Old Town Homes with East Exposure

Welcome to Old Town, a vibrant neighborhood nestled in the heart of Chicago, Illinois. Known for its rich history and charming streets, Old Town seamlessly blends the character of yesteryear with the conveniences of modern living. This picturesque area boasts a unique architectural style, featuring beautifully restored Victorian brownstones and contemporary condominiums, creating a diverse and inviting atmosphere.

One of the standout features of homes in Old Town is their east exposure. Imagine waking up every morning to the soft glow of sunrise filtering through your windows, filling your space with natural light. These east-facing homes not only provide a bright and airy ambiance but also offer stunning views of the city skyline and Lake Michigan, making them a perfect retreat for anyone who appreciates the beauty of urban living.

Old Town is not just about beautiful homes; it is also a thriving community filled with charming boutiques, trendy restaurants, and lively entertainment options. Stroll down Wells Street, where you'll find a delightful mix of shops and eateries, or explore the historic Old Town Triangle, a designated landmark district that showcases the neighborhood's rich architectural heritage.

Families and professionals alike are drawn to Old Town for its excellent schools and proximity to the Loop, making commuting a breeze. With easy access to public transportation, parks, and cultural landmarks, Old Town truly offers a lifestyle that balances the excitement of city living with the warmth of a close-knit community.

Discover your dream home in Old Town today, where history meets modernity, and every sunrise brings new possibilities!

Newest Old Town Homes with East Exposure

$699,900

3 Beds ⋅ 2 Baths ⋅ 12672942 MLS ⋅ NEW Status

Nestled on a quiet, tree-lined street in the heart of coveted Old Town, this beautifully appointed 3-bedroom, 2-bathroom home spans approximately 1,800 square feet of turnkey living space. Seamlessly pairing timeless character with modern peace of mind, the interior showcases fresh paint, hardwood floors, and elegant custom built-ins throughout. The kitchen is outfitted with stainless steel appliances, while both refreshed bathrooms deliver clean, spa-like comfort. Major mechanical upgrades ensure effortless ownership, including a furnace 2024, water heater 2026, and in-unit laundry machine 2025. Outside, relax or entertain on one of two private back porch terraces framed by skyline views-a rare outdoor sanctuary in the neighborhood. One dedicated garage parking space is included. Unbeatable location meets daily convenience: step outside and walk to Mariano's, Target, Wells Street's renowned dining and nightlife, Second City, and Lincoln Park. Commuting is effortless with rapid access to both the Brown and Red Lines, Lake Shore Drive, and I-90/94, placing the Loop, River North, and the Gold Coast just minutes from your front door.

1355 N Mohawk Street Unit #3N, Chicago

$875,000

2 Beds ⋅ 2 Baths ⋅ 12783945 MLS ⋅ NEW Status ⋅ Old Town BLDG.

Perched among the treetops overlooking the heart of Old Town's vibrant Wells Street, this spectacular, sun-drenched, extra-wide 2BR/2BA condo is situated in an intimate boutique elevator building and offers the ultimate in urban residential living! Enjoy parking inside the attached heated garage and arriving effortlessly at your front door where you will step inside and be amazed at the home's expansive open-concept layout and magazine-caliber interior showcasing a 24FT wide LR/DR with sweeping east-facing windows, cozy private balcony, and a fireplace with elegant 11FT wide custom mantle with built-in shelving. Opening directly into this delightful space is the home's stunning DREAM kitchen with Sub-Zero and Wolf (gas cook-top/hood/wall-oven) appliances, thick granite countertops with breakfast bar seating, backsplash with under-cabinet lighting, and gorgeous custom cabinetry with premium details and components like full-height butler's hutch, pull-out pantry shelving, appliance garage w/electric outlet, large drawers, pull-out trash, and more. Beautiful dark-walnut stained solid hardwood floors run throughout the home and lead to the luxurious and sprawling primary suite complete with two custom-organized walk-in closets and an 11' x 6' private balcony nestled amid the treetops. The sumptuous marble bath offers split dual-vanities with abundant storage and thick marble countertops with cove edging, a whirlpool tub, and a separate shower with a rain head. The spacious second bedroom features custom millwork, designer wall coverings, a large organized closet, and is located conveniently across from the second full marble bath. Completing the picture is an extra-large laundry room with side-by-side washer/dryer and built-in cabinetry, and one available private parking space ($25K) with adjacent additional storage. Well-run professionally managed association. Unbeatable location across from Jeni's Ice Cream and steps to all the shopping, dining and nightlife on Wells, and only a short stroll to Lake Michigan, Lincoln Park, Gold Coast, and the very best of Chicago.

1414 N Wells Street Unit #406, Chicago

$465,000

2 Beds ⋅ 2 Baths ⋅ 12775616 MLS ⋅ ACTIVE Status ⋅ Old Town Square BLDG.

Gorgeous, freshly painted 2BR/2BA penthouse in a charming brick walk-up courtyard building, tucked away on a quiet cul-de-sac. This sun-filled home features hardwood floors throughout, a private balcony, and an open-concept layout ideal for both everyday living and entertaining. The spacious kitchen flows seamlessly into the living and dining areas, with ample room for a full dining table and sectional. The inviting living room includes a gas fireplace and access to the balcony overlooking the serene courtyard. The generously sized primary suite easily fits a king bed and offers double closets along with an en-suite bath featuring dual vanities. The second bedroom comfortably accommodates a queen bed and is conveniently located next to the second full bathroom. Additional highlights include a tandem parking spaces (front to back) in a gated lot and access to a shared rooftop deck with stunning skyline views. Pet-friendly and investor-friendly with rentals allowed. Unbeatable location just steps from Wells Street dining, shopping, and entertainment. INVESTOR FRIENDLY **Please note, this is a 4th floor walk-up unit.**

301 W Scott Street Unit #204, Chicago

$370,000

2 Beds ⋅ 1 Baths ⋅ 12764375 MLS ⋅ PRICE CHANGE Status ⋅ Old Town Square BLDG.

This beautifully maintained home features hardwood flooring throughout and a cozy wood-burning gas fireplace in the living room. The open kitchen is a standout, with granite countertops, an under-mount sink, and a stylish backsplash. In-unit washer/dryer and organized closets add everyday convenience. 2nd bdrm does not have a window, could also be a great office or den space! A tandem exterior parking space is included, along with an outdoor area perfect for grilling or relaxing and a common roof deck. This Old Town gem is set in a private gated courtyard right across from a park. This home offers the best of Old Town living - minutes from shops, restaurants, grocery stores, and much more.

301A W Goethe Street Unit #201, Chicago

230 W Division Street Unit #1501, Chicago

$599,000

2 Beds ⋅ 2 Baths ⋅ 12712603 MLS ⋅ ACTIVE Status

Experience elevated city living in this exceptional designer corner penthouse, ideally situated in one of Old Town's most sought-after residential buildings - The Venetian. This stunning 2BR/2BA + Den is located in the heart of Old Town. It offers unbelievable southern & western skyline views from the open living/dining rooms which open to your wrap around balcony. It is an entertainers dream! Adorned with Brazilian cherrywood flooring, the home boasts soaring 11-foot ceilings which give the space a grandness that truly set it apart. The primary suite has both northern and western exposure with beautiful views of Lake Michigan. It features a massive walk-in closet with custom built in's and a large marble bathroom with dual vanity & shower/tub combo. The 2nd bedroom also features lake views as well as a large closet with built in's. There is also a large partially enclosed den that functions as a great office/flex space. The building has a top notch fitness center, rooftop deck, beautiful garden terrace, and 24 hour door person. Heated deeded garage parking for Additional $30k.

230 W Division Street Unit #1501, Chicago

$749,900

3 Beds ⋅ 2 Baths ⋅ 12751067 MLS ⋅ ACTIVE Status

WELL DESIGNED AND OVERSIZED THREE BEDROOM CONDO IN OLD TOWN OFFERS A SPACIOUS AND FUNCTIONAL FLOORPLAN. THIRD FLOOR UNIT WITH TREE LINED VIEWS AND GREAT NATURAL LIGHT. UPDATED KITCHEN WITH WHITE CABINETRY, MARBLE COUNTERTOPS AND BACKSPLASH, FISHER & PAYKEL APPLIANCES, AND ISLAND WITH BREAKFAST BAR. LARGE LIVING ROOM WITH GREAT WINDOWS, GAS FIREPLACE WITH TRAVERTINE SURROUND, AND SEPARATE DINING AREA. XL PRIMARY SUITE WITH WALK-IN CLOSET, MARBLE BATH WITH DUAL SINK VANITY, AND ACCESS TO REAR DECK. SPACIOUS SECONDARY BEDROOMS AND RENOVATED FULL BATH WITH WALK-IN STEAM SHOWER. SIDE BY SIDE LAUNDRY. THIS UNIT FEATURES HARDWOOD FLOORING THROUGHOUT, CUSTOM TRIM WORK, CROWN MOLDING, WAINSCOTING, RECESSED LIGHTING, 9' CEILINGS, AND GENEROUS STORAGE THROUGHOUT. PRIVATE ROOF DECK WITH PERGOLA, BUILT-IN DINING TABLE, AND VIEWS OF OLD TOWN. GARAGE PARKING INCLUDED. WALKABLE TO WELLS ST, LINCOLN PARK, TRANSPORTATION, AND MORE.

1547 N Hudson Avenue Unit #3, Chicago

1360 N Sandburg Terrace Unit #2701C, Chicago

$534,900

2 Beds ⋅ 2 Baths ⋅ 12761116 MLS ⋅ ACTIVE Status

Presenting this spectacular brand new gut renovated rare two bedroom two bathroom, corner unit with balcony on the 27th floor of Cummings House. Be the first to live in this unit with a modern open floor-plan that takes advantage of the wide open views across the city and lake. The workmanship and finishes are to the highest standards. Central to the unit is the open chef's kitchen where you can enjoy cooking and entertaining while taking in the stunning views.The custom cabinets are white gloss flat panel with black accent hardware, under-cabinet LED lighting. Quartz counters and a large island with waterfall edge and breakfast bar. High end appliances - French-door refrigerator, Bosch panel dishwasher, Sharp microwave drawer, slide-in range. Finished with black/gold lighting and new recessed led lights. The kitchen flows into the dining area which has a matching white gloss flat panel built-in credenza with additional cabinet storage. The open spacious living room has two full exposures of windows creating a bright airy feel. The large balcony has sliding doors from the living room to provide the perfect outdoor extension of the living space, relax enjoying a lake breeze with lake views to the east, city skyline to the south and beautiful sunsets to the west. The floor plan provides for a split layout of the two bedrooms and bathrooms. The bedrooms are both very spacious and have professionally organized closets with automated lights, recessed LED lighting overs the beds, they also have space to accommodate a desk area. The bathrooms are fully rehabbed- new walk-in shower with rain head and body sprays, sliding glass door, fully tiled in contemporary style, new vanity with quartz top, finished with black/gold accented fixtures, hardware, large mirror & lighting. Throughout the unit there are new wide plank light wood color floors, new electrical, new plumbing, new recessed led lighting. Painted throughout with contemporary soft color palette. There is plenty of storage in the unit, all professionally organized, also a storage cage is included in the building. Cummings House is a well run building with good reserves, many recent major updates completed including new elevators and renovated hallways & laundry room, facade restoration. There's a rooftop sundeck, 24 hour door staff, maintenance & management are onsite. Monthly assessment includes heat, TV cable and high speed (1GB) internet service (everything except electricity). Leased parking in attached parking garage currently has a waitlist. Sandburg Village amenities include 2 outdoor pools & sundecks, tennis courts, hospitality rooms- (some additional fees) The landscaped courtyards, play lot, commercial facilities provide a welcoming community environment. Highly desirable location, convenient for transportation - 1 block to train/subway, buses at door, access to Lake Shore Dr, bike path. Nestled between Gold Coast / Old Town, close to downtown, Lincoln Park. Enjoy all attractions of the neighborhood - restaurants, nightlife, shopping, new Jewel, Lakefront trail, beach, Investor friendly building (no rental cap, no Airbnb) Pets allowed.

1360 N Sandburg Terrace Unit #2701C, Chicago

1455 N Sandburg Terrace Unit #808B, Chicago

$279,000

1 Beds ⋅ 1 Baths ⋅ 12727241 MLS ⋅ ACTIVE Status ⋅ Sandburg Village BLDG.

Welcome to Unit 808B at 1455 N Sandburg, a meticulously positioned one-bedroom, one-bathroom corner residence that captures the very best of Gold Coast living. Perched on the northeast corner of the building, this home is flooded with natural light, further enhanced by a private north-facing balcony that serves as your own personal retreat for morning coffee or evening relaxation. Inside, the layout is both functional and inviting, aboundant closet space to include a Walk-in closet in the bedroom, centered around classic parquet hardwood floors that add a layer of warmth and texture to the space. The kitchen is designed for those who love to entertain or stay connected while cooking, featuring a convenient pass-through that opens directly into the dedicated dining area. This thoughtful configuration ensures the living spaces feel airy and interconnected, maximizing every square foot of the floor plan. Living at Sandburg Village offers a lifestyle defined by its robust amenities. Residents have access to two beautifully maintained common pools and professional-grade tennis courts, providing a resort-like atmosphere right in the heart of the city. With its prime corner orientation and crisp interior details, Unit 808B is a standout opportunity to experience a sophisticated urban lifestyle.

1455 N Sandburg Terrace Unit #808B, Chicago

$485,000

2 Beds ⋅ 1 Baths ⋅ 12754756 MLS ⋅ ACTIVE Status

This beautifully updated 2-bedroom condo in a boutique 4-unit building in desirable Old Town checks every box that matters in real estate: price, value, and location. Between the low property tax ($4,779 in 2025) and modest HOA dues ($245/month), the overall cost of ownership here comfortably beats renting a comparable unit in the neighborhood. Numerous major updates, including designer kitchen(2025), water heater (2023), new roof, furnace / air conditioning, and maintenance-free high efficiency Andersen windows (all in 2020), alleviate just about all other financial worries. Nothing about this home is generic; rather, it showcases exquisite detail, including elegant tray ceilings, refinished hardwood floors, fresh neutral paint throughout, and new carpeting in both spacious bedrooms. In-unit laundry and deeded / gated parking space included. Common amenities include a massive roof top deck with sweeping Chicago skyline views. Location undeniably second to none. This quiet nook on the outskirts of the vibrant Old Town entertainment district is 5 min. to Brown line Sedgwick stop, 10 min to Redline North / Clybourn, 20 min. to North Ave Beach, and everything in between! A block away, set in a backdrop of iconic Chicago skyline, brand new beautifully designed Chicago Park No. 598 at 1514 N. Larrabee, easily rivals a historic Oz park, featuring a playground, adult outdoor fitness area, running track, state-of-the- art dog park, and vast green spaces. An extra perk for this amazing location is permit street parking always and readily available. This unmatched synergy of value and premier location offered by this incredible condo simply cannot be replicated.

1407 N Mohawk Street Unit #1, Chicago

$480,000

2 Beds ⋅ 2 Baths ⋅ 12753995 MLS ⋅ ACTIVE Status ⋅ Old Town Square BLDG.

Discover your dream urban retreat in the heart of Chicago's dynamic Old Town with this captivating top-floor, 2-bedroom, 2-bathroom sanctuary. Step into luxury as you enter this meticulously crafted residence boasting an updated kitchen, sleek hardwood flooring throughout the main living area, and the cozy ambiance of a gas fireplace. Embrace the serenity of your own private balcony with treetop and courtyard views, perfect for unwinding after a busy day in the city. Indulge in the comfort of the primary bedroom, featuring a spacious walk-in closet and an ensuite bathroom for ultimate relaxation. A generously sized second bedroom awaits, accompanied by another full bathroom steps away. Ascend to the common roof deck and be mesmerized by panoramic views of Chicago's iconic skyline, a breathtaking backdrop to your urban lifestyle. Your slice of heaven awaits just one floor above you. Don't miss the opportunity to make this gem your own and experience the epitome of city living in style. 2 parking spaces (tandem space, front to back) included!

301 W Goethe Street Unit #304C, Chicago

1455 N Sandburg Terrace Unit #2306B, Chicago

$319,900

1 Beds ⋅ 1 Baths ⋅ 12753898 MLS ⋅ ACTIVE Status ⋅ Gold Coast Galleria BLDG.

Welcome to this stunning, fully renovated 1-bedroom, 1-bathroom condo perfectly situated on the border of Gold Coast and Old Town! This updated residence features breathtaking east-facing views, modern finishes, and a bright, open layout designed for effortless city living. Throughout the home, you'll find an expansive kitchen with island seating, ample closet space, an electric fireplace, and a stylishly renovated bathroom. The well maintained community offers an impressive array of amenities, including a 24-hour doorperson, outdoor swimming pools, pickleball courts, a rooftop deck showcasing spectacular skyline and lake views, and a lush, landscaped courtyard. The location is hard to beat being just a few blocks to Wells Street, Lincoln Park, the Lakefront, and Division St. Whether you're searching for your first home, a city retreat, or a move-in-ready investment, this exceptional condo delivers the perfect combination of style, convenience, and location. Don't miss the opportunity to call one of Chicago's most sought-after neighborhoods home! No rental cap, parking available for lease through the building.

1455 N Sandburg Terrace Unit #2306B, Chicago

1360 N Sandburg Terrace Unit #1106C, Chicago

$295,000

1 Beds ⋅ 1 Baths ⋅ 12736182 MLS ⋅ ACTIVE Status

Ideally situated in the heart of Sandburg Village, this 1-bedroom residence at Cummings House offers comfortable city living with a private balcony and beautiful skyline and lake views. The northeast-facing home is filled with natural light and features hardwood floors throughout, an open-concept living area, and a kitchen with abundant cabinetry and a convenient breakfast bar with seating. The bedroom offers beautiful views, while the marble-tiled bathroom and fresh paint throughout give the home a clean, refreshed feel. Residents of Cummings House enjoy an impressive collection of full-service amenities, including an outdoor pool with cabanas, private tennis and pickleball courts, a rooftop deck with panoramic city views, doorman, 24-hour on-call maintenance, on-site garage parking, bike storage, laundry facilities, and a dedicated package and receiving room. Set near the Gold Coast, Old Town, and Lincoln Park, this location puts some of Chicago's best dining, shopping, entertainment, and outdoor recreation within easy reach. North Avenue Beach and the lakefront paths are nearby. Enjoy restaurants such as Small Cheval, Happy Camper, and the 3 Arts Club along with the Chicago History Museum, Second City, and Zanies for entertainment. Your neighborhood grocery options include Fresh Market, Aldi, and Potash Market. Convenient access to the Red and Brown Lines, as well as Clark and LaSalle bus routes, makes getting around the city effortless. Enjoy the best of city living from this beautiful home in one of Chicago's most established residential communities.

1360 N Sandburg Terrace Unit #1106C, Chicago

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