View All Jefferson Park Chicago IL Homes with Rooftop Deck Listings

5759 N Elston Avenue, Chicago
$740,000
8 Beds ⋅ 5 Baths ⋅ 12796696 MLS ⋅ NEW Status
OVER $200,000 IN IMPROVEMENTS over the last three years! This is not a flip, just a well-managed and exceptionally improved opportunity in Jefferson Park featuring a legal 2-flat with a finished English garden unit. A rare find! Especially with BOTH upper units offering 3 bedrooms and 1.5 baths. Extensively updated in 2024-2025, this turnkey property delivers the space, condition, and income potential investors and owner-occupants are looking for. Both legal units feature spacious layouts, separate dining rooms, additional kitchen/dining areas, recessed lighting, and beautifully updated kitchens with quartz countertops, stainless steel appliances, and ample cabinetry. Updated bathrooms and modern finishes make these units stand out. The improvements go well beyond cosmetics, including a new roof, windows, gutters, tuckpointing, flooring, kitchens, bathrooms, and an upgraded rooftop deck over the garage-all completed in 2024-2025. Enjoy the benefits of substantial recent investment without the immediate expense of major renovations. The income is already working for you! Unit 1 is leased at $2,650/month, and Unit 2 at $2,400/month, generating $5,050/month or $60,600 annually in current gross rental income. The finished garden unit is currently vacant and offers 2 bedrooms and 1 full bath, presenting additional flexibility for an owner-occupant, extended household, or potential rental income, subject to applicable zoning, permits, and legal occupancy requirements. If approved for rental use, estimated rent of $2,300/month could bring potential gross income to $7,250/month or $87,000 annually. Explore the short-term rental opportunity! AirDNA market data provided by the seller indicates an average daily rate of $116 and 69% occupancy. At those market benchmarks, a qualifying short-term rental could generate approximately $29,200 in gross annual booking revenue for one unit. Combined with the existing leases, the property presents a potential gross revenue opportunity of approximately $89,800 annually, assuming the garden unit is legally approved for short-term rental use and achieves the stated market performance. Actual results will vary, and gross revenue excludes operating expenses. Additional features include rear decks, a rooftop deck over the 2-car garage, shared outdoor space, and coin-operated laundry. Enjoy convenient access to the Kennedy Expressway (I-90/I-94), O'Hare International Airport, and the Jefferson Park transportation hub, with CTA Blue Line and Metra connections. Nearby shopping and everyday conveniences include Jefferson Park Plaza, Gladstone Corners, Mariano's, and Jewel-Osco, along with neighborhood restaurants, cafes, parks, and local businesses.

5759 N Elston Avenue, Chicago

5317 N Nagle Avenue, Chicago
$595,000
4 Beds ⋅ 5 Baths ⋅ 12171501 MLS ⋅ CLOSED Status
Beautifully renovated, turnkey, 4-bedroom (currently used as a 5 bedroom)/4.1-bathroom single-family home that offers the perfect layout for multi-generational living, larger families, or generating rental income for the clever house hacker who wants to reduce their mortgage. The front of the house, built in 2010, features 3 spacious bedrooms, and 3 full baths, two of which are en-suite, while the back includes a private in-law/guest suite complete with a full kitchen, 1.1 bathroom, family room, and separate entrance. This space is ideal for extended family, guests, or a quiet work-from-home retreat. Recent updates include a new roof at the rear of the home, two modern kitchens with 42" shaker-style cabinets, sleek quartz countertops, stainless steel appliances, new bathrooms, refinished hardwood floors and more. The entire home has been freshly painted and boasts a new front porch and zoned HVAC for maximum comfort. Convenience is key with main-floor laundry, plus an additional laundry room in the basement where you will find an additional guest bedroom, gym, or office. The massive rooftop deck is perfect for entertaining. 2-car garage with overhead door. Easy access to the expressway and O'Hare, with Taft High School just a short few minute walk away. This home offers style, function, and the unique ability to lower your housing costs with this gorgeous 3-level setup that can evolve as your needs do.

5317 N Nagle Avenue, Chicago

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Jefferson Park, Chicago IL · Curated MLS Search

Homes with Rooftop Deck in Jefferson Park, Chicago IL

An editorially curated view of every active homes with rooftop deck listing in Jefferson Park, Chicago IL. Updated in real time from the local MLS, presented without the noise.

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