Vintage homes for sale & real estate in Uptown, IL

Vintage Home for sale in Uptown, IL:

Discover a rare opportunity with this exquisitely updated 3-unit multi-family property, originally built in 1910, located in the heart of Sheridan Park between Ravenswood and Uptown. Adding to the allure is the prized, adjoining secret garden-a serene oasis tucked away from the bustling city. With its lush greenery and tranquil charm, it offers a rare retreat in an urban setting, providing a perfect escape for relaxation and enjoyment. This additional lot also holds potential for future development or can remain as a cherished garden, enhancing the property's uniqueness. Seamlessly blending historic charm with modern conveniences, this property offers endless potential for both homeowners a

Vintage Home for sale in Uptown, IL:

Come see this spacious, updated 1 bedroom with one of the best views in the entire building and the neighborhood! You have 6 windows facing SE with unobstructed views of the lakefront, downtown and Navy Pier Fireworks! You are going to love the massive rooftop deck with 360 views of the lake/city with easy access from this unit just down the hall and up 1 flight of stairs. This is a full amenity building featuring full-time door staff, on-site management, large workout facility, beautifully landscaped courtyard, community room, package/parcel receiving Plenty of storage with wall to wall closets in the bedroom and additional storage down the hall. Why rent when you can own for the same m

Vintage Home for sale in Uptown, IL:

This is the one you've been waiting for! Finally, an incredibly bright, spacious & affordable 2BR condo located on the 2nd floor of a very well managed courtyard building. The 722 tier is centrally located between the two courtyards, which means you will enjoy abundant light from the east, south and west exposures! Buena is a gorgeous tree-lined street with direct access under LSD to the Lakefront paths for those who enjoy walking, running and/or cycling along the lake. Available for the 1st time in nearly 22 years, the entire unit was just freshly painted! The new owner will enjoy a full-size washer and dryer in the unit! Additionally, this unit offers thermopane windows, generous cl

Vintage Home for sale in Uptown, IL:

This historic 1909 home unifies the very best of historic integrity and a modern lifestyle. Designed in a four square Georgian style, hallmarks of this home are the clean lines of the exterior and the welcoming front porch. The original exterior cladding has been restored and complemented with new cedar cladding on the rear addition. Oriented on a 30' X 132' lot, you will also enjoy a verdant, private oasis in the rear yard relaxing under the canopy of a mature White Burr Oak. The 2.5 car garage was thoughtfully designed and executed to reflect a delightful cottage. A rare find in urban living. The interior is an immaculate homage to the home's history. While much of it is newer, the owner'

Vintage Home for sale in Uptown, IL:

Check out this spacious 3rd floor 2 bed 2 bath corner unit condo in the Uptown neighborhood. This unit has the east side lake views. Walk into the inviting bright living room with parquet flooring, freshly painted throughout. Updated modern kitchen with tile flooring, white shaker cabinetry, quartz countertops, and newer stainless steel appliances. Enjoying relaxing baths in the jacuzzi tub. The building offers a shared laundry room, gym, 24-hr doorman, bike storage, and on-site parking. Just steps away from Lake Michigan and a great location to shopping, restaurants and more. Call and schedule your showing today.

Vintage Home for sale in Uptown, IL:

Bright & spacious Shoreline Park corner one bedroom condo with open floor plan! Generously sized living room with space for a dining table or desk. Kitchen with subway tile backsplash & island with breakfast bar. Large bedroom with an entire wall of closets plus two additional hall closets & separate storage locker included. Brand new luxury vinyl flooring in living area and bedroom and freshly painted with neutral colors. Full amenity building features two rooftop decks with lake/park views, fitness center, community/game room with pool table, ping pong & air hockey, business center, bike room, 24-hour door staff, multiple laundry facilities, courtyard with tables a

Vintage Home for sale in Uptown, IL:

Freshly updated and rehabbed, this top floor, south-facing condo will give you plenty of natural light while overlooking the beautiful courtyard on a gorgeous, tree-lined street in Uptown. The unit boasts brand new flooring throughout, brand new paint throughout, BRAND NEW high-end Fisher & Paykel refrigerator and brand new dishwasher. Other updates include new track lighting, new ceiling fan, and switch and dimmer upgrades throughout. The stunning, custom-built bathroom features floor-to-ceiling granite slabs and tiles, Jado shower fixtures, a Duravit pedestal sink, Robern mirror, recessed lighting and a Pocher soak tub. There is also a large deck off the kitchen with plenty of outdo

Vintage Home for sale in Uptown, IL:

Discover Timeless Elegance at 5000 North Marine Dr. Welcome to the Aquitania, a vintage gem nestled along Chicago's picturesque parks and lakefront. This exquisite, spacious 1000 SF one-bedroom, one-bath residence offers a blend of historic charm and modern comfort, making it the perfect home for full-time living or as an in-town. Experience all the activities that Uptown has to offer with restaurants, shopping, parks and easy lakefront access within walking distance. This unit has been recently updated with new engineered bamboo floors, a totally gut-rehab bathroom, new bedroom and living room windows, closets have built-in organizers by California Closets. The bedroom, flooded with natura

Vintage Home for sale in Uptown, IL:

Welcome home to the historic Aquitania, where elegance and modern convenience meet in the heart of Margate Park. The gleaming lobby's vintage details invite you in and the welcoming door staff provide assistance 24 hours a day. The unit's marble entryway opens to the spacious living room, where the grand windows flood the room with natural light. The pristine oak floors flow from the living room into the bedroom through french doors. The bedroom boasts a large closet and direct access to the shining marble bathroom. The chef's kitchen features Subzero fridge, Viking stove, Bosch dishwasher and plenty of storage. The dining area shares the same newer porcelain tile with space for a large din

Vintage Home for sale in Uptown, IL:

Experience vibrant city living at 1059 W Foster Ave, nestled in the heart of Andersonville near Uptown, Chicago. This charming condo is just two blocks from Lake Michigan, offering easy access to scenic lakefront trails, beaches, and parks. Enjoy a dynamic neighborhood with a mix of trendy restaurants, cafes, and entertainment venues, all within walking distance! With excellent public transportation options and proximity to downtown, this location blends urban convenience with peaceful relaxation. Updated 2 bd/2 bth first floor condo with combination washer/dryer in unit. Main bedroom offers en-suite accommodations. FRESH interior paint throughout, warm oak-stained flooring, neutral plush c

Vintage Home for sale in Uptown, IL:

Welcome home to this beautiful and bright 1-bedroom, 1-bathroom condo in Chicago's historic MDA building just steps from Lake Shore Drive and Foster Beach! This newly-painted unit offers one of the more spacious layouts, including a large living room, separate dining room for hosting friends and family that can also be used as an office/den/multipurpose room, ample-sized bedroom with plenty of closet storage, and a newly updated bathroom. So many building amenities including a doorman, fitness center, party/common room, on-site management, bike room, and additional storage locker. Enjoy the beautifully landscaped courtyard with a striking Art Deco fountain where you can sit and relax, read,

Vintage Home for sale in Uptown, IL:

Charming move-in ready courtyard building home with updates around every corner. Be wow'ed by the spacious and lovely living area complete with decorative brick fireplace, large windows and space for a large sectional. Flow into the eat-in kitchen to find refinished cabinets, window with treetop views, easy access to the private balcony, newer refrigerator and dishwasher and room for a dining area. You will love the hardwood floors, large closet and lush green views from the primary bedroom! Find hardwood floors and great natural light in the second bedroom, a great flexible space for any number of uses. Prime Uptown/Margate Park location close to Montrose Beach and Harbor, Margate Park, Pu

Vintage Home for sale in Uptown, IL:

Welcome to your new home in the heart of Uptown! This sunny garden unit boasts 2 beautiful bedrooms. It includes a comfortable living area, a separate dining room, a full bathroom, and a modern kitchen featuring granite countertops and stainless steel appliances. Enjoy the convenience of an in unit washer and dryer in a pet friendly building. With its prime location just minutes from the Argyle Red Line stop, the lakefront, parks, shopping, and dining options, this condo places you right in the center of the city's vibrant offerings. Don't miss out on this gem! * * INVESTORS WELCOME, RENTALS ARE ALLOWED * *

Vintage Home for sale in Uptown, IL:

Prime location within top rated Ravenswood elementary school district, walking distance to Chase Park, multiple cafes, nightlife, brown line, red line and a Metra stop and Marianos! Stunning 6 bedroom, 3 full & 2 half bath home, loaded with designer touches on an OVERSIZED lot, is an entertainer's dream. Three levels of luxe living spaces overlook a spacious backyard, anchored by a gorgeous Magnolia tree. The newly renovated main level features coffered ceilings, traditional millwork and hand-scraped wood floors. The updated chef's kitchen sparkles with white cabinets, white quartz countertops, a 6-burner Viking stove and double oven, Sub-Zero refrigerator, Bosch dishwasher, and beve

Vintage Home for sale in Uptown, IL:

Bright and Airy One Bedroom Condo. Boasting Skylights and Hardwood Floors Throughout. Washer/Dryer In Unit. Newer Furnace and Water Heater. One Block From The Lakefront/Montrose Beach, Bicycle Paths/Walking Paths, Restaurants, and Shopping. Close To Train/Red Line.

Vintage Home for sale in Uptown, IL:

Welcome to this investor-friendly, updated condo in the vibrant Buena Park neighborhood! This charming condo offers a huge sunny living room, gorgeous hardwood flooring, and a convenient galley kitchen with granite counters and stainless steel appliances. The split bedroom design provides ample privacy and comes with plenty of closet space. Recent upgrades include a new HVAC system and an in-unit washer/dryer (2023). The bathroom features a whirlpool tub and a bidet. Just a 15-minute walk to the Lakefront Trail, Wrigley Field, and Southport Corridor! Close to Jewel, Target, Aldi, and Walgreens for ultimate convenience. This condo combines comfort, convenience, and charm - a perfect place to

Vintage Home for sale in Uptown, IL:

Margate Park. Perfect for first time buyers! Spacious, corner one bedroom with lovely tree top views of the lakefront. Features hardwood flooring throughout, high ceilings, separate dining area, large bedroom with walk-in closet and window AC. The building features evening/weekend door staff, 24hr maintenance, exercise room, storage and steps to the lake, shopping, nightlife, transportation and everything that Margate Park/ Edgewater have to offer.

Vintage Home for sale in Uptown, IL:

Come check out this gut-rehabbed 2-flat + finished basement in Uptown / Andersonville! Located on a 25x180 sq. ft. lot on a quiet residential street, this property is the perfect place for a new owner in search of a big backyard to call home. 4870 N Magnolia was recently renovated with all new utilities and interior finishes. The bathrooms feature brand new finishes and the property still shows its original style and character. The first floor is a 2br/1ba apartment, second floor is 3br/1ba, and the basement has a sink and additional bedroom, allowing for a potential 3rd unit or duplex down with the first floor. Basement even features a cellar for additional storage or creative wine cellar!

Vintage Home for sale in Uptown, IL:

Sunny and spacious Uptown 1-bedroom home in a well maintained, classic Chicago brick building on a quiet tree-lined street- and it's a couple blocks from the lake! The morning person will love the sunshine flooding through the unobstructed east facing windows in the living room and sun room. This perfect layout includes a separate dining room in addition to the living room and sun rooms, and the sizable bedroom comfortably accommodates various bed layouts as well. The kitchen has granite counters, stainless steel appliances, and solid cabinet storage. The monthly assessments are $306, and there is a separate storage unit and a bike room in the basement as well as a deeded exterior parking s

Vintage Home for sale in Uptown, IL:

RARELY AVAILABLE 2BR/2.5BA DUPLEX THAT LIVES LIKE A TOWNHOME. HUGE UPPER LEVEL W/ HARDWOOD FLOORS, OPEN KITCHEN W/ STAINLESS APPLIANCES, GRANITE COUNTERTOPS & BREAKFAST BAR. SEPARATE DINING ROOM, LIVING ROOM & MASTER W/ EN SUITE BATH W/ DOUBLE VANITY. LOWER LEVEL FAMILY ROOM, 2ND BEDROOM & FULL BATH. IN-UNIT LAUNDRY, PRIVATE DECK. GATED ASSIGNED PARKING SPOT & STORAGE LOCKER INCLUDED IN PRICE! FURNACE AND A/C BOTH REPLACED IN 2022. IDEAL LOCATION STEPS FROM PUBLIC TRANSPORTATION, WRIGLEY FIELD, THE LAKE, RESTAURANTS, AND SHOPPING.

Vintage Home for sale in Uptown, IL:

Welcome to your bright and spacious 2-bedroom, 1-bathroom condo in the historic MDA building, just steps from Lake Shore Drive and Foster Beach! This newly renovated unit features ample-sized bedrooms with plenty of closet space and a newly updated bathroom. The MDA building offers a range of fantastic amenities, including a doorman, fitness center, party/common room, on-site management, bike storage, and an additional storage locker. Enjoy the beautifully landscaped courtyard with its striking Art Deco fountain, where you can relax, read, or take part in community events like morning coffee talks, happy hours, yoga sessions, gardening days, and holiday parties. With convenient access to ex

Vintage Home for sale in Uptown, IL:

Just steps from the Park and Lake Michigan, this bright and spacious one-bedroom condo at Shoreline Park is a true gem! Located in a quiet, mid-sized building with a welcoming lobby, first-floor laundry, storage, and two garage parking, this condo offers everything you need. The spacious floor plan features new hardwood floors (2019) throughout the living room and bedroom, while the kitchen boasts a breakfast bar with tons of cabinet and counter space. The bathroom was also remodeled in 2019, adding modern touches to the home. With a tremendous lakefront location, just steps from the Red Line, Express Buses, and all the dining and nightlife that Uptown, Edgewater, and Andersonville have to

Vintage Home for sale in Uptown, IL:

Orchard House: Experience the high ceilings and vintage wood of this beautifully renovated 1910 home, situated in an amazing location just minutes away from North Michigan Ave by car and three blocks from the lakefront. Sitting on half an acre of garden space landscaped by Scott Byron, this four-story house comprises 5 bedrooms, 4.5 baths, a 3 car garage, a fully finished walk out basement with an illuminated zebrawood bar, fireplaces throughout, custom kitchen with banquette and luxury appliances, two sun rooms, new deck off the main bedroom, all new utilities, and much more added during a year-long, over $500k renovation. The floor plan hearkens back to the years of pre-cookie cutter hous

Vintage Home for sale in Uptown, IL:

Renovated, Contemporary, and Sun-Soaked 2-Bedroom Condo in Prime Uptown Location Blocks from Montrose Beach and Lake Michigan! Enjoy Open-Concept Living Complete with Tall Ceilings, Fantastic Windows, and an Abundance of Natural Light. Pristine Finishes include New Flooring, Paint, and Fixtures Throughout, and Modern Kitchen with Quartz Countertops, White Shaker Cabinets, and SS Appliances. Upgraded Bath with Beautiful Shower Tile, New Lighting, and New Medicine Cabinet. Separate Dining Room and Living Room, Each with Space for Desk or Peloton. Two Spacious Bedrooms, Plentiful Closets, including a Walk-in Closet in the Primary Bed. Classic Brick Building with Outdoor Patio on Quiet One-Way

Vintage Home for sale in Uptown, IL:

One of Chicago's best finds, this treasured residence - an entire floor in an intimate boutique building designed by famed architect Benjamin Marshall - exudes opulence and offers practicality. Rich in preserved architectural details, the one-of-a-kind square floor plan elegantly works for both entertaining and day-to-day living. The formal rooms all flow from the main gallery: A glamorous living room framed by a marble fireplace and windows on all sides; a large dining room with extensive molding and decorative windows; and a library/bedroom with an arched entry and built-in shelving. A welcomed surprise for vintage residences, the fabulous chef's kitchen opens to an enormous great room fo

Vintage Home for sale in Uptown, IL:

Discover this charming 1 bedroom, 1 bath condo located right across Lake Michigan! The unit has been freshly painted and the kitchen boasts new appliances. The open concept living area is perfect for entertaining. Amenities of the building include a 24 hour doorman, rooftop deck, business center, and fitness center. Situated in a vibrant neighborhood, you'll enjoy easy access to local dining, shopping, and public transportation. Don't miss out on this fantastic opportunity to live in one of Chicago's most desirable areas! This is a HomePath property.

Vintage Home for sale in Uptown, IL:

Steps to Lake Michigan this high floor 1 bedroom 1 bathroom condo in the most desirable tier in the building. Showered in natural light from abundant windows. Fantastic layout offers plenty of space for living and dining. Kitchen with breakfast bar. Wood floors throughout. Great closet space. Unit was just painted and is ready to move right in and call it home. Tenants allowed, most recent rent was $1350 for a 3 year lease. This location can't be beat at this price. Steps to the lake, public transportation, Wrigley, shopping, dining and nightlife. Rental parking available. Assessments cover everything! No gas or electric bill!

Vintage Home for sale in Uptown, IL:

This fully-rehabbed, prime first floor condo boasts 2 bedrooms, 1 bathroom, and a meticulously-maintained interior, completed in 2023. Freshly painted with many upgrades makes this unit ready to move in and occupy. Unit features spacious bedrooms, hardwood floors, ceiling fans, central heat/air, and common laundry (shared by 2 units only). New HVAC system installed on the roof in 2020, backed by a 10-year heat exchanger warranty. Healthy 11-unit association with ample reserves of $27,446.21, and an operating account of $18,443.17, totaling $45,889.38, as of July 23, 2023. 1 unit is rented right now. 2 units allow to be rented at a time. If more than 2 units want to be rented out, they will

Vintage Home for sale in Uptown, IL:

Fabulous Art Deco building with beautiful fountain & garden courtyard. Across the street from the park and lake. Convenient and spacious first-floor unit with no adjoining neighbors. New Kitchen and remodeled bathroom. Parquet floors throughout. The large bedroom has lots of closet space. Laundry and storage located on the same floor just a few steps away from the unit. Great location close to transportation and shopping. HOA includes HEAT, TV/cable, water, Door person, and access to the exercise room.

Vintage Home for sale in Uptown, IL:

Enjoy stunning unobstructed views of the Lake and Lincoln Park. This extraordinarily elegant and graceful apartment is in the Aquitania! This home is designer owned and has custom window treatments throughout, all new plastered walls, replaced original woodwork and hardwood floors and a beautifully renovated kitchen with all new Bertazonni appliances (2022) with incredible views! This gorgeous home has new Pella Architect Series windows (Jan 2023), only three units per floor and concrete between floors makes for extremely quiet living also professionally organized closets plus large additional storage space located near service elevator . The Aquitania is listed in the national Register Of

Vintage Home for sale in Uptown, IL:

Set on an enormous 65x165 lot on a tree-lined street in the idyllic Hutchinson Historic District, this magnificent gated estate - rich in original detailing and filled with abundant natural light - presents the opportunity for wonderfully grand entertaining coupled with the ease and conveniences of modern day living. Enter the home through a private drive and Porte cochere, and savor the priceless treasures that await: grand rooms filled with intricate carved moldings, detailed leaded windows, and original built-ins. The entry hall is flanked by a formal dining room on one side and a fabulous living room centered on a breathtaking fireplace on the other. Spanning the entire width of the fro