Kenwood, Chicago IL · Curated MLS Search

Homes with Guest House in Kenwood, Chicago IL

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

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Kenwood Market — Homes with Guest House Comparison

Live MLS data — Kenwood vs. Homes with Guest House

Kenwood
Homes with Guest House
inventory
Active Listings
29
1
Sold (Past 6 Mo.)
33
0
Under Contract
4
0
pricing
Avg. List Price
$1,048,934
$1,675,000
Cost / Sq. Ft.
$239
$558
typical home
Living Area
2,863 ft²
3,000 ft²
Avg. Beds
3.7
4.0
Avg. Baths
3.1
4.0
Days on Market
76
39

Homes with Guest House in Kenwood: Market Data

Data as of (MLS snapshot; listings below update live)

As of October 20, 2026, Chicago Real Estate Source's review of MLS data shows 1 active listing for Kenwood homes with guest house. Listings like these do not come up often in Kenwood. That is about 3% of the 29 active listings in Kenwood across every property type. In a market this small, a listing alert is the most reliable way to hear about the next one.

Homes with Guest House in Kenwood, Chicago IL, October 20, 2026
MeasureValue
Active listings1
All active listings in Kenwood, every property type29

Homes with Guest House in other neighborhoods

Market questions

How many Kenwood homes with guest house are on the market?

There was 1 active listing for Kenwood homes with guest house as of October 20, 2026, based on Chicago Real Estate Source's review of MLS data.

How do Kenwood homes with guest house stack up against other neighborhoods?

As of October 20, 2026, there was 1 active listing for Kenwood homes with guest house. In the same search, Chicago had 22 homes with guest house for sale at a median list price of $600,000, Aurora had 3 homes with guest house for sale and Evanston had 2 homes with guest house for sale.

How do Kenwood homes with guest house compare with all active listings in Kenwood?

As of October 20, 2026, there was 1 active listing for Kenwood homes with guest house, out of 29 active listings in Kenwood across every property type.

Listing data courtesy of Midwest Real Estate Data LLC.

Next Steps in Kenwood, Chicago IL

View All Kenwood Chicago IL Homes with Guest House Listings

1203 E 50Th Street, Chicago
$1,675,000
4 Beds ⋅ 4 Baths ⋅ 12711971 MLS ⋅ ACTIVE Status
Designed by renowned modernist architect Tony M. Grunsfeld, this mid-century gem highlights architect's love for clean lines, minimalist design and above all, natural flow from inside to the outside world. This house built in 1965, has been recently fully renovated. When entering the house one is immediately drawn to the expansive living room with its' three floor-to-ceiling double glass doors that open the space onto a lush, oversized backyard full of blooming flowers. Spacious chef's kitchen, features lots of counter space and storage, beautiful cabinets and high end appliances . This delightful space is flooded with light from a set of floor-to-ceiling glass doors and opening to the light filled living room. First level features also an office/guest bedroom and a half bath. Four spacious bedrooms are all located on the second floor. Primary bedroom has en-suite bathroom with double sink and two large walk-in closets. Additional two bedrooms and one office (originally a bedroom) share a beautiful bathroom with a bathtub. Comfortable family room and a gym are located in the basement. In addition, there is a large storage space, mechanical area and laundry as well as additional half bath on the lower level. All wooden floors are oak, while the entry hall floor is covered with stone ties. This is a unique home with simple beauty, inviting, light filed space and a very comfortable interior. Recent major updates: HVAC system 2022, new sewer line to the street, direct vent gas fireplace 2024.

1203 E 50Th Street, Chicago

1150 E 49Th Street, Chicago
$1,600,000
5 Beds ⋅ 5 Baths ⋅ 12421410 MLS ⋅ CLOSED Status
Custom renovation in Historic Kenwood! Sophisticated single-family home offers a perfect blend of mid-century charm and modern living. Large garden is a lovely oasis which includes a private pergola and formal dining area. Dine al fresco with family and friends using the large outdoor cooking area and expansive front yard. The home was completely reconstructed to the studs by the owner. The home features an open floor plan with intimate spaces filled with natural light and pre wired for entertainment through the house. Upon entering, you are welcomed by an elevated family room with a room-sized skylight, complemented by custom shelving and built-ins for both comfort and organization. This room boast floor-to-ceiling windows, creating a bright and airy atmosphere. The sunken living room features a vaulted ceiling, dual skylight, and modern double crystal chandeliers with pairing wall sconces. The dining room is adorned with a crystal chandelier and double archway doors. The room includes a built in custom wet bar and comfortably seats 12-14. Enjoy after-dinner wine or tea on the private enclosed patio. The sophisticated kitchen is a chef's dream, equipped with double ovens, microwave drawer, ample cabinetry, and a custom-designed built in armoire housing a Subzero refrigerator and pantry space. An oversized porcelain island and Wolf appliances complete this stunning culinary space, making it perfect for entertaining and cooking. On the second level, four of the five bedrooms are spacious and filled with natural light, with three featuring elegantly designed attached bathrooms. Custom closets are thoughtfully configured for optimal space usage. The primary bedroom is a standout, boasting a luxurious walk-in shower for two, a separate modern Victoria & Albert tub, a generous custom walk-in closet, and a private toilet room. The lower level offers 10-foot ceilings and contemporary spaces designed for relaxation and fun, including a game room, gym, guest bedroom, half bath, and a laundry room. Two attached heated garages provide convenient access from a gated, private entryway and heated driveway. A custom outdoor porch to patio perfect for outdoor cookouts, garden parties, and relaxation. Boasting white hydrangeas and other blooming flowers and trees all spring and summer long. Additional features include remotely operated skylights and custom door coverings, heated floors throughout, and numerous built-in custom closets for ample storage. This exquisite home seamlessly combines luxury and functionality, making it a must-see for discerning buyers.

1150 E 49Th Street, Chicago

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