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44220 Cowboy Hill Ln, Chiloquin, OR 97624

$579,000
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Property Description

Imagine waking up to sweeping mountain and forest views with 20 peaceful acres outside your door. This beautifully maintained 2,742 sqft horse property offers the space and freedom to embrace country living. Inside, natural light, vaulted ceilings and hardwood floors create a warm, welcoming feel. The main-level primary suite is a private retreat with walk-in closet, tiled shower, jetted soaking tub, backyard access and adjoining office or sitting room. An open kitchen with island and stainless appliances flows into inviting gathering spaces, while two pellet stoves and an enclosed sunroom add warmth and charm. Outside, fully fenced and gated acreage blends open ground with mature trees and beautiful territorial views. A barn, corral, attached garage and impressive 4-car shop/garage with workbenches and 220V power offer room for horses, projects, vehicles and toys. Central A/C, forced-air heat and a metal roof add year-round comfort to this special country retreat. Serenity awaits you!

44220 Cowboy Hill Ln | MLS# 786780802

This single family home located at 44220 Cowboy Hill Ln, Chiloquin, OR 97624 is currently listed for sale with an asking price of $579,000. This property was built in 1999 and has 3 bedrooms and 2 full and 1 partial baths with 2742 sq. ft. Search Chiloquin real estate on juli.bendpremierrealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Crawl Space
Cooling: Central Air
Fenced: Yes
Fireplaces: 2
Fuel Type: Electricity
Garage: 7 car attached
Heating: Forced Air, PelletStove
Home Style: Contemporary, Craftsman
Lot Size: 20.02 Acres
Roof Type: Metal
Stories: 2.0
Taxes: $4,244
Year Built: 1999
Square Feet: 2,742

Feature Descriptions

Accessibility: Garage on Main, Ground Level, Main Floor Bedroom w-Bath, Minimal Steps, Natural Lighting, Utility Room On Main, Walk-in Shower
Bathroom: 1.1 (Main), 1.0 (Upper)
Days on Site: 46
Exterior: Lap Siding, Wood Siding
Exterior: Barn, Corral(s), Fenced, Outbuilding, Patio, Porch, Poultry Coop, RV Parking, Second Garage, Yard
Fireplace: Pellet Stove
Hot Water: Electricity
Interior: Ceiling Fan(s), Hardwood Floors, Laundry, Skylight, Soaking Tub, Tile Floor, Vaulted Ceiling(s), Wall to Wall Carpet
Kitchen: Cook Island, Cooktop, Dishwasher, Disposal, Free-Standing Refrigerator, Microwave, Pantry, SolidSurfaceCountertop, Stainless Steel Appliance(s)
Lot: Gated, Gentle Sloping, Level, Pasture, Secluded, Trees
Parking Notes: Attached, Detached, Oversized, Driveway, OffStreet
Sewer: Standard Septic
Special View Info: Mountain, Territorial, Trees/Woods
Square Footage: 1842 (Main), 900 (Upper)
Water: Private, Well

Local Schools

High School: Chiloquin
Middle School: Chiloquin
Elementary School: Chiloquin

Listed By / Shown By

Listed By

Agency Name: ICON Real Estate Group
Agency Contact: ICON@TheICONREGroup.com

Shown By

Agent Name: Juli Porterfield | Broker
Agent Phone: (541) 280-6451
Agency Title: Bend Premier Real Estate

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Estimated Payment

$ 3,450.28 per month $2,927.74 Principal & Interest $353.67 Property Tax $168.88 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 11/11/2026. The listing information on this page last changed on 11/11/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 11/11/2026 12:08:45 AM EST) or RMLS (last updated Wed 11/11/2026 12:04:24 AM EST) or COAR/MLSCO (last updated Wed 11/11/2026 12:01:18 AM EST). Real estate listings held by brokerage firms other than Bend Premier Real Estate may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

The content relating to real estate for sale on this web site comes in part from the IDX program of the RMLS of Portland, Oregon. Real estate listings held by other brokerage firms are marked with the RMLS logo, and detailed information about these properties includes the names of the listing brokers. Listing content is copyright © 2026 RMLS, Portland, Oregon. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

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