Homes for Sale near Milestone Democratic School

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  /24

  $184,900

  • 2 Beds
  • 2 Baths
  • 1,060 Sq Ft

  1007 N Sunnyvale Ln Unit C, Madison, WI 53713

  Spacious first floor 2 bedroom, 2 bath condo offers comfortable, and low maintenance living. The open living room features laminate floor, a wood burning fireplace and patio doors leading to the community pool and clubhouse. The kitchen showcases butcher block countertops, stainless steel shelving, and stainless steel appliances. Primary suite complete with private full bath. Additional features

  Scott Elert RE/MAX Preferred

  1007 N Sunnyvale Ln Unit C, Madison, WI 53713
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  /71

  $3,043,000

  $157K PRICE DROP

  • 6,654 Sq Ft

  120 N Franklin St, Madison, WI 53703

  Rare opportunity to own the 120–126 N. Franklin St portfolio, a 6-unit, 27-bedroom side-by-side investment property in a premier rental location near James Madison Park. This exceptionally well-maintained portfolio offers strong in-place income, consistent tenant demand, and easy leasing year after year. The property currently generates $315,254 in annual income with pro forma projections of

  Imani Jones EXIT Realty HGM

  120 N Franklin St, Madison, WI 53703
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  /7

  $129,900

  $4K PRICE DROP

  • Land
  • 10,454 Sq Ft
  • $541,250 per Acre

  540 Buss Rd, Cottage Grove, WI 53527

  Build your dream home in the desirable Shady Grove neighborhood, where small-town charm meets everyday convenience. This homesite offers close proximity to schools and an ideal setting for a peaceful, slower-paced lifestyle, without giving up easy access to big-city amenities. Enjoy a welcoming, tight-knit community feel with friendly neighbors, nearby parks, trails, and natural spaces, perfect

  Aeryn Barry Tim O'Brien Homes LLC

  540 Buss Rd, Cottage Grove, WI 53527
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  /51

  $859,900

  Open Sat 1PM - 3PM $9K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,593 Sq Ft

  10 Vienna Cir, Madison, WI 53718

  Open House this Saturday the 25th 1:00--3:00!!Elegant,well maintained 3 bedroom/2bath ranch on half acre. Phenomenal saltwater in-ground pool,and professionally landscaped.WIFI capable,16 -zone lawn irrigation system,3-car garage, and central vacuum. Hardwood floors throughout. Living room boasts gas fireplace, remote opening/closing skylights with vaulted ceilings bathing the home in natural

  Vern Acker RE/MAX Preferred

  10 Vienna Cir, Madison, WI 53718
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  /11

  $809,900

  • 3,296 Sq Ft

  110 S Bassett St, Madison, WI 53703

  Great downtown 3-unit in an unbeatable location! New roof in 2025, newer furnace and updated electrical which are separately metered. Just blocks from the Capitol Square, James Madison Park & Kohl Center. Residents will love the inviting front porches ideal for entertaining, with easy access to downtown dining, shopping, entertainment, and the lakefront. Fully rented until August of 2027. This is

  Ken Seifert Realty Executives Capital City

  110 S Bassett St, Madison, WI 53703
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  /54

  $380,000

  $70K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,968 Sq Ft

  4802 Onyx Ln, Madison, WI 53714

  4 BEDROOM UNDER $385k!! AND Seller is offering $6,000 closing cost credit to buyers!This updated 4-bedroom home offers the perfect blend of space, comfort, and convenience. The main level features a spacious living room open to a dining area with ample space for large gatherings, and an eat-in kitchen with plenty of room to enjoy casual dinners. A bonus main level living space provides extra

  Sandy Joudrey NextHome Midwest

  4802 Onyx Ln, Madison, WI 53714
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  /28

  $440,000

  • 3 Beds
  • 2.5 Baths
  • 1,612 Sq Ft

  5852 Tranquility Trail, Madison, WI 53718

  Welcome home to this inviting 3-bedroom, 2.5-bath two-story home offering a functional layout and room to grow! All three bedrooms are conveniently located upstairs, including a spacious primary suite featuring a walk-in closet and private ensuite bath. The main level provides comfortable living and entertaining spaces, along with the convenience of a half bath. The unfinished basement offers

  Autumn Garrigan MHB Real Estate

  5852 Tranquility Trail, Madison, WI 53718
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  /5

  $627,700

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,045 Sq Ft

  The Hoffman Plan at Pheasant Crossing, Middleton, WI 53562

  Calling all culinary connoisseurs, avid readers, and design devotees. Arrange the shelves with timeless Mark Twain classics or your most cherished finds. Fill the expansive kitchen with gourmet cookware and rare, beautifully crafted tools. With more space comes a more effortless kind of luxury—where everything has its place, and so do you. Meet The Hoffman. Energy expert certified: Third-party

  Veridian Homes Builder

  6801 S Towne Dr Unit 39023559, Middleton, WI 53562
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  /2

  $194,000

  • Land
  • 11,325 Sq Ft
  • $746,154 per Acre

  2995 London Ave, Cottage Grove, WI 53527

  Beautiful full walk-out lot that backs up to a large pond and open space. Located in the highly desirable Westlawn Estates neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2995 London Ave, Cottage Grove, WI 53527
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  /68

  $325,000

  • 4 Beds
  • 1.5 Baths
  • 1,400 Sq Ft

  4707 Camden Rd, Madison, WI 53716

  Nice 4-bedroom, 1,5 bath home in the Monona school district is ready to buy! There have been extensive improvements done! The kitchen completely gutted & redone in 2022. Offers stainless steel appliance, beautiful cabinetry, tile back splash & under cabinet lighting. Living & dining rooms with new drywall, lighting, flooring & paint & trim. Upstairs are 4 bedrooms, bath & refinished oak hardwood

  Brenda Murphy First Weber Inc

  4707 Camden Rd, Madison, WI 53716
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  /37

  $179,900

  Open Sun 11AM - 1PM $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft

  6402 Milwaukee St Unit 207, Madison, WI 53718

  Simple Living, Exceptional Value! Experience the ease of low-maintenance condo living in this inviting 1-bedroom, 1-bath home with a versatile bonus room perfect for a home office, hobby space, or extra storage. The open-concept layout features a stylish kitchen with stainless steel appliances, breakfast bar seating, and a comfortable living area that opens to your private balcony—ideal for

  Matt Kornstedt Stark Company, REALTORS

  6402 Milwaukee St Unit 207, Madison, WI 53718
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  /2

  $189,000

  • Land
  • 15,246 Sq Ft
  • $540,000 per Acre

  2006 Wellington Place, Cottage Grove, WI 53527

  Beautiful wooded walkout lot with East backyard exposure. Located in the highly desirable Westlawn Estates neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2006 Wellington Place, Cottage Grove, WI 53527
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  /35

  $449,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,151 Sq Ft

  641 E Dayton St Unit 1, Madison, WI 53703

  Welcome to this bright and airy 2-bedroom, 2-bath townhouse-style condo in the heart of Madison! Ideally located just blocks from Lakes Mendota and Monona, this home offers easy access to the UW campus, UW Hospital, Breese Stevens Field, and all the dining, shopping, and entertainment that downtown Madison has to offer. The thoughtfully designed floor plan features a bedroom and full bathroom on

  Elissa Zollin EXP Realty, LLC

  641 E Dayton St Unit 1, Madison, WI 53703
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  /90

  $2,000,000

  $300K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,473 Sq Ft

  4523 Winnequah Rd, Monona, WI 53716

  Fresh Opportunity...NEW MARKET ADJUSTMENT OFFERS EXCEPTIONAL BUY! Stunning classical w/endless upgrades & amenities. Seller's travels to Europe, especially Italy & Greece, inspired his design of the classic elements of the home. I define it as a masterpiece; unique & truly one of a kind! Enjoy 3 levels of living. MAIN: Laundry, Half Bath, Office, DR is open to the $350k Kitchen Remodel w/high end

  Jules Bowes EXP Realty, LLC

  4523 Winnequah Rd, Monona, WI 53716
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  /4

  $112,900

  • Land
  • 4,791 Sq Ft
  • $1,026,364 per Acre

  4785 Brassica Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4785 Brassica Rd, Fitchburg, WI 53711
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  /50

  $536,500

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  The Sawyer Plan at Rosewood Fields, McFarland, WI 53558

  A home as resourceful as you are. The flex room may be the perfect home office today, but it can easily transform into a creative craft studio tomorrow. The kitchen offers ample space for preparing elegant feasts, and the island is ready for quick morning routines. When it’s time to unwind, retreat to the spacious primary suite, complete with a private bath designed for comfort and calm. Welcome

  Veridian Homes Builder

  6437 Tuscobia Trail Unit 36476241, McFarland, WI 53558
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  /42

  $715,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,663 Sq Ft

  1130 E Gorham St Unit 1, Madison, WI 53703

  Exceptional east side residence just moments from the lake, parks, and downtown Madison, offering a rare blend of historic character and refined modern updates. This beautifully maintained home features a new detached 3-car garage (2021) with potential for future ADU/finished space above, updated electrical and plumbing (2018), and updated windows throughout much of the home. The remodeled

  Chris Ziegler Redfin Corporation

  1130 E Gorham St Unit 1, Madison, WI 53703
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  /40

  $399,900

  $80K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,412 Sq Ft

  3142 Larsen Rd, Madison, WI 53711

  Nestled on a private 1 acre lot on a dead end road near the nature preserve, Christy's Landing, and our awesome bike trails, this home is just minutes from downtown Madison. There is a 1 car garage on the lower level, with a heated 2 car (24x26) detached garage out back just perfect for the hobbyist! Main floor primary was opened up to make it a current 2 bedroom home, however seller is giving a

  Mike Bailey EXP Realty, LLC

  3142 Larsen Rd, Madison, WI 53711
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  /50

  $499,900

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft

  309 W Washington Ave Unit 905, Madison, WI 53703

  Live in the heart of downtown Madison, just three blocks from Capitol Square. Rarely available, 2-bedroom, 2-bath residences with two parking stalls at Capitol West seldom come to market, making this a unique opportunity to enjoy one of the city's most sought-after condominium communities. Thoughtfully appointed interiors pair warm oak flooring and cabinetry with granite countertops, and Kohler

  Trey Sprinkman Sprinkman Real Estate

  309 W Washington Ave Unit 905, Madison, WI 53703
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  /24

  $640,000

  • 2,560 Sq Ft

  2069 Winnebago St, Madison, WI 53704

  Prime Near East Side 3-unit investment opportunity just steps from Schenk's Corners. Full of character, this well-maintained property features hardwood floors, formal dining rooms in the first and second-floor units, inviting porches, a private third-floor balcony, and three off-street parking spaces. Recent improvements include major electrical updates, vinyl siding, ceiling repairs, deck and

  Sarah Gabrielse Devout Real Estate Group, LLC

  2069 Winnebago St, Madison, WI 53704
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  /10

  $164,900

  • Land
  • 6,534 Sq Ft
  • $1,099,333 per Acre

  4767 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4767 Lacy Rd, Fitchburg, WI 53711
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  /63

  $624,900

  Open Sat 11AM - 1PM $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,402 Sq Ft

  100 Farwell Dr, Cottage Grove, WI 53527

  Beautifully maintained, open concept Ranch in sought after Coyle Highlands neighborhood. This house is the largest in the neighborhood offering comfort and privacy. Many updates including, deck paint '26, new carpet & LVP in LL '24, disposal '25 furnace '22, sump pump '22, refrigerator '22, dishwasher '24, microwave '24 & dryer '21 to name a few. Living room features stunning stone fireplace,

  Jaclyn Cunningham First Weber Inc

  100 Farwell Dr, Cottage Grove, WI 53527
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  /34

  $589,900

  $10K PRICE DROP

  • 7 Beds
  • 3 Baths
  • 2,280 Sq Ft

  114 W Olin Ave, Madison, WI 53715

  Rare opportunity to own one of Madison's few true seven bedroom homes, offering exceptional flexibility for multigenerational living, home offices, or evolving lifestyle needs. Built with enduring quality and meticulously maintained by the same family since it was constructed, this spacious brick home features a floor plan rarely found in today's market. The sun filled main level welcomes you

  Erika Haar CCL Management

  114 W Olin Ave, Madison, WI 53715
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  /48

  $859,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 2.5 Baths
  • 2,305 Sq Ft

  2017 Wellington Place, Cottage Grove, WI 53527

  Estimated completion by the end of June 2026. This stunning, custom-built, brand-new ranch-style home by Maverick Homes offers 2,305 square feet of modern living space designed for both comfort and elegance. Situated on a generous lot, the property provides ample space for outdoor activities and future landscaping opportunities. The three-car garage offers plenty of room for vehicles and

  Matt Winzenried Realty Executives Cooper Spransy

  2017 Wellington Place, Cottage Grove, WI 53527
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  /90

  $774,999

  $10K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,118 Sq Ft

  517 Buss Rd, Cottage Grove, WI 53527

  Step inside this immaculate, impressive Colonial 5 bedroom, 3.5 bath offering over 4000 sq ft on main level & an unfinished lower level for great expansion, includes a bath rough in & egress window. This open floor plan offers a very large kitchen w/lots of beautiful maple cabinets, walk-in pantry, upgraded GE SS appliances, an oversized island bar & a lovely morning room. Open & airy

  Nancy Riemenapp First Weber, Inc

  517 Buss Rd, Cottage Grove, WI 53527
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  /25

  $545,000

  Open Sun 11AM - 1PM $45K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,287 Sq Ft

  29 Westend Cir, Madison, WI 53704

  Motivated seller - Open Sunday from 11am to 1pm. Move-in ready and located at the end of a quiet cul-de-sac, this beautiful home offers privacy with a new in 2024, fenced backyard and an outstanding floor plan. The soaring vaulted great room and gourmet kitchen create the perfect space for everyday living and entertaining. Brand new roof May 2026, All new windows 2024. It also features 4 spacious

  Brad Acker Brad Acker

  29 Westend Cir, Madison, WI 53704
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  /12

  $5,990,000

  • Land
  • 9.8 Acres
  • $611,224 per Acre

  3080 County Road Mm, Fitchburg, WI 53711

  REDEVELOPMENT OPPORTUNITY - Prime location on the corner of Clayton Rd. & Highway MM in Fitchburg, WI. Priced at just $5,990,000, this 9.8-acre parcel offers endless potential for redevelopment. Situated on a beautiful hilltop, with breathtaking views of downtown Madison, Lake Monona, and the surrounding countryside, the property is just minutes away from the proposed development of the Dane

  James Stopple Madison Property Management, Inc.

  3080 County Road Mm, Fitchburg, WI 53711
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  /61

  $2,999,999

  • 4 Beds
  • 3 Baths
  • 3,578 Sq Ft

  155 E Wilson St Unit 702, Madison, WI 53703

  Architect-owned dual-level penthouse offers a serene retreat where high modernism meets panoramic lake views. Personally designed by renowned architect Kenton Peters, the home focuses on airy, expansive, environmentally layered spaces with carefully curated interiors that balance grand entertaining with intimate living. A main-level bedroom suite offers exceptional flexibility, complete with an

  Maria Antoinette Cannarella Restaino & Associates

  155 E Wilson St Unit 702, Madison, WI 53703
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  /60

  $435,000

  • 3 Beds
  • 2.5 Baths
  • 1,463 Sq Ft

  1001 Glacier Hill Dr, Madison, WI 53704

  Welcome home to this beautifully situated 3-bedroom, 2.5-bath property on a desirable corner lot with mature trees and unobstructed views of Glacier Hill Park. Enjoy the privacy of the backyard retreat, perfect for relaxing or entertaining, with a dinette featuring a patio door that opens directly to the outdoor space. Fresh paint throughout, and new front porch pillars (2026). Major improvements

  Ikbal Bieff Restaino & Associates

  1001 Glacier Hill Dr, Madison, WI 53704
• 

  

  /90

  $419,900

  Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,743 Sq Ft

  613 Whitehall Dr, Madison, WI 53714

  No showings until open house on Sunday 7/26 at 2:00 pm. Beautiful Ranch in popular Heritage Heights. Not much to do here but move in and enjoy your new home! The roof, gutters, furnace, central air and water heater have been taken care of in the last 2 years. The beautiful and large eat in kitchen with breakfast bar has recently been updated as well as both bathrooms. Downstairs in partially

  Michele Killerlain Restaino & Associates

  613 Whitehall Dr, Madison, WI 53714
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  /59

  $425,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,466 Sq Ft

  400 Frost Woods Rd, Monona, WI 53716

  CHARMING MONONA RANCH! Welcome home to this well-maintained classic ranch in excellent condition. The bright living room includes solid hard wood floors, a large picture window and plenty of room for that large sectional you’ve been wanting. A few more steps takes you to the functional eat in kitchen with painted cabinets. Three bedrooms on the main floor sit next to the updated main bathroom.

  The Lavik Home Team EXP Realty, LLC

  400 Frost Woods Rd, Monona, WI 53716
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  /43

  $579,900

  • 3 Beds
  • 2 Baths
  • 2,003 Sq Ft

  5514 Maddy Pass, Madison, WI 53718

  Like new and absolutely stunning, this 3-bedroom ranch offers the perfect blend of style and comfort. Vaulted ceilings and abundant natural light create a bright, open feel throughout the thoughtfully designed floor plan. The elegant kitchen features stainless steel appliances, a sleek tile backsplash, and quartz center island that overlooks the spacious living and dining area, making

  Dustin Laufenberg MHB Real Estate

  5514 Maddy Pass, Madison, WI 53718
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  /10

  $169,900

  • Land
  • 6,534 Sq Ft
  • $1,132,667 per Acre

  4759 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4759 Lacy Rd, Fitchburg, WI 53711
• 

  

  /10

  $117,900

  • Land
  • 6,534 Sq Ft
  • $786,000 per Acre

  4766 Lacy Rd, Fitchburg, WI 53711

  Build your dream home in Terravessa, a thoughtfully planned Fitchburg community featuring parks, green space, walking and biking trails, and nearby lake access. Conveniently located near shopping, event venues, in-neighborhood dining, cafés, and school. Served by the Oregon School District and connected to the greater Madison trail network, including the Southwest Commuter Trail. Lot sale is

  Aeryn Barry Tim O'Brien Homes LLC

  4766 Lacy Rd, Fitchburg, WI 53711
• 

  

  /23

  $900,000

  • 2,697 Sq Ft

  124 N Franklin St, Madison, WI 53703

  Rarely do you find a 2-flat with this much size, income, and upside all in one package! Located right next to James Madison Park, this 8-bedroom property is already generating over $7,100/month with potential to push rents beyond $8,200/month. The oversized units, off-street parking, unbeatable location, and classic charm make these apartments incredibly easy to rent year after year. Well

  Imani Jones EXIT Realty HGM

  124 N Franklin St, Madison, WI 53703
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  /63

  $750,000

  • 1,730 Sq Ft

  137 Proudfit St, Madison, WI 53715

  Opportunity awaits with this charming 2-unit investment property in a highly desirable Madison location! Featuring a vacant 4-bedroom, 2-bath unit, this property offers excellent flexibility for an owner-occupant or the ability to maximize rental income with a new tenant. The second unit is a cozy 1-bedroom, 1-bath apartment, providing an additional income stream. Full of timeless character and

  Rose Freidel First Weber Inc

  137 Proudfit St, Madison, WI 53715
• 

  

  /22

  $432,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft

  309 W Washington Ave Unit 212, Madison, WI 53703

  This condo in the heart of downtown offers floor to ceiling windows, balcony and beautiful views. Open concept kitchen features breakfast bar, quartz counters, gas range and GE stainless appliances. Engineered wood flooring in main living area. Primary bedroom has walk-in closet and organizers. Large bathroom with dual vanity, separate tub and tiled walk-in shower. Storage unit located on same

  Marc Gerothanas First Weber Inc

  309 W Washington Ave Unit 212, Madison, WI 53703
• 

  /2

  $189,000

  • Land
  • 14,374 Sq Ft
  • $572,727 per Acre

  2994 London Ave, Cottage Grove, WI 53527

  Beautiful wooded walk-out lot with a full South backyard exposure. Located in the highly desirable Westlawn neighborhood. Building permit available now.

  Andrew Homburg Homburg Realty Inc

  2994 London Ave, Cottage Grove, WI 53527
• 

  

  /7

  $133,900

  • Land
  • 10,890 Sq Ft
  • $535,600 per Acre

  543 Buss Rd, Cottage Grove, WI 53527

  Build your dream home in the desirable Shady Grove neighborhood, where small-town charm meets everyday convenience. This homesite offers close proximity to schools and an ideal setting for a peaceful, slower-paced lifestyle, without giving up easy access to big-city amenities. Enjoy a welcoming, tight-knit community feel with friendly neighbors, nearby parks, trails, and natural spaces, perfect

  Aeryn Barry Tim O'Brien Homes LLC

  543 Buss Rd, Cottage Grove, WI 53527
• 

  

  /8

  $125,000

  • Land
  • 7,840 Sq Ft
  • $694,444 per Acre

  Lot 4 Wyalusing Dr, Madison, WI 53718

  Rare opportunity in Madison’s sought-after Reston Heights Subdivision! Hard-to-find single-family lots in a master-planned community with parks, greenspace, and trails. Lots will be ready to build by mid-November — bring your own builder and design your dream home! Enjoy green space bordering these lots and a large park across the street. Prime location near the Door Creek Corridor, new schools,

  Mark Nortman First Weber Inc

  Lot 4 Wyalusing Dr, Madison, WI 53718

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