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4226 Sheffield Rd, Madison
$369,000
3 Beds ⋅ 2 Baths ⋅ 2028909 MLS ⋅ ACTIVE UNDER CONTRACT Status
Some homes just have a feel to them, and this is one of them. Just minutes from the Arboretum, this bungalow blends warmth, character, and unexpected space into a home that's anything but ordinary. The layout flows effortlessly from the welcoming front porch through the living room and kitchen before opening into the light-filled great room. Here, soaring vaulted ceilings, oversized windows, and reclaimed wood beams frame the space and continue into the primary bedroom to create a striking architectural focal point. Upstairs, the loft offers the flexibility to serve as a home office, art studio, or exercise room. Outside, the private patio provides a peaceful place to relax or entertain, surrounded by mature landscaping. Recent improvements—including a new roof, appliances, carpet, and fresh paint—mean you can simply move in and start enjoying both the home and its fantastic location near trails, parks, and downtown.

4226 Sheffield Rd, Madison

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

3160 S High Point Rd, Madison
$425,000
2 Beds ⋅ 2 Baths ⋅ 2028895 MLS ⋅ ACTIVE UNDER CONTRACT Status
Welcome home to this beautiful private end-unit condo on Madison's highly desirable West Side! Offering 2 bedrooms, 2 full baths, and a spacious loft, this home features an open-concept layout designed for both comfortable everyday living and effortless entertaining. The inviting kitchen features a large center island, open to the bright living and dining areas. Enjoy your morning coffee or unwind at the end of the day from the screened porch or adjoining private deck. The versatile loft provides the perfect space for a home office, or guest retreat. The heated attached garage offers exceptional convenience with ample storage, plus an additional dedicated storage room for all your extras. Ideally located near shopping, dining, parks, bike paths, and everything Madison's West Side has to offer, this move-in-ready condo combines comfort, privacy, and an unbeatable location.

3160 S High Point Rd, Madison

6683 Charlie Grimm Rd, Windsor
$269,900
2 Beds ⋅ 1 Baths ⋅ 2028893 MLS ⋅ ACTIVE Status
Enjoy carefree living with no condo fees in this beautifully updated half-duplex overlooking picturesque Lake Windsor Country Club and the Yahara River. The bright, open-concept design features luxury flooring, fresh paint, and large windows that fill the home with natural light while showcasing peaceful golf course views. The remodeled kitchen offers granite countertops, subway tile backsplash, stainless steel appliances, abundant cabinetry, and a spacious breakfast bar that opens to the living and dining areas. Two generously sized bedrooms, an updated full bath, and a convenient main-level laundry room provide comfortable everyday living. Step through the patio doors to a private patio where you can relax and enjoy the scenic setting. Attached 1-car garage, mature landscaping, and an ideal Windsor location just minutes from Madison complete this exceptional property.

6683 Charlie Grimm Rd, Windsor

155 E Wilson, Madison
$749,000
2028886 MLS ⋅ ACTIVE Status
Contemporary, unique office condominium in the heart of vibrant downtown Madison boasts an amazing Capitol view and Lake Monona steps away. Designed by world class architect Kenton Peters, the space and building is an innovative, inspiring work office environment or location for small retail or other commercial use. The office allows 15 or more teammates to work in creative, semi private spaces in 2870 sq ft. A large conference room and lobby are beautifully designed with stunning ‘forever’ views of the Capitol. A galley kitchen, 2 bathrooms on the 1st floor with street access makes the space extremely accessible. Loft office area and storage throughout. Includes 1 undergound parking space and 6 cooperative-use outdoor spaces. Move right in and get to work as spaces are set to go, no build out needed. A solid real estate investment that is unmatched for its striking upscale design and functionality. Storage unit availability TBD. Possible re-zoning for residential use.

155 E Wilson, Madison

4074 Whistle Rock Cir, Windsor
$729,900
3 Beds ⋅ 2 Baths ⋅ 2028868 MLS ⋅ ACTIVE Status
Some homes check the boxes. This one welcomes you home the moment you step through the front door, where beautiful wood beams will greet you and it only gets better from there. Thoughtfully designed with a sought-after split-bedroom layout, this ranch home blends warm inviting spaces with exceptional craftmanship highlighted by dramatic floor-to-ceiling stone fireplace, Amish-crafted custom cabinetry, an oversized center island, an impressive walk-in pantry, and a covered porch featuring a stunning wood ceiling. The private primary suite offers a beautifully tiled walk-in shower, dual vanities, and a spacious walk-in closet. The exposed lower level is ready for your dream rec room, additional bedrooms, home office, fitness room, or entertaining space. Tour today and discover why this home won’t just check your boxes…it will capture your heart.

4074 Whistle Rock Cir, Windsor

809 Harbor House Dr Unit 4, Madison
$225,000
2 Beds ⋅ 2 Baths ⋅ 2028833 MLS ⋅ ACTIVE Status
Beautiful 1st floor 2 bedrooms, 2 bath in the desirable Harbor House Condominiums. Kitchen features Cherry cabinets, S/S appliances, glass inserted cabinets with tile flooring in the kitchen and baths. In-unit washer/dryer. LPV Flooring throughout the unit. 4 heated underground parking stalls and storage unit. Clubhouse with fantastic amenities year-round: 24-hour fitness center, basketball, tennis and volleyball courts, swimming pool, hot tub, and a relaxing spa. Perfectly situated near the Beltline & EPIC, with a wide variety of dining, entertainment & shopping options nearby. Furnace and central air in the unit. Enjoy a maintenance-free lifestyle with trash removal, snow removal, and lawn care handled by the condo association. Don’t miss your chance to call this gem home.

809 Harbor House Dr Unit 4, Madison

304 St Teresa, Monona
$370,000
3 Beds ⋅ 2 Baths ⋅ 2028821 MLS ⋅ ACTIVE Status
MONONA LIVING WITH THE SPACE & FEEL OF A HOME! Discover this beautifully updated 3-bedroom condo offering the privacy and comfort of a half-duplex in a small, 2-unit association! Enjoy your own private entrance, driveway, patio, backyard space & storage shed. Inside, you'll love the gorgeous hardwood floors, vaulted living room ceiling, abundant natural light & updated kitchen with stainless steel appliances. Major improvements include a NEW ROOF (2022), renovated bathroom (2025), fresh interior paint, new carpeting, updated lighting, doors & more! Conveniently located just off Monona Dr, near bike trails, shopping, dining & public transportation. A wonderful opportunity to enjoy the Monona lifestyle with more space, privacy & flexibility than a traditional condo. BONUS! Seller is including a Universal Home Protection Basic Home Warranty for added peace of mind! Schedule your showing today!

304 St Teresa, Monona

2395 White Oak Trl, Dunn
$1,599,999
4 Beds ⋅ 5 Baths ⋅ 2028815 MLS ⋅ ACTIVE Status
This one-of-a-kind home sits on nearly three wooded acres in an old growth neighborhood, tucked on a quiet street, with downtown Madison around 15 minutes away. The 5,263 sq ft Contemporary carries a finished walkout lower level, 2 family rooms with custom gas fireplaces, and two screened porches: one opens directly off the office with a hot tub built in for four-season use. Beyond the attached garage, two detached garages complete the property, including a custom toy garage built for the collector: car lift, epoxy floors, and a finished upper level where you can host a guest for the night or just hang out. The kitchen holds a breakfast bar, island, and full appliance suite, and the primary suite includes a walk-in shower with marble countertops. Wet bar, whole-home water softener, natural gas heat, and private well and septic with a full sprinkler system with fire protection, and alarm system to help lower you insurance cost. Come tour the house today!

2395 White Oak Trl, Dunn

54 S Bryan St, Madison
$375,000
3 Beds ⋅ 2 Baths ⋅ 2028371 MLS ⋅ ACTIVE UNDER CONTRACT Status
Looking for an affordable way into Madison’s East Side? Start here. This 3-bedroom, 2-bath bungalow offers an inviting mix of original character, useful updates, and room to make it your own. Refinished hardwood floors, abundant natural light, a main-level bedroom, and an easy-flowing layout create a comfortable place to call home. Big-ticket improvements include a newer roof, 200-amp electrical service, solar power system, and washer. Enjoy coffee on the screened front porch, evenings on the back deck, and a generous yard shaded by mature trees. A detached garage and long driveway add valuable parking. Close to parks, Garver Feed Mill, restaurants, shopping, and downtown, this well-located home is an appealing choice for a first-time buyer or investment property.

54 S Bryan St, Madison

700 Paradise Dr, Stoughton
$599,900
3 Beds ⋅ 3 Baths ⋅ 2028799 MLS ⋅ ACTIVE Status
Big on Space. Big on Updates. Big on Possibilities! This updated Stoughton ranch delivers 2,849 sq. ft. of living space on one love with oversized rooms and an expansive layout. Kitchen features granite countertops, stainless steel appliances, abundant cabinetry, and a large island. Generous living and dining areas, gas fireplace, 3 bedrooms, 2.5 baths, and main floor laundry make living effortless. Major updates: newer roof, triple-pane windows, central A/C, new flooring, in-floor radiant heat, and oversized attached garage. Lower level is framed, drywalled, wired, and has radiant heating - ready for more living space. Outside: fully fenced yard, in-ground pool, and an expansive stamped concrete patio. Space to spread out. Updates to appreciate. Possibilities to make it yours!

700 Paradise Dr, Stoughton

321 Sauk Creek Dr, Madison
$715,000
4 Beds ⋅ 4 Baths ⋅ 2028797 MLS ⋅ ACTIVE UNDER CONTRACT Status
This inviting home offers generous space, flexible rooms, and comfort for everyday living, working, and entertaining. A welcoming 2-story foyer creates an immediate sense of home, while the sunken front living rm adds character and the dining area features convenient built-ins. Spacious kitchen offers an island, ample cabinetry, stainless appliances, and an eat-in area that flows into the family rm with a wood-burning stove. Upstairs, the generous primary suite includes two walk-in closets, a private bath with double sinks, a separate vanity, whirlpool tub, and walk-in shower. Two additional bedrooms, a full bath with vaulted ceiling & skylight, and a versatile loft complete the upper level. Walkout basement provides even more usable space with a large rec rm, 4th bedrm, full bath, and excellent storage. Main-floor laundry, screened porch, deck, patio, oversized 2-car garage a plus! Furnace & A/C updated in 2018, roof in 7/26, complete this well-rounded home in a convenient location!

321 Sauk Creek Dr, Madison

3710 Johnson Dr, Deerfield
$399,000
2 Beds ⋅ 1 Baths ⋅ 2028794 MLS ⋅ ACTIVE UNDER CONTRACT 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

912 Pebblebrook Dr, Waunakee
$795,000
4 Beds ⋅ 3 Baths ⋅ 2028773 MLS ⋅ ACTIVE UNDER CONTRACT Status
Located in sought-after ranch home in Meadowbrook, just 2 blocks from the neighborhood pool, clubhouse, park, and Meadows of Six Mile Creek Golf Course, this beautifully maintained ranch offers space, style, and function. Awesome Covered front porch is perfect for summer days. The gourmet kitchen features granite countertops, a large island, 6-burner gas range, stainless appliances, and glass tile backsplash. Vaulted and tray ceilings with rope lighting, hardwood floors, and a gas fireplace highlight the open great room. Spacious owner's suite includes backyard access, walk-in closet, double vanity, makeup station, and soaking tub. Finished exposed lower level boasts a tavern-style full bar, rec room with theater and game areas, 4th bedroom, full bath, and abundant storage. Enjoy a huge flat backyard with brick patio, invisible fence, covered front porch, 3-car garage, mudroom with lockers, main floor laundry, solid-core 5-panel doors, and freshly painted trim throughout.

912 Pebblebrook Dr, Waunakee

6628 Offshore Dr, Madison
$250,000
2 Beds ⋅ 2 Baths ⋅ 2028760 MLS ⋅ ACTIVE Status
Welcome home to this beautifully maintained 2-bedroom, 1.5-bath condo in one of the west side's most sought-after communities! The open-concept main level offers a bright and inviting layout, perfect for both everyday living and entertaining. You'll love the spacious bedrooms and the convenience of an attached garage with direct access to the kitchen. Enjoy a low-maintenance lifestyle in a well-managed and well-maintained condo association featuring fantastic amenities, including a clubhouse, swimming pool, and community events. Just steps from Mineral Point Park, this highly walkable location puts you close to parks, schools, bus routes, the mall, restaurants, grocery stores, and so much more. This condo is one you won't want to miss! No showings until Sunday July 26th.

6628 Offshore Dr, Madison

416 Stoneridge Ter, Deforest
$525,000
4 Beds ⋅ 4 Baths ⋅ 2028754 MLS ⋅ ACTIVE UNDER CONTRACT Status
This expansive 4-bed, 3.5 bath home has so much to offer! The large open living room is full of light and opens into the bright and cheery family room and spacious kitchen that is great for creating a feast! The home features laundry on the main floor, with easy access to the 2 bedrooms. The primary suite boasts a large walk-in closet and en-suite bathroom with double vanity. In the lower level, you will find another living space with a fireplace and a room that could be finished as a kitchenette, making this level perfect for entertaining or as a space for live-in or visiting guests. The lower level also features 2 more bedrooms and a walkout to the gorgeous yard on just over a quarter acre. There is tons of storage and lots of opportunity! Looking for a home workshop or space for your hobbies? The extra-large garage is the perfect space to put all your toys or tools. Come check this one out today as gems like this don't come up often.

416 Stoneridge Ter, Deforest

2310-2312 Post Rd, Madison
$400,000
2028722 MLS ⋅ ACTIVE UNDER CONTRACT Status
Strong investment opportunity in a highly desirable Madison location! Consistent rental demand driven by proximity to the Cannonball Trail, Jenni & Kyle Preserve, shopping, dining, parks, schools & public transit. Conveniently located w/quick access to the Beltline, Downtown Madison, UW-Madison, Epic, Verona, Fitchburg & numerous major employers. Property features private driveways, separately fenced yards, separated poured concrete basements, poured concrete foundation & ductwork in both units. Unit #2312 offers 4 BRs, including a massive primary BR w/sliding door leading to a private patio, plus a full BA w/tub/shower combo. Recent updates include a new water softener (26), new window in #2312, and new LR & DR windows in #2310. Unit #2312 also has sump pumps in both the basement & garage. This duplex presents an excellent opportunity to increase cash flow and build long-term equity in one of Madison's most convenient rental corridors. Please reach out to Burke to schedule a tour.

2310-2312 Post Rd, Madison

710 N Star Dr, Madison
$450,000
4 Beds ⋅ 3 Baths ⋅ 2028715 MLS ⋅ ACTIVE Status
Brand-new roof, kitchen appliances, carpet, and paint! Welcome home to this beautifully updated 4-bedroom, 2.5-bath home in the heart of Grandview Commons. Fresh paint and brand-new carpet throughout give the home a bright, move-in-ready feel. Enjoy peace of mind with a brand-new roof and new kitchen appliances, including a refrigerator, stove/oven, and dishwasher. The spacious two-story layout offers room for everyone, featuring a kitchen island that's perfect for gathering, walk-in closets, and an attached two-car garage. Relax on the backyard deck, enjoy nearby neighborhood parks, and take advantage of convenient access to schools, shopping, restaurants, and the bus line. A rare combination of modern updates, comfort, and an unbeatable location—this exceptional home is ready for its next owner!

710 N Star Dr, Madison

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.

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