Madeline Flanagan Real Estate Agent - @properties Christie's International Real Estate

916 Enfield Dr Unit 5A2, Northbrook, IL Pending $406,000 - co-listed by Madeline Flanagan — Pending $406,000 • Co-Listing Agent

Madeline Flanagan listing agent for 953 W Montana St Unit 3, Chicago, IL - sold for $940,000 — Sold $940,000

4939 N Damen Ave Unit 304, Chicago, IL For Sale $649,000 - listed by Madeline Flanagan — For Sale $649,000

Madeline Flanagan buyer's agent for 912 Burnham Ct, Glenview, IL - sold for $810,000 — Sold $810,000

830 Forest Ave Unit B, Evanston, IL For Sale $379,000 - listed by Madeline Flanagan — For Sale $379,000

Madeline Flanagan

Winnetka IL

@properties Christie's International Real Estate

24 Closed Sales

$32.5M Total Value

$345K - $4.7M Price Range

$1.4M Average Price

Prior 5 years

About Madeline

Maddie Flanagan brings nearly 20 years of real estate expertise and a boutique, client-first approach to Chicago and North Shore homes. A lifelong local with deep roots in Evanston and Lincoln Park, Maddie combines sharp market insight, standout marketing skills, and a passion for design to deliver seamless, high-touch service. Her background in wholesale sales and communications ensures every transaction is organized, strategic, and personalized—making her a trusted guide in every step of the buying or selling journey.

Home Types: House, Condo, Townhouse

Years of Experience: 6

Education: Miami University

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	5
Total Value	$8,870,000
Average Sale Price	$1,774,000
Price Range	$870K - $4.7M

Buyer Deals
Total Deals	1
Total Value	$810,000
Average Sale Price	$810,000

Seller Deals
Total Deals	8
Total Value	$13,195,000
Average Sale Price	$1,649,375
Price Range	$390K - $4.7M

Buyer Deals
Total Deals	2
Total Value	$1,155,000
Average Sale Price	$577,500
Price Range	$345K - $810K

Seller Deals
Total Deals	21
Total Value	$30,636,332
Average Sale Price	$1,458,873
Price Range	$350K - $4.7M

Buyer Deals
Total Deals	3
Total Value	$1,905,000
Average Sale Price	$635,000
Price Range	$345K - $810K

5 Year View

Areas Madeline is Experienced In

Madeline's Listings and Deals

Madeline's Active Listings

$649,000
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
4939 N Damen Ave

Unit 304

Chicago, IL
Experience elevated living in this beautifully designed 2-bedroom, 2-bath residence in a boutique elevator building in the heart of Ravenswood. Offering the perfect blend of luxury, convenience, and thoughtful design, this newer construction home features an open-concept floor plan with wide-plank oak hardwood floors, oversized windows that flood the space with natural light, and a stunning

Madeline Flanagan @properties Christie's International Real Estate

$379,000
- 1 Bed
- 1.5 Baths
- 1,400 Sq Ft
830 Forest Ave

Unit B

Evanston, IL
Beautifully updated and move-in ready, this charming residence offers the perfect blend of modern improvements and timeless appeal in a highly desirable Evanston location. This 1 bed + den, 1.5 bath has a functional floor plan that is filled with natural light and offers comfortable living for everyday enjoyment. Thoughtfully refreshed throughout, the current owner has completed numerous

Madeline Flanagan @properties Christie's International Real Estate

Co-Listing Agent

$406,000

Pending
- 2 Beds
- 2 Baths
916 Enfield Dr

Unit 5A2

Northbrook, IL
Located in the beautiful and quiet Northbrook Greens subdivision, this spacious and updated 2-bedroom, 2-bathroom unit with attached 1-car garage offers the perfect blend of comfort and convenience. This sun-filled home features an open floor plan with a living room that flows into the dining area and kitchen. The sleek kitchen offers newer cabinets and appliances. Both Bedrooms are generously

Madeline Flanagan @properties Christie's International Real Estate

Recently Sold

$940,000

Sold Aug 6, 2026
- 3 Beds
- 2 Baths
- 1,900 Sq Ft
953 W Montana St

Unit 3

Chicago, IL
- 3% Above List
- 13 Days On Market
- $495/SF
- Current Est. Value $906K
Madeline Flanagan @properties Christie's International Real Estate

$950,000

Sold Oct 6, 2025
- 5 Beds
- 3 Baths
- 2,800 Sq Ft
244 Elm St

Glenview, IL
- 3 Days On Market
- $339/SF
- Current Est. Value $1M
Madeline Flanagan @properties Christie's International Real Estate

$870,000

Sold Jul 31, 2025
- 3 Beds
- 3 Baths
- 2,097 Sq Ft
1415 Burr Oak Dr

Glenview, IL
- 5% Above List
- 6 Days On Market
- $415/SF
- Current Est. Value $1M
Madeline Flanagan @properties Christie's International Real Estate

$390,000

Sold Jun 25, 2025
- 2 Beds
- 2 Baths
- 1,169 Sq Ft
154 School St

Unit 202

Libertyville, IL
- 5% Below List
- 2 Days On Market
- $334/SF
- Current Est. Value $409K
Madeline Flanagan @properties Christie's International Real Estate

$635,000

Sold Apr 22, 2024
- 2 Beds
- 2.5 Baths
2251 N Wayne Ave

Unit A3

Chicago, IL
- 3% Above List
- 3 Days On Market
- Current Est. Value $715K
Madeline Flanagan @properties Christie's International Real Estate

$788,000

Sold Apr 1, 2024
- 3 Beds
- 2 Baths
1908 W Belmont Ave

Unit 3

Chicago, IL
- 1% Below List
- 3 Days On Market
- Current Est. Value $837K
Madeline Flanagan @properties Christie's International Real Estate

$650,000

Sold Dec 8, 2023
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
210 E Pearson St

Unit 7C

Chicago, IL
- 2 Days On Market
- $361/SF
- Current Est. Value $663K
Madeline Flanagan @properties Christie's International Real Estate

$415,000

Sold Sep 20, 2023
- 4 Beds
- 2.5 Baths
- 2,800 Sq Ft
435 Swan Ct

Deerfield, IL
- 2% Below List
- 5 Days On Market
- $148/SF
- Current Est. Value $444K
Madeline Flanagan @properties Christie's International Real Estate

$585,000

Sold Sep 27, 2021
- 2 Beds
- 2.5 Baths
- 1,800 Sq Ft
2315 W Wabansia Ave

Unit 3SW

Chicago, IL
- 2% Below List
- 7 Days On Market
- $325/SF
- Current Est. Value $742K
Madeline Flanagan @properties Christie's International Real Estate

Agent License: Illinois 475187852

Madeline Flanagan

(855) 941-4365

Nearby Homes

Madeline Flanagan

About Madeline

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Areas Madeline is Experienced In

Madeline's Listings and Deals

Madeline's Active Listings

Recently Sold