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3670 Jenson Ln, Deerfield
$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
2 S Western Ave, 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
108 N Washington St, 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
512 Central Ave, 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
307 Meadowlark Cir, 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
9 N Washington St, 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
407 Kleine 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
39 London Rd, 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
233 Whitetail Ln Unit 26, 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
16 Legreid St, 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
249 Whitetail Ln Unit 22, 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
253 Whitetail Ln Unit 21, Deerfield
$427,000
3 Beds ⋅ 3 Baths ⋅ 2028906 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.

253 Whitetail Ln Unit 21, Deerfield
261 Whitetail Ln Unit 19, 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
265 Whitetail Ln Unit 18, 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
269 Whitetail Ln Unit 17, Deerfield
$460,000
2 Beds ⋅ 3 Baths ⋅ 2028903 MLS ⋅ ACTIVE Status
Vacant lot with Acorn building contract - estimated completion is 7-mos from construction start; occupancy is approximately 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.

269 Whitetail Ln Unit 17, Deerfield
221 Whitetail Ln Unit 29, Deerfield
$458,500
3 Beds ⋅ 3 Baths ⋅ 2028902 MLS ⋅ ACTIVE Status
Vacant lot with Acorn building plan - estimated completion is 7-mos from construction start. Occupancy is estimated May 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.

221 Whitetail Ln Unit 29, Deerfield
226 Whitetail Ln Unit 8, Deerfield
$435,000
3 Beds ⋅ 3 Baths ⋅ 2028901 MLS ⋅ ACTIVE Status
Vacant lot w/ Cherry Suites building plan-estimated completion date is 7-mos from construction start - the goal is Occupancy in April 2027. You will love this open floor plan. Rear views are east/south over the canopy of trees in the environmental corridor and into the marshes. Wake up each morning to the sunrise and birds trilling in the woods. Walk the Glacial Drumlin State Trail, just steps outside your door. Condo is not FHA warrantable. This unit is a Sedona Red with natural stone accents. All images are artistic renderings.

226 Whitetail Ln Unit 8, Deerfield
3710 Johnson Dr, Deerfield
$425,000
2 Beds ⋅ 1 Baths ⋅ 2028794 MLS ⋅ ACTIVE Status
A truly one-of-a-kind property that must be experienced in person to appreciate its peaceful setting. Nestled on 1.6 private wooded acres, you'll enjoy a rare level of privacy where you can't see neighboring homes in any direction. Watch deer, wild turkeys, foxes, and countless birds from your own backyard while enjoying the serenity of a quiet, lightly traveled road—all just 25 minutes from Madison. Inside, the home has been thoughtfully updated while preserving its warm, natural character. The remodeled 2026 kitchen, fresh paint throughout, updated lighting, and custom live-edge wood shelving complement the home's extensive use of real wood and natural materials. With very little drywall and no carpet, the home offers a distinctive feel that's difficult to find in newer construction. If you've been searching for a home that offers true privacy, abundant wildlife, handcrafted character, and modern updates, this is a rare opportunity.

3710 Johnson Dr, Deerfield
3613 County O Rd, Deerfield
$325,000
4 Beds ⋅ 2 Baths ⋅ 2028433 MLS ⋅ ACTIVE Status
Welcome home to this beautifully updated, move-in ready 4-bedroom home where charm, space, and versatility come together! Designed for today's lifestyle, the main level features a formal dining room, expansive living room, stylish kitchen with breakfast bar, sun-filled sunroom, and a convenient main-floor bedroom. Upstairs, you'll find three spacious bedrooms, centrally located laundry, a versatile bonus landing, and a half bath. The finished lower level offers the perfect rec room, complete with an egress window, while a second egress window provides an exciting opportunity to add a 5th bedroom. The enclosed mudroom connects to the attached 3-car garage for added convenience. Outside, enjoy a fenced backyard, spacious deck, and inviting front porch. Just steps from the Glacial Drumlin State Trail, this home offers the perfect blend of comfort, functionality, and an unbeatable location!

3613 County O Rd, Deerfield
217 Whitetail Ln Unit 30, Deerfield
$457,900
2 Beds ⋅ 3 Baths ⋅ 2027876 MLS ⋅ ACTIVE Status
Vacant lot with building plan - completion is approximately 7-months from start of construction; estimated May 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.

217 Whitetail Ln Unit 30, Deerfield
222 Whitetail Ln Unit 7, Deerfield
$430,000
3 Beds ⋅ 3 Baths ⋅ 2027875 MLS ⋅ ACTIVE Status
Vacant site with building plan - complete within 7-mos of construction start, approximately April 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.

222 Whitetail Ln Unit 7, Deerfield
402-404 S Main St, Deerfield
$348,500
2025881 MLS ⋅ ACTIVE Status
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.

402-404 S Main St, Deerfield
254 Whitetail Ln Unit 13, Deerfield
$435,500
3 Beds ⋅ 3 Baths ⋅ 2024623 MLS ⋅ ACTIVE Status
Knoll Crest plan Complete: Nov/Dec 2026. 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.

254 Whitetail Ln Unit 13, Deerfield
262 Whitetail Ln Unit 15, Deerfield
$460,000
2 Beds ⋅ 2 Baths ⋅ 2022305 MLS ⋅ ACTIVE Status
Under construction; estimated completion Nov/Dec 2026. Wow!! Your lucky day has arrived! The last expanded Black Walnut plan in Drumlin Woods is back on the market. With a wider second room on the main floor and larger closet, this is truly a 2-bedroom on the main floor. You also have wider windows for views into the woods and a screen porch facing east, this condo has it all. Every morning wake up to birds in the trees and views over the environmental corridor into the marshes to the east. Finish the lower level with two more rooms, a rec room, full bath and walk out. Call listing agent about incentives for an accepted offer by September 30th!

262 Whitetail Ln Unit 15, Deerfield
210 Whitetail Ln Unit 5, Deerfield
$460,500
3 Beds ⋅ 3 Baths ⋅ 2021408 MLS ⋅ ACTIVE Status
Vacant Site w/ Building Plan-Completion is approx 6-7 mos from start of construction. Hickory plan in a wooded setting near the Glacial Drumlin State Trail, this condo offers a rare connection to the outdoors with peaceful views into the surrounding canopy. Large windows bring in natural light, highlighting the changing seasons. The open layout creates comfortable everyday living with a calm, nature-forward feel. Enjoy convenient access to walking, biking, and year-round recreation just moments away. Whether heading to work, dining, or entertaining, the location supports easy commutes to Madison, Milwaukee, and surrounding communities. Private outdoor space extends the living experience, creating an ideal spot to relax and recharge. Take in the quiet beauty of this scenic natural setting daily. Designed for easy living with an inviting indoor-outdoor connection throughout the condo. Condo is NOT FHA warrantable. See additional docs for FAQ and floor plan details.

210 Whitetail Ln Unit 5, Deerfield
214 Whitetail Ln Unit 6, Deerfield
$465,900
3 Beds ⋅ 3 Baths ⋅ 2020980 MLS ⋅ ACTIVE UNDER CONTRACT Status
VACANT Site with Hickory building plan. Completion is 6-7 mos from start of construction; weather dependent. Welcome to the Hickory; a one-of-a-kind opportunity to live atop a scenic drumlin, surrounded by native oak savannah, just moments from Glacial Drumlin State Trail. Love biking, hiking, bird watching? This is your ideal home. Start mornings w/ a sunrise walk & sounds of birds calling in the marshes & wetlands. End the day on a porch. Main-floor living condo offers an open-concept full of natural light—perfect for relaxing or entertaining. Garage enters into a convenient mudroom w/ adjacent laundry. You have views into the woods and room to entertain. Don't miss this unique opportunity. Condos are NOT FHA warrantable. See condo docs for details and floor plans.

214 Whitetail Ln Unit 6, Deerfield
225 Whitetail Ln Unit 28, Deerfield
$419,000
2 Beds ⋅ 2 Baths ⋅ 2001619 MLS ⋅ ACTIVE Status
Black Walnut plan. You can finish the lower level with 2-bedrooms,1-full bath and rec room. *469,000-$489,000+ (*depending upon selections) = 2,224 finished SF . Welcome to the Black Walnut; a one-of-a-kind opportunity to live atop a scenic drumlin, surrounded by native oak savannah, just moments from Glacial Drumlin State Trail. Love biking, hiking, bird watching? This is your ideal home. Start mornings w/ a sunrise walk & sounds of birds calling in the marshes & wetlands. End the day on a porch, watching the sun set. Main-floor living condo offers an open-concept full of natural light—perfect for relaxing or entertaining. Enjoy zero-step entry from the garage into a convenient mudroom w/ adjacent laundry. Main bedroom has HUGE WIC closet & full bath. If you finish the LL: rec room, 2-beds & full bath w/ a patio; you'll have tons of room to entertain. Don't miss this unique opportunity. Spectrum available.

225 Whitetail Ln Unit 28, Deerfield

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.