Paige Dooley, Broker - Compass

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United States
Winnetka, IL
Paige Dooley, Broker - Compass

Dynamic real estate professional with extensive marketing, sales, negotiation and service experience

Dynamic real estate professional with extensive marketing, sales, negotiation and service experience. A total "hands-on" broker capable of providing successful strategies for property marketing.

05/12/2026

📈 North Shore Q1 2026 Market Update
The numbers are in, and the North Shore is delivering. Strong buyer demand, rising median sale prices, and sellers consistently landing at — or above — their original list price.

If you’re thinking about your next move, this is the kind of market that rewards being prepared. Reach out and let’s discuss your options.

💬 Comment “REPORT” and I’ll send you the full Chicagoland Q1 2026 market breakdown.

05/06/2026

A privilege to bring this extraordinary piece of Winnetka history to market.

More to come — message me for early details.

Learn more about the new walking tour and homes built by William Aitken at

500 Maple, Winnetka

05/05/2026

Coming Soon • May 19th | East Winnetka

A timeless Georgian on the Village Green. Set on lush 0.4-acre grounds with sweeping views, this architecturally significant classic has been meticulously restored and thoughtfully expanded blending historic charm with modern luxury. Steps to town, train, beaches, and schools, with a private garden oasis all your own.

500 Maple St, Winnetka
5 BD | 3.2 BA

CO-LIST .compass

05/04/2026

Just listed in Winnetka — a rare opportunity on a half acre spanning three lots near the Indian Hill train.

This 1835 farmhouse was thoughtfully renovated in 2004 with a new kitchen, family room addition, finished basement, and more — all while preserving the original character that makes this home unforgettable.

The renovation brought the best of modern living — a chef’s kitchen with SubZero, Wolf, and Bosch appliances, a sun-drenched family room wrapped in windows, and a finished lower level with high ceilings and natural light. But the original details are what make you stop and stare: wide plank hardwood floors, a paneled library with an authentic fireplace, a curved staircase in the foyer. Four bedrooms, screened porch, stone patio with fire pit, heated attached garage, and a private fenced yard behind a circular drive.

Location. Space. Charm. Potential. It’s all here.

211 Church Rd, Winnetka | $1,750,000

Co-list .compass

05/03/2026

Broker Open and showings begin May 5. A rare opportunity: A bright and beautiful, historic 4+BR/3.1BA home spanning 3 lots near Indian Hill Train and several parks and schools! The 1/2 acre yard (149’ wide) surrounding the home creates a setting that feels truly expansive.

Well-cared-for home in one of Winnetka’s most desirable and walkable locations. A must-see opportunity to create something truly special.

211 Church Rd, Winnetka

Listed with .compass

05/02/2026

✨ Open House Sunday | 12–2 • 1040 Arbor Lane, Northfield $699,000
A rare offering in Meadowlake. This beautifully renovated townhome in New Trier pairs serene pond views with a freshly reimagined 2025 kitchen and two stunning new baths. Designed for the way you want to live!

Join us on Sunday!

Address

Winnetka, IL
60093

Website

https://www.compass.com/agents/chicago/paige-dooley/

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