Old Town Real Estate

Old Town Real Estate

Old Town, located in the heart of Chicago, Illinois, is a vibrant and historic neighborhood that offers residents a unique blend of old-world charm and modern amenities. Situated in Cook County, Old Town is a coveted area known for its rich history, diverse culture, and bustling entertainment scene.

With its tree-lined streets and well-preserved Victorian-era architecture, Old Town exudes a timeless appeal that attracts both locals and visitors alike. The neighborhood is renowned for its historic landmarks, including the iconic Second City comedy club and the Chicago History Museum, which showcase the area's cultural significance.

In addition to its historical significance, Old Town is home to a thriving arts and entertainment scene. The neighborhood is dotted with art galleries, theaters, and music venues, providing residents with a plethora of cultural experiences. The annual Old Town Art Fair, one of the oldest and most prestigious art fairs in the country, draws art enthusiasts from all over to admire and purchase unique artworks.

Old Town also boasts a vibrant dining and shopping scene. The neighborhood is known for its eclectic mix of restaurants, ranging from cozy cafes to upscale eateries, offering a wide variety of cuisines to suit every palate. Additionally, residents can explore a diverse range of boutiques, specialty shops, and local markets, making Old Town a shopper's paradise.

With its prime location and easy access to public transportation, Old Town offers a convenient and connected lifestyle. Residents can enjoy the benefits of living in a close-knit community while being just a short commute away from downtown Chicago and its countless attractions.

Whether you're drawn to its rich history, cultural offerings, or vibrant atmosphere, Old Town is a neighborhood that truly has it all. Experience the best of Chicago living in this charming and dynamic community.

Newest Listings in Old Town

$1,250,000
3 Beds ⋅ 4 Baths ⋅ 12717282 MLS ⋅ NEW Status
This 2400 square foot 3 bed, 3 1/2 bedroom condo located in a four-unit extra-wide building tucked back on a deep leafy lot, offers quiet luxury in a prime Old Town location, just steps from Lincoln Park. Built in 2008, with one residence per floor and exquisite attention to classic detail, this solid masonry home has the solid bones one would expect to find in vintage buildings - while offering all the advantages of modern construction. Features include exclusive elevator access to the unit, wide-plank hardwood floors, 9 foot ceilings, crown moldings and a wood burning fireplace with gas starter. This home also boasts 3 en-suite bedrooms with custom closets; including a primary suite with his-and-hers walk in closets and a huge primary bathroom with double sinks, whirlpool tub and oversized shower. The open kitchen is a cook's dream, with loads of storage space, high end appliances and a large breakfast bar. An amply sized laundry room with new side-by side he washer and dryer and a private back terrace perched amongst old growth trees, complete the serene, homey ambiance. One attached garage space (accessed from a heated driveway) included. Located within walking distance of Latin School and Lincoln Park. Just steps from the best dining, shopping, theaters and beaches Old Town, Gold Coast and Lincoln Park have to offer. Professionally managed. Pets of all sizes welcome! Note the low assessments!

1418 N Lasalle Drive Unit #3, Chicago
$1,450,000
3 Beds ⋅ 4 Baths ⋅ 12713927 MLS ⋅ NEW Status
One of the defining features of this home is its setting within Old Town Village East - a private, tree-lined horseshoe street that offers guest parking, a rarity in Chicago, and a gated alley where neighbors gather and children play. It is a neighborhood that offers an uncommon sense of community while remaining just minutes from the heart of the city. The home has been thoughtfully renovated with an emphasis on both design and functionality. The first floor was completely reconfigured to improve the original layout, including a remodeled kitchen, relocated powder room, and the addition of a walk-in pantry, creating a more practical and cohesive living space. The main level features custom millwork and wainscoting, while updated lighting, fixtures, switches, outlets, and integrated recessed lighting throughout provide a clean, contemporary aesthetic. Hardwood floors were added to the upstairs bedrooms, and the finished lower level includes two additional bedrooms and a spacious spa-inspired bath, offering exceptional flexibility for guests, extended family, or work-from-home needs. Ideally situated within walking distance of Old Town's restaurants and several of Chicago's most respected schools, including Latin, Walter Payton College Prep, Catherine Cook School, and Immaculate Conception/St. Joseph School (ICSJ), this home combines thoughtful renovations with an exceptional neighborhood setting. A private deck and landscaped outdoor space extend the living area outdoors, complemented by a detached two-car garage. Extensive recent capital improvements further enhance the home's appeal (Roof, Gutters, HVAC (2025/2026).

344 W Scott Street, Chicago
$530,000
2 Beds ⋅ 1 Baths ⋅ 12707332 MLS ⋅ RE-ACTIVATED Status
Nestled on a quiet, tree-lined street in the heart of Chicago's highly sought-after Old Town neighborhood, this beautifully updated 2-bedroom, 1-bath condo offers the perfect blend of timeless character and modern convenience. Complete with a gated parking space, private rooftop deck, and easy street parking for guests, this home is an exceptional opportunity. Inside, you'll be captivated by the architectural charm, including elegant tray ceilings, gleaming refinished hardwood floors, fresh paint throughout, and brand-new carpeting in both bedrooms. The professionally designed kitchen, completely renovated in 2025, is the centerpiece of the home, featuring stunning quartz countertops, custom cabinetry, an undermount sink, and a new refrigerator, creating a sophisticated and functional space for everyday living and entertaining. Major mechanical updates provide peace of mind, including a new furnace and air conditioning (2020), new roof (2020), and Anderson windows (2020). Additional conveniences include an in-unit washer and dryer and ample storage throughout. The location is second to none. Enjoy a peaceful treelined residential setting while being just a 7-minute walk to the Brown Line, making commuting downtown effortless. You'll also be just moments from the exciting new Park No. 598 at 1514 N. Larrabee, featuring a dog park, playground, walking paths, and outdoor fitness amenities. Surrounded by the renowned restaurants, boutiques, coffee shops, and vibrant nightlife of Old Town, Lincoln Park, and the Near North Side, this home truly offers the best of city living. This move-in-ready condo checks every box. Don't miss your chance to own a beautifully updated home in one of Chicago's most desirable neighborhoods!

1407 N Mohawk Street Unit #1, Chicago
$395,000
2 Beds ⋅ 1 Baths ⋅ 12712810 MLS ⋅ ACTIVE Status

1455 N Sandburg Terrace Unit #2009, Chicago
$4,600,000
10 Beds ⋅ 10 Baths ⋅ 12556436 MLS ⋅ ACTIVE Status

Chicago
$680,000
3 Beds ⋅ 2 Baths ⋅ 12700297 MLS ⋅ ACTIVE Status
Welcome to this spacious 3-bedroom, 2-bath residence in a boutique elevator building at the crossroads of Old Town and Lincoln Park, taking in the best of both neighborhoods! Featuring an open layout with dark hardwood floors, granite countertops, stainless steel appliances, a built-in wine fridge and a custom gas fireplace, this home offers both comfort and functionality. The generous primary suite includes organized closets and a spa-inspired bath with a dual vanity, soaking tub, and separate shower, while two additional bedrooms provide excellent flexibility. Enjoy two private terraces plus a shared rooftop deck with city views. Additional highlights include in-unit laundry, 1 outdoor parking space included, additional storage unit, and bike storage. Ideally located just steps from the Brown Line, Wells Street, restaurants, shopping, parks, and the lakefront.

409 W North Avenue Unit #2E, Chicago
$750,000
2 Beds ⋅ 2 Baths ⋅ 12686934 MLS ⋅ ACTIVE Status
Welcome home to this sun-drenched 2-bedroom, 2-bathroom condo in a boutique elevator building in the heart of Old Town. South-facing windows and soaring ceilings flood the space with natural light, starting with an wide formal foyer finished with custom wall treatments. The updated white kitchen features granite countertops, a tile backsplash, under-cabinet lighting, and a generous peninsula perfect for casual dining-plus a new stove, refrigerator, and dishwasher installed in 2023. It flows seamlessly into an expansive living and dining room anchored by a gas fireplace, and out to a south-facing balcony with sweeping city views, ideal for morning coffee or evening drinks. The primary suite is a true showstopper: at 19 feet wide, it rivals bedrooms in single-family homes, complete with a custom walk-in closet and a spa-like marble bath featuring double sinks, a separate shower and tub, and a linen closet. The second bedroom, also south-facing, is equally gracious, and a well-appointed hall bath rounds out the layout. Both bedrooms have newer carpeting, installed in 2024. Additional highlights include 8-inch wide-plank wood floors, abundant custom closet storage throughout, an in-unit stackable washer/dryer, and a Nest thermostat. A storage unit and heated garage spot #G-16 are included. This well-managed, pet-friendly (max of 3 pets) brick building added a new video doorbell security system. Enjoy an unbeatable location just steps from shopping, restaurants, the lake, and the park. Rentals permitted with a minimum 1-year lease. Monthly HOA: $676.36 ($637.95 / unit & $38.78 / parking) & 2024 Taxes: $14,083.56 w/no exemptions ($13,276.74 /unit & $806.82 / garage parking)

1429 N Wells Street Unit #502, Chicago
$4,600,000
12703290 MLS ⋅ ACTIVE Status
Premier Old Town Development & Cash-Flow Opportunity | Double or Triple Lot Package. An unmatched development canvas awaits in the heart of Old Town, one of Chicago's most coveted and historic enclaves. This rare offering features a flexible double or triple-lot footprint situated on a premier, tree-lined residential street. The package combines immediate high-yield rental income with immense ground-up development potential for a landmark residential or commercial project. The Development Footprint: Rare double or triple-lot ideal for luxury single-family homes, high-end condominiums, or commercial assets. Ready Accessibility: Features an existing curb cut, significantly simplifying site planning and construction logistics. Favorable Zoning: Versatile zoning parameters accommodate diverse architectural visions and maximize buildable square footage. The Income Generator (1455 N. Sandburg) Turnkey Asset: A beautiful, fully leased brick multi-family building anchoring the third parcel to provide immediate carrying income. Upper-Level Units: Three pristine, layout-efficient 2-bedroom, 2-bathroom apartments commanding premium neighborhood rents. Garden-Level Space: An expansive 5-bedroom, 5-bathroom footprint, currently optimized as high-end office space. A Location Without Equal Transit-Oriented: Located just steps from the Sedgwick CTA Brown Line station and express buses on LaSalle Street for effortless commuting. Gold Coast & Lake Access: Walking distance to the shores of North Avenue Beach and the vast green spaces of Lincoln Park. Lifestyle & Amenities: Minutes from the world-class dining, boutique shopping, and vibrant nightlife lining iconic Wells Street.

1455-59 N Sedgwick Avenue, Chicago
$575,000
2 Beds ⋅ 3 Baths ⋅ 12701805 MLS ⋅ ACTIVE Status
Elegant and rare 2 bedroom, 2.5 bath duplex-down condo in the heart of Old Town. This bright and airy home offers an ideal floor plan with generous living and entertaining space across two levels. Recent updates include windows, appliances, furnace, and high-efficiency water heater, providing modern comfort and energy efficiency for years to come. The main level features an open concept living and dining area with abundant natural light which includes a private balcony for seamless indoor and outdoor entertaining. The lower level offers two well-appointed bedrooms and ample storage. The primary suite includes a private bath with a luxurious shower and excellent closet space. Enjoy the convenience of an unbeatable location near parks, restaurants, shopping, and public transportation. Despite its proximity to the train, the unit is remarkably quiet; train noise is virtually unnoticeable from inside the home. 1 outdoor parking spot is included in the price. A rare opportunity to own a move-in-ready and turn-key residence in an unbeatable location.

308 W Evergreen Avenue Unit #1R, Chicago
$275,000
2 Beds ⋅ 1 Baths ⋅ 12701664 MLS ⋅ ACTIVE Status
Sun- Filled, South Facing 2 Bedroom with views of the City and Courtyard. Features impressive hardwood floors, a modern kitchen with granite counters and breakfast bar, New Oven/Range, and New Bedroom Carpeting. An array of Amenities include: 24-hour Door Person, Elevator, Rooftop, Exercise Room, Health Club, 2 Swimming Pools and Sundeck. Rental Garage parking space available. On site Laundry Facilities, Tennis Courts and Bike Room included. This location is an excellent choice for residing in the Old Town Gold Coast Area and steps away from the Lakefront, Lincoln Park, Dining, Shopping, and Public Transportation. Sandburg Village presents a wonderful opportunity to experience the City of Chicago at its finest.

1460 N Sandburg Terrace Unit #803A, Chicago
$340,000
1 Beds ⋅ 1 Baths ⋅ 12697701 MLS ⋅ ACTIVE Status

1560 N Sandburg Terrace Unit #2708J, Chicago
$285,000
1 Beds ⋅ 1 Baths ⋅ 12654505 MLS ⋅ ACTIVE Status ⋅ Sandburg Village BLDG.
Welcome home to this updated south facing condo with sweeping skyline city views from this high floor condo in Old Town. Nothing to do but move in and enjoy city living! This location cannot be beat, Lincoln Park, Wells Street, North Avenue Beach and Michigan Avenue are all right outside your front door. Features include an open kitchen floorplan with extra wide layout, new flooring and fresh paint throughout, granite countertops, stainless steel appliances, and an oversized bedroom that easily fits a king size bed. Built-in 1962, Alcott House is pet friendly and offers 24/7 Doorstaff, on-site management and engineering staff, common laundry, sundeck, fitness center, new hallways, bike room, receiving room and a beautiful sophisticated lobby to welcome you home. Sandburg Village offers two pools and private tennis courts for a small additional yearly fee. Rental parking is available with a wait list, check SpotHero for other nearby options. Sorry, in unit laudry is not permitted. Book your private viewing today. don't miss out on this fantastic opportunity!

1460 N Sandburg Terrace Unit #2303A, Chicago
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