5745 Bittersweet Place, Madison
$530,000 - 3 Beds, 2 Baths, 1,781 Sf
MLS® # 2015613, 36 days, Offer-Show
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 a wide 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
4 Properties Found. Page 1 of 1.
5517 Terre Haute Avenue, Madison
$415,000 - 6 Beds, 2 Baths, 2,229 Sf
MLS® # 2017921, 30 days, Active
413 N Rosa Road, Madison
$390,000 - 3 Beds, 2 Baths, 1,582 Sf
MLS® # 2014431, 82 days, Offer-No Show
Recent Glen Oak Hills/Crestwood Sales
| Address | Sold Price | Sold Date | Bed | Bath | Sqft. | Price Per Sqft |
|---|---|---|---|---|---|---|
| 5524 Park Way | $370,000 | 2026-04-14 | 3 | 2.00 | 1635 | $226 |
| 5518 Belin Street | $470,000 | 2026-04-10 | 2 | 2.00 | 1347 | $349 |
| 401 Merrill Crest Drive | $450,000 | 2026-02-02 | 2 | 2.00 | 1298 | $347 |
| 5422 Gettle Avenue | $501,000 | 2026-01-27 | 4 | 2.50 | 2293 | $218 |
| 5449 Old Middleton Road | $350,000 | 2026-01-23 | 3 | 2.00 | 1317 | $266 |
| 5450 Gettle Avenue | $305,000 | 2025-12-01 | 2 | 1.00 | 775 | $394 |
| 5521 Gettle Avenue | $415,000 | 2025-10-01 | 4 | 1.00 | 1310 | $317 |
| 5529 Belin Street | $375,000 | 2025-08-29 | 3 | 1.00 | 1152 | $326 |
| 5620 Crestwood Place | $561,000 | 2025-08-28 | 4 | 2.00 | 1880 | $298 |
| 401 Merrill Crest Drive | $475,000 | 2025-08-22 | 2 | 2.00 | 1298 | $366 |
| 5612 Crestwood Place | $570,000 | 2025-08-20 | 4 | 2.50 | 2431 | $234 |
| 5425 Gettle Avenue | $440,000 | 2025-08-18 | 4 | 2.00 | 1344 | $327 |
| 5749 Bittersweet Place | $555,000 | 2025-07-31 | 3 | 2.50 | 2480 | $224 |
Crestwood/Glen Oak Hills Real Estate Stats
Current Listings
- With Accepted Offers: 2
- Without Accepted Offers: 2
- Total Active Listings: 4
- % with Accepted Offers: 50%
- Months of Inventory: 1.8
Sold 04/16/2025 - 04/16/2026
- Total Sold Listings: 13
- Highest Sold Price: $570,000
- Lowest Sold Price: $305,000
- Average Sold Price: $449,000
- Median Sold Price: $450,000
* 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.
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. Owen Park offers a network of trails meandering though wooded and prairie environments. Two smaller parks - Bordner and Glen Oak Hills - are located within the neighborhood boundaries. Both Crestwood Elementary and Stephens Elementary offer playgrounds for more recreation.
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.
More Neighborhoods Near Crestwood & Glen Oak Hills
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West Side Neighborhoods
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.