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 *
27
Recent sales
$250K-$925K
Price range
$485K
Median price
5
Years experience

Recent Listings & Sales

Address Sold Date Sold Price Represented
1872 Hope St
Ashland, OR 97520
4/24/2026 $557,000 Buyer
2175 Delta Waters Rd
Medford, OR 97504
4/23/2026 $305,000 Seller
1604 Palermo St
Medford, OR 97504
2/27/2026 $505,000 Buyer
166 Mountain View Dr
Ashland, OR 97520
2/26/2026 $383,000 Buyer
295 S First St
Talent, OR 97540
1/30/2026 $510,000 Seller

Transaction History *

Seller Deals

Total Deals
4
Total Value
$2,339,900
Median Sale Price
$554,950
Price Range
$305K - $925K

Buyer Deals

Total Deals
23
Total Value
$10,707,740
Median Sale Price
$468,000
Price Range
$250K - $740K

Sales Volume Timeline

Jen Annen’s production volume for the past 3 year period Q2 ’23 Q2 2023: $0 Q3 ’23 Q3 2023: $0 Q4 ’23 Q4 2023: $0 Q1 ’24 Q1 2024: $0 Q2 ’24 Q2 2024: $0 Q3 ’24 Q3 2024: $0 Q4 ’24 Q4 2024: $502K Q1 ’25 Q1 2025: $2.6M Q2 ’25 Q2 2025: $1.9M Q3 ’25 Q3 2025: $2.3M Q4 ’25 Q4 2025: $2M Q1 ’26 Q1 2026: $2.9M Q2 ’26 Q2 2026: $862K Q2 2023 Total Sales $0 Q3 2023 Total Sales $0 Q4 2023 Total Sales $0 Q1 2024 Total Sales $0 Q2 2024 Total Sales $0 Q3 2024 Total Sales $0 Q4 2024 Total Sales $502K Q1 2025 Total Sales $2.6M Q2 2025 Total Sales $1.9M Q3 2025 Total Sales $2.3M Q4 2025 Total Sales $2M Q1 2026 Total Sales $2.9M Q2 2026 (Apr 1-Jun 2) Total Sales $862K

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

  • 15 sales past 3 years
  • 98 days on market
  • $526K median price

Medford

  • 8 sales past 3 years
  • 43 days on market
  • $360K 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.