Shayna Rupp is a trusted REALTOR(R) and top producer in Western Montana, serving clients across Ravalli County (the Bitterroot Valley) and Beaverhead County. Licensed since 2018, Shayna has helped more than 100 buyers and sellers and has closed $55M+ in career sales volume, consistently ranking among the Top 25 agents in the Bitterroot Valley. She is the founder and supervising broker of Double Black Diamond Real Estate, the 2025 winner of Bitterroot's Best Brokerage, and Shayna herself was voted Bitterroot's Best Realtor. With specialties in new construction, investment properties, residential sales, first-time homebuyers, cabins, legacy properties, and riverfront/water-rights transactions, Shayna brings unmatched local expertise and boots-on-the-ground knowledge to every client.
Community Involvement
Darby Community Partner board member and active member of the community and Darby School district.
HOBBIES/INTEREST
I love to ski/snowboard, cross country ski, hike, bike, kayak, camp and hunt. A true Montana outdoors "woman"
FAMILY
Wife and mama of 3 beautiful humans, a whole lotta chickens, some dogs, some goats and a couple cows. Proud Homestead and 4H mom.
Read More About Shayna
Specialties
Sellers
Buyers
Residential Property
Commercial Property
Awards
2026
TOP AGENT
Hamilton, MT
2026
TOP AGENT
Corvallis, MT
2026
TOP AGENT
Stevensville, MT
Other Awards
Bitterroots Best Realtor AND Real estate Brokerage for 2025
Note: Reviews may include other agents on their team
What clients say about this agent....
Professional
Communicative
Responsive
Knowledgeable
Trustworthy
Hard working
Outstanding
Attentive
Ryan A.
Review for Member: Shayna Rupp
October 11, 2025
Shayna and the whole team at Double Black Diamond are who you want in your corner Have been a client of DBD twice and will be again in the future There is a reason they were just voted BITTERROOTS BEST Thank you Shayna
Dillion W.
Review for Member: Shayna Rupp
October 1, 2025
As first time homebuyers we were nervous and overwhelmed by the process but working with Shayna made all the difference From our very first conversation it was clear that we were in good hands She took the time to explain every step in detail answered all of our many questions with patience and clarity and never once made us feel like we were on our ownWhat we appreciated most was how proactive and responsive Shayna was Whether it was helping us understand the market coordinating viewings or walking us through the offer and closing process she was always one step ahead and kept everything moving smoothlyWe felt supported and informed throughout the entire journey and we ended up in a home we love If youre a first time buyer or any kind of buyer we cant recommend Shayna enough Thank you for making such a stressful process feel manageable and exciting
Spencer C.
Review for Member: Shayna Rupp
September 8, 2025
It was awesome working with the the double black diamond crew Helped whenever there was questions and made the buying process as stress free as possible Would recommend
Corey O.
Review for Member: Shayna Rupp
June 11, 2025
I am a Broker in the Kalispell area I recently worked with Shayna on a transaction I cant say enough great amazing wonderful things about her She is on top of everything she has great problem solving skills and she is kind and professional I will definitely refer clients her way in the future and know that they are being taken care of 1000 I have to say that in 22 years of selling real estate there are very few agents I have dealt with that have the capabilities that Shayna and her team do I know that without her on the other side of this transaction we never would have made it to the closing table If you are a buyer or selling in the greater Darby area definitely use her for all of your real estate needs She will ensure you are taken care of and will do an amazing job with every single aspect of the transaction
Samantha M.
Review for Member: Shayna Rupp
May 9, 2025
Shayna leads Double Black Diamond Real Estate with integrity vision and a genuine passion for helping others Her knowledge of the Bitterroot Valley is unmatched and she goes the extra mile to ensure her clients feel supported every step of the way What really sets her apart is how much she cares not just about closing a deal but about building lasting relationships and giving back to the community If youre looking for someone who will work tirelessly on your behalf and treat you like family Shayna is the one to call