4,788Sq. Ft.
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- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 3Total Baths
- 2,830Sq. Ft.
- Single Family
- Active
- Updated 20 hours ago
- 2Beds
- 1Total Bath
- 782Sq. Ft.
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- Condo
- Active
- Updated 3 days ago
- 3Beds
- 2Total Baths
- 1,500Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 5Total Baths
- 5,456Sq. Ft.
- Single Family
- Active
- Updated 5 days ago
- 3Beds
- 2Total Baths
- 1,453Sq. Ft.
Listed by Don Cornelius (414) 559-1835
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 3Total Baths
- 1,801Sq. Ft.
Listed by Tameka Winters (262) 444-9481
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5550 N Hollywood Ave, Whitefish Bay, WI 53217 (MLS# 1949605) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5550 N Hollywood Ave is currently listed for $1,075,000 and was received on February 13, 2026. Want to learn more about 5550 N Hollywood Ave? Do you have questions about finding other Single Family real estate for sale in Whitefish Bay? You can browse all Whitefish Bay real estate or contact a Coldwell Banker agent to request more information.