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 short drive from the vibrant city of Madison, Deerfield offers residents a tranquil lifestyle surrounded by picturesque landscapes and a close-knit community atmosphere. With its rich history, friendly neighbors, and an abundance of recreational opportunities, it’s no wonder Deerfield is a sought-after destination for families and professionals alike.

The village boasts an array of amenities, including local shops, parks, and schools, all contributing to its welcoming environment. Enjoy leisurely strolls along the scenic trails or spend weekends exploring nearby lakes and nature reserves. Deerfield is also known for its annual community events, fostering a sense of belonging and camaraderie among residents.

For those seeking an affordable home in this idyllic setting, Deerfield offers a variety of options under $500,000. Whether you’re in the market for a cozy single-family home, a modern townhouse, or a charming starter property, you’ll find a range of choices to suit your needs. These homes often feature spacious yards, contemporary designs, and access to excellent schools, making them perfect for families looking to settle down.

Discover the perfect balance of suburban tranquility and urban accessibility in Deerfield, where your dream home awaits. Explore the available listings today and experience the warmth and beauty of this delightful community!

Newest Deerfield Homes under $500,000

$338,500

2034659 MLS ⋅ ACTIVE Status

402-404 S Main - Multi-family opportunity with all the updates! Check out this duplex with a 3 AND 4 bedroom unit both with 1.5 baths! Nearly everything has been re-done/updated/replaced. Brand new roof, new windows, new electrical, new kitchen cabs & tops and appliances, new bathrooms, new flooring & more! Both units are vacant - perfect for owner occupy & you get to pick you renter(s)! Estimated rents based on size of units & lack of available inventory in area. Big basement with separate laundry hook-ups. Plenty of off street parking and big yard. Great opportunity to start or add to your portfolio.

404 S Main St, 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

$409,900

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

$499,900

4 Beds ⋅ 3 Baths ⋅ 2029940 MLS ⋅ ACTIVE Status

This updated and well maintained modern two-story colonial offers the perfect blend of classic style and contemporary comfort. The spacious, functional floor plan features bright and inviting living areas with numerous updates throughout, making this home move-in ready. Generously sized bedrooms provide plenty of space for guests, or a home office. Outside, enjoy a large backyard with room for entertaining, gardening, pets, or play, plus a convenient storage shed for lawn equipment and tools. The impressive 3 car garage provides plenty of space for toys, storage, and or a workshop. With its modern updates, traditional colonial charm, spacious lot, and exceptional garage space, this home offers all the features of today's homes. Located a short distance from schools!

304 N Atwood Ln, Deerfield

$450,000

5 Beds ⋅ 3 Baths ⋅ 2029625 MLS ⋅ ACTIVE Status

Amazing 1.28-acre retreat located just 20 min from the Beltline or East Towne, offering the perfect blend of space & convenience. This 5-bedroom, 2.5-bath home features thoughtful upgrades throughout, including a primary suite with separate jetted tub & stand-up shower. The second full bathroom boasts a tub, stand-up shower, & dual vanity. The garage provides convenient access to the basement, adding versatile storage. Step outside to a generous backyard with a fenced-in area ideal for pets. A wooded section at the rear provides privacy, relaxation & wildlife viewing. Situated near the Glacial Drumlin Bike/Snowmobile Trail, this property provides endless opportunities for outdoor recreation. Recent updates include a newer central air system, windows, sliding glass doors, front door, deck, patio, stove & paint. Waiting for your best offer to move right in, this home combines comfort, privacy, and location in one remarkable package.

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

$430,000

3 Beds ⋅ 3 Baths ⋅ 2028905 MLS ⋅ ACTIVE Status

Vacant lot with a Knoll Crest plan: estimated completion is January 2027. Tucked near the end of a private lane in a wooded setting near the Glacial Drumlin State Trail, this condo offers a rare connection to nature with peaceful eastern views into the surrounding canopy. Large windows bring in beautiful natural light, framing the changing seasons, creating a calm, nature-forward feel throughout the home. Enjoy morning coffee with sunrise light and birdsong, or unwind in the private outdoor space that extends the living experience. The open layout is designed for comfortable everyday living with an inviting indoor-outdoor connection. With convenient access to walking, biking, and year-round recreation just moments away, this scenic setting feels tucked away while still supporting easy commutes to Madison, Milwaukee, and surrounding communities. Two optional entries on floor plan see additional docs for layouts. NOT FHA approved.

261 Whitetail Ln Unit 19, Deerfield

$457,500

3 Beds ⋅ 3 Baths ⋅ 2028904 MLS ⋅ ACTIVE Status

Vacant lot with Acorn building plan - estimated completion is 7-mos from construction start. Occupancy is estimated June 2027. The Acorn is a two-story condo unit with optional bedroom or lower level layouts, and optional kitchen layouts. See floor plan in attached documents. In unit laundry can be upstairs in the primary bedroom suite or in the lower level - or both! Primary suite has a flex room for potential office space or a secluded retreat. This unit will have morning light in the primary bedroom and afternoon light in the main floor and lower level. Look out into the marshes or watch the sunset over the top of the Village to the west. Close to the Glacial State Drumlin Trail and in nature - come enjoy the serenity of this home. Condos are not FHA warrantable at this time.

265 Whitetail Ln Unit 18, Deerfield

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Deerfield Homes under $500,000

Newest Deerfield Homes under $500,000

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