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4725 N Kenmore Avenue, Chicago
$825,000
8 Beds ⋅ 3 Baths ⋅ 12754863 MLS
Rare opportunity to own a solid brick legal 3-unit building in Chicago's Uptown neighborhood on beautiful tree-lined Kenmore Avenue. Situated on an oversized lot, this Uptown multi-unit property offers outstanding potential for an investor, owner-occupant, or future single-family home conversion. Spacious units feature abundant natural light, generous room sizes, and separate living and dining spaces. Each unit has separate heating and cooling systems and individual utilities. The vacant top-floor unit features a bright 2-bedroom, 1-bath layout, dramatic stairwell accented by a skylight, and in-unit laundry. The first- and second-floor units each offer 3 bedrooms and 1 bath. The unfinished basement provides additional untapped potential with great ceiling height and two separate entrances. Detached 2-car garage. Prime Uptown Chicago location near the Wilson Red and Purple Line CTA station, multiple bus routes, lakefront parks and trails, restaurants, coffee shops, grocery stores, and the Uptown Entertainment District. An exceptional opportunity to own a brick 3-unit investment property in one of Chicago's most vibrant North Side neighborhoods.

4725 N Kenmore Avenue, Chicago

4858 N Kenmore Avenue Unit #3N, Chicago
$799,000
3 Beds ⋅ 2 Baths ⋅ 12752054 MLS
This impeccably maintained 3-bedroom, 2 bath penthouse pairs sophisticated modern design w/ exceptional private outdoor space in the heart of Uptown! Soaring 11' ceilings & oversized windows flood the home w/ natural light. Hardwood flooring throughout, 8-foot solid core doors & clean architectural lines create a contemporary feel throughout. The sleek European kitchen is a chef's dream, featuring integrated panel refrigerator & dishwasher, Thermador/Bosch appliances, white quartz countertops, marble backsplash, under cabinet & pendant lighting, & a generous breakfast bar w/ seating for four. The expansive open concept living and dining space is fantastic for entertaining, anchored by a striking custom fireplace & opening directly to a private terrace w/ gas hookup for a grill. The serene primary suite provides ample room for a King-sized bed, professionally organized walk-in closet, & a luxurious primary bathroom w/ heated porcelain floors, a floating double vanity & an oversized walk-in shower w/ a rain head. Two guest bedrooms, a beautiful hall bathroom, & a huge laundry closet with side-by-side Whirlpool washer/dryer set complete the main living level. The full-floor rooftop is a true urban oasis w/ panoramic city view, pergola & fire pit, contemporary planters, irrigation, & artificial turf. Adjacent to the roof deck is a bonus room that would make an ideal office or workout space. This boutique, seven-unit building is professionally managed with a spacious garage w/ bike storage. Walk to the Lake, Aragon Ballroom, Green Mill, Lawrence and Argyle Red Line "L" stations, and so much more!

4858 N Kenmore Avenue Unit #3N, Chicago

4921 N Kenmore Avenue Unit #1, Chicago
$725,000
3 Beds ⋅ 3 Baths ⋅ 12757940 MLS
Vintage charm meets contemporary comfort in this well cared for and graciously renovated 3-bedroom, 3 bath duplex with over 2,300 square feet of beautifully finished living space. Located on a tree-lined street in the heart of Uptown just a block from the renovated Argyle Red Line stop and a short walk to North Lincoln Park and the lake, you'll find yourself at home with impressive 11-foot ceilings and expansive windows creating an abundance of natural light. The minute you step inside, you're welcomed into the open living and dining area with the warmth and coziness of the elegant fireplace, all adjacent to the well-appointed kitchen with 42'' maple cabinets, honed granite countertops, breakfast bar and stainless-steel appliances. With hardwood floors throughout, the main floor also features full guest bath, custom-designed laundry space, sitting area/reading nook and primary ensuite with tastefully designed, spa-like bath with radiant floor heating and marble tile that was a complete gut-remodel in 2021. And you'll love stepping outside onto your expansive covered rear deck, perfect for entertaining or quiet relaxation on a summer day. The lower-level features home office space, another gut-remodel full bath (2024) and two additional bedrooms, offering comfortable privacy for other members of the family or hosting overnight guests. Other updates include new dishwasher and microwave (2026), new washer & dryer (2023), new central air conditioner (2022) and new furnace (2021). Secure exterior parking with deeded space and dedicated storage with additional area for bikes. Pet-friendly, self-managed building. Just steps from Argyle Street, this sought-after Uptown neighborhood is an easy walk to public transportation; Lincoln Park, beaches, running and bike paths, and playgrounds; trendy cafes and restaurants; local shops; iconic concert venues like the Aragon Ballroom and Green Mill Jazz Club, and so many other cultural offerings not only in Uptown, but also in nearby Andersonville and Edgewater. In this location, in this meticulously cared for and thoughtfully renovated spacious duplex, this is truly a unique opportunity.

4921 N Kenmore Avenue Unit #1, Chicago

927 W Agatite Avenue Unit #3S, Chicago
$650,000
2 Beds ⋅ 2 Baths ⋅ 12710094 MLS
Look no further than this exceptional corner condo, where elevated city living meets an extraordinary outdoor lifestyle. Meticulously maintained and bathed in natural light from southern exposure, this sophisticated split two-bedroom residence offers two private outdoor spaces, including an impressive 500-square-foot private rooftop deck with newly installed Trex decking and stunning Chicago skyline views. The rooftop is equally suited for entertaining, relaxing, or working from home (WiFi access point ready). Inside, the thoughtfully designed floor plan showcases beautiful hardwood floors, detailed moldings, custom designer lighting, smart-home technology, and a cozy gas fireplace. The sun-filled living room opens directly to a second private deck, also refinished with Trex decking-an inviting retreat for morning coffee or evening cocktails. The chef's kitchen is designed for both everyday living and entertaining, featuring stainless-steel appliances, striking 42-inch white milled cabinetry, durable soapstone countertops, generous prep space, an oversized breakfast bar, and a large walk-in pantry. The serene primary suite easily accommodates a king-size bed, two nightstands, and additional furnishings, while the professionally organized walk-in closet provides exceptional storage. The spa-inspired primary bath features an oversized stone shower, deep soaking tub, dual undermount-sink vanity, and abundant storage. The spacious second bedroom offers an organized closet and is complemented by a beautifully appointed full guest bath with an oversized standing shower. Additional highlights include in-unit washer/dryer and a dedicated parking space equipped with a newly installed Level 2 EV charger. Set within a full-brick building, this exceptional home offers both timeless quality and modern convenience. Ideally located in the sought-after Montrose Harbor/Buena Park neighborhood, enjoy easy access to Lake Michigan, Montrose Beach, the park, off-leash dog park, running and biking paths, and the newly proposed Trader Joe's. Convenient transportation options include Lake Shore Drive, the Wilson Red Line station, and express bus service. An abundance of neighborhood coffee shops, restaurants, pubs, gyms, theaters, Target, and Jewel are all close by. An exceptional home offering private rooftop living, refined interiors, and an enviable location just steps from the lake. Welcome home!

927 W Agatite Avenue Unit #3S, Chicago

1321 W Winnemac Avenue Unit #2E, Chicago
$599,900
2 Beds ⋅ 2 Baths ⋅ 12766694 MLS
Welcome to this gorgeous Andersonville 2 bedroom + office, 2 bathroom condo that is beautifully maintained and truly move-in ready! Located in a classic vintage Chicago building that was gut-rehabbed in 2006, this home blends timeless character with high-quality modern finishes throughout. The spacious open floor plan is ideal for both everyday living and entertaining, featuring a large living room with a gas fireplace framed by custom built-ins. Elegant details throughout include coffered ceilings, exposed brick, and beautiful hardwood floors. The bright and inviting sunroom provides an additional living space with walls of windows offering abundant natural light and beautiful treetop views. The well-appointed kitchen features 42" wood cabinetry, upgraded stainless steel appliances, and generous counter space. The spacious primary suite offers a gorgeous en-suite bathroom with a deep soaking tub, separate shower, dual vanities & radiant heated flooring. A standout feature of this home is the dedicated built-in office, thoughtfully designed to maximize space and filled with natural light from patio doors that open directly to your private deck-perfect for working from home or enjoying a quiet morning outdoors. A separate laundry room and pantry provide excellent additional storage and garage parking is included in the price. Enjoy everything Andersonville has to offer right outside your door with an incredible selection of restaurants, shopping, nightlife and entertainment nearby - including Bar Roma, The Magic Lounge, Hopleaf, Tala House and countless other neighborhood favorites. You're also just minutes from the restaurants and shops along Argyle Street. Convenient access to public transportation, including the Red Line and the Metra, makes commuting easy, while the lakefront, parks, beaches and miles of walking and biking trails are less than a mile away. Beautifully updated, thoughtfully designed and surrounded by everything that makes Andersonville special-this is a home that truly has it all!

1321 W Winnemac Avenue Unit #2E, Chicago

5055 N Clark Street Unit #2S, Chicago
$599,000
2 Beds ⋅ 2 Baths ⋅ 12733138 MLS
Stunning Extra-Wide 2BR/2BA Condo in the Heart of Andersonville. Set in an all brick-and-limestone boutique building, this unit includes a SPACIOUS, OVERSIZED and SEPARATE 1.5 car garage (18.5 ft. W X 19 ft. D X 12.67 H) with abundant storage located inside the building. Move right into this mint-condition, condo offering 1,500 square feet of meticulously maintained open living space. Every detail has been thoughtfully considered - from the high ceilings and oversized windows to the upgraded lighting that fills the combined living/dining area with warmth and light. The chef's kitchen was remodeled in 2017 with painted cabinetry, quartz countertops, an extended island, new backsplash, and new sink, complemented by a newer refrigerator (2020) and stove (2017). Also refreshed in 2017: refinished/stained floors, freshly painted walls, a custom living room built-in, and a stylish fireplace wrap - giving the whole home a cohesive, move-in-ready feel. Retreat to the private primary suite, complete with a spacious walk-in closet and a hotel-caliber marble bath boasting a double vanity, jacuzzi tub, and separate shower. Major systems have been thoughtfully maintained, including a newer condenser, evaporator coil & refrigerant (2017) and water heater (2018), plus a washer/dryer replaced in 2023 - offering real peace of mind for the next owner. The location can't be beat - steps from Clark Street's best dining, shopping, and entertainment, with easy access to the Red Line, Metra, the lake, bike trail, and beach.

5055 N Clark Street Unit #2S, Chicago

823 W Lakeside Place Unit #3E, Chicago
$520,000
3 Beds ⋅ 2 Baths ⋅ 12720695 MLS
Timeless vintage architecture meets refined modern living in this exceptional top-floor residence, nestled on a picturesque tree-lined street just a half block from the lake. Set within an intimate six-unit greystone dating to the early 1900s, this sun-drenched home showcases the craftsmanship vintage enthusiasts cherish, including original millwork, cove moldings, soaring 10-foot ceilings, five-panel wood doors, decorative mantels, coffered dining room ceilings, custom radiator covers, original honeycomb tile, a classic clawfoot tub, and two fireplaces. Offering exceptional flexibility, the expansive 3-bedroom, 2-bath floor plan can easily accommodate a fourth bedroom, home office, or additional living space. Modern updates include SpacePak central air (2021), Bosch in-unit laundry, radiant heat, private storage, and a covered deck perfect for outdoor entertaining. A garage parking space is included. Located in a meticulously maintained, 100% owner-occupied building with a strong association (no rentals permitted), this rare residence offers the perfect blend of historic elegance and contemporary comfort just moments from the lakefront, beaches, neighborhood dining, and all that Uptown has to offer-including the highly anticipated Trader Joe's coming soon. Cat-friendly building. Welcome home!

823 W Lakeside Place Unit #3E, Chicago

4925 N Glenwood Avenue Unit #3E, Chicago
$430,000
2 Beds ⋅ 2 Baths ⋅ 12738026 MLS
Welcome home to a truly special Andersonville residence where classic Chicago character meets contemporary style. This beautifully designed 2-bedroom, 2-bathroom condo offers thoughtfully arranged living space with soaring ceilings, warm hardwood floors, abundant natural light, and distinctive architectural details throughout.The spacious living room is the heart of the home, offering an open and inviting setting for both everyday living and entertaining. A charming sunroom extends from the living space, creating a versatile spot for morning coffee, a reading nook, or home office while overlooking the quiet treelined street.The separate dining room makes a statement with its dramatic exposed brick wall, adding warmth and authentic Chicago character. Large windows and hardwood floors complement the space, while the adjacent kitchen keeps cooking and entertaining effortlessly connected. Both bedrooms are generously sized, with the primary bedroom offering a comfortable retreat and the second bedroom providing flexibility for guests, a home office, or additional living space. Two full bathrooms add convenience and functionality. An expansive outdoor deck extends the living space and provides an ideal setting for dining, entertaining, or relaxing. Combined with the home's spacious rooms, sunroom, exposed brick, and thoughtful layout, this home offers the charm of a vintage Chicago condo with both comfort and functionality. Ideally located in Andersonville, one of Chicago's most sought-after North Side neighborhoods, you'll be surrounded by an exceptional selection of restaurants, cafes, boutiques, entertainment, parks, and everyday conveniences, with easy access to public transportation and everything the North Side has to offer.

4925 N Glenwood Avenue Unit #3E, Chicago

810 W Lakeside Place Unit #107, Chicago
$299,900
2 Beds ⋅ 1 Baths ⋅ 12753511 MLS
This beautiful courtyard building featuring a two bed, one bath condo is just steps from the lakefront and Montrose harbor. With an open floor plan, hardwood floors throughout and an outdoor deck space, this home is not to be missed. Each room provides ample closet space, the bathroom is updated and the living room features an electric fireplace. The building includes: two laundry rooms, a community exercise room, storage locker (#24) and nearby parking garages. In unit laundry cannot be added. Rentals and pets ARE welcome! (Unit is currently rented through April 30, 2027. Current rent is $2,100. Good tenants, great investment opportunity.) Parking available at Wise Memorial Garage, $150 per month and daily rates as well.

810 W Lakeside Place Unit #107, Chicago

918 W Sunnyside Avenue Unit #1B, Chicago
$285,000
2 Beds ⋅ 1 Baths ⋅ 12753202 MLS
****Highest and Best Due by 7pm Sunday Sept. 13th****Rarely Available Uptown condo!!! Chicago living at it's best in this sun-soaked 2 bed / 1 bath condo, perfectly placed on a quiet tree-lined street in the heart of Uptown. Fully updated in 2022, this vacant, move-in-ready home combines modern style, cozy vibes, and city energy all in one smart space. 2022 Renovation - fresh finishes, updated kitchen + bath Natural Light Goals - huge windows, airy layout Hardwood Floors - sleek, clean, and easy to style Stainless Steel Appliances - modern + functional A+ Location - walk to the lake, CTA, gym, groceries, bars, & brunch Tree-Lined Street Feels - peaceful block, urban access First-Floor Walk-Up - easy in, easy out (no endless stairs!) Whether you're nesting or investing, this Uptown condo is the best deal in the building and ready for its next owner. Schedule your showing today - opportunities at this price move fast!

918 W Sunnyside Avenue Unit #1B, Chicago

1258 W Winona Street Unit #4B, Chicago
$225,000
1 Beds ⋅ 1 Baths ⋅ 12763794 MLS
BEST AND FINAL DUE MONDAY AT 3PM. - Recently rehabbed Andersonville 1 Bedroom Penthouse on a tree-lined one-way street. East-facing light-filled home with modern open floor plan with generous room dimensions and vintage charm. Open kitchen with beautiful cherry cabinets, granite countertops, and stainless steel appliances. Marble bathroom, private deck off living room, common deck off kitchen, in-unit washer and dryer, and large extra storage room. 7 min walk to public transit and blocks away from everything Andersonville has to offer. Street parking and off-site rental options are available. Roof recoated in 2025, new butterfly entrance system, furnace and AC from 2024, laundry 2021. HOA 287. Tax 4036.30. Built in 1927 and fully gutted in 2004. Rentals allowed-rental cap of 4 units-currently 3 rented. Must live in the unit for 1 year before renting. 40k in reserves - no specials planned

1258 W Winona Street Unit #4B, Chicago



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