599 Greenleaf Ave, Glencoe, IL 60022
OFF MARKET

599 Greenleaf Ave
Glencoe, IL 60022

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

$2,651,600

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $18,062/mo*
Refinance Your Home

$2,651,600

Trulia Estimate
as of May 30, 2026
Est. Refi. Payment $18,062/mo*
Refinance Your Home
5 Beds
6 Baths
5,000 sqft
(on 0.35 acres)

Local Information

Map showing home location
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-- mins to
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Description

     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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
HOA
None
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Home Details for 599 Greenleaf Ave

Interior Features

Levels, Entrance, & Accessibility
Stories: 2

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 History for 599 Greenleaf Ave

DatePriceEventSource
10/25/2012$2,250,000ListingRemovedAgent Provided
09/14/2012$2,250,000Listed For SaleAgent Provided
09/15/2011$1,905,000Sold
MRED as distributed by MLS GRID #07799051
05/07/2011$2,250,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2023
Tax$17,661
Assessment$737,560
Home facts updated by county records

Comparable Sales for 599 Greenleaf Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
540 Green Bay Rd, Glencoe, IL
0.25
Single-Family Home
$2,377,500
01/16/26
5
5.5
4,800
626 Greenleaf Ave, Glencoe, IL
0.10
Single-Family Home
$1,575,213
06/30/25
4
3.5
3,253
677 Greenleaf Ave, Glencoe, IL
0.14
Single-Family Home
$3,230,000
04/17/26
5
6
7,785
693 Greenwood Ave, Glencoe, IL
0.43
Single-Family Home
$1,900,000
10/10/25
6
4.5
5,258
555 Vernon Ave, Glencoe, IL
0.31
Single-Family Home
$1,715,000
06/02/25
5
3.5
3,753
670 Longwood Ave, Glencoe, IL
0.17
Single-Family Home
$2,220,000
11/03/25
5
4
2,793
730 Longwood Ave, Glencoe, IL
0.28
Single-Family Home
$1,350,000
01/13/26
4
3.5
4,818
260 Lincoln Dr, Glencoe, IL
0.43
Single-Family Home
$1,975,000
05/04/26
5
4.5
3,824
146 Beach Rd, Glencoe, IL
0.26
Single-Family Home
$1,650,000
02/24/26
5
4
3,642
343 Washington Ave, Glencoe, IL
0.36
Single-Family Home
$2,021,000
01/28/26
5
4.5
3,296

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Assigned Schools

These are the assigned schools for 599 Greenleaf Ave.
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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 50 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

  • 88 % 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
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  • 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
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  • Shert929
    "Most places here are dog friendly accept for the condos. Plenty of places to walk a dog. Great community for pets and people. "
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  • 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
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  • 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
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  • Deborah B.
    "This is a lovely Community with old fashioned values. Jens Jensen Landscaping delight local parks. "
    1
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599 Greenleaf Ave, Glencoe, IL 60022 is a 5 bedroom, 6 bathroom, 5,000 sqft single-family home built in 1869. This property is not currently available for sale. 599 Greenleaf Ave was last sold on Sep 15, 2011 for $1,905,000. The current Trulia Estimate for 599 Greenleaf Ave is $2,651,600.