Oakland Heights Homes for Sale

Welcome to Oakland Heights, a charming subdivision nestled in the heart of Madison, Wisconsin! This inviting community in Dane County is perfect for those seeking a blend of suburban tranquility and urban convenience. Oakland Heights boasts a picturesque landscape with tree-lined streets, well-maintained parks, and a welcoming atmosphere that makes it an ideal place to call home.

The homes for sale in Oakland Heights offer a diverse range of architectural styles and sizes, ensuring there’s something for everyone. From cozy single-family homes perfect for first-time buyers to spacious properties for growing families, each residence is designed with comfort and style in mind. Many homes feature modern amenities, open floor plans, and beautifully landscaped yards, providing a perfect backdrop for both relaxation and entertaining.

Living in Oakland Heights means you’re just a stone’s throw away from the vibrant culture and amenities that Madison has to offer. Enjoy nearby shopping, dining, and recreational activities, all while being surrounded by the natural beauty of the area. With easy access to major highways and public transportation, commuting to downtown Madison or exploring the stunning landscapes of Wisconsin is a breeze.

Whether you’re looking to settle down in a friendly neighborhood or invest in a promising real estate opportunity, Oakland Heights is a community that welcomes you with open arms. Discover your dream home today in this delightful Madison subdivision and experience the perfect blend of comfort, convenience, and community spirit!

Newest Oakland Heights Homes for Sale

$724,900

4 Beds ⋅ 2 Baths ⋅ 2029238 MLS ⋅ ACTIVE Status

Looking for a beautifully remodeld Single Family home thats checks all the boxes - then this is it! Enjoy a walkable lifestyle just steps from Monroe Street's shops, cafe's and restaurants, with easy access to Camp Randall, Henry Vilas Zoo, Vilas Park, SW Bike Path, bus line, and the University of Wisconsin. This charming open floor plan features large picture windows, fireplace, well appointed Kitchen, and new addition adding a main floor family room. Upstairs offers four bedrooms plus an Office/Den cool bedrooms with lofts. The fenced yard and two parking spaces prepped and ready for a two car garage to be added. You'll love this perfect blend of modern updates, timeless character, and unbeatable locaton! Addition and remodel completed 5 years ago. Roof 5 years, Refrigerator ('26) Oven ('26) Washer/Dryer ('21) Windows ('18, '21) Deck ('21) AC ('18) Water Heater ('22) Electrical ('18).

1013 Oakland Ave, Madison

$664,900

4 Beds ⋅ 1 Baths ⋅ 2028322 MLS ⋅ ACTIVE Status

Charming Vilas neighborhood home blending timeless character with thoughtful updates! Beautifully refinished hardwood floors and original trim pair perfectly with new windows throughout, creating a bright and inviting feel. The spacious main level offers a bedroom, large open kitchen, and comfortable living spaces ideal for everyday living and entertaining. Upstairs, you'll find three additional bedrooms, a full bath, and a convenient laundry area tucked into the primary bedroom's walk-in closet. High-efficiency home systems provide modern comfort and peace of mind. Located just minutes from Vilas Park, Lake Wingra, the UW hospitals, bike paths, and Monroe Street's popular shops and restaurants, this home offers the perfect combination of charm, updates, and an unbeatable location!

1422 Chandler St, Madison

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This information, provided by seller, listing broker, and other parties, may not have been verified. Copyright 2026 South Central Wisconsin MLS Corporation. All rights reserved. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify perspective properties consumers may be interested in purchasing.