16396 Skyline Dr, Bend, OR 97703
PENDING
3D VIEW
1.89 ACRES

16396 Skyline Dr
Bend, OR 97703

  • 4 Beds
  • 6 Baths
  • 3,401 sqft (on 1.89 acres)

$2,450,000

Est. Mortgage $13,320/mo*
Get Pre-Qualified

$2,450,000

Est. Mortgage $13,320/mo*
Get Pre-Qualified
4 Beds
6 Baths
3,401 sqft
(on 1.89 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Just minutes from the westside of Bend, this peaceful sanctuary provides 4181sf of living spaces for relaxing, entertaining and enjoying the views and sounds of Tumalo Creek in this park-like setting. The 3401sf main home has an airy great room with natural light, open kitchen, wet bar, wood stove and large doors that open to a covered deck and expansive paver patio for seamless indoor-outdoor living. The primary suite has a private deck overlooking the creek. There is a secondary suite, bonus room and two additional bedrooms with a shared bath. The 835sf two-car garage has a 10ft overhead door and mudroom for staging outdoor adventures. A 780sf guest house/office has two additional garage bays, 1.5 baths, laundry and two decks. This artfully-designed retreat in a one-of-a-kind location is filled with majestic old-growth Ponderosas and has 283ft of private creek frontage. Bordering the Deschutes National Forest, this is a dream property for people who love privacy and the outdoors.

Home Highlights

Parking
4 Car Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$720
Listed
34 days ago

Home Details for 16396 Skyline Dr

Active Status

MLS Status: Pending

Interior Features

Interior Details
Wet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 6
Dimensions and Layout
Living Area: 3401 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Disposal, Dryer, Microwave, Oven, Range, Range Hood, Refrigerator, Washer, Water Heater, Wine RefrigeratorDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,Forced Air,Heat Pump,Propane,Wood,ZonedHas CoolingAir Conditioning: Central Air,Heat Pump,ZonedHas HeatingHeating Fuel: Electric
Fireplace & Spa
No Fireplace
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Skylight(s), Vinyl Frames, Wood FramesFlooring: Concrete, Hardwood, OtherCommon Walls: No Common Walls
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Concrete, Hardwood, Other
View
Has a ViewView: Creek/Stream, Forest, Panoramic, Ridge, Territorial
Security
Security: Carbon Monoxide Detector(s), Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: CompositionPatio / Porch: Covered, Covered Deck, Deck, Patio, Porch, Rear PorchOther Structures: Guest House, Second Garage, Shed(s), StorageExterior: Fire Pit, RV DumpFoundation: Slab
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Asphalt,Attached,Driveway,Garage Door Opener,Gravel,Heated Garage,RV Access/Parking
Frontage
WaterfrontWaterfront: Creek, WaterfrontRoad Frontage: Shared AccessRoad Surface Type: GravelOn Waterfront
Water & Sewer
Sewer: Septic Tank, Standard Leach Field
Farm & Range
Not Allowed to Raise HorsesDoes Not Include Irrigation Water Rights

Days on Market

Cumulative Days on Market: 15Days on Market: 34

Property Information

Year Built
Year Built: 2003
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Northwest
Building
Construction Materials: Frame, ICFs (Insulated Concrete Forms)Not a New ConstructionHas Additional Parcels
Property Information
Parcel Number: 106965Additional Parcels Description: TL 1810000000205 APN 197196

Price & Status

Price
List Price: $2,450,000Price Per Sqft: $720
Status Change & Dates
Off Market Date: Sat Apr 25 2026

Media

Location

Direction & Address
City: BendCommunity: Skyline
School Information
Elementary School: William E Miller ElemJr High / Middle School: Pacific Crest MiddleHigh School: Summit High

Agent Information

Listing Agent
Listing ID: 220218998

Building

Building Area
Building Area: 3401 Square Feet

Community

Community Features: Access to Public Lands, Trail(s)Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.89 Acres

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 220218998Water ViewWater View: Creek/Stream

Additional Information

Access to Public LandsTrail(s)
Last check for updates: about 23 hours ago
Listing courtesy of Duke Warner Realty ERA Powered, (541) 382-8262
Source: Oregon Datashare, MLS#220218998
Also Listed on Oregon Datashare.

Price History for 16396 Skyline Dr

DatePriceEventSource
04/27/2026$2,450,000PendingOregon Datashare #220218998
04/10/2026$2,450,000Listed For SaleOregon Datashare #220218998
12/16/2025$2,650,000ListingRemovedOregon Datashare #220207883
08/29/2025$2,650,000PendingToActiveOregon Datashare #220207883
08/18/2025$2,650,000PendingOregon Datashare #220207883
08/18/2025$2,650,000Listed For SaleOregon Datashare #220207883
10/16/2024$2,995,000ListingRemovedOregon Datashare #220182245
06/25/2024$2,995,000PriceChange
Oregon Datashare #220182245
05/09/2024$3,250,000Listed For SaleOregon Datashare #220182245

Similar Homes You May Like

Skip to last item
Skip to first item

New Listings near 16396 Skyline Dr

Skip to last item
  • Results are loading
Skip to first item

Comparable Sales for 16396 Skyline Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
16390 Skyliners Rd, Bend, OR
0.11
Single-Family Home
$995,000
09/16/25
3
3
2,998

Assigned Schools

These are the assigned schools for 16396 Skyline Dr.
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 Bend

At least 665 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 84 % Say car is needed

  • 79 % Say people would walk alone at night

  • 78 % Say yards are well-kept

  • 77 % Say parking is easy

  • 75 % Say there's wildlife

  • 75 % Say there's holiday spirit

  • 71 % Say kids play outside

  • 68 % Say it's quiet

  • 68 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 53 % Say they plan to stay for at least 5 years

  • 48 % Say it's walkable to restaurants

  • 42 % Say it's walkable to grocery stores

  • 33 % Say streets are well-lit

  • 30 % Say there are community events

Learn more about our methodology.
  • Daemon Heydon
    "Great place to live, relax and enjoy the outdoors. Lived here in the 80’s and moved back 8 years ago. Bigger but still lovely."
    0
    Flag
  • Crystal
    "I have lived many places yet this neighborhood makes me feel it is the safest I have ever lived in. I am female and regularly walk to restaurants, grocery stores, music halls, Downtown Bend, Drake Park etc and I always feel safe and feel a sense of community and caring for others and our furry friends. The sense of community is amazing and genuine!"
    0
    Flag
  • Anne B Christmas
    "I have miles and miles of trails outside my house. It’s perfect for dogs. There are areas that are wonderful for off leash running Wonderful for off leash running. "
    0
    Flag
  • Rome Hill
    "The people are nice and so are the dogs. Would love to live here. Great people, great community. I love this neighborhood"
    0
    Flag
  • Roesslerc
    "Great town. Close to mountains but currently over priced. Very worried about the future of home worth in this market "
    0
    Flag
  • Christopher.parsonst
    "Dogs seem super welcome. I love it immensely. Lots of great trails nearby. Summer is amazing and being near downtown makes everything so walkable."
    0
    Flag
  • Angimoe
    "It’s very walkable and pets are welcome. Animals are on leashes and everyone cleans up after their dogs."
    0
    Flag
  • Annette Solis
    "I’ve lived here for an over a year. The location is excellent but overpriced and impossible to land a great spot."
    1
    Flag
  • Shanda
    "Quiet, family and pet friendly, lots of walkers and bicyclists, large lots, neighbors look out for each other. "
    0
    Flag
  • Lureesk
    "Car is needed for commute. However, there are parks and restaurants that you can walk to. Public transportation is available."
    0
    Flag
  • Bart
    "It’s a fantastic place to live and recreate. Neighbors are terrific, and the homes are beautiful. So lucky to be here."
    0
    Flag
  • Jonathan Trimm
    "I’ve lived here for 3 years and never had any problems with neighbors or their dogs. The houses are all well maintained and people take care of their property."
    1
    Flag
  • Joellee Davis
    "The Christmas parade and the Neighborhood hero Joey Johnson. Lots of space. We often see wildlife from our window. Tall forest trees "
    0
    Flag
  • SD
    "Quiet & safe neighborhood where there are tons of kids of all ages out playing every day. Perfect neighborhood for a family"
    0
    Flag
  • Trulia User
    "You’ll love the new off leash dog park at Alpenglow Park! There are also lots of trails in the area."
    1
    Flag
  • Trulia User
    "I’ve lived here about 18 months. It’s a nice, convenient neighborhood. The Larkspur and Alpenglow parks add so much to the quality of life. "
    2
    Flag
  • Trulia User
    "Private setting, and kids can play freely in the cul-de-sac. Great neighborhood. All the neighbors are all good friends."
    0
    Flag
  • Trulia User
    "It’s a community. People watch out for each other. Children have others to play with. Pet friendly. "
    1
    Flag
  • Trulia User
    "Neighbors are interested in being neighborly. We share garden bounty, help each other out, care about being a friendly community."
    1
    Flag
  • Trulia User
    "There are sidewalks in most neighborhoods, but not a great deal of shade. The new park, Aspenglow, has nice fenced areas for off-leash dogs. "
    0
    Flag
  • Trulia User
    "There is access to public transportation and within walking distance to shopping or the Old Mill District."
    1
    Flag
  • Trulia User
    "Good neighborhood for families and for getting to know bend and all its greatness. Very easy access to downtown and old mill district."
    0
    Flag
  • Trulia User
    "Very family friendly neighborhood with a park and and an elementary school within the neighborhood. "
    0
    Flag
  • Trulia User
    "lots of places to walk thru neighborhoods but lots of people have their dogs not leashed or don't pick up after their dog poop"
    0
    Flag
  • Trulia User
    "Amazing neighborhood to raise kids. Beautiful homes and well cared for. A lot of pride of ownership. "
    0
    Flag
  • Maxorsini
    "Good place and safe place for kids. The park it’s really nice and the neighborhood it’s clean and safe."
    0
    Flag
  • Michelle K.
    "Alley access means that sidewalks aren’t crossed with driveways. It’s very safe for kids riding bikes and walkers. "
    2
    Flag
  • Alexandra H.
    "Trick or treating is great and the neighbors are all very friendly. It’s a rather quiet neighborhood & there’s lots of kids around. Super family friendly "
    1
    Flag
  • Trulia User
    "Lots of families and family centered things to do in Bend. Good schools, lots of parks, wonderful community Parks and Recreation programs "
    0
    Flag
  • Phillip W.
    "my work is roughly 5 minutes away from home, easy freeway access. Living in Bend has gotten harder for commuting as population increased."
    2
    Flag
  • Cindee R.
    "Easy access to downtown Bend. Traffic is busy but walking is nice. Lots of great little stores around. "
    0
    Flag
  • Melissa
    "Pretty private and quiet. No community events but has old Bend charm and feel. Super convenient to stores but then so peaceful. "
    0
    Flag
  • Bryan B.
    "Easy commute. Hardly any traffic, easy to downtown, Redmond or shops in cascade shopping center. More characters here😋"
    2
    Flag
  • Sioux T.
    "beautiful peaceful homes in a area where you are 10 minutes from the heart of town but feel like you are in the middle of nowhere...."
    1
    Flag
  • Valdiviafam
    "Seems to have plenty of public transit. Traffic flows well. Easy access to highway and parkway. Area has roundabouts and lots of people in this area bike quite a bit."
    0
    Flag
  • Kathleen C.
    "Seems very neighborly- people seem to be open to meeting new people. The homes are a nice mix of small and large, old and new."
    1
    Flag
  • Andrewlangenbach
    "We have great friends to hat live here and know all the fun outdoor activities to do. This is a wonderful place for outdoor activities year round. "
    0
    Flag
  • Michelle
    "I love this neighborhood. Families are out playing ball with their kids and fur babies every day. Folks stop to say hello and shot the breeze any chance they can get. Their is truly a sense of community. "
    3
    Flag
  • Bucky H.
    "everyone here looks out for each other, I know my neighbors on a first name bases, and consider them friends."
    0
    Flag
  • Blake S.
    "Great place to live close to the rivers and hiking trails. The golf course is maintained and beautiful to play on. "
    0
    Flag

LGBTQ Local Legal Protections

Duke Warner Realty ERA Powered, (541) 382-8262
© 2026 Oregon Datashare (KCAR | MLSCO | SOMLS). All rights reserved. The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Oregon Datashare. Real estate listings held by IDX Brokerage firms other than Zillow Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange thumbnail logo and detailed information about them includes the name of the listing Brokers. Information provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. The consumer will not copy, retransmit nor redistribute any of the content from this website. Information provided is deemed reliable, but not guaranteed. This content has last been updated on 2026-05-14 23:20:07 PDT
16396 Skyline Dr, Bend, OR 97703 is a 4 bedroom, 6 bathroom, 3,401 sqft single-family home built in 2003. This property is currently available for sale and was listed by Oregon Datashare on Apr 10, 2026. The MLS # for this home is MLS# 220218998.