Welcome to the Highland Woods Condo Association Website

Our Community

The Highland Woods Condos are nestled in the woods alongside Old Middleton Road. The 55 condo homes were built between 1984 and 1987 and offer distinct contemporary styling that blends with the woods. Highland Woods Condominiums was a project of TMB Development, a Wisconsin company engaged in real estate investment and development. TMB partners were Charles Trainer, Daniel McCarty and Thomas Beach, and they worked with Carley Capital Group and Robert Sieger Architects of Madison to develop the 8-acre site while preserving the area’s natural wooded environment. Phase 1 was completed in September 1984 (including the 5 units at the bottom of GTR). Additional phases were completed through Fall 1987.

The main street winding through the small condo community is shaped like a horseshoe, resulting in two exit/entrances at Old Middleton Road. The streets are lined with an assortment of flowering crabapples, magnolias, towering oaks and black walnuts, complimented by colorful flower gardens, shrubbery and decorative grasses.

Unlike more traditional condo communities, Highland Woods includes a combination of attached, two unit structures as well as free standing, single-family homes. The owners share in the maintenance of the "common areas" through a monthly condo fee. These areas include the streets, driveways, designated visitor parking, the majority of the property and the woods itself.

Individual owners are responsible for exterior building maintenance and approximately five feet of property surrounding their unit. This provides the owners with an opportunity to create and tend flower gardens or other decorative plantings that conform to the overall landscaping of the property.

Yes, many have referred to the Highland Woods condos as the "best kept secret in Madison," as our precious woods provides a bit of country elegance here in the city!

What's New

Posted 11/4/2019:
-- AFTER HOURS MAINTENANCE -- If you have any "after hours" emergency needs, call the Prima main phone at 441-5420. This will notify the ON-CALL Prima staff member. Be as detailed as possible with your message. For non-emergency requests, please submit through your online portal.

Posted 4/26/18:
-Updated Recycling Guidelines can be found in the "Homeowners Information" page.

HWCA Meeting Notices


December 8, 2020
7:00 pm - 8:00 pm

Meeting to be held Via Zoom. Link will be sent to all owners via email.

2019-2020 Board Members

Kathleen Grant, President
Maureen Galitski, Vice President
Glen Broderick, Treasurer
Beth Swanson, Secretary

Pat White & LSC Chair
Molly Khalil
Becky Kordahl

Community Members Log-in

If you haven’t done so, please contact the Management Company to get your secure login information in order to access the Latest news and use the members only sections. (Note: The member’s only sections are secured from public view and are indicated by asterisk on the menu).

Community Management

Prima Property Management became the "Property Manager" for the Highland Woods Condo Association effective October 1, 2011. Dylan Duhr is the primary contact.

At no cost to homeowners, online payments can be made through the owner portal. Contact Prima to receive an invitation to the portal if you have not already done so.

If you mail your condo fees please use this address:

Highland Woods Condominium Association
C/O Prima Management
PO Box 620422
Middleton, WI 53562-0422

Prima Office Location:
6273 University Ave., Suite E
Middleton, WI 53562