Jen Annen

Gateway Real Estate

Looking to sell your property, buy a new home, or just need some expert real estate advice?

About
"We have had several realtors over the years in which we have purchased houses, and I can honestly say that Jennifer was the best realtor we have had in these processes." - DS, buyer

Jennifer Annen is a top-producing REALTOR at Gateway Real Estate, a trusted real estate office located at 5 N Main St in downtown Ashland, Oregon. Jen has insightful knowledge of Southern Oregon real estate, where she serves clients across Ashland, Talent, Medford, and the greater Rogue Valley, helping buyers and sellers achieve successful results with unmatched local insight and client-first service.

Jen holds a Bachelor of Arts in Law and Society from the University of California, Santa Barbara, and she is known for her sharp negotiation skills, professional integrity, and hands-on support. She specializes in residential homes, luxury properties, investment real estate, and buildable land throughout Jackson County.
Highlights *
42
Recent sales
$250K - $1.09M
Price range
$468K
Median price
5
Years experience

Recent Listings & Sales

Address Sold Date Sold Price Represented
610 Orchard St
Ashland, OR 97520
10/19/2026 $900,000 Buyer
917 Rebecca Dr
Phoenix, OR 97535
10/14/2026 $362,500 Buyer
107 Manzanita St
Ashland, OR 97520
10/1/2026 $983,720 Buyer
472 Scenic Dr
Ashland, OR 97520
9/24/2026 $642,500 Buyer
39 N Mountain Ave
Ashland, OR 97520
8/28/2026 $449,000 Seller

Transaction History *

Seller Deals

Total Deals
7
Total Value
$4,224,900
Median Sale Price
$510,000
Price Range
$305K - $1.09M

Buyer Deals

Total Deals
35
Total Value
$17,181,060
Median Sale Price
$468,000
Price Range
$250K - $984K

Sales Volume Timeline

Jen Annen’s production volume for the past 3 year period Q1 ’24 Q1 2024 (Jan 1–Mar 31, 2024): $0 Q2 ’24 Q2 2024 (Apr 1–Jun 30, 2024): $0 Q3 ’24 Q3 2024 (Jul 1–Sep 30, 2024): $0 Q4 ’24 Q4 2024 (Oct 1–Dec 31, 2024): $502K Q1 ’25 Q1 2025 (Jan 1–Mar 31, 2025): $3.1M Q2 ’25 Q2 2025 (Apr 1–Jun 30, 2025): $1.9M Q3 ’25 Q3 2025 (Jul 1–Sep 30, 2025): $2.6M Q4 ’25 Q4 2025 (Oct 1–Dec 31, 2025): $2M Q1 ’26 Q1 2026 (Jan 1–Mar 31, 2026): $3.3M Q2 ’26 Q2 2026 (Apr 1–Jun 30, 2026): $1.4M Q3 ’26 Q3 2026 (Jul 1–Sep 30, 2026): $4.5M Q1 2024 Total Sales $0 Q2 2024 Total Sales $0 Q3 2024 Total Sales $0 Q4 2024 Total Sales $502K Q1 2025 Total Sales $3.1M Q2 2025 Total Sales $1.9M Q3 2025 Total Sales $2.6M Q4 2025 Total Sales $2M Q1 2026 Total Sales $3.3M Q2 2026 Total Sales $1.4M Q3 2026 Total Sales $4.5M

Sales volume is shown for complete quarters only.

Ratings & Reviews
5.0 (17)

reachemmachristine
Oct 13, 2026

Listen, I am not your typical buyer. Highly self reliant, suspicious in general. Not a business oriented nor savy human let's say. So it is very special that we found a realtor who really saw this in me, respected that aspect, understood this, and adjusted appropriately to make me feel confident. Jen built trust, she explained why certain decisions would be advantageous for us as the buyer. I mean took the time, sincerely. Jen is a real honest good hearted human first, and then she does real-estate too. For those who hate bs-ers, Jen is your agent.

Zillow Verified

Charlotte Schroeder
Aug 7, 2026

Working with Jen was an absolute pleasure from start to finish. She made the process of buying a home, which was clear across the country and sight unseen, smooth and relatively easy. Her knowledge of the market, attention to detail, and clear communication helped me make such a life changing purchase with confidence. She was always available, scheduled FaceTimes and videos at my convenience, and provided thoughtful guidance throughout the process. Not only did Jen provide assistance and guidance throughout the purchasing process, she continued to provide recommendations and resources to help get me settled in. I highly recommend her services for any real estate purchase or investments. You could do no better than to enlist Jen Annen.

Zillow Verified

Isabella Lefkowitz
Jul 9, 2026

Having Jen as my realtor while purchasing my first home was an incredible experience, and I truly couldn't have asked for a better person to guide me through such an important milestone.

From the very beginning, she was patient, kind, and attentive, taking the time to answer every question and guide me through each step of the process. What I appreciated most was how she balanced her expertise with genuine respect for my own ideas and perspective. She trusted my instincts while providing thoughtful guidance and knowledge whenever I needed it, which made me feel confident and supported throughout the entire journey.

Jen was also incredibly responsive. Whenever I wanted to view a home, she was quick to make it happen, and I always felt like I was a priority. When it came time to negotiate, she advocated strongly on my behalf and stood firm whenever I asked her to, making sure my interests were represented every step of the way.

Buying a first home can feel overwhelming, but Jen made the process feel manageable and exciting. Her professionalism, dedication, and genuine care made all the difference.

I highly recommend Jen to anyone looking to buy or sell a home. I'm incredibly grateful for everything she did, and I look forward to staying in touch long after closing.

Zillow Verified

Rebecca Sandgren
Feb 15, 2026

Jen is knowledgeable about the local market and proactive in coordinating needed repairs and vendor connections. She remained responsive and steady during a complex transition. Her attention to staging and presentation helped position the property effectively. Overall, she provided solid guidance through the process.

Zillow Verified

sk8tr girl3
Feb 10, 2026

Buying and selling a house can be so fraught. Jen made it just... happen.

Jen Annen has the experience and knowledge that made our triplex sale really smooth. There were many issues that arose, none of them caused by Jen. When our first offer failed a contingency, she was able to approach previously interested parties and get a new offer to us within days. The questions that came up in the course of home showings, required handyman work, and during escrow were answered quickly (does she even sleep) and thoroughly.

The patience needed to be a seller's agent is significant, and Jen's was phenomenal--with us, our renter, the buyer's agent, and during escrow. It also made things much easier that she knew the right people for the various issues that came up, including our the title company, and was able to tell us what tasks were necessary, and what we could push back on.

I am in another state (CA) and she dealt with that with no issues--happy to text or call when needed, handle things through email, even signing the closing documents.

I recommend Jen Annen, Real Estate Professional, very highly. She is worth her weight in gold.

Zillow Verified

Professional Info

Brokerage

Gateway Real Estate
5 North Main Street
Ashland, OR 97520

Licensed

Licensed REALTOR®
OR 201257903

Awards

  • Top Agent Zillow Premier

Specialties

  • First-time buyers
  • Foreclosures & Short sales
  • Investment & property management
  • Luxury properties
  • Relocation

Designations

  • ABR®

Education

University of California, Santa Barbara
Bachelor’s Degree, Law & Society

Top Cities *

Ashland

  • 26 sales past 3 years
  • 46 days on market
  • $513K median price

Medford

  • 11 sales past 3 years
  • 18 days on market
  • $346K median price

Talent

  • 4 sales past 3 years
  • 23 days on market
  • $466K median price

*Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.