Deerfield Homes under $500,000

Welcome to Deerfield, Wisconsin – a charming village nestled in the heart of Dane County, where small-town charm meets modern convenience. Just a stone’s throw from the vibrant city of Madison, Deerfield offers residents a peaceful retreat while keeping them connected to urban amenities. With its picturesque landscapes, friendly community, and a commitment to preserving its rich history, Deerfield is the perfect place to call home.

For those seeking affordable housing options, Deerfield boasts an impressive selection of homes priced under $500,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, you’ll find a variety of properties that cater to your needs. From cozy single-family homes with spacious yards to contemporary townhouses, Deerfield offers a diverse range of choices that fit any lifestyle.

The community is known for its excellent schools, beautiful parks, and a plethora of recreational activities. Residents enjoy easy access to hiking and biking trails, as well as local events that foster a strong sense of community. With a welcoming atmosphere and friendly neighbors, Deerfield is not just a place to live; it’s a place to thrive.

If you’re ready to find your dream home in Deerfield, explore the listings under $500,000 today. With affordable options in a vibrant community, you’ll discover the perfect blend of comfort and convenience. Come experience all that Deerfield has to offer – your new home awaits!

Newest Deerfield Homes under $500,000

$450,000

3 Beds ⋅ 2 Baths ⋅ 2033514 MLS ⋅ ACTIVE Status

Privacy, open space + memorable sunset views define this thoughtfully updated two-story home on just over 2 acres. The great room draws you in with soaring ceilings, a wood fireplace + extra windows that fill the space with natural light. The spacious kitchen includes an island, breakfast bar + generous cabinet storage. The main level also includes a primary bedroom with a private deck overlooking the backyard, full bath + laundry. Upstairs, two additional bedrooms share a full bath, while a versatile loft provides space for a den or home office. Recent exterior updates include a new roof, gutters, composite deck + exterior lighting. The wooded lot has been opened to frame the sunset views, with a freshly seeded yard ready to enjoy. The natural setting beyond the cleared areas invites wildlife watching, while convenient access to Madison keeps everyday amenities close at hand. Some photos are virtually staged.

3670 Jenson Ln, Deerfield

$319,900

3 Beds ⋅ 1 Baths ⋅ 2032875 MLS ⋅ ACTIVE UNDER CONTRACT Status

There’s a lot to love about this charming Craftsman, where original woodwork and a welcoming front porch give the home plenty of character, while thoughtful updates make it easy to settle in and enjoy. The main level offers comfortable gathering spaces, a modern kitchen with ss appliances and a bedroom that makes a great home office. Upstairs, 2 more bedrooms each feature expanded walk-in closets & fresh finishes. Updates include new electrical in most of the home, along with a refreshed front porch featuring cedar posts, new flooring an lighting. The lower level adds useful storage and laundry, with potential to create a 2nd bathroom and relocate laundry to the main level. Outside, new landscape curbing adds a finished touch around the home, while the 2 garages provide 3 total spaces for vehicles, hobbies or storage. Enjoy mornings on the porch, evenings in the yard, and the convenience of being close to Deerfield’s local spots, like Deerfield Coffeehouse, with easy interstate access.

2 S Western Ave, Deerfield

$419,900

5 Beds ⋅ 3 Baths ⋅ 2031501 MLS ⋅ ACTIVE Status

Completely renovated and completely ready for you to move in and enjoy. This wonderfully updated tri-level home features 5 BR, 3BA and almost 1900 square feet of living space. Enjoy the evenings in an updated large living room, dinners in a dining area with a fireplace, hangout in the kitchen around the island or find your space outside on the covered patio...Brand new roof, new siding, flooring throughout, windows, lighting fixtures and the list goes on. Two newer furnaces and central air units giving you efficiency of zoned heating and cooling. Outdoor covered patio for the cookouts or just relaxing overlooking the private yard. This is definitely a must see.

108 N Washington St, Deerfield

$375,000

4 Beds ⋅ 2 Baths ⋅ 2031375 MLS ⋅ ACTIVE UNDER CONTRACT Status

Great oversized corner lot w/ a large backyard for entertaining & the kids to run around in! Located in a quiet neighborhood in the thriving Village of Deerfield & only minutes to Madison! Walking distance to Glacial Drumlin trail and community park. 3 Bedrooms have original wood floors; the 4th has a darker laminate similar to the rest of the main level. The lower level could be updated to match the main level - open it up to create a spacious Rec room. Intercon is installing fiber optic for high-speed internet in neighborhood in corner of lot that WILL be repaired once finished. Appliances new in 2017; new water heater 1/19/2018. Super easy access to I94 & Hwy. 12

512 Central Ave, Deerfield

$359,900

3 Beds ⋅ 2 Baths ⋅ 2031096 MLS ⋅ ACTIVE UNDER CONTRACT Status

OPEN HOUSE CANCELLED DUE TO ACCEPTED OFFER- This well-maintained 3-bedroom, 2-bathroom ranch home is situated on a quiet cul de sac and move-in ready! The primary bedroom features a private ensuite bath, while the spacious eat-in kitchen opens via sliding doors to an expansive backyard—ideal for outdoor entertaining and family cookouts. Looking for extra space? The basement is already framed and wired with electrical, offering incredible potential to finish the space and double your square footage. Key updates include a new roof installed in 2025 with 50-year shingles and a transferable warranty. The water heater, water softener, refrigerator, and oven have all been updated within the last 3 years. Furnace was just cleaned and checked! Conveniently located within walking distance of local parks and schools, and just minutes from Madison!

307 Meadowlark Cir, Deerfield

$425,000

5 Beds ⋅ 3 Baths ⋅ 2030799 MLS ⋅ ACTIVE UNDER CONTRACT Status

Rarely does a 5-bedroom, 3-bath ranch pair sweeping western views with flexible living space and an easy connection to the outdoors. Set on a hilltop lot, it captures memorable sunsets. The updated kitchen includes stainless steel refrigerator and oven, tile backsplash, breakfast bar, and an open connection to the main dining area. The formal dining room can also serve as a spacious living area. The main level includes a primary suite with newly updated bath, two additional bedrooms, a full bath, and mudroom/laundry area. The walkout lower level offers a light-filled rec room with tray ceiling, two additional bedrooms, a flex room for an office, gym, or hobby space, and another full bath. Outside, landscaped grounds surround a firepit area and storage shed. Enjoy room to relax, entertain, and take in the view, all in a thriving community just minutes from Madison.

9 N Washington St, Deerfield

$387,500

3 Beds ⋅ 3 Baths ⋅ 2030006 MLS ⋅ ACTIVE UNDER CONTRACT Status

Updated kitchen, great indoor-outdoor living and a backyard with no neighbors directly behind! Enjoy cooking in the updated kitchen with farmhouse sink, custom hickory cabinets, abundant storage, solid-surface counters and slate appliances. Spacious living room with fireplace opens to the dining area and oversized deck - perfect for entertaining or relaxing. Upstairs you'll find 3 bedrooms, including a primary suite with walk-in closet and private bath. Lower-level has family room(open joists for ceiling), roughed in bath and walks out to a large cement patio and big backyard. Oversized, extra-deep garage has room for a full-size truck, toys and storage. Located in a thriving village near great schools, Glacial Drumlin Trail, Goose Lake and just minutes from Madison's east side!

407 Kleine St, Deerfield

$450,000

5 Beds ⋅ 3 Baths ⋅ 2029625 MLS ⋅ ACTIVE Status

Amazing 1.28 Acre property just 20 minutes from the Beltline. You'll find everything you need in this 5 bedroom, 2.5 bath home. Great Upgrades: Primary suite has both jetted tub & stand-up shower. Second bathroom has separate tub & stand up shower as well as a dual vanity. Garage has separate access to basement. Giant backyard with a fenced in area for your furry friends, plus wooded area at the far back. Tons of wildlife and room to play or relax. Located just off the Glacial Drumlin Bike / Snowmobile Trail. Recent Updates: Newer Central Air, Windows, Sliding Glass Doors, Front Door, Deck, Patio, Stove. Move in ready and ready for your best offer!

39 London Rd, Deerfield

$455,000

2 Beds ⋅ 2 Baths ⋅ 2029599 MLS ⋅ ACTIVE UNDER CONTRACT Status

Vacant lot w/ Black Walnut v2 building plan - estimated completion is Feb 2027. Great layout with views west over the tree canopy. Unit is ideal for main floor living. You're only minutes from the Glacial Drumlin State Trail. Ideal location for those who commute to Madison/Milwaukee yet want a quiet place to call home. Green space surrounds this cond. You'll feel like you're living in the woods. Finish the lower level for more room and spaces for guests. Walk out in the lower level adds lot of light.

233 Whitetail Ln Unit 26, Deerfield

$339,900

3 Beds ⋅ 2 Baths ⋅ 2028932 MLS ⋅ ACTIVE Status

Enjoy touches of the past while having the peace of mind of the many updates featured in this lovingly maintained home in the heart of Deerfield! Adorable 3-season porch opens into the foyer with open stairway, charming woodwork and convenient coat closet. New LVP flooring throughout main level. Updated kitchen with Drexel oak cabinets, built in wine rack, granite countertops and stainless sink/appliances. Pass thru from kitchen to formal dining room with wainscoting. Large living room with built-ins and knotty pine accents. Convenient main level powder room. Upper level features three bedrooms and full bath. Fully fenced yard gives the feeling of privacy for you to enjoy the firepit area or included hot tub. Newer 2-car detached garage, meticulously crafted retaining walls and beautiful landscaping bring the finishing touches! Updated electrical. New windows in 2022. New roof and gutters in 2018 with warranty transferrable to new buyer. UHP Home Warranty included for peace of mind!

16 Legreid St, Deerfield

$425,500

3 Beds ⋅ 3 Baths ⋅ 2028907 MLS ⋅ ACTIVE Status

Vacant site with a Cherry Suites plan - complete within 7-mos of construction start, approximately July 2027. Sweet!!!! The Cherry Suites is revamped! Come explore the woods at Drumlin Woods. Invite nature in through this open concept floor plan. You're overlooking the environmental corridor and walking trails to the east. Enjoy morning sunrises with a cup of steaming coffee while sitting on your deck. See floor plans and more details in the attached documents. Condo is not FHA warrantable.

249 Whitetail Ln Unit 22, Deerfield

$427,000

3 Beds ⋅ 3 Baths ⋅ 2028906 MLS ⋅ ACTIVE Status

253 Whitetail Ln Unit 21, Deerfield

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