Woodlawn, Chicago IL · Curated MLS Search

Homes with Garden in Woodlawn, Chicago IL

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

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Woodlawn Market — Homes with Garden Comparison

Live MLS data — Woodlawn vs. Homes with Garden

Woodlawn

Homes with Garden

inventory

Active Listings

Sold (Past 6 Mo.)

Under Contract

pricing

Avg. List Price

$427,689

$898,994

Cost / Sq. Ft.

$207

$302

typical home

Living Area

1,723 ft²

1,979 ft²

Avg. Beds

4.0

5.5

Avg. Baths

3.0

Days on Market

142

Homes with Garden in Woodlawn: Market Data

Data as of October 20, 2026 (MLS snapshot; listings below update live)

Chicago Real Estate Source's review of MLS data as of October 20, 2026 shows 2 active listings for Woodlawn homes with garden. Listings like these do not come up often in Woodlawn. These listings made up about 3% of the 58 active listings in Woodlawn, across every property type. With so few listings, setting up a listing alert is the easiest way to learn of the next one.

Homes with Garden in Woodlawn, Chicago IL, October 20, 2026
Measure	Value
Active listings	2
All active listings in Woodlawn, every property type	58

Homes with Garden in other neighborhoods

Chicago: 50 active, median $583,500
Oak Lawn: 6 active
Logan Square: 4 active
West Ridge: 4 active
Arlington Heights: 3 active

Market questions

How many Woodlawn homes with garden are on the market?

There were 2 Woodlawn homes with garden for sale as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do Woodlawn homes with garden stack up against other neighborhoods?

As of October 20, 2026, there were 2 Woodlawn homes with garden for sale. In the same search, Chicago had 50 homes with garden for sale at a median list price of $583,500, Oak Lawn had 6 homes with garden for sale and Logan Square had 4 homes with garden for sale.

How do Woodlawn homes with garden compare with all active listings in Woodlawn?

As of October 20, 2026, there were 2 Woodlawn homes with garden for sale, out of 58 active listings in Woodlawn across every property type.

Listing data courtesy of Midwest Real Estate Data LLC.

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View All Woodlawn Chicago IL Homes with Garden Listings

$599,000

3 Beds ⋅ 2 Baths ⋅ 12746760 MLS ⋅ ACTIVE Status

COUNTRY HOME & FARM PROPERTY ON 10+ ACRES! Discover a truly unique property offering over 10 acres of fenced and thoughtfully used land, ideal for livestock, horses, gardening, and those looking to embrace a self-sufficient country lifestyle. The spacious home features 3 bedrooms and 2 baths, an updated kitchen with new appliances, a large master suite with a balcony plus new skylights including automatic shade openers . A brand-new roof adds peace of mind, while the attached 2-car garage, pole barns and fenced backyard provide additional convenience and storage. The property is fully fenced and designed for livestock, with multiple pastures and pens ready for continued agricultural use. The large, fully stocked pond features three aerating fountains, two docks and has recently been riprapped around the perimeter, providing a wonderful recreational setting while enhancing the pond's shoreline. Plus a waterfowl-duck building just off the large pond. A second smaller pond is conveniently located near the large garden area and is used for watering the gardens adding another unique feature to this exceptional property. Multiple barns and outbuildings provide abundant space for tractors, equipment, livestock supplies, feed, storage, and more. An additional Harvest Station building, constructed in 2018, is equipped with water and electricity, offering a versatile space for agricultural, gardening, or homestead needs. The current owner has lived off the land for the past 3 decades and has continually improved the property, including adding new fence posts, electric fencing, automatic feeders, and other improvements designed to make homesteading easier. Much of what you need to continue raising livestock, waterfowl or horses, and enjoying a country lifestyle is already in place. Whether you're looking to continue the existing livestock operation, raise horses, grow your own food, or simply enjoy the privacy and freedom of country living, this property offers an incredible opportunity. Established homesteads with this level of infrastructure, acreage, ponds, barns, fencing, and improvements are truly hard to find.

5378 E Houston Road, Woodlawn

$1,198,988

8 Beds ⋅ 4 Baths ⋅ 12749117 MLS ⋅ ACTIVE Status

This beautiful, rare, and meticulously maintained vintage greystone is a fantastic, solid investment opportunity and an investor's dream! An ideal turnkey operation, it features two 3BR rentals plus a fully-furnished, top-rated, 2BR Airbnb, allowing several options for the buyer: enjoy income from the popular Airbnb and the fully-rented units; reside in a unit (or two) and reduce your mortgage payments through value-added rentals; or transform the entire building into your single family dream home! This spacious and sun-drenched beauty retains its vintage charm with 10' ceilings, hardwood floors, huge double hung windows, built-ins, and some original moldings. The main level 3BR, 1 bath features a wood burning fireplace with built-in mantel and bookshelves, full kitchen, in-unit W/D hookup, and window blinds. The second level 3BR, 1.5 bath was fully rehabbed in late 2019 with all new kitchen and baths, refinished floors, new in-unit W/D, built-out closets, new light fixtures, new wood blinds, new HVAC. The open plan, inviting 2BR, 1 bath, garden-level Airbnb (since July, 2018) with private entrance is fully furnished and has all the extra amenities guests expect, making it a top-rated (4.9/5) destination with Superhost designation. First and second level units open onto private decks with newly-rebuilt and sealed back stairs, including easy access to the roof via pull-down stairs on the second level deck, plus 15' x 8' secured storage area under the stairs. The Airbnb opens out the private back door to a storage area featuring full-size washer and dryer, then into the huge, secure and private backyard. Enjoy a green, urban oasis with mature landscaping, two large patios, and path leading to the masonry 2.5 car garage with extra storage space above (or retain the current garage renter for the extra income). The new roof (7/2019) is fitted with 9.0 kW Roof Mount Solar PV Array solar panels, offsetting utility costs. The location is the icing on the cake! Just steps from the University of Chicago law school and the Renee Grossman Residential Commons, and a stone's throw from the Green Line and Jewel-Osco, this property offers community, connectivity, and convenience. Only 3/4 mile from Jackson Park, the transformative Obama Presidential Center, and the vibrant lakefront, this location offers investment stability and exciting growth potential. Schedule your private showing now!

6109 S Greenwood Avenue, Chicago

$425,000

9 Beds ⋅ 3 Baths ⋅ 12002885 MLS ⋅ CLOSED Status

Purchase this extremely rare, versatile, 2-unit building located 1/2 a block from the University of Chicago campus in the thriving Woodlawn community and use it as an excellent performing rental, airbnb or reclaim its status as a single family home. Your options are limitless! The building is composed of (one) 6 bed/2 bath (2 bedrooms on the main floor and 4 bedrooms on the 2nd floor) unit and (one) 3 bed/1 bath garden unit. There are a total of 9 bedrooms and 3 full bathrooms (1 full bathroom conveniently located on each floor). Each unit has a private entrance and there is a private backyard with a 1-car garage. There is also free laundry. With new construction all around, this is an investment you don't want to miss.

6115 S Drexel Avenue, Chicago

$385,900

8 Beds ⋅ 3 Baths ⋅ 11908620 MLS ⋅ CLOSED Status

Introducing this exceptional 2 flat Graystone with Garden unit, composed of a 4 bed/1 bath on 2nd floor, 3 bed/1 bath on main floor and a 1 bed/1 bath garden. Each unit features a private entrance to the residence and a beautiful fully fenced in backyard perfect for relaxing & enjoying the outdoors or ample entertaining space. With updated and extremely spacious units, every level can enjoy hardwood floors, high ceilings, abundance of natural light, and potential to have a home office, fitness room, guest room, art studio, game room, craft room...the possibilities are endless! This property presents an incredible investment opportunity (projected rent of $1,000+ for the 1st and 2nd floor units and $875+ for the Garden unit) while tenants can enjoy everything Woodlawn and Hyde Park have to offer. Or seamlessly blend owner occupant convenience, income generating potential, and equity building for the future! Perfectly located along the developing 63rd Street corridor, walking distance to The University of Chicago and The Obama Presidential Library, nearby gorgeous Lake Michigan & beaches including Jackson Park Harbor, Downtown Chicago, CTA and Metra stations, expressways, shopping, restaurants, entertainment, and museums! Detached 2 car garage and permitted street parking are available.

6147 S Drexel Avenue, Chicago

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