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16440 Fair Mile Road, Sisters, OR 97759 | Ryan Realty — Central Oregon Real Estate

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Bend · Oregon541.703.3095

16440 Fair Mile Road

$2.0M6 bd · 6 ba · 2,945 sqft

16440 Fair Mile Road, Sisters, OR 97759 · Junipine Acres $1,995,000

16440 Fair Mile Road

Sisters, OR 97759 · Junipine Acres

● Active8 days on market$677/sqft

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About this home

Description

Junipine Acres · For sale

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541.703.3095 matt@ryan-realty.comBend · Oregon

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© 2026 Ryan Realty LLC · Principal Broker Matt Ryan · Licensed in Oregon · Equal Housing Opportunity

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Listings data provided by Oregon Data Share and Morgan Data Shuttle. Information deemed reliable but not guaranteed. Principal Broker license 201206613.

Exceptional 5-Acre Multigenerational Estate in Sisters! This unique, fully fenced and gated property features two separate residences connected by an oversized dream shop, making it perfect for multigenerational living or rental income. The centerpiece is a luxury barndominium featuring three bedrooms, each with its own private en-suite bathroom. Connected through the shop is the second residence, a beautifully maintained traditional home with three bedrooms and two and a half bathrooms. At the heart of it all is the massive central shop, a hobbyist's dream equipped with a vehicle lift and abundant storage. The five-acre grounds offer ultimate privacy, professional landscaping, a stunning koi pond, multiple garage spaces, and ample room for RVs or pets. Offering unmatched versatility and shop-focused living, this rare estate delivers the ultimate Central Oregon lifestyle just minutes from town.

Facts

Property details

Overview

Bedrooms: 6
Bathrooms: 6
Living area: 2,945 sq ft
Property type: Single Family Residence
Year built: 2009
Property age: 17 years
Style: Craftsman, Northwest

Interior

Levels: Two
Building area: 2,945 sq ft
Fireplace: Yes

Exterior & lot

Lot size: 5.37 acres
Lot features: Corner Lot, Drip System, Fenced, Landscaped, Level, Rock Outcropping, Sprinkler Timer(s), Sprinklers In Front, Sprinklers In Rear, Water Feature, Wooded
View: Neighborhood, Pond
Construction: Frame
Roof: Composition
Foundation: Stemwall
Waterfront: Yes

Systems & utilities

Sewer: Septic Tank, Standard Leach Field

Financial

Price / sq ft: $677
HOA: $0 per month
Annual taxes: $11,082
Tax year: 2025

Listing

MLS number: 220223800
County: Deschutes
Parcel: 135141

Listing courtesy of Ponderosa Properties, agent Thomas Arends

Data last updated July 10, 2026

Based on information from Oregon Data Share. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listing information is for consumers personal, non-commercial use only.

Education

Schools

Elementary

Middle

High

Estimate

Monthly payment

A rough estimate, not a quote. A real number comes from a lender.

Home price

Down payment %

Rate %

Term (years)

Principal + interest$10,618/mo

Property taxes$924/mo

Homeowners insurance$554/mo

Total monthly (PITI)$12,096

Loan amount $1,596,000 · $399,000 down · 30 year term

For investors

Rental analysis

Monthly cash flow, cap rate, and cash-on-cash return at this price. Every number is an estimate you can adjust to your own financing and rent.

Purchase & financing

Purchase price

$

Rehab budget (optional)

$

Down payment20% · $399,000

Interest rate

%

Loan term

Income

Monthly rent

$

Estimate $2,799 ($2,525–$3,225) · HUD Fair Market Rent (FY2025), Deschutes County, 4BR. Edit to your own number.

Vacancy

%

Operating expenses

Property taxes (yearly)

$

Insurance (yearly)

$

Management (% of rent)

%

Maintenance (% of rent)

%

Capital reserves (% of rent)

%

HOA (monthly)

$

Cash flow

-$9,503/mo

Cap rate

0.7%

Cash on cash

-28.6%

Cash needed

$399,000

At $1,995,000 with 20% down, this property runs $9,503 per month negative. Adjust the price, down payment, or rent to find what works.

Monthly cash flow

Gross rent$2,799

Vacancy (5%)- $140

Operating income$2,659

Operating expenses- $1,544

Net operating income$1,115

Loan payment- $10,618

Cash flow-$9,503

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Estimates only, not investment advice or a guarantee of rent, value, or return. Figures depend on the numbers you enter and current market conditions. Verify with your lender, tax advisor, and a Ryan Realty broker before you rely on them.

Location

Where this home sits

In Sisters, at the foot of the Three Sisters.

Climate

Climate risk

We pull climate risk data from FEMA flood maps, the Deschutes County wildland-urban interface map, and NOAA heat trends. Detailed scoring for this property is on request.

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Investment

Vacation rental

We compute vacation rental projections from comparable short-term rentals in the same community, weighted by bed count, view, and amenities. A custom projection for this property is on request.

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Talk to a broker

Questions about this home?

Tour requests usually get a same-day reply. No pressure, no obligation.

Matt Ryan

Owner & Principal Broker #201206613

541.703.3095 matt@ryan-realty.com

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Garage

16 spaces