Homes for Sale near Milestone Democratic School

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  /37

  $450,000

  • 2 Beds
  • 1 Bath
  • 1,114 Sq Ft

  309 W Washington Ave Unit 310, Madison, WI 53703

  Live in the heart of it all with this downtown condo offering unbeatable access to everything that makes the city shine. Walk to the Capitol Square, enjoy the farmers markets, top restaurants, coffee shops, boutiques, and year-round events. Inside, enjoy a light-filled, low-maintenance space designed for easy city living. With secure entry, access to bike paths and lakes, and the energy of

  

  Kelley Muselman

  Realty Executives Cooper Spransy

  (608) 351-0896

  309 W Washington Ave Unit 310, Madison, WI 53703
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  Explore Milestone Democratic School

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  /31

  $459,000

  • 3 Beds
  • 1 Bath
  • 1,261 Sq Ft

  4803 Shore Acres Rd, Monona, WI 53716

  Welcome home to this beautifully maintained 3-bedroom, 1-bath Cape Cod nestled on a spacious lot in the heart of Monona! This home perfectly blends classic charm with modern comfort, featuring refinished original hardwood floors throughout the main-floor living room and two bedrooms, along with a cozy wood-burning fireplace to enjoy on chilly evenings. Upstairs offers an additional bedroom with a

  

  Vikki Triggs

  Cold Water Realty

  (608) 560-5361

  4803 Shore Acres Rd, Monona, WI 53716
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  /39

  $445,000

  • 4 Beds
  • 3 Baths
  • 2,473 Sq Ft

  6318 Seven Pines Ave, Madison, WI 53718

  NO showings until 04/09: This tri-level offers a modern blend of updates with versatile living space. The beautifully renovated kitchen opens to a bright, sunny floor plan, ideal for everyday living and entertaining. Enjoy the coffee/wine bar. This layout provides distinct gathering spaces for both formal and casual occasions. A separate 4th bedroom with ensuite right off the lower level rec room

  

  Sona Olson

  Real Broker LLC

  (608) 713-0525

  6318 Seven Pines Ave, Madison, WI 53718
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  /82

  $715,000

  • 5 Beds
  • 3.5 Baths
  • 4,458 Sq Ft

  3630 T Bird Way, Cottage Grove, WI 53527

  Perched on a hilltop with breathtaking sunrise and sunset views, this beautiful 5-bedroom home on .83 acres blends space, privacy, and extensive updates including a new roof and windows. Inside, you'll find 9-foot ceilings, new flooring, an updated kitchen, and a remodeled upstairs bathroom. Enjoy multiple outdoor living spaces, including a custom-built deck, upper-level three-season porch, and

  

  Michael Leeson

  Realty Executives Cooper Spransy

  (608) 465-4167

  3630 T Bird Way, Cottage Grove, WI 53527
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  /25

  $1,500,000

  • Land
  • 2.28 Acres
  • $657,895 per Acre

  2735 Rimrock Rd, Fitchburg, WI 53713

  Looking for a turnkey investment opportunity? Olive Tree Residences presents a shovel-ready multifamily condominium development opportunity in Fitchburg, WI. PDD/SIP zoning approval was granted and recorded September 2025, providing certainty for the approved 20-unit program. Plans call for 2–3 bedroom units (approx. 1,700–2,500 SF) with 2.5–3.5 baths and attached 2-car garages—well positioned

  

  Rachel Kvasnica

  RE/MAX Preferred

  (608) 200-4930

  2735 Rimrock Rd, Fitchburg, WI 53713
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  /37

  $200,000

  • 1 Bed
  • 1 Bath
  • 904 Sq Ft

  101 Metro Terrace Unit 304, Madison, WI 53718

  East Side Ease--All the Perks. Step into airy, vaulted ceilings and a 1BR + Den layout that makes everyday living feel easy. The stainless galley kitchen and bar-height counter are perfect for quick breakfasts or catch-ups with friends. A true in-unit laundry room keeps life uncluttered with storage for the "everything else." The primary suite brings room to breathe and a generously sized double

  

  Jason Iverson

  Mode Realty Network

  (608) 292-4266

  101 Metro Terrace Unit 304, Madison, WI 53718
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  /23

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,457 Sq Ft

  10 Wynbrook Cir, Madison, WI 53704

  Welcome home to this delightful ranch, ideally located near parks, bus lines, and shopping. This inviting property offers both comfort and convenience, featuring an attached 2-car garage and a partially fenced patio—perfect for relaxing or entertaining. Step inside to a bright and cheerful interior, highlighted by a spacious living room and a large eat-in kitchen—ideal for everyday living and

  

  Jennifer Geils

  Stark Company, REALTORS

  (608) 299-4836

  10 Wynbrook Cir, Madison, WI 53704
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  /86

  $1,950,000

  • 6 Beds
  • 6.5 Baths
  • 5,374 Sq Ft

  752 E Gorham St, Madison, WI 53703

  VRP: $1,950,000-$2,195,000. Wake to sunlight streaming thru tall windows as the house stirs to life. Share stories & meals in the charmingly elegant kitchen, where history meets comfort. This Gothic Revival stone manor blends true craftsmanship w/ thoughtful updates for today’s living. Relax by 1 of 9 gas fireplaces. Climb the carved staircase to the cupola for views over the city. Original

  

  Sona Olson

  Real Broker LLC

  (608) 975-2898

  752 E Gorham St, Madison, WI 53703
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  /2

  $300,000

  • Land
  • 0.2 Acre
  • $1,500,000 per Acre

  380 Munn Rd, Madison, WI 53713

  .2 acre lot in the City of Madison. Seller is unsure on location of laterals.

  

  Monte Reyment

  Take Action Realty Group, LLC

  (608) 765-9225

  380 Munn Rd, Madison, WI 53713
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  /30

  $349,900

  • 2 Beds
  • 1 Bath
  • 977 Sq Ft

  1429 Macarthur Rd, Madison, WI 53714

  Discover this meticulously maintained updated gem. Prime East Side Madison location nestled in a peaceful spot just minutes from the action, this home offers the best of both worlds--a quick 10 minute drive to downtown Madison's vibrant heart, yet tucked away & peaceful. Step outside and enjoy walkable convenience: coffee shops, scenic walking paths, a nearby dog park, and even a dog-friendly

  

  Lena Oberwetter

  Real Broker LLC

  (608) 523-9083

  1429 Macarthur Rd, Madison, WI 53714
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  /34

  $189,500

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft

  6402 Milwaukee St Unit 107, Madison, WI 53718

  PRICE ADJUSTMENT! Motivated Seller. Cute & Cozy! Stylishly updated condo on Madison's eastside with an unbeatable location near parks, bike paths, restaurants, grocery stores & easy interstate access. This bright, open-concept unit is designed for effortless living & entertaining. Recent improvements include a remodeled pantry, custom closet shelving, freshly painted bathroom cabinetry, new

  

  Deanna Prochaska

  EXP Realty, LLC

  (608) 802-7293

  6402 Milwaukee St Unit 107, Madison, WI 53718
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  /3

  $160,000

  • Land
  • 0.23 Acre
  • $695,652 per Acre

  6418 Driscoll Dr, Madison, WI 53718

  Eastside 4 unit lot with approved plans ready to build, in a area of new Single & Multifamily Development. Very strong rental market and rents. All 3 bedroom units with 2 car garages. City is requiring a storm water drainage pipe along the rear of the lot closest to Milwaukee St to obtain building permit.

  

  Jim Wilson

  Restaino & Associates

  (608) 879-6280

  6418 Driscoll Dr, Madison, WI 53718
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  /21

  $3,700,000 New Construction

  • 6,202 Sq Ft

  4719 Burma Rd, Mc Farland, WI 53558

  12 units of new Apartments near McFarland High School. Beautiful wooded setting backing up to the Indian Mound park. 8 Units of 2 bedroom 1 bath units with private entrance and 1 car garage. set at the back of the lot give private quiet living. Units include spacious kitchen with full appliance package, plus washer dryer tankless water heaters and individual HVAC units. The 4 unit building offers

  

  Jim Wilson

  Restaino & Associates

  (608) 561-9882

  4719 Burma Rd, Mc Farland, WI 53558
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  /36

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,211 Sq Ft

  1014 Spaight St Unit 9, Madison, WI 53703

  Welcome to the Farwell Condominiums, a wonderful place to call home! The location can't be beat, near Lake Monona and everything Willy St has to offer, shops, restaurants and a quick bike ride to downtown!!! You will fall in love with the tasteful updates these sellers have done over the years including the hallway bath and kitchen! This unit is particularly special w/3 bedrooms, 2 full baths & a

  Tobi Silgman Lauer Realty Group, Inc.

  1014 Spaight St Unit 9, Madison, WI 53703
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  /40

  $1,999,900

  • 5 Beds
  • 3.5 Baths
  • 3,306 Sq Ft

  5728 Lake Edge Rd, Mc Farland, WI 53558

  Exquisite lakefront home w/nearly 70 ft of west facing frontage on Lake Waubesa! Spacious 5-bdrm, 3.5-bath home offers an open floor plan w/soaring ceilings, heated tile floors & cherry cabs throughout. Grand entry features 2 story foyer w/wrought-iron staircase. Chef's kitchen includes pantry, granite counters, large island w/breakfast bar & prep sink, SS appliances w/gas range & tile

  Luke Bruckner Collective Real Estate Group

  5728 Lake Edge Rd, Mc Farland, WI 53558
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  /59

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  1433 Spaight St, Madison, WI 53703

  A true Madison gem in the heart of the Marquette Bungalow Historic District, this 3 bed, 2 bath home retains the classic charm of yesteryear while adding thoughtful renovations throughout. Once a 2 flat, the main floor hosts 2 bedrooms and a full bath. Oak hardwood flooring throughout, with ornamental brick fireplace, leaded glass windows and classic arches. Custom hardwood countertops in the

  Mark Gladue Lauer Realty Group, Inc.

  1433 Spaight St, Madison, WI 53703
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  /45

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 1,923 Sq Ft

  7115 Reston Heights Dr, Madison, WI 53718

  Don't miss this charming, move-in ready 2 story home in one of the area's most high demand neighborhoods! Offering 3 spacious bedrooms plus a versatile loft perfect for a home office or second living area. Designed for today's lifestyle, this home combines space, style, and functionality in all. The private primary suite is a true retreat with a walk-in closet, dual vanity, and an oversized 3⁄4

  Pamela Braun Keller Williams Realty

  7115 Reston Heights Dr, Madison, WI 53718
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  /63

  $1,175,000

  • 2 Beds
  • 2 Baths
  • 2,088 Sq Ft

  360 W Washington Ave Unit 1413, Madison, WI 53703

  Perched above downtown Madison on the 14th floor, this breathtaking penthouse offers sweeping views of Lake Mendota, Lake Monona, the Capitol, and the city skyline from three private balconies. Floor-to-ceiling windows bathe the open-concept living space in natural light, anchored by a warm gas fireplace and custom built-ins. The beautifully appointed kitchen features granite countertops, custom

  Tony Tucci Realty Executives Cooper Spransy

  360 W Washington Ave Unit 1413, Madison, WI 53703
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  /62

  $719,900

  • 4 Beds
  • 1.5 Baths
  • 1,785 Sq Ft

  512 S Ingersoll St, Madison, WI 53703

  Show Sunday, 4/5. Gorgeous Marquette Victorian with extensive updates! Classic 3 season porch leads you into the architecturally stunning character this home showcases. Original staircase, woodwork, pocket doors, and expansive windows adorn the main floor with spacious parlor, living, and dining rooms. Continue on to the renovated kitchen with white cabinetry, stone countertops, stainless steel

  Asher Masino Lauer Realty Group, Inc.

  512 S Ingersoll St, Madison, WI 53703
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  /40

  $209,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,666 Sq Ft

  1309 Tompkins Dr Unit D, Madison, WI 53716

  Showings begin 4/4/26. Great opportunity to step into homeownership on Madison’s east side! This 3-bedroom, 1.5-bath townhome offers a functional layout with large windows that bring in natural light and all three bedrooms conveniently located upstairs. The lower level provides potential for future finishing, adding even more value. Private patio, pet-friendly association, and a convenient

  Dominic Colosimo EXP Realty, LLC

  1309 Tompkins Dr Unit D, Madison, WI 53716
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  /42

  $350,000

  • 1 Bed
  • 1 Bath
  • 1,011 Sq Ft

  333 W Mifflin St Unit 2130, Madison, WI 53703

  Experience downtown Madison living at Metropolitan Place, where style, convenience, and comfort come together effortlessly. This beautifully updated condo offers an open, airy layout highlighted by new luxury vinyl plank flooring that adds a fresh, modern feel throughout. The kitchen provides great functionality, granite counters, and opens to living area, making it ideal for entertaining or

  Brandon Buell Realty Executives Cooper Spransy

  333 W Mifflin St Unit 2130, Madison, WI 53703
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  /54

  $590,000

  • 4 Beds
  • 2.5 Baths
  • 2,761 Sq Ft

  6202 Rivercrest Dr, Mc Farland, WI 53558

  Lake Life Without the Price Tag — Walk to the Water from This Stunning Colonial! Love living in Indian Mound with easy access to parks, boat launch, dining, & schools. Space for all with an open, flexible layout built for entertaining. Enjoy a recently updated kitchen w/ granite countertops, stainless steel appliances, an XL peninsula, & ample pantry space. The Great Room You’ve Been Waiting For

  Alexandra Broz EXP Realty, LLC

  6202 Rivercrest Dr, Mc Farland, WI 53558
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  /70

  $879,900

  • 4 Beds
  • 2.5 Baths
  • 3,544 Sq Ft

  6207 Indian Mound Dr, Mc Farland, WI 53558

  Situated at one of the finest settings in the Village, this custom-built, one-owner home has all the things you have been looking for! Fantastic in-ground Pool and yard landscaping is one-of-a-kind. Backing up to Indian Mound Park offers tranquility and privacy yet only minutes walk through the peaceful park to the Middle and High Schools! Meticulously maintained and re-modeled this gem is

  Jeff Schraml Century 21 Affiliated

  6207 Indian Mound Dr, Mc Farland, WI 53558
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  /44

  $629,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,362 Sq Ft

  5613 Glorious Dr, Madison, WI 53718

  Move-in ready new construction - 4-bedroom, 2.5-bath two-story with a well-planned layout and thoughtful details throughout. The main level features a private office, spacious great room with a fireplace, and an open kitchen and dining area. The kitchen includes a walk in pantry, ample cabinetry, and stainless steel appliances including a gas range stove, dishwasher, refrigerator, and microwave

  Diane Filkouski Real Broker LLC

  5613 Glorious Dr, Madison, WI 53718
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  /34

  $599,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,342 Sq Ft

  5617 Glorious Dr, Madison, WI 53718

  Move-in ready new construction - 4-bedroom, 3-bath ranch with an open-concept layout. The main level features a spacious living room connected to the kitchen and dining area. The kitchen includes stainless steel appliances—microwave, gas range, dishwasher, and refrigerator—along with ample cabinetry and a pantry. The primary suite offers a walk-in closet and private bath. Two additional bedrooms

  Diane Filkouski Real Broker LLC

  5617 Glorious Dr, Madison, WI 53718
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  /29

  $264,900 Open Thu 5PM - 7PM

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft

  10 Kings Mill Cir Unit 309, Madison, WI 53718

  Turn-key 2 bed, 2 bath condo in Richmond Hill Estates on Madison’s east side! This well-maintained unit features an open layout with vaulted ceilings, wood-style floors, and great natural light. The kitchen includes a breakfast bar, pantry, and full appliance package, flowing easily into the living and dining areas. Spacious primary suite offers a walk-in closet and private bath with walk-in

  John Reuter Integrity Homes - Real Broker LLC

  10 Kings Mill Cir Unit 309, Madison, WI 53718
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  /44

  $370,000

  • 3 Beds
  • 1.5 Baths
  • 1,981 Sq Ft

  4702 Retana Dr, Madison, WI 53714

  Show 3/31. Spacious Ranch home, perched on a corner lot, offers a great quiet locale just blocks from Heritage Sanctuary/Park and Kennedy Elementary! Main floor boasts tile foyer, huge living room w/south facing bank of windows & oak hardwood floors. Kitchen with oak cabinetry, SS dishwasher, solid surface counter tops, breakfast bar and open to dining and elevated deck for BBQ’s and

  Liz Lauer Lauer Realty Group, Inc.

  4702 Retana Dr, Madison, WI 53714
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  /44

  $719,900

  • 4 Beds
  • 3 Baths
  • 3,112 Sq Ft

  816 Damascus Trail, Cottage Grove, WI 53527

  Welcome home to this beautifully upgraded ranch that’s only 6 years old & truly move-in ready. From the moment you walk in, you’ll appreciate the bright, open floor plan filled with natural light, vaulted ceilings & luxury vinyl plank flooring. The inviting living room features a cozy gas fireplace & the kitchen doesn’t cut corners offering custom cabinetry, granite countertops & backsplash &

  Tonya Nye Stark Company, REALTORS

  816 Damascus Trail, Cottage Grove, WI 53527
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  /67

  $1,150,000

  • 3,628 Sq Ft

  939 Spaight St, Madison, WI 53703

  Show 4/1.Grand Marquette Victorian, currently configured as a two flat, sits on a corner lot with sweeping views of Lake Monona and a stunning professionally designed garden which was featured in Olbrich Magazine. The lot size at 6,795 or 35x194 has potential to be split to allow the addition of an additional single family or 2 flat (see City of Madison email in docs). This rare property offers

  Liz Lauer Lauer Realty Group, Inc.

  939 Spaight St, Madison, WI 53703
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  /26

  $429,900

  • 2 Beds
  • 1 Bath
  • 1,055 Sq Ft

  309 W Washington Ave Unit 606, Madison, WI 53703

  Experience stylish downtown living at Capitol West in the heart of Madison. This highly desirable 2-bedroom condo offers an open, inviting layout with warm wood floors, and a sophisticated, city-forward feel. The kitchen features contemporary cabinetry, solid surface countertops, stainless steel appliances, and a breakfast bar that works well for casual meals or entertaining. Large windows fill

  Seth Pfaehler The McGrady Group, LLC

  309 W Washington Ave Unit 606, Madison, WI 53703
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  /52

  $359,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,830 Sq Ft

  3329 Webb Ave, Madison, WI 53714

  Showings begin 4/4/26. Step into this super cute 1950's ranch in one of Madison’s east side neighborhoods known for its fun, vibrant vibe and easy access to local favorites! Beautiful hardwood floors run throughout much of the main level, while newer windows bring in tons of natural light. The spacious living room features large windows and plenty of room to stretch out - perfect for relaxing or

  Dominic Colosimo EXP Realty, LLC

  3329 Webb Ave, Madison, WI 53714
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  /38

  $439,900

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft

  3386 Brugger Place, Mc Farland, WI 53558

  Showings begin 4/4. This well-laid-out tri-level sits on a generous lot in McFarland and delivers room for everyone and everything! The main level keeps things easy with a bright dining area and semi-open, updated kitchen featuring granite counters incl. breakfast bar. Head upstairs to a spacious living room and two comfortable bedrooms, including a primary with a walk-in closet. Walk-through

  Brandon Buell Realty Executives Cooper Spransy

  3386 Brugger Place, Mc Farland, WI 53558
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  /26

  $189,900

  • 2 Beds
  • 1 Bath
  • 852 Sq Ft

  7 Sherman Terrace Unit 6, Madison, WI 53704

  Welcome home to Sherman Terrace, a well-kept Madison community where easy living is built right in. This two-bedroom, one-bath garden-style condo has been freshly updated so you can settle in with complete peace of mind. The layout is comfortable and functional, and the main living area flows naturally into the dining space, giving you a great setup for everyday meals or casual entertaining. The

  Brandon Buell Realty Executives Cooper Spransy

  7 Sherman Terrace Unit 6, Madison, WI 53704
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  /28

  $339,900

  • 3 Beds
  • 2 Baths
  • 1,381 Sq Ft

  3513 Burke Ave, Madison, WI 53714

  This east side gem is full of character and ready for you! Step through the cheerful enclosed front porch, complete with built-in bench seating and wraparound windows, and you'll already feel at home. Inside, hardwood floors carry you through a bright, airy living room and into a sun-drenched dining room made for long dinners and good company. The kitchen keeps things light and easy with a

  Brandon Buell Realty Executives Cooper Spransy

  3513 Burke Ave, Madison, WI 53714
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  /51

  $350,000

  • 3 Beds
  • 2.5 Baths
  • 1,960 Sq Ft

  2414 Commercial Ave, Madison, WI 53704

  Fully updated 3-bedroom townhouse in Eken Park with over $60,000 in recent improvements. New furnace, AC, water heater, and garage door. Remodeled kitchen with new cabinets, countertops, refrigerator, dishwasher, and disposal. New bathroom, flooring throughout, and ceiling fan. Gas fireplace with new mantel. 1,960 sq ft across three levels including private basement storage and attached 2-car

  Timothy Flores LPT Realty

  2414 Commercial Ave, Madison, WI 53704
• 

  

  /29

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,189 Sq Ft

  3233 Quincy Ave, Madison, WI 53704

  Showings begin Wednesday April 1 at 5pm. Well-maintained bi-level home ideally located close to bus line & all the conveniences of Madison’s east side. Numerous updates over the years provide peace of mind, including roof, windows, appliances, water heater (2022), & furnace (2014). Finished LL adds valuable living space w/spacious rec room or use as 4th bedroom w/double closets (Closet organizers

  Mary Schultz Century 21 Affiliated

  3233 Quincy Ave, Madison, WI 53704
• 

  

  /27

  $425,000

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  6144 Stoney Oak Ln, Madison, WI 53718

  No showings until open house. Welcome home to this nicely upgraded property in the desirable Grandview Commons neighborhood. Featuring an open-concept floor plan, great laundry/mud room, along with a spacious pantry. The bright and inviting main living area leads to a deck and fully fenced backyard perfect for relaxing or hosting family and friends. This home includes three spacious bedrooms and

  Jamie Zimmer MHB Real Estate

  6144 Stoney Oak Ln, Madison, WI 53718
• 

  

  /86

  $1,100,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 2,785 Sq Ft

  260 Kensington Dr, Madison, WI 53704

  Welcome to this beautifully updated home in sought-after Maple Bluff! Offering more space than meets the eye, this 4-bedroom, 2.5-bath home features a brand-new kitchen with stainless steel appliances. The spacious primary suite includes a walk-in closet and a luxurious bath with heated floors. Enjoy a cozy gas fireplace, and the dedicated office with built-ins. Storage abounds with ample closets

  Jenny Bunbury-Johnson Bunbury & Assoc, REALTORS

  260 Kensington Dr, Madison, WI 53704
• 

  

  /35

  $419,000

  • 2 Beds
  • 1.5 Baths
  • 1,390 Sq Ft

  21 Powers Ave, Madison, WI 53714

  Show 4/2. Charming bungalow full of character and timeless appeal! This home features beautiful wood floors, original moldings, and a large sunroom with a wood-burning stove that opens up to walkout deck and expansive yard on double lot. The updated full bath includes heated floors, and the kitchen offers stainless steel appliances and a functional layout with a breakfast bar that opens to

  Michael Weiss MHB Real Estate

  21 Powers Ave, Madison, WI 53714
• 

  

  /25

  $600,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  129 Dunning St, Madison, WI 53704

  Step into timeless charm w/this beautifully maintained 1925 home, where classic character meets thoughtful modern updates. Nestled on a quiet street, this home offers the perfect blend of historic appeal and today’s conveniences. The refinished hardwood floors showcase the home’s original craftsmanship, adding warmth & elegance thruout. The fully renovated kitchen is a standout feature, complete

  Robin Taylor Restaino & Associates

  129 Dunning St, Madison, WI 53704

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