Cook County · Illinois

Homes for sale in Crestwood.

There are 26 homes for sale in Crestwood right now, with a median list price of $307,450. Every active listing below updates live from the MLS.

homes for sale

$307K

median list price

$183

median price / sq ft

123 days

avg. days on market

How the Crestwood market is moving.

Closed MLS sales — last 12 months.

178 homes closed in Crestwood over the last 12 months. Updated continuously from the MLS.

Active listings in Crestwood.

See all 26 homes →

5343 Waterbury Court #2403, Crestwood, IL 60418

Active New 📸 21

$169,900

2 bd · 1 ba · — sqft

5343 Waterbury Court #2403

Crestwood, IL 60418

Active New 📸 21

$279,900

3 bd · 1 ba · 1,650 sqft

3904 W 137th Street

Crestwood, IL 60418

Active 📸 32

$350,000

4 bd · 1.5 ba · 1,471 sqft

5428 138th Street

Crestwood, IL 60418

Active 📸 23

$170,000

2 bd · 1 ba · 1,000 sqft

14016 Waterbury Drive #1404

Crestwood, IL 60418

Active

$149,900

2 bd · 1 ba · 950 sqft

12809 Carriage Lane #12

Crestwood, IL 60418

Active 📸 22

$149,900

2 bd · 1 ba · 1,052 sqft

5701 129th Street #2D

Crestwood, IL 60418

Active

$200,000

2 bd · 2 ba · 1,154 sqft

5025 139th Place #512

Crestwood, IL 60418

Active

$167,000

2 bd · 1 ba · — sqft

5739 129th Street #1B

Crestwood, IL 60418

About the Crestwood market.

Crestwood is one of the communities dwello Home Group covers across Cook County and the broader Chicago and Northwest Indiana market. The listings on this page are pulled live from the MLS and refreshed continuously, so what you see is what's genuinely available right now.

Whether you're buying your first home, moving up, or selling, a local dwello agent can give you a real read on Crestwood — pricing, neighborhoods, schools, and how fast homes are actually moving. Reach out any time; there's no pressure and no obligation.

Browse Crestwood by property type.

Houses

Single-family homes

Townhomes & Condos

Attached + low-maintenance

Nearby areas.

Chicago 8782 Evanston 217 Des Plaines 216 Orland Park 201 Schaumburg 194 Calumet City 181 Oak Lawn 166 Palatine 164

Crestwood real estate questions.

How many homes are for sale in Crestwood, IL?

As of May 2026, there are 26 active listings in Crestwood, Illinois, plus 26 more under contract. The listings on this page update straight from the MLS, so they reflect current inventory.

What is the median home price in Crestwood?

The median list price of active homes in Crestwood is currently $307,450, or roughly $183 per square foot. Prices vary widely by neighborhood, size, and condition — browse the active listings above for live pricing.

Does dwello Home Group serve Crestwood?

Yes. dwello Home Group is based in Chicago's south suburbs and Northwest Indiana and works with buyers and sellers across the wider region, including Crestwood. Get in touch and we'll connect you with the right agent.

How fast do homes sell in Crestwood?

Active listings in Crestwood have been on the market an average of 123 days. 32 homes have closed there in the last 90 days. Well-priced homes in good condition tend to move noticeably faster than average.

How do I schedule a showing in Crestwood?

Open any listing on this page and use the "Schedule a showing" button, or contact dwello Home Group directly. A local agent will set up the tour and walk you through every step — financing, offers, inspections, and closing.

Thinking about Crestwood?

Tour a home, get a straight answer on pricing, or just ask a question. A local dwello agent is ready when you are.

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