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Old Town Chicago Real Estate Search

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Old Town Real Estate Offers Historic Chicago Gems

Enjoy the arts on Old Town real estate.Check out Old Town real estate to live in the heart of historic Chicago. It is the location of many of the city’s older, Victorian-style buildings, including St. Michael’s Church, one of only seven structures to survive the Great Chicago Fire. Today, anyone beginning an Old Town real estate search will find a great variety of housing options. There are many lovely older homes with brick facings and artistic stone work. You can also find historic row houses which have been updated into condo buildings, while great care was taken to preserve details like built-in cabinetry, stained glass windows, stone work, and detailed woodwork.

Explore Old Town Chicago and Find a Thriving Arts Scene

In addition to historic construction, house-hunters will find plenty of new construction in Old Town, some designed in keeping with established styles, while other buildings have struck a bolder, more modern look. There are many new condo buildings with sleek lines, open floor plans, and sunny balconies. They also have hardwood floors, stone countertops, top of the line appliances, and spa-like master suites.

Old Town Chicago is a wonderfully walkable area and public transit options are plentiful. The arts thrive in the neighborhood, especially stand up comedy. Two noteworthy venues are Zanies Comedy Club and The Second City. The Old Town Art Fair is held annually in June and is sponsored by the Old Town Triangle Association. The art fair includes around 250 nationally known artists who exhibit their work, as well as food, live music, and children’s activities. The Old Town Art Center is another local fixture. It offers gallery space to artists, as well as classes and workshops to the public. You’ll also find a great restaurant scene, with lots of locally owned and beloved restaurants, cafes, bars, and pubs. As the area gentrifies, more national chains are moving in, too.

Call the office today so we can show you Old Town!

Search Old Town Chicago Real Estate

Our website features the best Old Town Chicago real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Old Town Chicago Homes for Sale

1550 N Clark Street Unit #701, Chicago image
1550 N Clark Street Unit #701, Chicago $3,350,000

Fifteen Fifty on the Park is Chicago's newest and most exciting luxury condominium building in the Gold Coast. Fifteen Fifty On The Park features 32 residences offering ...

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  • 4 Beds
  • 5 Baths
  • MRD11680536 MLS
  • ACTIVE Status
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1550 N Clark Street Unit #401, Chicago image
1550 N Clark Street Unit #401, Chicago $2,700,000

ONLY A FEW UNITS REMAIN! Fifteen Fifty on the Park is Chicago's newest and most exciting luxury building in where Lincoln Park meets Gold Coast. Fifteen Fifty On The Park...

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  • 4 Beds
  • 5 Baths
  • MRD11680534 MLS
  • ACTIVE Status
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1550 N Clark Street Unit #503, Chicago image
1550 N Clark Street Unit #503, Chicago $2,400,000

Fifteen Fifty on the Park is Chicago's newest and most exciting luxury building in where Lincoln Park meets Gold Coast. Fifteen Fifty On The Park features 32 residences o...

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  • 3 Beds
  • 4 Baths
  • MRD11680531 MLS
  • ACTIVE Status
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1550 N Clark Street Unit #303, Chicago image
1550 N Clark Street Unit #303, Chicago $1,950,000

ONLY A FEW UNITS REMAIN! Fifteen Fifty on the Park is Chicago's newest and most exciting luxury building in where Lincoln Park meets Gold Coast. Fifteen Fifty On The Park...

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  • 3 Beds
  • 4 Baths
  • MRD11680532 MLS
  • ACTIVE Status
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1526 N Wieland Street Unit #4N, Chicago image
1526 N Wieland Street Unit #4N, Chicago $1,600,000

Introducing W8 Old Town! Halcyon Development presents eight distinct new residences in luxury boutique building. Extra-wide 3 bed/2.1 bath penthouse on triple lot with h...

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  • 3 Beds
  • 3 Baths
  • MRD11366940 MLS
  • ACTIVE Status
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1522 N Wieland Street, Chicago image
1522 N Wieland Street, Chicago $1,600,000

Introducing W8 Old Town! Halcyon Development presents eight distinct new residences in luxury boutique building. 1522 Wieland is W8's duplex down which features its very ...

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  • 3 Beds
  • 3 Baths
  • MRD11704157 MLS
  • ACTIVE Status
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1526 N Wieland Street Unit #3S, Chicago image
1526 N Wieland Street Unit #3S, Chicago $1,325,000

Introducing W8 Old Town! Halcyon Development presents eight distinct new residences in luxury boutique building. Extra-wide 3 bed/2.1 bath on triple lot with highlights ...

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  • 3 Beds
  • 3 Baths
  • MRD11640358 MLS
  • ACTIVE Status
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1222 N Orleans Court, Chicago image
1222 N Orleans Court, Chicago — Old Town Village East $899,900

Expansive all brick townhome tucked away in a secluded enclave located in coveted Old Town. Walking distance to amazing shops, fitness and restaurants on Wells Street tha...

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  • 3 Beds
  • 4 Baths
  • MRD11710091 MLS
  • NEW Status
  • Old Town Village East Bldg.
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337 W Scott Street, Chicago image
337 W Scott Street, Chicago $890,000

Four story brick townhouse with 2600 square feet has 3 bedrooms plus office (or 4th bedroom), 2 baths plus powder room, built 2004 and this is first resale since. Well ma...

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  • 4 Beds
  • 3 Baths
  • MRD11671949 MLS
  • ACTIVE Status
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1542 N Wieland Street Unit #3, Chicago image
1542 N Wieland Street Unit #3, Chicago $800,000

Penthouse located in Old Town! Duplex offering 3 bedrooms plus a family room, living room offers 23' ceilings, fireplace, hardwood floors, & open layout. Kitchen w/island...

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  • 3 Beds
  • 3 Baths
  • MRD11625520 MLS
  • ACTIVE Status
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1430 N La Salle Drive Unit #G2, Chicago image
1430 N La Salle Drive Unit #G2, Chicago $780,000

This beautiful 2 bed, 2.5 bath END unit lives like a single-family home with 3 spacious levels and a stunning, private outdoor space with sweeping views of the city skyli...

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  • 2 Beds
  • 3 Baths
  • MRD11683319 MLS
  • ACTIVE Status
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1410 N Sandburg Terrace, Chicago image
1410 N Sandburg Terrace, Chicago $759,000 ▼

Gold Coast townhome in an incredible location! Spacious 3 bedroom, 2 bathroom tucked away in Sandburg Village with easy access to shopping and dining in both the Gold Coa...

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  • 3 Beds
  • 2 Baths
  • MRD11669576 MLS
  • ACTIVE Status
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1429 N Wells Street Unit #703, Chicago image
1429 N Wells Street Unit #703, Chicago $699,000

Spectacular south-facing penthouse level home with fabulous unobstructed city views in the most sought after Old Town boutique elevator building! Great open two bedroom/t...

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  • 2 Beds
  • 2 Baths
  • MRD11711242 MLS
  • NEW Status
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230 W Division Street Unit #905, Chicago image
230 W Division Street Unit #905, Chicago $599,000

Fully renovated, turnkey 1600sf southeast corner unit with wrap around balcony and 10 foot ceilings in the heart of Old Town. New hardwood floors, new refinished white ca...

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  • 2 Beds
  • 2 Baths
  • MRD11706319 MLS
  • NEW Status
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1406 N Mohawk Street Unit #A, Chicago image
1406 N Mohawk Street Unit #A, Chicago $550,000 ▼

Nothing else like it on the market. If home is where the heart is your heart will love to call this unit home. Two bedrooms, two full baths and a family room, easily con...

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  • 2 Beds
  • 2 Baths
  • MRD11678694 MLS
  • ACTIVE Status
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1212 N Wells Street Unit #705, Chicago image
1212 N Wells Street Unit #705, Chicago $465,000

An exquisite two-bedroom, two-bathroom condo located in the heart of Old Town. A spacious foyer greets you as you enter the unit, and hardwood flooring runs throughout th...

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  • 2 Beds
  • 2 Baths
  • MRD11703606 MLS
  • ACTIVE Status
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1560 N Sandburg Terrace Unit #2301J, Chicago image
1560 N Sandburg Terrace Unit #2301J, Chicago $462,000

A unique opportunity at James House. This beautiful South West corner residence features incredible city views with amazing sunsets in this 2 bedroom/2 bath condo. It was...

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  • 2 Beds
  • 2 Baths
  • MRD11671478 MLS
  • ACTIVE Status
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1212 N Wells Street Unit #204, Chicago image
1212 N Wells Street Unit #204, Chicago $450,000

Live at the Neapolitan located on historic Wells St in the heart of Old Town. With its functional layout and stylish finishes, this stylish 2 bedroom/2 bathroom offers a ...

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  • 2 Beds
  • 2 Baths
  • MRD11704373 MLS
  • ACTIVE Status
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1560 N Sandburg Terrace Unit #2810J, Chicago image
1560 N Sandburg Terrace Unit #2810J, Chicago — James House $449,900

Spectacular newly gut rehabbed two bedroom unit with balcony and stunning views from the 28th floor at James House. Be the first to live in this beautiful unit, among the...

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  • 2 Beds
  • 1 Baths
  • MRD11709062 MLS
  • ACTIVE Status
  • James House Bldg.
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1309 N Wells Street Unit #1405, Chicago image
1309 N Wells Street Unit #1405, Chicago $449,000

Welcome home to this rarely available 2 bedroom/2 bathroom PENTHOUSE located in the heart of vibrant Old Town! Your spacious split floor plan boasts a recently updated wh...

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  • 2 Beds
  • 2 Baths
  • MRD11703856 MLS
  • ACTIVE Status
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1560 N Sandburg Terrace Unit #506J, Chicago image
1560 N Sandburg Terrace Unit #506J, Chicago — James House $424,900

Stunning newly gut rehabbed two bedroom unit with balcony at James House. Be the first to live in this unit, among the many new features is the in-unit washer & dryer. Th...

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  • 2 Beds
  • 1 Baths
  • MRD11704995 MLS
  • ACTIVE Status
  • James House Bldg.
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1309 N Wells Street Unit #1202, Chicago image
1309 N Wells Street Unit #1202, Chicago $415,000

Beautiful 2 bedroom / 2 bathroom corner unit available in Michaels Terrace, located in the heart of Old Town. The home offers an open floor plan great for entertaining, n...

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  • 2 Beds
  • 2 Baths
  • MRD11710605 MLS
  • NEW Status
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1444 N Orleans Street Unit #5J, Chicago image
1444 N Orleans Street Unit #5J, Chicago $389,900

Spacious 2 bed, 2 bath condo located in the heart of Old Town in boutique elevator building with attached and heated garage parking! Lovely open concepts cook's kitchen f...

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  • 2 Beds
  • 2 Baths
  • MRD11633911 MLS
  • ACTIVE Status
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1444 N Orleans Street Unit #7C, Chicago image
1444 N Orleans Street Unit #7C, Chicago $379,000

Incredible 2 bed/2 bath condo on a centrally located street in Old Town. This condo has great floor to ceiling windows looking north which provides amazing natural light ...

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  • 2 Beds
  • 2 Baths
  • MRD11702824 MLS
  • ACTIVE Status
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1360 N Sandburg Terrace Unit #601C, Chicago image
1360 N Sandburg Terrace Unit #601C, Chicago $379,000

A must see 2 bedroom, 2 bathroom 1200 SF southeast corner unit in Chicago's most historic Old Town & Gold Coast neighborhood. With plenty of natural light pouring in thro...

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  • 2 Beds
  • 2 Baths
  • MRD11679013 MLS
  • ACTIVE Status
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1212 N Wells Street Unit #1503, Chicago image
1212 N Wells Street Unit #1503, Chicago $375,000

Beautiful one bedroom condo available at sought after Neapolitan building in center of Old Town! This extra large one bedroom, 1 and 1/2 bathroom condo was tastefully upd...

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  • 1 Beds
  • 2 Baths
  • MRD11702538 MLS
  • ACTIVE Status
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1360 N Sandburg Terrace Unit #2710C, Chicago image
1360 N Sandburg Terrace Unit #2710C, Chicago — Sandburg Village $339,900

Stunning brand new two bedroom, high (27th) floor unit at Cummings House. The unit has been gut rehabbed and meticulously renovated. Be the first to live in this unit wit...

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  • 2 Beds
  • 1 Baths
  • MRD11700077 MLS
  • ACTIVE Status
  • Sandburg Village Bldg.
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1212 N Wells Street Unit #902, Chicago image
1212 N Wells Street Unit #902, Chicago $337,500

1 Bedroom + Den located in the heart of the Old Town! East facing unit with balcony and great city views. Unit has a spacious bathroom, large bedroom, living room & kitc...

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  • 1 Beds
  • 1 Baths
  • MRD11709534 MLS
  • NEW Status
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1455 N Sandburg Terrace Unit #2306B, Chicago image
1455 N Sandburg Terrace Unit #2306B, Chicago — Gold Coast Galleria $304,900

Look no further, Buy NOW! Large contemporary, high floor, sun-drenched 1 bed/1 bath + home office condominium with breath-taking Lake and City Skyline Views right on the...

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  • 1 Beds
  • 1 Baths
  • MRD11694232 MLS
  • ACTIVE Status
  • Gold Coast Galleria Bldg.
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247 W Scott Street Unit #305, Chicago image
247 W Scott Street Unit #305, Chicago $300,000

Tucked away location in the heart of everything for this warm and inviting Old Town unit. Bright and open with tall ceilings and hardwood floors throughout the unit plus ...

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  • 1 Beds
  • 1 Baths
  • MRD11704202 MLS
  • ACTIVE Status
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1560 N Sandburg Terrace Unit #907J, Chicago image
1560 N Sandburg Terrace Unit #907J, Chicago — James House $299,900

This is a stunning newly gut rehabbed one bedroom unit in popular James House. Be the first to live in this unit, among the many new features is in-unit washer/dryer. The...

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  • 1 Beds
  • 1 Baths
  • MRD11700025 MLS
  • ACTIVE Status
  • James House Bldg.
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1255 N Sandburg Terrace Unit #1801, Chicago image
1255 N Sandburg Terrace Unit #1801, Chicago — Eliot House $286,000 ▲

Converted Junior 2 Bedroom and 1 Bathroom Condo with A Large East Facing Balcony, Brazilian cherry hardwood floor thru-out the unit, gourmet kitchen w/42" euro cabinets, ...

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  • 2 Beds
  • 1 Baths
  • MRD11708889 MLS
  • ACTIVE Status
  • Eliot House Bldg.
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1560 N Sandburg Terrace Unit #1708, Chicago image
1560 N Sandburg Terrace Unit #1708, Chicago — Sandburg Village $285,000 ▼

Mesmerizing Lake Michigan and Gold Coast views from every window. Walk out the sliding glass door onto your covered private balcony that sprawls 19 feet in width, room f...

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  • 1 Beds
  • 1 Baths
  • MRD11626234 MLS
  • ACTIVE Status
  • Sandburg Village Bldg.
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1560 N Sandburg Terrace Unit #3503, Chicago image
1560 N Sandburg Terrace Unit #3503, Chicago $279,500 ▼

LOCATION, LOCATION. Just renovated , modern, one bedroom with spectacular West City view from your private balcony .Brand new kitchen , open to living/dinning room, count...

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  • 1 Beds
  • 1 Baths
  • MRD11632846 MLS
  • ACTIVE Status
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1560 N Sandburg Terrace Unit #4311, Chicago image
1560 N Sandburg Terrace Unit #4311, Chicago — James House $279,000

Live on Top of the world at the highest floor of the James House! This west facing beauty is light and bright. Completely vast, unobstructed views of spectacular sunsets ...

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  • 1 Beds
  • 1 Baths
  • MRD11710905 MLS
  • NEW Status
  • James House Bldg.
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1560 N Sandburg Terrace Unit #1104J, Chicago image
1560 N Sandburg Terrace Unit #1104J, Chicago — Sandburg Village $275,000 ▼

Welcome Home! You'll be greeted by the courteous staff at Sandburg's premier James House each time you arrive. Elegant lobby, multiple elevators, and recently renovated c...

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  • 1 Beds
  • 1 Baths
  • MRD11643279 MLS
  • ACTIVE Status
  • Sandburg Village Bldg.
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1444 N Orleans Street Unit #6E, Chicago image
1444 N Orleans Street Unit #6E, Chicago — Royalton Towers $275,000 ▼

Ideal large layout for a 1 bedroom condo in Old Town. This will check every box on your list: IN-UNIT laundry, balcony, doorman building, workout room, kitchen island, h...

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  • 1 Beds
  • 1 Baths
  • MRD11491916 MLS
  • ACTIVE Status
  • Royalton Towers Bldg.
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1455 N Sandburg Terrace Unit #2002, Chicago image
1455 N Sandburg Terrace Unit #2002, Chicago — Bryant House $259,000

This wonderful high floor south east corner one bedroom in the most desirable tier is now available! This unit offers awesome city views in the unit and from your privat...

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  • 1 Beds
  • 1 Baths
  • MRD11704680 MLS
  • ACTIVE Status
  • Bryant House Bldg.
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1255 N Sandburg Terrace Unit #2803E, Chicago image
1255 N Sandburg Terrace Unit #2803E, Chicago — Sandburg Village $239,900

Lovely one bedroom that can easily be used as a two bedroom. The unit was just painted and is immaculate. Lovely Kitchen is opened to living area. Very unique space. ...

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  • 1 Beds
  • 1 Baths
  • MRD11694583 MLS
  • ACTIVE Status
  • Sandburg Village Bldg.
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1455 N Sandburg Terrace Unit #2006B, Chicago image
1455 N Sandburg Terrace Unit #2006B, Chicago — Sandburg $235,000

Gold Coast/Old Town Perfection! Large, 850 sqft, 1Bed/1Bath move in ready condo with breathtaking Skyline views, Lake views & immense privacy! Wonderful layout has a sepa...

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  • 1 Beds
  • 1 Baths
  • MRD11705809 MLS
  • ACTIVE Status
  • Sandburg Bldg.
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1360 N Sandburg Terrace Unit #2707, Chicago image
1360 N Sandburg Terrace Unit #2707, Chicago $234,900

High floor(27th) fully rehabbed Jr. one bedroom with large balcony offering amazing city views. Kitchen layout redesigned with white Shaker cabinets, quartz counter tops,...

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  • 1 Beds
  • 1 Baths
  • MRD11704457 MLS
  • ACTIVE Status
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1212 N Lasalle Drive Unit #1906, Chicago image
1212 N Lasalle Drive Unit #1906, Chicago $229,900 ▼

PRICE DROP-MOTIVATED SELLERS. BRING ALL OFFER!!!LIVE ON THE EDGE!! On the edge of two of Chicago's most desirable neighborhoods - Old Town and the Gold Coast - This full ...

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  • 1 Beds
  • 1 Baths
  • MRD11679068 MLS
  • PRICE CHANGE Status
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1212 N Lasalle Street Unit #2505, Chicago image
1212 N Lasalle Street Unit #2505, Chicago $219,900 ▼

Gorgeous skyline views from this SOUTH-FACING high, 25th, floor 1 bedroom condo at the LaSalle Private Residences! Brand new, beautiful wood flooring and fresh paint as o...

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  • 1 Beds
  • 1 Baths
  • MRD11622211 MLS
  • ACTIVE Status
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1455 N Sandburg Terrace Unit #2204B, Chicago image
1455 N Sandburg Terrace Unit #2204B, Chicago — Bryant House $215,000

Charming, warm & inviting Gold Coast/Old Town one bedroom facing East on high floor. Large windows allow plenty of sunshine with views of the lake and skyline. Galley ki...

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  • 1 Beds
  • 1 Baths
  • MRD11708539 MLS
  • ACTIVE Status
  • Bryant House Bldg.
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1255 N Sandburg Terrace Unit #209, Chicago image
1255 N Sandburg Terrace Unit #209, Chicago $215,000 ▼

Ideally located in-town one bedroom condo available in iconic Sandburg Terrace. Steps from the Lake in Chicago's Gold Coast and close to Old Town's restaurants, shopping ...

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  • 1 Beds
  • 1 Baths
  • MRD11646197 MLS
  • ACTIVE Status
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1355 N Sandburg Terrace Unit #203D, Chicago image
1355 N Sandburg Terrace Unit #203D, Chicago — Sandburg Village $189,000

Junior one bedroom in prime building in Sandburg Village overlooking a beautifully landscaped courtyard with sunset views. Features include hardwood floors throughout, op...

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  • 1 Beds
  • 1 Baths
  • MRD11710218 MLS
  • NEW Status
  • Sandburg Village Bldg.
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1255 N Sandburg Terrace Unit #2106, Chicago image
1255 N Sandburg Terrace Unit #2106, Chicago $1

Great opportunity on this condo unit. It offers approximately 810 square feet of living space with 1 bedroom and 1 bathroom. Good floor plan. May require some enhancemen...

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  • 1 Beds
  • 1 Baths
  • MRD11706503 MLS
  • AUCTION Status
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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2023 MRED LLC. All rights reserved.

Based on information submitted to the MRED as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MRED. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

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