377 Sunset Rd, Winnetka, IL 60093
Property image
Property image
OFF MARKET

377 Sunset Rd
Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 5,200 sqft

$2,351,600

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $15,792/mo*
Refinance Your Home

$2,351,600

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $15,792/mo*
Refinance Your Home
5 Beds
4.5 Baths
5,200 sqft

Local Information

  • Map ViewExplore the area around 377 Sunset Rd.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

Step into this dreamy, custom built home and you will feel like you have been transported to the sunny California coast...This exquisitely designed home exudes serene, beachy vibes with elements of urban sophistication and perhaps even a dash of mid-century modern woven in. Clean, contemporary, transitional and open, it is truly the epitome of casual elegance and lives beautifully on all 4 levels of its phenomenal, sun filled living space. The gorgeous, step down Kitchen with island and table area features a spectacular wall of floor to ceiling windows and doors overlooking the gorgeous back yard. The spacious Master BR suite with vaulted ceiling and spa like Master BA rivals the best of SoCal boutique hotels. Exceptional decor, finishes and craftsmanship. Truly turnkey. The absolute best location! Hear the waves lap against the shores of Lake Michigan. Steps to Greeley, New Trier, Elder Beach, dog beach, Indian Hill Park and Metra. Truly a one of a kind and very special. FABULOUS!
377 Sunset Rd, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 5,200 sqft single-family home built in 2004. It last sold for $1,425,000 on Jun 12, 2019. It is currently off market. The Trulia Estimate is $2,351,600, with a rent estimate of $7,517/month.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 377 Sunset Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 11Types of Rooms: Walk In Closet, Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Slate
Security
Security System

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: WoodPatio
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: split level

Community

Units in Building: 1

Lot Information

Lot Area: 9500 sqft

Price History for 377 Sunset Rd

DatePriceEventSource
06/12/2019$1,425,000Sold
MRED as distributed by MLS GRID #10279494
04/12/2019$1,495,000PendingAgent Provided
03/15/2019$1,495,000PriceChange
Agent Provided
02/22/2019$1,545,000Listed For SaleAgent Provided
05/19/2014$1,400,000Sold
MRED as distributed by MLS GRID #08561716
03/20/2014$1,530,000PriceChange
Agent Provided
01/14/2014$1,585,000PriceChange
Agent Provided
10/18/2013$1,695,000Listed For SaleAgent Provided
07/09/1997$480,000Sold
N/A

Market trends in Winnetka

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
7MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$1,470,000
Home facts updated by county records

Comparable Sales for 377 Sunset Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
373 Sunset Rd, Winnetka, IL
0.01
Single-Family Home
$1,380,000
06/26/26
5
3.5
3,465
350 Elder Ln, Winnetka, IL
0.06
Single-Family Home
$2,100,350
08/08/25
5
4
5,675
91 Abbottsford Rd, Winnetka, IL
0.25
Single-Family Home
$2,009,100
05/15/26
5
4.5
5,231
153 Bertling Ln, Winnetka, IL
0.18
Single-Family Home
$2,750,000
04/22/26
5
4.5
6,150
318 Sunset Rd, Winnetka, IL
0.12
Single-Family Home
$1,797,000
08/12/25
4
3.5
3,165
321 Woodland Ave, Winnetka, IL
0.19
Single-Family Home
$2,600,000
09/18/25
6
5
4,698
314 Woodland Ave, Winnetka, IL
0.20
Single-Family Home
$1,995,000
01/30/26
4
4
3,700
165 Fuller Ln, Winnetka, IL
0.24
Single-Family Home
$2,450,000
05/08/26
5
5.5
4,994
174 Woodland Ave, Winnetka, IL
0.13
Single-Family Home
$1,515,000
05/01/26
3
2.5
3,248
643 Abbotsford Rd, Kenilworth, IL
0.37
Single-Family Home
$2,692,148
12/16/25
5
4.5
5,088

Nearby homes

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Assigned Schools

These are the assigned schools for 377 Sunset Rd.
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 Winnetka

At least 78 Trulia users voted on each feature.

  • 94 % Say people would walk alone at night

  • 90 % Say it's dog friendly

  • 88 % Say kids play outside

  • 88 % Say there's holiday spirit

  • 87 % Say there are sidewalks

  • 82 % Say yards are well-kept

  • 81 % Say it's walkable to restaurants

  • 80 % Say parking is easy

  • 78 % Say there's wildlife

  • 75 % Say it's quiet

  • 74 % Say car is needed

  • 72 % Say there are community events

  • 71 % Say they plan to stay for at least 5 years

  • 71 % Say it's walkable to grocery stores

  • 70 % Say neighbors are friendly

  • 67 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • DRD
    "Great schools and public works. Incredible beaches. Great fire and police systems. Amazing playing fields for kids’ sports. "
    0
    Flag
  • allisonbowersbrown
    "Park district, block parties, parades, fireworks. Neighborhood get together, school and church events. "
    0
    Flag
  • Jillian D.
    "I take the metra and walk to work. It’s easy and about as fast in the train to Chicago as it is in a car. Going west without a car is not as doable though. "
    1
    Flag
  • Acparacchini
    "Great dog beach, easy walk to town with coffee shops, restaurants, etc and bring the dog! 4th of July parade and everyone brings their dogs "
    0
    Flag
  • Phil L. .
    "Great parks, families and restaurants. Easy walk to restaurants , train, and interesting stores. Lots of people out walking, running or on bikes. "
    0
    Flag
  • Jillian D.
    "I take the train and walk. There are usually window seats available on the Metra when I leave winnetka at 7:21. "
    1
    Flag
  • Jillian D.
    "There are lots of green parks for doggos to play at! There’s also lil fountains where you can get water for people and dogs in the summer. "
    2
    Flag
  • Sarahvaile687
    "Winnetka music festival, summer music in the park...there are plenty of events hosted by the community."
    1
    Flag
  • Winnetka mom
    "I’ve lived here for 14 years and Winnetka is the most warm, welcoming neighborhood I’ve ever lived in!"
    1
    Flag
  • Benjamin J. D.
    "They would like it. It’s a great community with tons of parks. Move here! You won’t regret it. It’s like living in a Rockwell painting."
    1
    Flag
  • Mklein
    "Lived here for 22 years. Raised our family here. Would do it again given the chance. Great mix of people from different backgrounds and heritage. Only downfall is politically backwards and cannot get anything done in the village that’s required to stay current with infrastructure or lifestyle. "
    5
    Flag
  • Sbardoni29
    "Wonderful place to live. Gorgeous homes and great apartment living above shops and restaurants. So close to the lake and Metra runs right through city to downtown. "
    0
    Flag
  • Coveyandclay
    "family friendly and perfect for children! parks are wonderful and schools are best in country. park district facilities are top notch"
    0
    Flag
  • Coveyandclay
    "great parks and lots of kids playing there all the time. very family friendly. many kids events put on by park district also."
    0
    Flag
  • Erin K. C.
    "Very dog friendly. There is a great private dog beach that is well maintained with a dog wash and passholder only gate. All dogs are required to be well behaved and up to date on all shots. "
    0
    Flag
  • Acparacchini
    "Lived in Winnetka essentially since I was 9! Great place to raise a family. Beautiful homes, great town, great beaches, excellent schools, easy transportation to the city! "
    2
    Flag
  • Gabriel
    "Safe, quiet and architecturally nice. A great place to live and raise a family. Great schools and close to the lake. "
    0
    Flag
  • mtoyama60
    "Wonderful neighborhood close to lake and town and highly rated schools. Family community. Quiet residential street. Great investment."
    0
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  • Patty E.
    "I want to move here ,whith my kids."
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

44 pet-friendly rentals in Winnetka, IL

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23 rentals with air conditioning in Winnetka, IL

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41 rentals with a washer/dryer in Winnetka, IL

Homes for sale near 377 Sunset Rd

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Off Market Homes Near 377 Sunset Rd

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