View All Jefferson Park Chicago IL STR Income Homes Listings

$399,000
2 Beds 3 Baths 12735325 MLS CONTINGENT Status
MULTIPLE OFFERS RECEIVED - HIGHEST AND BEST BY 8/28, 2PM; MOVE-IN READY, classic charm meets modern! If you want a completely redesigned home, this one is not to miss! Remodeled just three years ago, this Jefferson Park/Gladstone Park property sits on an extra wide 70 ft corner Chicago lot, offering more outdoor space, more privacy, and a layout that lives larger than expected. With an open concept main level, updated finishes throughout, and three levels of flexible living space, this home is an ideal fit for buyers moving up from a condo or apartment, downsizers seeking comfort without sacrificing space, or investors looking for a strong rental or Airbnb opportunity. Step inside to a bright, seamless main floor with refinished hardwood floors that feel so satisfying to walk on, updated modern lighting, and an airy flow between living, dining, and the remodeled kitchen. The kitchen features two-tone soft close shaker cabinetry, quartz counters, Frigidaire stainless appliances, and a cook's dream pot filler-perfect for everyday meals or weekend entertaining. A convenient half bath on the main level adds comfort for guests and flexible living. Upstairs, you'll find two comfortable bedrooms and an updated full marble bath with modern finishes and smart mirros. The finished lower level creates a full second living zone with a family room, full bath, and a wet bar with undermount refrigerator-ideal for game nights, extended stay guests, or a teen retreat. The generous layout also offers flexibility for a true third bedroom if desired, giving buyers even more options for guests, extended family, or private living quarters. With its privacy and amenities, the lower level also offers appealing potential for Airbnb or short-term rental income. Outside, enjoy a peaceful yard with mature peach, apple, and fig trees, a charming garlic patch, and thoughtful perennial plantings that add beauty without demanding heavy maintenance. And with a flat water bill, that is right, no water meter. You can water as much as you like-perfect for gardeners, hobby growers, or anyone who loves a lush outdoor space. The covered front porch offers a quiet spot to unwind and enjoy the neighborhood. Parking is easy and convenient thanks to a dedicated parking pad off the alley, with an alley approach that feels like your own private driveway-and plenty of street parking for visitors. And for buyers considering future expansion, the extra-wide lot offers the potential to add a garage if desired. Located moments from parks, schools, local shops, the 22 min walk to the Blue Line, Metra, and 90/94, this turnkey home blends modern updates, flexible space, and a welcoming layout in one of the Northwest Side's most beloved neighborhoods. Get ready to move in and start making cherished memories.

5150 N Moody Avenue, Chicago

$210,000
1 Beds 1 Baths 12606675 MLS CLOSED Status
* Check out the video & the 3D walk-through of this home * Stunning & cozy 1 bedroom, 1 bathroom top-floor condo in desirable JEFFERSON PARK location! This remodeled 2nd-floor condo overlooks the tree-lined street and has the perfect mix of vintage charm & modern updates. This one-bedroom unit is not your traditional small unit; it's the size of a two-bedroom unit. Step into this unit and enjoy the extra-wide, open living room with hardwood floors throughout & large southwest-facing windows that bring in lots of natural light. Condo living at its best, with a brand new kitchen featuring stainless steel appliances, timeless shaker-style cabinetry, backsplash with custom tilework, granite countertops, breakfast bar, and a charming private deck off the separate dining room that is perfect for grilling, relaxing, entertaining, or watching your plants grow. The remodeled bathroom features a modern look, high-quality finishes, and a large shower with custom tilework. Generously sized primary bedroom with ample closet space and gets great light. The unit has ample storage, plus an additional large private storage closet, a common laundry room, and a bike room in the basement. Completely remodeled in 2025, this impeccable home features meticulous attention to detail. Recent updates include: new kitchen cabinets, countertops, backsplash, hardware, and appliances (2025), new bathroom remodel, tile, shower glass, toilet, plumbing fixtures, vanity, and mirror (2025), new paint throughout the unit (2025), new fans and light fixtures (2025), refinished hardwood floors (2025). Please ask your agent for the full list of improvements to the unit and the building. Low HOA assessment of $285 per month includes heat, water, hot water, common insurance, exterior maintenance, lawn care, garbage, & snow removal. Easy permit street parking. Proactive association with approx. $13,786 in reserves. Converted to condos in 2001. All BRICK building. 8 total units, 6 owner-occupied, 2 rentals. Rentals allowed (Owner must occupy the unit for 12 months prior to renting. No short-term rentals). Cats & dogs allowed (No breed or weight restrictions. No pets allowed for renters). Fall in love with all Jefferson Park offers - Easy access to transit (Blue Line, Metra, & bus stops), 90/94 expressway, popular restaurants/bars/retail, coffee shops, and green space. Welcome home! MULTIPLE OFFERS RECEIVED. Please submit highest & best by Monday 04/06 @ 11 am.

4941 N Lester Avenue Unit #4, Chicago

$585,000
5 Beds 3 Baths 11905478 MLS CLOSED Status
Incredibly well maintained and updated by long term owner! Spacious two apartments plus full finished basement with additional kitchen, bath and rec room. Main floor unit features 3 large bedrooms, beautiful octagon front room, formal dining, extra den/office , and cute kitchen with custom cabinetry, new fridge, and brand new flooring! It is occupied by same (16+ years) tenants who are willing to stay under new ownership. Upper second floor unit is owner occupied and simply meticulous! Features eat in updated kitchen with 42 " cabinets, granite countertops, expanded pantry/"butler's closet" in enclosed porch, white doors and trims and refinished hardwood floors throughout! Building has double pane vinyl windows throughout and updated just recently all 3 water heaters. NEW roof on the house and garage in 2022. Back staircase recently renovated freshly repainted, and new door installed to tenant's unit. Nicely organized laundry in the basement with 2 sets of full size washers & dryers. Separate utilities gas, water, electric meters for all 3 levels are conveniently located in spacious utility room. Detached 2 cars solid brick garage and nice patio, fenced in backyard, and garden to sit & relax completes the picture here! This is perfect property for live in owner or for stable investment with positive cash flow. Such a solid home in fantastic location just where Jefferson Pk & Forest Glen meet with walk-able short distance to Forest Glen METRA Station, Blue Line, Marianos, Sturbucks & more. Easy access to I90/94. Don't miss this one! Call for details & schedule your private showing today!

5221 N Lockwood Avenue, Chicago

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Jefferson Park, Chicago IL · Curated MLS Search

STR Income Homes in Jefferson Park, Chicago IL

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

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