Jen Annen Real Estate Agent - Gateway Real Estate

487 Rock St, Ashland, OR For Sale $600,000 - co-listed by Jen Annen — For Sale $600,000 • Co-Listing Agent

Jen Annen listing agent for 9 Hillcrest St, Ashland, OR - sold for $1,090,000 — Sold $1,090,000

1019 Talent Ave, Talent, OR For Sale $185,000 - listed by Jen Annen — For Sale $185,000

Jen Annen buyer's agent for 960 Oak St, Ashland, OR - sold for $709,100 — Sold $709,100

808 Pompadour Dr, Ashland, OR For Sale $1,299,000 - listed by Jen Annen — For Sale $1,299,000

Jen Annen

Ashland OR

Gateway Real Estate

37 Closed Sales

$18.5M Total Value

$330K - $1.1M Price Range

$498.9K Average Price

Prior 5 years

About Jen

JEN ANNEN - REALTOR
First time home buyers, relocating to Southern Oregon, selling your home in the Rogue Valley -
Ashland - Talent - Phoenix - Jacksonville - Medford
I am here to guide and advise you through this process from start to finish. I moved to Ashland, Oregon over 20 years ago for the nature, the skiing, the beauty, the schools, and family life and I have loved every year more and more. I look forward to meeting with you.

Home Types: House, Townhouse, Multifamily, Condo

Years of Experience: 5

Education: Masters in Educational Psychology, CSU Long Beach, and Bachelor of Arts, Law & Society, University of California Santa Barbara, UCSB

Transaction History

1 Year
2 Year

Seller Deals
Total Deals	8
Total Value	$4,647,065
Average Sale Price	$580,883
Price Range	$305K - $1.1M

Buyer Deals
Total Deals	19
Total Value	$8,850,840
Average Sale Price	$465,834
Price Range	$250K - $710K

1 Year View by Quarter

Seller Deals
Total Deals	8
Total Value	$4,647,065
Average Sale Price	$580,883
Price Range	$305K - $1.1M

Buyer Deals
Total Deals	29
Total Value	$13,811,840
Average Sale Price	$476,270
Price Range	$250K - $740K

Areas Jen is Experienced In

Jen's Listings and Deals

Jen's Open Houses

Co-Listing Agent

$600,000

Open Sat 11AM - 1PM
- 4 Beds
- 2.5 Baths
- 1,624 Sq Ft
487 Rock St

Ashland, OR
Beautiful, charming, updated craftsman in the historic Skidmore Academy district with close to proximity to downtown Ashland, Lithia Park, shops, and dining. The peaceful 'Pollinator Garden' has abundant, beautiful perennials, many fruit trees, and a separate octagon shaped office/art/yoga studio. Both front and back yards/gardens have sprinkler systems for low maintenance gardening. High quality

Jen Annen Gateway Real Estate

Jen's Active Listings

$185,000
- Land
- 0.25 Acre
- $740,000 per Acre
1019 Talent Ave

Talent, OR
Location, location, location... south Talent, close to shops, restaurants, and downtown Talent and Ashland! Beautiful mountain views on this .25 acre, fully fenced, level lot with water, sewer, and electric available. Zoning of RM-22 allows for residential multi-family, high density build, home plus ADU, lots of options. Talent irrigation rights on .20 of an acre are available at $166 per year.

Jen Annen Gateway Real Estate

$1,299,000
- 5 Beds
- 5.5 Baths
- 4,935 Sq Ft
808 Pompadour Dr

Ashland, OR
Live the Southern Oregon Dream! Welcome to an extraordinary Ashland estate where breathtaking views of Mount Ashland, the Cascades, downtown Ashland, and surrounding vineyards create a spectacular backdrop. Nestled behind a private gated entrance on 5 acres, 1.6 TID irrigated, this custom-built 5 bedroom, 6 bath home offers luxury, privacy, and versatility. Whether you're seeking a peaceful

Jen Annen Gateway Real Estate

Recently Sold

$1,090,000

Sold Sep 18, 2026
- 4 Beds
- 3 Baths
- 2,381 Sq Ft
9 Hillcrest St

Ashland, OR
- 4 Days On Market
- $458/SF
- Current Est. Value $1M
Jen Annen Gateway Real Estate

$449,000

Sold Aug 28, 2026
- 3 Beds
- 2 Baths
- 1,134 Sq Ft
39 N Mountain Ave

Ashland, OR
- 5 Days On Market
- $396/SF
- Current Est. Value $494K
Jen Annen Gateway Real Estate

$346,000

Sold Aug 4, 2026
- 3 Beds
- 1 Bath
- 1,323 Sq Ft
1650 Grand Ave

Medford, OR
- 1% Below List
- 1 Day On Market
- $262/SF
- Current Est. Value $372K
Jen Annen Gateway Real Estate

$305,000

Sold Apr 23, 2026
- 2 Beds
- 1 Bath
- 1,046 Sq Ft
2175 Delta Waters Rd

Medford, OR
- 5 Days On Market
- $292/SF
- Current Est. Value $306K
Jen Annen Gateway Real Estate

$510,000

Sold Jan 30, 2026
- 3 Beds
- 2 Baths
- 1,620 Sq Ft
295 S 1st St

Talent, OR
- 1% Above List
- 5 Days On Market
- $315/SF
- Current Est. Value $508K
Jen Annen Gateway Real Estate

$925,000

Sold Jan 5, 2026
- 5 Beds
- 5 Baths
- 3,339 Sq Ft
252 B St

Ashland, OR
- 2% Above List
- 3 Days On Market
- $277/SF
- Current Est. Value $843K
Jen Annen Gateway Real Estate

$599,900

Sold Dec 26, 2025
- 5 Beds
- 3 Baths
- 2,388 Sq Ft
899 Timberlake Dr

Ashland, OR
- 14% Below List
- 111 Days On Market
- $251/SF
- Current Est. Value $624K
Jen Annen Gateway Real Estate

Other Experience

First Time Homebuyers, Investments, Luxury Homes

Agent License: Oregon #201257903

Frequently Asked Questions

Who is Jen Annen, and what is their real estate background?

How many homes has Jen Annen sold in Ashland, OR?

What areas does Jen Annen serve?

How can I contact Jen Annen?

Jen Annen

(949) 731-6189

Gateway Real Estate

(949) 731-6189

Nearby Homes

Jen Annen

About Jen

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Areas Jen is Experienced In

Jen's Listings and Deals

Jen's Open Houses

Jen's Active Listings

Recently Sold

Other Experience

Frequently Asked Questions

Who is Jen Annen, and what is their real estate background?

How many homes has Jen Annen sold in Ashland, OR?

What areas does Jen Annen serve?

How can I contact Jen Annen?