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5 Beds ⋅ 3 Baths ⋅ 12683557 MLS ⋅ CLOSED Status

Classic Chicago charm meets an unbeatable Rogers Park location at 7529 N. Winchester. This handsome brick two-flat sits on an oversized lot and offers spacious layouts filled with vintage character, hardwood floors, and abundant natural light. A full basement provides additional living and storage space, while the detached garage and expansive backyard offer endless possibilities for entertaining, gardening, or relaxing outdoors. Nestled on a quiet tree-lined street, you'll enjoy easy access to parks, beaches, restaurants, shopping, and public transportation. Just minutes from Loyola University, downtown Evanston, and Lake Michigan, this is a fantastic opportunity for owner-occupants and investors alike. Experience the best of city living in one of Chicago's most vibrant and diverse neighborhoods. Roof (2021), Windows (2018), Back Porch Siding (2026), HWH (2022).

7529 N Winchester Avenue, Chicago

$225,000

2 Beds ⋅ 1 Baths ⋅ 12648850 MLS ⋅ RE-ACTIVATED Status

There's a lot to love about this 2 bedroom / 1 bathroom condo on the top floor of a charming brick building. You get the best of both worlds with classic Chicago architecture on the outside and modern finishes on the inside. The living room makes an impression with a tray ceiling, ceiling fan, gas fireplace, and a balcony that's perfect for morning coffee or winding down after work. Enjoy the real hardwood floors run throughout. With no unit above you, the sunlight is generous and the quiet is real. The kitchen is built for someone who actually cooks - black granite counters with plenty of prep space, cherry cabinets, and stainless appliances. A large second outdoor space off the kitchen is great for entertaining or getting some fresh air as you cook. A washer and dryer are tucked right into a closet, and additional storage in the basement means you'll never feel cramped. Both bedrooms are split and nearly equal in size, each with ample closet space - a layout that works whether you have a roommate, a home office, or just appreciate having room to breathe. The bathroom is a genuine retreat: a whirlpool tub, a window for natural light, and finishes that hold up well a full two decades after the building's interior gut renovation. Outside, you're on a quiet, tree-lined street in one of Chicago's most character-rich neighborhoods. Warren Park is close by for green space, the Rogers Park branch library is a short walk, and the Rogers Park Metra station on the UP-North Line is just two blocks away - putting downtown in under 30 minutes. The Clark Street bus adds a second transit option right at your doorstep.

7050 N Damen Avenue Unit #3S, Chicago

$378,000

3 Beds ⋅ 2 Baths ⋅ 12497781 MLS ⋅ CLOSED Status

Set on a quiet, tree-lined street in Rogers Park, this oversized three-bedroom, two-bath 1931 condo spans 1,900 square feet in an orange-rated, architecturally significant six-flat. Recognized in the Chicago Historic Resources Survey for its contribution to the city's built heritage, the building blends vintage character with thoughtful updates, offering generous room sizes, abundant natural light, and solid construction throughout. Original mosaic tile greets you in the foyer, leading into a gracious living room with hardwood floors and large north-facing windows. A decorative fireplace anchors the space, with original wood trim and built-ins adding warmth and detail. The formal dining room is full-scale and designed for entertaining. Just beyond, a charming butler's pantry includes a built-in breakfast nook and connects the dining room to a spacious, vintage kitchen with ample cabinet storage and workspace. The primary bedroom comfortably fits a king-sized bed and sitting area, while the second and third bedrooms offer flexibility for guests, work-from-home setups, or additional family members. Both full baths feature vintage tile and are in clean, well-preserved condition. Hardwood floors run through most of the home, with carpet in one of the bedrooms and ceramic tile in the foyer, kitchen, and pantry. Ornate light fixtures, wall sconces, and plaster walls add warmth and charm creating a cohesive, vintage character that reveals a subtle Spanish Revival influence. Additional features include generous closet space, private storage, in-building laundry, bike room, and a private single-car garage. Heat is included in the monthly assessment. The building is pet-friendly and self-managed. Close to the Red Line, bus routes, the lakefront, and neighborhood spots along Howard and Ridge, this home offers exceptional space and character in one of Chicago's most diverse and historic neighborhoods.

2109 W Jarvis Avenue Unit #1, Chicago

$700,000

3 Beds ⋅ 3 Baths ⋅ 12412647 MLS ⋅ CLOSED Status

Step into a piece of Rogers Park history with this beautifully preserved 3-bedroom, 2.5-bath Prairie Style home-once the residence of Howard Ure, for whom Howard Street was named. This two-story gem blends timeless charm with modern updates, offering the best of both worlds. From the moment you arrive, you're welcomed by a charming enclosed front porch-an inviting spot to enjoy your morning coffee. Inside, the bright and spacious layout is ideal for everyday living and entertaining. The living room features a generously sized footprint and a well-maintained wood-burning fireplace, perfect for cozy evenings. Original stained glass windows and hand-crafted built-in cabinetry in the dining room add warmth, character, and artistry to the home. The renovated kitchen is both stylish and functional, boasting granite countertops, stainless steel appliances, and beautiful wood cabinetry. Well-appointed mudroom/pantry features custom cabinetry, ample counter space, open shelving, and natural light. Conveniently located off the kitchen with direct access to the deck perfect for additional storage, prep space, or a coffee station. Upstairs, the primary suite offers a peaceful retreat with two walk-in closets, an updated bath, and an attached sunroom or office space. Two additional bedrooms share a hall bath and offer ample closet space-one even features a unique closet with stairs leading to a full-sized attic, perfect for storage or future expansion.The spacious basement includes a large open area, a separate cellar, and an additional half bath offering plenty of room for storage, hobbies, or future expansion. Outside, the magic continues with a huge backyard garden filled with mature perennials, a paver patio, and a deck creating a park-like setting ideal for gatherings, birdwatching, or quiet relaxation under gorgeous old trees. The fully fenced yard connects to the neighboring lot for an expansive, serene feel. Additional features include hardwood floors throughout, an insulated attic ready for finishing, a full basement, a two-car garage with extra parking, and close proximity to the lakefront. Enjoy easy access to the Metra, CTA, schools, shops, restaurants, and parks. This is a rare opportunity to own a piece of local history in one of Chicago's most vibrant and walkable neighborhoods. Don't miss it!

1525 W Birchwood Avenue, Chicago

$345,000

3 Beds ⋅ 2 Baths ⋅ 12290339 MLS ⋅ CLOSED Status

**BRING YOUR DESIGNERS** Welcome to this SPACIOUS Rogers Park 3 bed / 2 bath vintage! This well-built, classic vintage unit offers an impressive 1800 square feet of living space in an intimate, self-managed building on a quiet, tree-lined street. You won't find buildings like this anymore-this is truly a rare gem and a STEAL at such an affordable price! With its timeless charm and original architectural details this three-bedroom, two-bathroom condo is waiting for you to bring your vision to life and transform it into your dream home. The oversized living room features beautiful bay windows that flood the space with natural light, a decorative fireplace, and built-in bookshelves on either side-perfect for cozy gatherings or relaxing evenings. The separate dining room is ideal for hosting meals or entertaining, and the spacious kitchen is ready for your renovation ideas to make it the perfect space for your inner chef. Plus, with a deeded garage parking spot included in the price, convenience is a breeze! Rogers Park is not only rich in history but also in culture, with amazing restaurants, cafes, Loyola University, and excellent transportation options including the CTA and Metra just moments away. It's no wonder Rogers Park was recently named one of the TOP FIVE Best Neighborhoods to live in the country, and the top neighborhood to live in the Midwest! Don't miss out on this rare find!

6549 N Ashland Avenue Unit #2, Chicago

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