599 Greenleaf Ave, Glencoe, IL 60022
OFF MARKET

$2,654,500

Trulia Estimate
  • 5 Beds
  • 6 Baths
  • 5,000 sqft (on 0.35 acres)

599 Greenleaf Ave, Glencoe, IL 60022

Est. Refi. Payment $18,180/mo*
Refinance Your Home
Currently Off Market - Sold Sep 15, 2011 for $1,905,000

Home Value

Trulia Estimate
$2.65M
Since last month
Increased$51K (+2%)
Since last year
Increased$180K (+7.3%)
Since last sale
Increased$751K (+39.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +100% in the last 10 years
MonthEstimated value
2026
August 2026$2.66M
July 2026$2.6M
June 2026$2.61M
May 2026$2.71M
April 2026$2.57M
March 2026$2.54M
February 2026$2.48M
January 2026$2.44M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
540 Green Bay Rd, Glencoe, IL
0.22
Single-Family Home
$2,377,500
01/16/26
5
5.5
4,800
693 Greenwood Ave, Glencoe, IL
0.40
Single-Family Home
$1,900,000
10/10/25
6
4.5
5,258
677 Greenleaf Ave, Glencoe, IL
0.14
Single-Family Home
$3,230,000
04/17/26
5
6
7,785
670 Longwood Ave, Glencoe, IL
0.19
Single-Family Home
$2,220,000
11/03/25
5
4
2,793
260 Lincoln Dr, Glencoe, IL
0.42
Single-Family Home
$1,975,000
05/04/26
5
4.5
3,824
730 Longwood Ave, Glencoe, IL
0.30
Single-Family Home
$1,350,000
01/13/26
4
3.5
4,818
430 South Ave, Glencoe, IL
0.45
Single-Family Home
$2,200,000
07/17/26
6
6.5
5,636
244 Lincoln Dr, Glencoe, IL
0.42
Single-Family Home
$1,875,000
08/03/26
4
4.5
3,705
146 Beach Rd, Glencoe, IL
0.27
Single-Family Home
$2,350,000
07/22/26
5
4
3,642
343 Washington Ave, Glencoe, IL
0.34
Single-Family Home
$2,021,000
01/28/26
5
4.5
3,296

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
589 Greenleaf Ave, Glencoe, IL 60022
0.04
$4,143,800
6
6
5,000
Off Market
626 Greenleaf Ave, Glencoe, IL 60022
0.08
$2,039,200
4
3.5
3,253
Off Market
212 Hawthorn Ave, Glencoe, IL 60022
0.09
$3,239,400
5
4.5
5,473
Off Market
264 Cedar Ln, Glencoe, IL 60022
0.11
$1,556,000
3
3
2,409
Off Market
621 Sheridan Rd, Glencoe, IL 60022
0.11
$2,975,000
6
6.5
5,903
For Sale
555 Sheridan Rd, Glencoe, IL 60022
0.13
$4,019,200
5
6
7,982
Off Market
243 Hazel Ave, Glencoe, IL 60022
0.13
$3,282,000
4
3
3,123
Off Market
677 Greenleaf Ave, Glencoe, IL 60022
0.14
$3,230,000
5
6
7,785
Recently Sold
140 Hazel Ave, Glencoe, IL 60022
0.14
$2,957,700
5
5.5
6,019
Off Market
516 Sheridan Rd, Glencoe, IL 60022
0.17
$5,972,600
5
5.5
5,020
Off Market
535 Old Green Bay Rd, Glencoe, IL 60022
0.18
$2,486,400
5
6
6,000
Off Market
126 Hazel Ave, Glencoe, IL 60022
0.16
$4,423,000
6
5.5
7,434
Off Market

Local Information

  • Map ViewExplore the area around 599 Greenleaf Ave.
  • Schools1 Preschool School3 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1869
Lot Size
0.35 acres
Living Area
5,000 sqft
Price/Sqft
$531
Parking
Garage

About this House

     When a leading North Shore decorator purchases one of Glencoe’s original historic mansions, good things are bound to happen. Perfectly restored to its original grandeur capturing the charm of yesteryear, the current owners have added all of the modern amenities so sought-after in today’s new construction. Architecturally significant Italianante-style vintage details such as enchanting gables,  fluted pilasters and exquisite moldings and decorative trims blend seamlessly with extensive renovations including a gorgeous gourmet kitchen, sparkling new baths and expanded third floor to name only a few together combining to achieve the best of both worlds! Plus this estate is located on a glorious .8 acre of lush manicured grounds in a premier “Greenleaf Avenue” location only blocks to the sandy shores of Lake Michigan and to town and train. It just doesn’t get any better!     A magnificent veranda wraps around almost the entire home and gives guests the first glimpse of special things to come. Enter into the gracious foyer and be greeted by 11+’ ceilings, gracefully curved archways and oversized windows everywhere. Both the adjoining living room and main floor library have original decorative cast iron fireplaces modernized with gas logs and the library has custom floor-to-ceiling built-ins.     Entertain large parties with ease in the banquet-sized dining room. A third fireplace will add a soft warm glow to any gathering and hand painted trompe de l’oiel and faux wainscoted walls demonstrate just some of the innovative decorative touches seen throughout this remarkable home. And, with room enough for a grand piano in the beautiful bay, either extend the party to include yet more guests or enjoy gentle musical sonatas while dining!     Cooks will love the stunning kitchen. All white cabinets abound with granite counters and top stainless appliances. There is a center island as well as a built-in computer/planning station and all of this opens to the enormous breakfast room overlooking and opening to the spectacular back grounds. Nearby is the warm and inviting family room: richly-hued walls add to the ambiance and there is a wall filled with custom bookcases and entertainment center.     There are five spacious bedrooms on the upper levels, four having their own renovated baths. The fifth bedroom is located on the 3rd level which has a sitting area as well as a fully re-reconstructed bath emulating years gone by. The romantic master suite has yet another fireplace and has been modernized with a fantastic walk-in organized closet with built-in dressers nearby and a luxurious new marble bath with Jacuzzi and separate shower.          The lower level includes a recreation room, a play/computer area and an exercise room as well as numerous storage areas. There are front and back staircases and up and down laundries, one of which is located on the 3rd level with another hook-up available in the main level mud room.     The expansive acreage has been beautifully designed by well-known landscape architect Scott Byron. Along with mature trees and bushes there are English gardens filled with ever-blooming perennials, a boxwood-bordered blue-stone and curved brick patio area, a picket fence-enclosed vegetable garden area with arbor entrance, an underground sprinkling system and open lush yard perfect for croquet or a future swimming pool!     Recessed lighting as well as stunning original moldings and quarter-sawn oak hardwood floors are throughout. Archival wall and custom window coverings have been thoughtfully decorated to reflect the age of the home. Everything has been updated since the 1991–1992 restoration: new ele
599 Greenleaf Ave, Glencoe, IL 60022 is a 5 bedroom, 6 bathroom, 5,000 sqft single-family home built in 1869. It last sold for $1,905,000 on Sep 15, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,654,500, with a rent estimate of $5,021/month.

Home Details for 599 Greenleaf Ave

Interior Features

Levels, Entrance, & Accessibility
Stories: 2
Interior Details
Number of Rooms: 9

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Stone
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1869
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.35 acres

Price and Tax history

DateEventPrice
Oct 25, 2012
Source: Agent Provided
ListingRemoved
$2,250,000
Sep 14, 2012
Source: Agent Provided
Listed For Sale
$2,250,000
Sep 15, 2011
Source: MRED as distributed by MLS GRID #07799051
Sold
$1,905,000
May 7, 2011
Source: Agent Provided
Listed For Sale
$2,250,000

Market trends in Glencoe

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
40
1MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Glencoe

At least 51 Trulia users voted on each feature.

  • 98 % Say it's dog friendly

  • 91 % Say people would walk alone at night

  • 89 % Say there are sidewalks

  • 86 % Say yards are well-kept

  • 85 % Say kids play outside

  • 84 % Say there's holiday spirit

  • 82 % Say parking is easy

  • 82 % Say there's wildlife

  • 80 % Say it's walkable to restaurants

  • 76 % Say it's quiet

  • 76 % Say car is needed

  • 70 % Say streets are well-lit

  • 69 % Say they plan to stay for at least 5 years

  • 67 % Say neighbors are friendly

  • 65 % Say it's walkable to grocery stores

  • 60 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Leo.garcia.5251
    "The community puts together fantastic events for families during holidays and have their independent special events which cater to everyone’s wants and needs I’ve never felt more at home in this community. "
    1
    Flag
  • Cristinaisabelle
    "I live in this neighborhood. Some of the best year-round programs for kids as well as great schools. Also a family friendly town with many events to bring people together. "
    0
    Flag
  • Shert929
    "The schools here are great. Tariff Center offers something for everyone. There’s a few great grocery stores and you’re close to the beach. Most of all it’s a quiet and safe area to live in. And as a bonus, Glencoe is close to Ravinia to see concerts and near to Highland Park. "
    0
    Flag
  • mcsampson
    "Great schools, parks and kids activities. The park district offers day care, after school activities and various camps. Glencoe also has a beach! "
    0
    Flag
  • Shert929
    "Most places here are dog friendly accept for the condos. Plenty of places to walk a dog. Great community for pets and people. "
    0
    Flag
  • Ji
    "Lovely street, a lot of greenery, friendly neighbors. Walking distance to lake,town and train. Schools are terrific and beautiful parks for families and young children."
    0
    Flag
  • gladnowtravel
    "It is a small, tight-knit community with phenomal schools, negligent crime, a remarkably attentive police force, nearby train service, a large forest preserve, two golf courses and a nationally reknown botanical garden, all within blocks of expressway access to downtown Chicago or other suburbs."
    0
    Flag
  • Deborah B.
    "This is a lovely Community with old fashioned values. Jens Jensen Landscaping delight local parks. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 599 Greenleaf Ave

  • What is 599 Greenleaf Ave estimated to be worth?
    Trulia's estimated value for 599 Greenleaf Ave in Glencoe, IL is $2,654,500.
  • What is the price history for 599 Greenleaf Ave?
    599 Greenleaf Ave in Glencoe, IL last sold for $1,905,000 in September 2011.
  • Is Glencoe a buyer's or seller's market?
    Glencoe is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Glencoe?
    Residents describe Glencoe, IL as dog-friendly, pedestrian-friendly, and well-kept. See recently sold homes in Glencoe, IL.
  • How big is the lot at 599 Greenleaf Ave?
    The lot at 599 Greenleaf Ave in Glencoe, IL is about 0.35 acres (15,344 sq ft).
  • Does 599 Greenleaf Ave have a garage?
    Yes, 599 Greenleaf Ave in Glencoe, IL has a garage.

Explore by feature - Air Conditioning

6 rentals with air conditioning in Glencoe, IL

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Glencoe, IL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 599 Greenleaf Ave

Skip to last item
Skip to first item

Homes for sale near 599 Greenleaf Ave

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item