Homes for Sale near O'Keeffe Middle

• 

  

  

  /41

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  309 N Brearly St, Madison, WI 53703

  Rare opportunity to own a charming home in one of Madison's most desirable neighborhoods, just a couple of blocks from Lake Mendota & minutes from downtown. A private driveway provides valuable off-street parking, a sought-after feature in this area. This inviting home is filled with character, featuring hardwood floors, built-in cabinetry in the dining room, an expanded and updated kitchen

  

  Tami McFarlane

  Restaino & Associates

  309 N Brearly St, Madison, WI 53703
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  Explore O'Keeffe Middle

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  /27

  $530,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,376 Sq Ft

  1227 Spaight St, Madison, WI 53703

  Historic charm meets incredible flexibility at 1227 Spaight Street! This inviting home is currently configured as a 2-unit property, featuring a spacious 3-bedroom unit plus a separate efficiency, ideal for rental income, owner-occupancy, guests, or a home office. Prefer single-family living? The property can be restored to its original single-family configuration, offering exceptional

  

  Tiffany Malone

  Compass Real Estate Wisconsin

  1227 Spaight St, Madison, WI 53703
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  /37

  $338,000

  $17K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,404 Sq Ft

  813 Powers Ave, Madison, WI 53714

  Opportunity knocks! This 3-bedroom, 2-bath home is full of potential and ready for your vision! Offering a great layout and the opportunity to build equity, this home features a new roof, newer furnace, updated electrical, and new LeafGuard gutters on the back of the home. Move in ready or bring your design ideas and add your own finishing touches to make this property truly special. Conveniently

  

  Lisa Fritz

  Cold Water Realty

  813 Powers Ave, Madison, WI 53714
• 

  

  

  /35

  $364,900

  • 4 Beds
  • 1 Bath
  • 1,040 Sq Ft

  2737 Union St, Madison, WI 53704

  Nestled in the heart of Madison's eclectic East side, the Purple Bungalow is where charm meets modern convenience. Recent updates include a brand-new roof and gutters, plus a new washer and dryer, giving you peace of mind and everyday convenience from day one. This beautifully updated home also boasts newly refinished hardwood floors, fresh interior paint, spacious & flexible living spaces filled

  

  Mary Browning

  Compass Real Estate Wisconsin

  2737 Union St, Madison, WI 53704
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  /20

  $405,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 952 Sq Ft

  405 Rogers St, Madison, WI 53703

  Charming 2-bedroom, 1-bath home in the heart of Madison's vibrant East Side! This prime location puts you within walking distance of some of the city's best restaurants, entertainment, and the lake; perfect for enjoying everything Madison has to offer right outside your door. Whether you're grabbing coffee at a neighborhood cafe, catching a show, or taking a sunset stroll along the water, this

  

  Tiffany Malone

  Compass Real Estate Wisconsin

  405 Rogers St, Madison, WI 53703
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  /90

  $1,795,000

  $455K PRICE DROP

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

  752 E Gorham St, Madison, WI 53703

  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. Each bedroom has its own full bathroom. Each bedroom has its own gas fireplace. Relax by 1 of 9 gas fireplaces. Climb the carved staircase

  

  Sona Olson

  Real Broker LLC

  752 E Gorham St, Madison, WI 53703
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  /42

  $445,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 987 Sq Ft

  1406 Jenifer St, Madison, WI 53703

  Don't miss this dream opportunity to live in the historic Marquette neighborhood. 1406 Jenifer Street invites you in through its charming side porch, past beautiful landscaping and a sprawling front yard tree that matches the street's whimsical tone. Inside, you're greeted by a cozy living room and hardwood flooring. The stylish eat-in kitchen adds a pop of color, featuring open shelving and a

  Isabella Lazzareschi Realty Executives Cooper Spransy

  1406 Jenifer St, Madison, WI 53703
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  /59

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,042 Sq Ft

  54 S Bryan St, Madison, WI 53714

  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

  Anna Trull Stark Company, REALTORS

  54 S Bryan St, Madison, WI 53714
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  /43

  $390,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  2682 South Ct, Madison, WI 53704

  Check out this super cute move in ready bungalow on a quiet street in the heart of Atwood. The open-concept layout is spacious and inviting, featuring wood floors throughout. Plenty of natural light and updated windows as well. The kitchen offers a new Beko induction range and granite countertops, providing ample space to entertain and host dinners. Outside you'll enjoy the private yard and the

  Joe Copeland Realty Executives Cooper Spransy

  2682 South Ct, Madison, WI 53704
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  /52

  $445,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,057 Sq Ft

  2614 St Paul Ave, Madison, WI 53704

  Show 8/6. Atwood Bungalow with tons of updates overlooking the community gardens and bike path! Incredible complete kitchen remodel with opened wall, new cabinets, granite countertops, and appliances! Spacious living room boasts woodburning fireplace, built-in bookshelves, and tons of natural light. Hardwood floors throughout living room, formal dining, and kitchen, guide you through to the back

  Asher Masino Lauer Realty Group, Inc.

  2614 St Paul Ave, Madison, WI 53704
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  /57

  $689,000

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft

  422 Sidney St, Madison, WI 53703

  Beautifully maintained home in the heart of Tenney-Lapham awaits a new owner! This lovingly cared for 3 bed/1.5 bath home blends original character with thoughtful updates throughout. Hardwood floors flow through the home, while the updated kitchen with breakfast bar opens nicely to the dining room. The freshly renovated four season sunroom provides a bright, inviting space to relax year round.

  Michael Maziarka Realty Executives Cooper Spransy

  422 Sidney St, Madison, WI 53703
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  /50

  $328,000

  $12K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  1014 Spaight St Unit 5, Madison, WI 53703

  Rare opportunity to purchase a spacious, 2-bedroom condo in Madison’s desirable Marquette Neighborhood! Perfectly situated w/a partial view of Lake Monona, this sun-filled & exceptionally quiet home is just 100 yards from Lake Monona, one block from Orton Park & only a few blocks from the vibrant Willy Street area. Enjoy easy access to the Willy Street Co-op, restaurants, boutique shops,

  Tobi Silgman Lauer Realty Group, Inc.

  1014 Spaight St Unit 5, Madison, WI 53703
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  /42

  $289,900

  $9K PRICE DROP

  • 2 Beds
  • 4 Baths
  • 1,910 Sq Ft

  1328 Carpenter St, Madison, WI 53704

  Rarely available—and easy to see why! This spacious end-unit townhouse condo backs to a beautiful wooded conservancy, offering privacy, peaceful views and an abundance of wildlife right outside your door. With a private entrance, 2 bedrooms plus den, 2 full and 2 half baths, there’s room to spread out. The large primary suite features a walk-in closet and private bath, while the charming loft is

  Renee Heine Lauer Realty Group, Inc.

  1328 Carpenter St, Madison, WI 53704
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  /33

  $400,000

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  2929 Atwood Ave Unit 204, Madison, WI 53704

  Welcome to this freshly painted townhouse-style condo in one of Madison’s most vibrant and walkable neighborhoods near Lake Monona! 2 bed/1.5 bath condo features an open-concept main level with hardwood floors, gas fireplace and spacious living, dining, and kitchen areas. A wall of windows fills the space with natural light. Upstairs offers two spacious bedrooms, convenient in-unit laundry and a

  Sherry McKee Stark Company, REALTORS

  2929 Atwood Ave Unit 204, Madison, WI 53704
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  /35

  $340,000

  $25K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 697 Sq Ft

  107 Sutherland Ct Unit 323, Madison, WI 53704

  Wonderful garden facing unit in Linden Cohousing! Built in 2019, this top floor unit features a lovely open floor plan, a sunny balcony, and well cared for finishes from this original owner. Enjoy rare features such as the stove hood vent that actually vents to the outdoors, and that the unit is ADA compliant (see accessibility report). Best of all, enjoy a thoughtful, interactive, and supportive

  Asher Masino Lauer Realty Group, Inc.

  107 Sutherland Ct Unit 323, Madison, WI 53704
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  /68

  $349,900

  $100K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,775 Sq Ft

  1212 E Johnson St, Madison, WI 53703

  Location, Location, Location. Enjoy the newly remodeled (per seller) 2nd floor of this 19th century home conveniently located in the heart of the Tenney Lapham neighborhood. Major bus stops & bike lanes are w/in a block, to get you to the Capital or University w/in minutes. A spacious kitchen, two distinct living areas, four bedrooms (one is currently used as a 2nd LR (Main level) and two baths

  Sheryl Schroeder Coldwell Banker Real Estate Group

  1212 E Johnson St, Madison, WI 53703
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  /32

  $325,000

  $70K PRICE DROP

  • 1 Bed
  • 1.5 Baths
  • 978 Sq Ft

  1029 Williamson St Unit 1, Madison, WI 53703

  Motivated seller! All the charm of a home on the Isthmus, fully updated in 2006 including an exterior foundation rebuild. Step into this fully updated condo in the heart of Willy st and feel right at ease; it's all been taken care of! A private entry with a porch leads into the large, flexible living space, which features large bay windows reflecting onto the bamboo floors and a gas fireplace.

  Lindsey Cooper Lauer Realty Group, Inc.

  1029 Williamson St Unit 1, Madison, WI 53703
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  /73

  $799,900

  $25K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,802 Sq Ft

  1233 E Johnson St Unit 4, Madison, WI 53703

  Timeless 1924 Craftsman beautifully blends historic character with exceptional modern updates just two blocks from Tenney Park and only one mile to the Capitol. This stunning 5-bedroom home features gorgeous original woodwork, hardwood floors, glass transom windows, and a cozy gas fireplace. The chef's kitchen is equipped with quartz countertops, a GE Café Series range, Bosch refrigerator, and

  Sarah Deischer Sprinkman Real Estate

  1233 E Johnson St Unit 4, Madison, WI 53703
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  /55

  $474,900

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft

  1211 Rutledge St Unit 5, Madison, WI 53703

  Enjoy the best of downtown Madison and lakefront living in this charming condo on the shore of Lake Monona. The inviting interior features a primary bedroom with en suite bath, a wall of windows overlooking the lake, and a den/office. Just a few blocks from Willy Street and downtown Madison, the location offers easy access to dining, shopping, and entertainment. Building amenities include access

  Jeff Drengler Sprinkman Real Estate

  1211 Rutledge St Unit 5, Madison, WI 53703
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  /30

  $229,900

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 778 Sq Ft

  3530 Ridgeway Ave, Madison, WI 53704

  A great place to call home! Walking distance to MATC, shopping and restaurants. Freshly painted, new carpet on steps and in bedrooms, new toilet, tub & surround and new flooring in bath, and a new kitchen countertop. 2nd bedroom does not have a closet. Full basement, 1 car garage and a partially fenced yard. Seller says roof is about 4 years old. Move in and add a bit of your own sweat equity

  Barb Stephani Restaino & Associates

  3530 Ridgeway Ave, Madison, WI 53704
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  /39

  $675,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,263 Sq Ft

  223 N Baldwin St, Madison, WI 53703

  Stunning all-brick home in the heart of Madison! Just across from Tenney Park, a short walk to Breese Stevens Field, Willy Street Co-op, an incredible selection of restaurants, & neighborhood amenities. Thoughtfully renovated down to the studs, the main level features solid walnut floors, a spacious gourmet kitchen with custom walnut cabinetry, Bosch double ovens & dishwasher, induction cooktop +

  Paul Haviland Stark Company, REALTORS

  223 N Baldwin St, Madison, WI 53703
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  /45

  $585,000

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,609 Sq Ft

  733 E Gorham St, Madison, WI 53703

  Perfect house in a prime location!! Welcome home to this charming 3 bed/1.5 bath 2 story directly across from James Madison park & Lake Mendota! Enjoy the lake/capital views on your front porch swing or enter inside to find hardwood floors leading you through the main lvl’s living rm, formal dining, sunroom & remodeled kitchen w/ ss apps & center island. Find all 3 beds upstairs along w/ updated

  Chris Barreau MHB Real Estate

  733 E Gorham St, Madison, WI 53703
• 

  

  /22

  $795,000

  • 2,630 Sq Ft

  928 Spaight St, Madison, WI 53703

  4 unit apartment complex located just 2 blocks off Williamson St. and 1 block from Lake Monona. Unit# 1 is 2 bed + 1 bath, unit #2 is a studio + 1 bath, unit #2 is 1 bed + bath and unit #4 is 1 bed + den with 1 bath. Shared laundry in basement, front porch, shared driveway access, 4 parking spaces behind property, walking distance to many local restaurants and only 1 mile from downtown Madison.

  James Stopple Madison Property Management, Inc.

  928 Spaight St, Madison, WI 53703
• 

  

  /20

  $339,000

  • 2 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  1029 Melvin Ct, Madison, WI 53704

  Welcome to this spacious 2-bedroom, 2.5-bath townhome-style condo in Creek Edge Condominiums on Madison's east side. With over 2000 sq ft across two floors and a finished LL, there's plenty of room to live, work and unwind. The lower lever was refreshed with new walls and carpet in 2015/16. Recent updates include a sump pump (2020); refrigerator, kitchen/living room LVP flooring and half-bath

  Nedra Bobo-Boyes Capella Realty Group, LLC

  1029 Melvin Ct, Madison, WI 53704
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  /43

  $535,000

  $60K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,039 Sq Ft

  1151 & 1153 Jenifer St, Madison, WI 53703

  Two parcels, one opportunity on Madison's near east side. This offering includes a thoughtfully updated 2-bedroom, 1-bath home with historic character plus the adjacent, newly created lot, sold together as a package. Residential zoning and separate parcel status give the next owner flexibility: Build a second home / add an accessory dwelling / hold as an oversized yard. Inside the home, the main

  Timothy Flores LPT Realty

  1151 & 1153 Jenifer St, Madison, WI 53703
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  /78

  $2,900,000

  $300K 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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  /40

  $439,700

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,400 Sq Ft

  1907 E Washington Ave, Madison, WI 53704

  Updated Madison home offering the perfect blend of modern updates, artistic character, and an exceptional location. This 3-bedroom, 2.5-bath home features a spacious primary suite with a large closet and an updated en-suite bathroom with a new shower. Thoughtfully maintained and extensively improved, this home offers peace of mind with numerous updates, including a new roof (July 2026), central

  Katia Blanchette Keller Williams Realty

  1907 E Washington Ave, Madison, WI 53704
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  /28

  $549,900

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft

  426 N Ingersoll St Unit 1, Madison, WI 53703

  Well-built home used as a 2-flat for many years. (See MLS #2032044). Great potential for converting to an owner occupied residence Newer refinished wood floors on main level. Large welcoming covered front porch, double entry with original front door. Formal dining room on main formerly used as primary BR. New roof and gutter guards ('26). Newer vinyl windows and siding, newer boiler. Large

  Gladys Simon First Weber Inc

  426 N Ingersoll St Unit 1, Madison, WI 53703
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  /20

  $309,000

  • 1 Bed
  • 1 Bath
  • 692 Sq Ft

  111 N Hamilton St Unit 203, Madison, WI 53703

  Experience downtown Madison living at its finest! This stunning end-unit condo offers breathtaking rooftop terrace views of the Capitol and Lake Mendota, where spectacular sunrises and sunsets create an unforgettable backdrop year-round. Located just steps from James Madison Park, State Street, the Capitol Square, and Madison's best dining, shopping, and entertainment, the location simply can't

  Andy Kramer Redfin Corporation

  111 N Hamilton St Unit 203, Madison, WI 53703
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  /36

  $475,000

  • 3 Beds
  • 3 Baths
  • 1,556 Sq Ft

  54 S Marquette St, Madison, WI 53704

  NEW roof, siding, gutters/downspouts and 200 amp electric service/breaker panel (charcoal grey siding and gutters/downspouts to be completed prior to closing)! Welcome to this charming 3 bedroom, 3 bathroom bungalow in Madison’s highly sought-after Atwood neighborhood. Thoughtfully designed with flexible living options, this home offers the opportunity for a single family layout or a separate

  Jordan Armentrout Pinnacle Real Estate Group LLC

  54 S Marquette St, Madison, WI 53704
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  /39

  $635,000

  • 2 Beds
  • 2 Baths
  • 1,314 Sq Ft

  137 E Wilson St Unit 314, Madison, WI 53703

  Downtown condominium ideally located in the heart of Madison, within walking distance to top-rated restaurants & vibrant entertainment. Enjoy easy access to scenic bike trails along Lake Monona, perfect for outdoor enthusiasts. This light-filled unit features abundant natural light throughout and private balcony with a convenient gas outlet—ideal for grilling or relaxing while taking in the city

  Maria Antoinette Cannarella Restaino & Associates

  137 E Wilson St Unit 314, Madison, WI 53703
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  /42

  $699,900

  $25K 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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  /37

  $665,000

  • 3,089 Sq Ft

  2954 Milwaukee St, Madison, WI 53704

  Investor Alert or Owner-Occupant Special! Prime Near East Madison 4-unit multifamily opportunity delivering high-yield cash flow! This 3,200 sq ft property combines historic charm with major capital updates: new roof (2022), new furnace (2024), new flooring, a brand-new renovated bathroom in Unit 1, and upgraded ventilation in all bathrooms. Features two 2-bedroom and two 1-bedroom sun-drenched

  Krista Potter First Weber Inc

  2954 Milwaukee St, Madison, WI 53704
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  /24

  $600,000

  $40K PRICE DROP

  • 2,560 Sq Ft

  2069 Winnebago St, Madison, WI 53704

  Prime Near East Side 3-unit investment opportunity just steps from Schenk’s Corners. This well-maintained property offers character, strong rental history, and highly desirable layouts, with 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. Major improvements include electrical updates, a

  Sarah Gabrielse Real Broker LLC

  2069 Winnebago St, Madison, WI 53704
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  /33

  $499,000

  $101K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  415 S Livingston St, Madison, WI 53703

  Welcome to the hearty of Madison's vibrant Willy St neighborhood! This charming two story home offers the perfect blend of historic character and urban convenience, just minutes from the Sylvee, Breese Stevens Field, downtown, the Capitol Square, and countless locally owned restaurants, coffee shops, breweries, and boutiques. Inside, you'll find spacious living areas filled with natural light,

  Chris Alexander NextHome Midwest

  415 S Livingston St, Madison, WI 53703
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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
• 

  

  /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
• 

  

  /55

  $450,000

  $109K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft

  2146 Winnebago St, Madison, WI 53704

  Many items are updated including siding, roofing, windows, doors, carpets, floors, screen porch, light fixtures and receptacles, central AC and furnace. Make this house on home on well known Winnebago street, which close to many small businesses. Room dimensions are estimated. Owner is a broker.

  Koua Vang Koua Vang

  2146 Winnebago St, Madison, WI 53704
• 

  

  /30

  $260,000

  • 1 Bed
  • 1 Bath
  • 737 Sq Ft

  334 Amoth Ct Unit D, Madison, WI 53704

  OPEN HOUSE this Saturday the 12th from noon until 2pm. Open floor plan condo with a large deck that sits behind mature pine trees and looks over the Capitol City Trail. Walk-in closet & laundry off the bedroom. Deeded parking spot. 100+ sq ft large private storage in basement. Recent serious capital improvements include -- new roof for entire association. Inside the unit is new HVAC (forced air)

  Caleb Payne Madcityhomes.Com

  334 Amoth Ct Unit D, Madison, WI 53704
• 

  

  /33

  $680,000

  $30K PRICE DROP

  • 3,192 Sq Ft

  14 N Franklin St, Madison, WI 53703

  Classic downtown 3-unit in an unbeatable location! New roof. Just blocks from the Capitol Square and James Madison Park, this well-maintained property offers the perfect combination of historic charm and investment potential. Residents will love the inviting front and back decks, ideal for relaxing or entertaining, while enjoying easy access to downtown dining, shopping, entertainment, and the

  Jeffrey Cullen Weichert, Realtors- Lakepoint

  14 N Franklin St, Madison, WI 53703

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