Rolling Meadows Homes under $500,000

Welcome to Rolling Meadows, a charming subdivision nestled in the heart of Madison, Wisconsin! This delightful community in Dane County offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and anyone looking to enjoy the best of both worlds.

Rolling Meadows is known for its picturesque landscapes, tree-lined streets, and friendly neighbors. With a strong sense of community, residents here take pride in their homes and the vibrant atmosphere that surrounds them. The subdivision features a variety of well-maintained homes, many of which are available for under $500,000, making it an attractive option for first-time homebuyers, growing families, and those looking to downsize without sacrificing comfort.

The homes in Rolling Meadows boast modern designs and thoughtful layouts, perfect for everyday living. Many properties feature spacious backyards, ideal for outdoor gatherings or simply enjoying the serene Wisconsin seasons. The community is also conveniently located near parks, schools, shopping, and dining, ensuring that everything you need is just a short drive away.

For those who appreciate an active lifestyle, Rolling Meadows offers easy access to local trails and recreational areas, perfect for walking, biking, or jogging. With its inviting atmosphere and affordable housing options, Rolling Meadows is a hidden gem in Madison that promises a fulfilling and enjoyable living experience. Come explore this wonderful community and find your dream home today!

Newest Rolling Meadows Homes under $500,000

$420,000

3 Beds ⋅ 2 Baths ⋅ 2033859 MLS ⋅ ACTIVE Status

Welcome to this fully renovated east side stunner, where everyday living feels easy & the updates are already in place! Light-filled rooms span a versatile layout w/ space to live, work & unwind at your own pace. Fresh paint, refinished hardwood, new trim, matte-black hardware & modern lighting create a clean, current interior. The kitchen is sure to impress, featuring updated cabinets, a modern backsplash, refinished butcher-block counters, a new faucet, plus newer appliances. The bathrooms have been refreshed w/ new vanities & updated fixtures. Peace-of-mind updates include a new roof, new A/C & thermostat, electrical upgrades, some window replacements, a new concrete driveway & front landing & a partially finished basement w/ heat source. Outside, a private fenced backyard, patio, w/ fresh landscaping & updated exterior lighting complete the setting! Nearby parks & easy access to downtown round out this warm, comfortable, move-in-ready home to call your own!

4713 Hermsmeier Ln, Madison

$425,000

3 Beds ⋅ 2 Baths ⋅ 2032764 MLS ⋅ ACTIVE Status

This well-maintained move-in ready 3 bed, 2 full bath home has a smart, tri-level layout offering so much space! Step into the tile entry drop zone from the 2 car attached garage. Greet company in the foyer off the spacious living room. Enjoy meals in the formal dining room, eat-in kitchen or al fresco in the screen porch! Soak in the outdoors on the deck or in the sprawling backyard w/raised garden beds & plenty of room to play. This property offers great storage space, a clean finished laundry room, and extra family room (or flex space- exercise, office, play, media room?) UPDATES include newer appliances, carpet, interior paint, upgraded gutters, water heater, front bay window, basement windows & BRAND NEW ROOF! See UPDATE SHEET For full list. Enjoy peace of mind w/a transferable Elite UHP Home Warranty! Quiet, established neighborhood w/mature trees. Near McGinnis park & playground. Only 2 blocks to Kennedy Elementary School & Park. Convenient to groceries, library, shops and more!

4702 Flint Ln, Madison

$380,000

3 Beds ⋅ 2 Baths ⋅ 2030773 MLS ⋅ ACTIVE UNDER CONTRACT Status

Fabulous location close to schools in lovely, tree-lined neighborhood! Tons of space throughout this well-maintained multi-level home! New roof in 2026! Hardwood floors throughout and NEW carpet in lower level of sun-filled family room with wood burning fireplace! Eat-in kitchen and dedicated dining room connect to large living room. Additional lower level space could be finished to add even more living area. Large fenced in yard with patio, mature trees and lush landscaping. Tons of potential inside and out in super-desirable Rolling Meadows location! Selling "As-Is". Open House on Sunday 9/27/26!

4810 Retana Dr, Madison

$434,000

3 Beds ⋅ 2 Baths ⋅ 2029303 MLS ⋅ ACTIVE Status

Welcome home to this beautifully updated 3 bedroom, 2 full bath home located in a highly desirable neighborhood close to shopping, dining, parks, schools, and all the amenities you need! Step inside to an inviting open-concept floor plan featuring original hardwood floors, brand new carpeting, and spacious living areas designed for both everyday comfort and entertaining. The finished basement offers additional living space - perfect for a family room, home office, playroom, or workout area. Outside you will love the huge fully fenced backyard, providing plenty of room for pets, kids, gardening or hosting summer gatherings. The four season porch is perfect to relax in with a gas fireplace. Major updates include roof in 2025, including eaves and downspouts.

4620 Hermsmeier Ln, Madison

$449,000

3 Beds ⋅ 2 Baths ⋅ 2026885 MLS ⋅ ACTIVE Status

Completely renovated spacious ranch on a large corner lot. Home has recent metal roo,f insulation blown in attic, air ducts professionally cleaned, Fresh paint throughout, refinished hardwood floors, new windows, dual sided wood burning fireplace. Brand New kitchen appliances, new tub surround/toilet/floor/granite in main bath, new lighting/fans vanities, electrical upgrades, New paint and landscaping to exterior, composite deck overlooking a large fenced in beautiful backyard with mature trees. Basement is clean and well lit for your needs. Can be easily converted to additional bedroom/office/fun space. Insulated Garage door and Garage windows are new.

4813 Flint Ln, Madison

Start Your Search

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.