Crestwood and Glen Oak Hills Homes

The Crestwood neighborhood is nestled up against Owen Conservation Park just west of Rosa Road on the west side of Madison, WI. The Glen Oak Hill neighborhood is located just to the east on the opposite side of Rosa Road. These well-established subdivisions offer an affordable selection of real estate with convenient access to the local schools and several neighborhood parks. Learn more about the Crestwood and Glen Oak Hills real estate market by checking out our property guide below.

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All Crestwood/Glen Oak Hills Real Estate Listings

All Crestwood/Glen Oak Hills Real Estate Listings

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Recent Glen Oak Hills/Crestwood Sales

Crestwood/Glen Oak Hills Real Estate Stats

Current Listings

  • With Accepted Offers: 0
  • Without Accepted Offers: 0
  • Total Active Listings: 0
  • % with Accepted Offers: N/A
  • Months of Inventory: 0.0

Sold 01/18/2020 - 01/18/2021

  • Total Sold Listings: 18
  • Highest Sold Price: $533,000
  • Lowest Sold Price: $270,000
  • Average Sold Price: $321,100
  • Median Sold Price: $295,000

* Source: IDX Active & Sold Listings

* Property Types: Single Family, Multi Family

Glen Oak Hills/Crestwood Real Estate

Most Crestwood and Glen Oak Hills properties were built between 1930 and 1970 - back when Cape Cod, bungalow, and ranch style designs made up much of the new home inventory. The homes in these twin neighborhoods tend to be modest in size, but high in character and charm. Many of the properties in the area feature the thick hardwood flooring and original built-in cabinets that are common to many mid-century homes. Most of the real estate in Glen Oak Hills and Crestwood is very affordable, with many properties in the area selling for $250,000 and under. 

Local Parks

This part of Madison is a great fit for the home buyer seeking a neighborhood with access to a wide variety of green spaces and parks. Owen Conservation Park and Garner Park are within walking distance of most Crestwood/Glen Oak Hills homes. Two smaller parks - Bordner and Glen Oak Hills - are located within the neighborhood boundaries. Both Crestwood Elementary and Stephens Elementary offer playgrounds for families with children. 

Local Schools

Depending on location, Glen Oak Hills and Crestwood properties are zoned to either Stephens Elementary (120 S. Rosa Road) or Crestwood Elementary (5930 Old Sauk Road). Both grade schools are within walking distance of most neighborhood homes. All households in the area are zoned to Jefferson Middle School and Memorial High School - both located several blocks to the west on Gammon Road. 

Vintage Madison

This part of Madison is home to Knoche's Grocery Store and the Oakcrest Tavern. Knoche's is an old-style neighborhood grocery store and butcher shop. The Oakcrest Tavern serves up some of the best burgers in town. Both Knoche's and The Oakcrest offer a link to the past, back when neighborhood pubs and grocery stores were the norm. 

Glen Oak Hills/Crestwood Neighborhood Photos

Crestwood and Glen Oak Hills residents appreciate the many local amenities that make this part of Madison so unique. One local treasure is Owen Park, which offers a network of trails meandering through wooded and prairie environments.

Owen Park near the Crestwood Neighborhood 

Kettle Pond is a smaller conservation park and one of the hidden gems in the Madison park system. 

Kettle Pond Madison WI

Bordner Park is located in the heart of Crestwood. This park offers a walking path, playground, tennis courts, and picnic space, too. 

Bordner Park Playground Madison WI

Glen Oak Hills Park and playground are tucked away in a private, wooded setting. 

Glen Oak Hills Park Madison WI

Garner Park, located at the intersection of Rosa Road and Mineral Point Road, is one of the most beautiful parks on Madison's west side. 

Garner Park Shelter Madison WI

Crestwood Elementary playground is a great place for the little ones. The playground offers a beautiful setting just off of Old Sauk Road. 

Crestwood School Playground - Madison WI

Glen Stephens Elementary, on Rosa Road, has its own playground and plenty of green space, too. 

Glen Stephens Elementary School Madison WI 

The family-owned Knoche's Grocery Store on Old Middleton Rd is a neighborhood institution known for its butcher shop.

Knoches Food Center Madison WI

Right across the street from Knoche's is the Oakcrest Tavern - the perfect place for a burger and a beer. 

More Neighborhoods Near Crestwood & Glen Oak Hills

Our online real estate guides offer a local perspective which you won't find anywhere else. 

Interested in the homes for sale in Glen Oak Hills and Crestwood, Madison, WI? Contact us anytime, and we'll introduce you to the available properties in the area. Thinking of selling in the neighborhood? Our customized marketing plan will help you sell your home quickly and for the highest possible market price. 

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