Uptown Homes under $750,000

Welcome to Uptown, one of Chicago's most vibrant and eclectic neighborhoods, where urban charm meets rich cultural history. Nestled along the shores of Lake Michigan, Uptown is a dynamic enclave that offers an inviting blend of residential comfort and lively entertainment. Known for its diverse community, Uptown is a melting pot of cultures, making it a delightful place to call home.

As you explore this thriving neighborhood, you’ll discover a variety of homes under $750,000, perfect for first-time buyers, young professionals, and families alike. From beautifully restored vintage condos to spacious single-family homes, Uptown’s real estate market provides a range of options that cater to different lifestyles and budgets. Many of these homes boast unique architectural features, reflecting the neighborhood’s rich history while incorporating modern amenities for today’s discerning buyers.

Uptown is not just about homes; it’s about a lifestyle. Residents enjoy easy access to lush parks, including the scenic Montrose Beach and the picturesque lakefront trail, ideal for outdoor enthusiasts. The neighborhood is also home to a thriving arts scene, with venues like the historic Aragon Ballroom and the Riviera Theatre hosting a variety of performances throughout the year. Dining options abound, from cozy cafés to trendy restaurants, ensuring that there’s always something new to savor.

With its affordable housing options, cultural vibrancy, and community spirit, Uptown is more than just a place to live; it’s a place to thrive. Come and discover the charm of Uptown, where your dream home awaits!

Newest Uptown Homes under $750,000

$415,000

2 Beds ⋅ 2 Baths ⋅ 12792081 MLS ⋅ NEW Status

Welcome to 1110 W Leland Ave, Unit 1B, a modern and elegant 2-bedroom, 2-bath condo offering a stylish blend of comfort and sophistication. The spacious open-concept layout features high ceilings, abundant natural light, rich hardwood floors, a cozy fireplace, and a beautifully updated kitchen with stainless steel appliances and a generous island. The thoughtfully designed primary suite includes a spacious bedroom and a modern bath with a walk-in shower. Ideally located near Montrose Beach, public transportation, dining, shopping, and entertainment, this exceptional home offers both contemporary living and everyday convenience. The monthly HOA fee is $451.86. As of October 18, 2026, the association reserves total $44,876.73, and there are no special assessments. Current projects include roof repairs, with the deposit paid and work scheduled to begin in early November 2026, as well as drywall repairs in common areas and units affected by rain leaks in July 2026. The association is working with its insurance company regarding the water damage repairs.

1110 W Leland Avenue Unit #1B, Chicago

$299,900

2 Beds ⋅ 1 Baths ⋅ 12791314 MLS ⋅ NEW Status

Available for immediate occupancy! Welcome to this inviting two-bedroom, one-bath condo in a charming vintage courtyard building in Uptown. Beautiful wood floors and a cozy electric fireplace anchor the open living and dining area, creating a welcoming space to relax or entertain. The well-appointed kitchen features rich wood cabinetry, stainless steel appliances and convenient pantry storage. An updated bathroom, generous closets and rear outdoor deck space add comfort and everyday convenience. Enjoy a walkable neighborhood near Clarendon Park, the scenic lakefront and Montrose Beach, with cafes, restaurants and everyday shopping nearby along Wilson Ave and Broadway. Building amenities include common laundry, an exercise room and a separate storage locker. The monthly assessment includes heat and water. Pets and rentals are welcome. Nearby off-site parking is available for rent at Weiss Memorial Hospital.

810 W Lakeside Place Unit #107, Chicago

4908 N Winthrop Avenue Unit #2S, Chicago

$495,000

3 Beds ⋅ 2 Baths ⋅ 12785296 MLS ⋅ NEW Status

This spacious Uptown condo seamlessly blends classic charm with modern updates and is bathed in natural light from the East and South exposures. The kitchen features 42-inch cabinets painted to give a more modern touch, with new hardware, a new dishwasher, all stainless steel appliances, and granite countertops including a breakfast bar. Beautifully refinished hardwood floors flow into the light-filled living area with plenty of space for a dining table, which now includes a custom built-in bookshelf, wood burning fireplace and direct access to a private balcony (the first of two!). Just re-painted, the condo also boasts a spacious primary suite that serves as a peaceful retreat, complete with ample closet space, direct access to the second private balcony, and an en-suite bathroom featuring double sinks and separate tub and shower. Additional highlights include a functional hall bath with a granite vanity, two additional bedrooms, in-unit laundry, additional storage, and an included secured assigned parking space. Nestled in a prime location just minutes from from the Argyle CTA Red Line station, Montrose Beach & Harbor, the Green Mill jazz club, historic music venues like the Riviera and Aragon, and the vibrant global dining along Argyle Street and Broadway.

4908 N Winthrop Avenue Unit #2S, Chicago

$285,000

2 Beds ⋅ 2 Baths ⋅ 12790721 MLS ⋅ NEW Status

Rarely available Uptown garden unit in vintage historical low-rise building. This freshly painted unit located in a quiet pocket of Uptown on a cul-de-sac street offers lots of space and plenty of light throughout. The open floorplan, solid, refinished hardwood floors, and high ceilings makes it a hard to find home. The kitchen features granite counters, custom cabinetry, stainless steel appliances, and a convenient breakfast bar. It opens to the spacious living room area with a cozy gas fireplace, and open window line. The primary suite has an en-suite bathroom, double-sinks, whirlpool tub, and lots of closet space. Enjoy your own private terrace space in the back as well. Washer/dryer in-unit, and assigned parking space. Large storage room on the same level. Sump pump and check valve to prevent backflow. Conveniently located within walking distance of all the area amenities, including lakefront trails, public transportation, and the vibrant restaurant scene. ACT FAST. ** This property may qualify for a $5,000 Chase Homebuyer Grant that can be used to reduce the cost of your Chase mortgage. Contact for more information** Offered as-is.

929 W Eastwood Avenue Unit #GW, Chicago

$522,900

2 Beds ⋅ 2 Baths ⋅ 12790183 MLS ⋅ NEW Status

Perched on the top floor, this beautifully updated penthouse offers the perfect blend of style, comfort, and city living. The airy open-concept layout is highlighted by soaring vaulted ceilings, skylights that flood the home with natural light, and rich hardwood floors throughout. The chef-inspired kitchen features granite countertops, custom cherry cabinetry, stainless steel appliances, abundant prep space, and a built-in pantry designed to seamlessly complement the kitchen's elevated aesthetic. The kitchen flows effortlessly into a spacious dining area and inviting living room anchored by a cozy fireplace, creating an ideal setting for entertaining or everyday living. Freshly painted and move-in ready, the home also boasts luxurious marble baths, including a spa-like primary bath with a whirlpool tub and steam shower. Enjoy outdoor living with both a private balcony and charming Juliette balcony, perfect for taking in the neighborhood atmosphere. Garage parking with an additional tandem exterior space completes this exceptional offering. Ideally situated in Chicago's vibrant Uptown neighborhood, you'll enjoy easy access to the lakefront, Montrose Beach, scenic running and biking trails, and some of the city's most beloved entertainment venues, including the historic Riviera Theatre and Aragon Ballroom. Recent building upgrades/maintenance: Roof - 2019, Tuck pointing and re-sealing - 2025, landscaping updated- 2023, new fence 2023, decks replaced-2016, stained 2024. Robust reserves.

917 W Lakeside Place Unit #3W, Chicago

$325,000

1 Beds ⋅ 1 Baths ⋅ 12787669 MLS ⋅ ACTIVE Status

Bright, sun-filled top-floor loft in the heart of Uptown. Soaring ceilings and oversized windows flood the open-concept layout with natural light. Highlights include in-unit laundry, central heat and A/C, generous closet space plus a separate storage unit, and a heated indoor garage parking space included in the price. Brand new stainless steel kitchen appliances as of October 2026. The location is hard to beat. You're minutes from Uptown landmarks like the Aragon Ballroom and the Green Mill. Andersonville, Lakeview, North Center, and Lincoln Square are all close by. The lakefront, CTA, dining, nightlife, and shopping are within easy reach, and the commute downtown is quick. A standout home in one of Chicago's most vibrant neighborhoods. Schedule your showing today!

4715 N Racine Avenue Unit #502, Chicago

$249,000

1 Beds ⋅ 1 Baths ⋅ 12779445 MLS ⋅ ACTIVE Status

Gorgeous top-floor residence offering exceptional natural light, soaring extra high ceilings, and parking included in the price. The bright, open kitchen features 42-inch maple cabinetry, stainless steel appliances, granite countertops, and a spacious island, along with a new gas range (2026) and refrigerator (2025). Expansive skylights fill the home with natural light, complemented by recessed lighting, beautiful hardwood floors throughout, and custom blinds. The stunning marble bathroom features a glass-enclosed shower, while the dishwasher and in-unit LG WashTower washer/dryer provide everyday convenience. Additional updates include a new building roof and two new skylights (2026), as well as a new furnace and A/C with a smart thermostat (2022). The building has also undergone extensive improvements, including significant tuck-pointing and masonry repairs, along with refurbished gates and fencing. A rare highlight is the building's only private outdoor deck, offering an exceptional opportunity to create your own private outdoor retreat. Ideally located just four blocks from the CTA, one block from the lake, and one block from a convenient dog park. Ultra-low assessments complete this exceptional offering.

835 W Lawrence Avenue Unit #3S, Chicago

$649,900

3 Beds ⋅ 2 Baths ⋅ 12785563 MLS ⋅ ACTIVE Status

A rare find in Uptown: newer construction in a neighborhood known for its vintage brick and greystone character. This sun-filled 3-bedroom, 2-bath home is turn-key and impeccably managed. The open kitchen features European cabinetry, an integrated panel-front refrigerator, Thermador/Bosch appliances, quartz countertops, and a spacious breakfast bar. It connects seamlessly to the living/dining area and opens to a large front balcony with a gas hookup for grilling. The primary suite includes an organized walk-in closet, oversized shower, heated porcelain floors, a floating double vanity, and linear drains. The second bath offers custom lighting and a deep soaking tub. Sustainable bamboo floors run throughout, and European turn-and-tilt windows provide sound insulation and energy efficiency, complemented by energy-efficient HVAC and a tankless water heater. Additional features include one garage parking space, bike storage, and a full-size Samsung washer/dryer. Location: two blocks to the lakefront, one block to the new Red Line Lawrence stop and a Divvy station, with express bus access downtown and Metra less than a mile away. Nearby restaurants, festivals, and a neighborhood school add to the area's appeal.

4858 N Kenmore Avenue Unit #2N, Chicago

$649,000

2 Beds ⋅ 2 Baths ⋅ 12783086 MLS ⋅ ACTIVE Status

Live in one of Chicago's most sought-after neighborhoods. This light filled, extra wide condo offers approximately 1,500 square feet of comfortable, modern living in the heart of vibrant Andersonville. The spacious main living area features a welcoming fireplace and flows seamlessly into an open concept kitchen with room for separate dining area. The kitchen has a large 6' island, granite countertops, and stainless-steel appliances that create an ideal space for cooking and entertaining. The home includes two full bathrooms, highlighted by a serene primary ensuite. Enjoy a double sink vanity, separate shower and a Jacuzzi tub for ultimate relaxation. Side-by-side in-unit washer and dryer adds everyday convenience, while private storage provides valuable extra space. Step outside to two private decks; one off the living room and one in the back. Hardwood floors run throughout, central AC and generous natural light. Updates include new HVAC 2026, washer/dryer 2026, cooktop 2025, refrigerator 2022, water heater 2021 and the unit is freshly painted throughout. The building has a video/voice intercom system connected to your phone for guests and deliveries. Gated parking is included and covered by a carport. Separate storage closet on the ground level. This condo blends space, comfort, and location all within one of Chicago's most beloved neighborhoods.

5055 N Clark Street Unit #3S, Chicago

$200,000

1 Beds ⋅ 1 Baths ⋅ 12753643 MLS ⋅ ACTIVE Status

INVESTOR AND PET FRIENDLY CHARMING ONE BEDROOM NEAR THE LAKE! ALL HARDWOOD FLOORS, 42" MAPLE CABINETS, STAINLESS APPLIANCES, IN-UNIT WASHER/DRYER. CENTRAL HEAT AND AC. HIGH FIRST FLOOR W/HUGE DECK OFF KITCHEN.3 BLOCKS TO RED LINE - CLOSE TO RESTAUANTS, SHOPPING AND BEACH.

827 W Lawrence Avenue Unit #1S, Chicago

1100 W Montrose Avenue Unit #502, Chicago

$525,000

2 Beds ⋅ 2 Baths ⋅ 12778498 MLS ⋅ ACTIVE Status

Check out this sun-filled 2-bedroom, 2-bath corner home with two deeded parking spaces in a boutique elevator building. Large windows flood the home with natural light, creating a bright and inviting living space. The spacious living room features a tiled gas fireplace and direct access to a charming private balcony. The open concept kitchen is beautifully appointed with Calacatta Classic quartz countertops, custom white cabinetry, stainless steel appliances, and a large island with seating. The generous primary suite offers two closets and a beautifully updated spa-like en-suite bath with custom tile work and ample storage. Additional highlights include updated kitchen and bathrooms, an in-unit washer and dryer, and peace of mind with major mechanical updates, including a new heating system installed in November 2025 and a new air conditioning system installed in July 2026. Two deeded exterior parking spaces are INCLUDED in the price. Ideally located just steps from the train and minutes from Montrose Beach, the Southport Corridor, Uptown, Wrigleyville, and Andersonville, with easy access to Lake Shore Drive for a quick commute. This is the one you've been waiting for-come take a look!

1100 W Montrose Avenue Unit #502, Chicago

$470,000

2 Beds ⋅ 2 Baths ⋅ 12760178 MLS ⋅ ACTIVE Status

Large, Top floor corner unit in a beautiful vintage building with amazing original detail and incredible natural light. Built in 1889; this 2 BD/2BA home features an open layout perfect for entertaining. Kitchen has ample storage, SS appliances, granite counters, and beautiful glass tile backsplash. Living room is flooded with natural light; shining through large, curved bay windows. Vintage built-in bookcases surround a tiled gas fireplace. Harwood floors throughout the living room and bedrooms (each with a large walk-in closet). In-unit washer/dryer. Central heat & air. Full-size storage unit in the building. The building is pet-friendly with not weight restrictions or breed restrictions. Front yard has automatic sprinkler system. Parking is secured and gated. exterior front and back video surveillance (Nest Cams) and electronic entry system. Walking distance to the lake, Starbucks, Target and the Red line.

4536 N Sheridan Road Unit #303, Chicago

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Uptown Homes under $750,000

Newest Uptown Homes under $750,000

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