Circa 1908 Single-Family Home In Chicago, Illinois For $659,900

4028 W Waveland Ave, Chicago, IL 60641

$659,900 | 1908 | 5 Beds | 3 Baths | 4,662 Sq. Ft. Loot

Old Irving Park has long been one of Chicago’s quietest treasures, a neighborhood where tree-shaded streets, historic architecture, and a strong sense of community come together to create a truly timeless residential experience. Tucked within this beloved pocket of the city sits a remarkable single-family home that stands out not only for its charm, but for its thoughtful modern updates and the versatility of its layout. This beautifully maintained residence, built in 1908 and offering an in-law arrangement ideal for multi-generational living or flexible lifestyle needs, represents the perfect blend of vintage Chicago character and contemporary comfort. It is the kind of home that instantly communicates warmth, functionality, and longevity—qualities that make a real estate listing truly memorable, especially for buyers searching for a property that feels both established and truly move-in ready.

Approaching the house, the first thing that catches the eye is the extra-wide lot, a rare and valuable feature in this area. It allows for an openness around the property that creates breathing room, natural light, and a sense of privacy that is often difficult to achieve within the city limits. The calm, tree-lined street sets the tone before one even reaches the front steps: peaceful, residential, and deeply rooted in the history of Chicago’s neighborhood grid. Over its more than 100 years, the home has been updated with care, ensuring that the original character is preserved where it matters while today’s conveniences are seamlessly integrated. This property is not simply a house for sale—it is a home crafted to support modern lifestyles while remaining sensitive to the architectural language of its era.

Inside, the first floor offers two bedrooms and a full bathroom, creating an immediate sense of accessibility and practicality. Whether used for guests, family members, or flexible bonus rooms, these spaces add dimension to the home’s layout. The updated finishes and careful renovations throughout the home ensure that nothing feels dated or neglected, a significant advantage for any buyer hoping to avoid the extensive work often associated with homes from the early 1900s. The living areas feel open yet comfortable, with windows that draw in natural light and layouts that support everyday living as well as larger gatherings. The home’s updates do not overshadow its roots; instead, they highlight the craftsmanship of the past while providing the conveniences today’s buyers expect in real estate.

The kitchen and dining areas serve as key centers of the home, designed to accommodate the rhythm of daily routines while offering enough space to host, cook, and connect. Updated appliances, clean lines, and thoughtful storage options allow these areas to function efficiently without sacrificing style or warmth. Throughout the home, the finishes strike a balance between modernity and compatibility with the 1908 structure—an intentional choice that preserves the home’s charm while ensuring it feels current. The result is a property that stands out among the homes listed for sale in this part of Chicago, appealing to those who appreciate history but require a space equipped for contemporary life.

Climbing the stairs to the second level, the home expands into a more private living space featuring three additional bedrooms and two full bathrooms. Each room is comfortably sized, offering flexibility whether they become sleeping areas, offices, creative spaces, or whatever evolving lifestyle needs may require. The presence of two bathrooms on this floor significantly enhances convenience, especially for families or shared living arrangements. It’s an aspect of the home’s design that reflects a thoughtful understanding of modern living patterns, where personal space and accessibility are essential.

One of the rarest and most desirable features of this home is the presence of in-unit laundry on both the first and second floors, a luxury that dramatically simplifies daily routines. For families, multi-generational households, or occupants using the in-law arrangement, this detail offers meaningful independence and comfort. Many buyers looking through today’s real estate market understand the value of efficiency, and this home’s layout ensures that convenience is built directly into its structure. Combined with the updated electrical, plumbing, and interior finishes, the property brings the peace of mind that comes from knowing a house has been carefully prepared for long-term living.

The second-floor bedrooms also benefit from the quiet ambiance of the neighborhood. Old Irving Park has always been known for offering a small-town atmosphere within the city—a trait that continues to attract buyers searching for a home that feels restful without distancing them from the conveniences of Chicago. The property’s location provides walking and biking access to nearby parks, local dining, coffee shops, and the popular Disney II Magnet School, making it especially appealing to families prioritizing proximity to educational and recreational resources. With many homes for sale in Chicago emphasizing access to transit, shops, and outdoor spaces, this property stands out for providing all three without compromising the quiet residential charm that defines the neighborhood.

In addition to the primary living spaces, the property includes a spacious 2-car detached garage, offering storage, convenience, and protection from Chicago’s weather. The extra-wide lot enhances the overall sense of scale, creating outdoor options for gardening, relaxation, or simply enjoying the peaceful energy of the neighborhood. Whether for backyard gatherings, a play area, or personal hobbies, the space supports a variety of uses and allows the home to function as a private retreat from the busyness of city life.

Beyond the living space itself, the basement plays a meaningful role in extending the home’s versatility. With an in-law arrangement possible, the lower level becomes more than storage or mechanical systems—it transforms into an area for additional living, working, or recreational activities. Whether used as guest quarters, an office, a private suite, or a creative workspace, it provides the kind of flexible functionality that buyers increasingly prioritize when evaluating homes listed for sale. Being able to carve out distinct zones within a single property is a valuable advantage, especially in a bustling real estate market where adaptability is key.

The home’s location strengthens its value even further. Old Irving Park offers quick access to I-90/94, making commuting efficient whether you are heading downtown, to the suburbs, or beyond. Public transportation—including multiple bus routes and nearby CTA and Metra options—ensures freedom for those who prefer to move around Chicago without relying on a car. At the same time, the immediate surroundings maintain the tranquility of a residential district, ensuring that the property provides both convenience and calm. It’s a balance that many buyers seek but rarely find in the same home for sale.

Restaurants, bakeries, small businesses, and essential services are located just minutes away, creating a walkable lifestyle without sacrificing the feel of a neighborhood community. Whether grabbing breakfast at a local café, picking up groceries, or enjoying a weekend outing, residents have easy access to the essentials of daily life. The home’s connection to these amenities helps define it as more than a structure—it is part of a living, evolving neighborhood that supports a high quality of life.

Buyers today are more focused than ever on finding a home that supports their lifestyle not only today, but in the years to come. This property delivers on that promise through its thoughtful updates, generous layout, historic character, and exceptionally convenient location. It is a rare combination in the Chicago real estate market, especially at this price point. For anyone searching for a house for sale that blends charm, modern convenience, stability, and neighborhood appeal, this residence stands out as an exceptional opportunity. The presence of multiple bathrooms, updated mechanicals, two laundry areas, recent renovations, and a flexible in-law arrangement positions the property as a smart long-term investment as well as a welcoming and comfortable home from day one.

The home’s nearly 5-bedroom, 3-bathroom configuration allows it to adapt to changing life circumstances, whether accommodating a growing household, creating space for guests, supporting hybrid work arrangements, or establishing a private setup for additional family members. In today’s market, where flexibility has become one of the most sought-after qualities in residential real estate, this home offers it naturally. The craftsmanship of the early 1900s, paired with carefully curated modern updates, creates a feeling of solidity and reliability that newer builds sometimes struggle to match. It is a place built to last, with every renovation reinforcing its structural and aesthetic strengths rather than masking or replacing them.

As buyers navigate the homes listed in Chicago and beyond, many find themselves seeking the perfect balance: a home with character that does not require overwhelming renovation; a house with history that still feels fresh; a residence that is spacious but not excessive; a property rooted in a neighborhood with identity, walkability, and access to transportation. This home satisfies all of these criteria, offering a rare and compelling blend of qualities that make it a standout option among current real estate listings.

Whether for a family searching for more space, a buyer seeking multi-generational flexibility, or someone looking for a truly move-in-ready home with strong long-term value, this property offers an exceptional opportunity. At its core, it is a home filled with warmth, updated with intention, and situated in one of Chicago’s most beloved neighborhoods. For anyone exploring the homes for sale in Old Irving Park, this residence represents not only a beautiful house but a lifestyle defined by comfort, convenience, and community. A realtor showcasing this listing would undoubtedly emphasize its unique combination of historic charm and modern upgrades, making it a compelling choice in today’s competitive real estate landscape.

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