5529 Greenleaf Dr, Madison, WI 53713
Property image
Property image
OFF MARKET

5529 Greenleaf Dr
Madison, WI 53713

Waunona
  • 3 Beds
  • 2 Baths
  • 1,809 sqft (on 0.26 acres)

$413,200

Trulia Estimate
as of Jul 9, 2026

$413,200

Trulia Estimate
as of Jul 9, 2026
3 Beds
2 Baths
1,809 sqft
(on 0.26 acres)

Local Information

  • Map ViewExplore the area around 5529 Greenleaf Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Fantastic home in the heart of Waunona! Located on a quiet street just a block away from Lake Monona, this impeccably maintained, Mid-Century home has had only two owners & is looking for its next! The main living area is expansive, boasts hardwood floors, loads of natural light & flows easily into the dining area, kitchen & great room (which has a cozy wood burning stove, vaulted ceilings & opens to the large, private, fenced yard, huge deck and hot tub). Super floor plan for both entertaining or retreating into your own space. A bonus is the retro vibe of the lower level rec room with fireplace! This gem is a quick walk to Esther Beach, and near walking/bike paths, downtown, bus lines, the Beltline, restaurants and shopping. Definitely a must see!
5529 Greenleaf Dr, Madison, WI 53713 is a 3 bedroom, 2 bathroom, 1,809 sqft single-family home in Waunona, built in 1961. It last sold for $400,000 on Feb 18, 2025 (4% above the $385,000 asking price). It is currently off market. The Trulia Estimate is $413,200, with a rent estimate of $2,797/month.

Home Highlights

Parking
1 Car Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
33 days ago

Home Details for 5529 Greenleaf Dr

Interior Features

Interior Details
Basement: Full,Full Size Windows/Exposed,Partially FinishedNumber of Rooms: 6Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 1809 Square Feet
Appliances & Utilities
Utilities: Cable Available, Internet - CableAppliances: Washer, Dryer, Water Softener IncludedDryerWasher
Heating & Cooling
Heating: RadiantHas CoolingAir Conditioning: Wall Unit(s),Window Unit(s)Has HeatingHeating Fuel: Radiant
Fireplace & Spa
Number of Fireplaces: 1Fireplace: 1 fireplace, Free Standing, Wood BurningSpa: Indoor Hot tubHas a FireplaceHas a Spa
Levels, Entrance, & Accessibility
Stories: 2Levels: Two, Bi-level

Exterior Features

Exterior Home Features
Patio / Porch: DeckFencing: FencedFoundation: Other
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 1Parking: 1 car,Access to Basement,Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 1529 Square Feet

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Vinyl Siding
Property Information
Not Included in Sale: Personal property of SellersIncluded in Sale: stove, range, dishwasher, refrigerator, hot tub, all window coverings, water softener, washer, dryer, window acParcel Number: 071030208344

Price & Status

Price
List Price: $385,000
Status Change & Dates
Off Market Date: Tue Jan 21 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: MadisonCommunity: Waunona
School Information
Elementary School: Call School DistrictElementary School District: MadisonJr High / Middle School: SennettJr High / Middle School District: MadisonHigh School: LafolletteHigh School District: Madison

Building

Building Area
Building Area: 1809 Square Feet

Lot Information

Lot Area: 0.26 acres

Offer

Listing Terms: Arms Length

Miscellaneous

BasementMls Number: 1992035Attribution Contact: Pref: 608-513-9635Above Grade Unfinished Area: 1529
Last check for updates: about 4 hours ago
Listed by Sue Janowitsch
Restaino & Associates
Bought with: Karen Gray, Dwellhop Real Estate, LLC
Source: SCWMLS, MLS#1992035

Price History for 5529 Greenleaf Dr

DatePriceEventSource
02/18/2025$400,000Sold
N/A
01/26/2025$385,000PendingWIREX MLS #1992035
01/21/2025$385,000Listed For SaleWIREX MLS #1992035
10/16/2018$254,900ListingRemovedAgent Provided
10/01/2018$254,900PriceChange
Agent Provided
09/28/2018$264,900PriceChange
Agent Provided
09/24/2018$269,900PriceChange
Agent Provided
09/14/2018$274,900PriceChange
Agent Provided
09/07/2018$280,000Listed For SaleAgent Provided
09/19/2016$208,000Sold
N/A
06/30/2016$209,900Listed For SaleAgent Provided

Market trends in Madison

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$415K
$8.83KMoM
Sale-to-List Price
101.7%
1.3%MoM
Price per sq ft
$250
$8MoM
Available listings
661
102MoM
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Property Tax and Assessment

Year2024
Tax$7,198
Assessment$367,700
Home facts updated by county records

Comparable Sales for 5529 Greenleaf Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2913 Waunona Way, Madison, WI
0.12
Single-Family Home
$556,000
08/19/25
3
2
1,908
3018 Harriman Ln, Madison, WI
0.15
Single-Family Home
$450,000
06/30/26
4
2
1,525
5526 Ethelwyn Rd, Madison, WI
0.09
Single-Family Home
$429,900
08/22/25
4
3
2,099
918 Moorland Rd, Madison, WI
0.80
Single-Family Home
$360,000
11/03/25
3
2
1,712
2202 Lake Point Dr, Madison, WI
0.64
Single-Family Home
$343,500
11/25/25
3
2
1,340
2706 Waunona Way, Madison, WI
0.30
Single-Family Home
$1,150,000
10/08/25
4
3
2,451
1905 Weber Dr, Madison, WI
0.80
Single-Family Home
$365,000
11/19/25
4
2
1,707
6 Arther Ct, Madison, WI
0.88
Single-Family Home
$392,000
09/17/25
3
2
1,552
2505 Badger Ln, Madison, WI
0.80
Single-Family Home
$350,000
04/24/26
3
2
1,248
2802 Wayland Dr, Madison, WI
0.84
Single-Family Home
$375,000
01/20/26
4
2
1,540

Nearby homes

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Assigned Schools

These are the assigned schools for 5529 Greenleaf Dr.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Waunona
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Waunona

At least 5 Trulia users voted on each feature.

  • 100 % Say parking is easy

  • 89 % Say yards are well-kept

  • 88 % Say it's dog friendly

  • 80 % Say it's quiet

  • 67 % Say there are sidewalks

  • 67 % Say people would walk alone at night

  • 64 % Say it's walkable to restaurants

  • 63 % Say they plan to stay for at least 5 years

  • 57 % Say there's holiday spirit

  • 56 % Say there's wildlife

  • 55 % Say neighbors are friendly

  • 50 % Say car is needed

  • 50 % Say kids play outside

  • 38 % Say streets are well-lit

  • 30 % Say it's walkable to grocery stores

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.

LGBTQ Local Legal Protections

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Homes for sale near 5529 Greenleaf Dr

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Off Market Homes Near 5529 Greenleaf Dr

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