Welcome to a rare opportunity in the heart of Issaquah! Nestled on a massive wooded lot in a highly sought-after community, this custom split-level home offers privacy, character, and endless potential all while being just minutes from shopping, dining, commuter routes, and everyday conveniences. Located near Timberlake Park and scenic walking trails, this original-owner home has been lovingly maintained and thoughtfully customized throughout the years. Step inside to soaring vaulted ceilings accented by enormous custom beams that span the length of the home, creating a warm and striking architectural centerpiece. The spacious layout offers incredible flexibility, including a partially finished basement with potential for a future duplex-style setup, second primary suite, or substantial additional finished square footage. The primary bedroom features its own private deck overlooking the peaceful natural surroundings, along with a bath off the primary for added comfort and privacy. A large 2-car garage offers extensive storage space, perfect for hobbies, outdoor gear, or workshop needs. Whether you're looking to move right in, customize further, or unlock the home's investment potential, this property combines location, lot size, and unique craftsmanship in a way that's hard to find in Issaquah. Don't Wait, make this house your home! Buyer to verify all information.
Listed by Douglas Drost
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Skyline Properties, Inc.
Listed by Joshua Buenavista
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Skyline Properties, Inc.
Last updated June 05, 2026
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Source: NWMLS #2532823
Listing Facts
TypeSingle-family
NeighborhoodGreenwood Point
Bedrooms3
Bathrooms5
Days on Prevu12
Taxes$11,625/year
Size1,710 sqft
Price per sqft$877
Amenities
Dishwasher
Washer/Dryer
Pets Allowed
Parking
Location
Mortgage Calculator
Listing History
06/04/2026
Listed by Skyline Properties, Inc.
$1,500,000
Property Details for 18408 SE 44th Street
Exterior
Construction
Property Condition: Fair
Roof: Flat, See Remarks
Structure Type: House
Year Built: 1965
Architectural Style: Craftsman
Construction Materials: Brick, Cement Planked, Wood Products
Interior Features: Second Kitchen, Bath Off Primary, Ceiling Fan(s), Dbl Pane/Storm Window, Dining Room, Fireplace, Sprinkler System, Vaulted Ceiling(s), Water Heater
Measurements
Living Area: 1,710
Rooms
Basement: Partially Finished, Unfinished
Bathrooms Full: 2
Bathrooms Half: 2
Bathrooms Three Quarter: 1
Bathrooms Total Integer: 5
Bedrooms Total: 3
Other
Location
Subdivision Name: South Lake Sammamish
Parking
Parking
Attached Garage: Yes
Covered Spaces: 2
Garage: Yes
Parking Features: Driveway, Attached Garage, Off Street, RV Parking
Parking Total: 6
Schools
Elementary School
Elementary School: Sunset Elem
High School
High School: Issaquah High
High School District: Issaquah
Middle or Junior School
Middle Or Junior School: Issaquah Mid
Utilities
Equipment
Has Heating: Yes
Sewer: Septic Tank
Water Source: Private
Frequently Asked Questions
How many bedrooms and bathrooms does this single-family home have?
There are 3 bedrooms and 5 bathrooms in this single-family home at 18408 SE 44th Street.
What schools are nearby to 18408 SE 44th Street?
Nearby schools include the Sunset Elem Elementary School, Issaquah Mid Middle School, and Issaquah High.
Does this single-family home have parking?
Yes, there are 6 parking spaces available for 18408 SE 44th Street.
What are the annual taxes for 18408 SE 44th Street?
Annual taxes for this single-family home are estimated at $11,625.
How does 18408 SE 44th Street compare to other single-family homes in Greenwood Point?
This single-family home is listed 65% below the average price for single-family homes in Greenwood Point and has been on the market for 10 less days than the typical home in this area.
What is the square footage on this single-family home?
According to the MLS, this listing is 1,710 sqft.
18408 SE 44th Street is a 3-bedroom, 5-bath single-family home for sale in Issaquah WA 98027. Available on Prevu for 12 days at $1,500,000. This residence features 1,710 square feet of living space, located in Greenwood Point. The median listing price for single-family homes in this area is $2,796,500. Nearby schools include Sunset Elem Elementary School, Issaquah Mid Middle School, and Issaquah High. Additional amenities include dishwasher, pets allowed, parking, and washer/dryer. Explore more single-family home listings in Issaquah.
Based on information from NWMLS and/or other sources. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by Prevu or the MLS. Information is provided exclusively for consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing.
Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.
