Backcountry San Diego Real Estate

Backcountry Real Estate.
Veteran Expertise.

Starlene Bennin and Ashlyn Windsor serve buyers, sellers, tenants, and property owners across rural San Diego and Riverside County — a mother-daughter team with deep roots in the veteran community.

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Starlene Bennin · Marine Veteran · DRE #01730188 · GRIAshlyn Windsor · Coast Guard Veteran · DRE #02224221Proudly part of Red Hawk Realty · DRE #01109566

Featured Properties

Backcountry San Diego listings — live MLS feed coming soon

Mountain View Ranch

Julian, CA

3 bed · 5.2 acres

Oak Grove Homestead

Santa Ysabel, CA

4 bed · 10 acres

Desert Sky Retreat

Ranchita, CA

2 bed · 20 acres

Why Veterans Choose the Backcountry

Most veteran real estate is suburban VA-loan work. We lean into the opposite — space, self-reliance, and the rural life a lot of us came home wanting.

Post-Service Freedom

Space, privacy, and the ability to live on your own terms — exactly what a lot of us came home wanting.

Off-Grid Capable

Solar-ready parcels, well and septic guidance, fire-zone know-how. Rural infrastructure isn't abstract to us.

VA Loan in Rural Markets

Appraisers, septic, water rights, manufactured-home quirks — we know where VA files get stuck and how to unstick them.

Room to Breathe

Julian to Ranchita to Warner Springs — acreage, horses, night skies, and neighbors who respect a fence line.

Local Expertise

Backcountry San Diego isn't one market — it's a dozen small ones. Here's where we work.

Julian

Mountain charm at 4,200 feet

Julian is the jewel of San Diego's backcountry — a historic gold mining town at 4,200 feet elevation, famous for its apple orchards, pies, and small-town charm. With a walkable Main Street, local wineries, and real four-season weather, Julian offers a lifestyle that feels worlds away from the coast while being just 60 miles from downtown San Diego.

Explore Julian

Santa Ysabel

Valley living in the heart of the backcountry

Santa Ysabel is the crossroads of the backcountry — a quiet valley community centered on the historic Santa Ysabel Ranch and the famous Dudley's Bakery. Located between Julian and Ramona on Highway 78/79, it's the geographic and cultural heart of backcountry San Diego. This is ranch country — open meadows, rolling hills, and a pace of life that rewards patience.

Explore Santa Ysabel

Ranchita

Where the desert meets the mountains

Ranchita sits at the eastern edge of San Diego's backcountry, where mountain terrain transitions to high desert. At 4,000+ feet, it offers larger parcels, genuine privacy, and a lifestyle suited to those who want space, quiet, and the ability to live on their own terms. This is where you go when you want land — real land.

Explore Ranchita

Ramona

Horse country with a hometown feel

Ramona is the gateway to the backcountry — close enough to urban San Diego for convenience, rural enough for horses, livestock, and elbow room. Known as the "Turkey Capital of the World," Ramona has grown into a thriving community with a wine country emerging in its valley, strong schools, and the infrastructure that makes rural living practical.

Explore Ramona

From Our Clients

Real words from people Starlene and Ashlyn have helped buy, sell, and relocate.

Starlene and Ashlyn were wonderful to work with. There were many rounds of negotiations in our land acquisition and they were both attentive and aggressive in getting us the property we wanted at the best possible price for our unique situation.

Krystal & Erick Tronboll

Backcountry land acquisition

Star and Ashlyn were great — had great recommendations of companies to use to get the property ready for selling. They were right there and available whenever I had questions or concerns regarding the sale. Highly recommend.

Karen Klawitter

Sold in Santa Ysabel, CA

As a military family, you don't always have the option to fly out and look at properties. Based on many conversations, Star found us our house — because she truly listens when you speak! We bought our house sight unseen and laid eyes on it the day we got our keys.

Lisa Stehle

Military family · Bought in Oceanside, CA

Discipline. Integrity. Service.

Starlene Bennin is a Marine veteran who built her real estate career the same way she served — with discipline, integrity, and a commitment to the people around her. Ashlyn Windsor is a San Diego County native who served for six years in the U.S. Coast Guard and brings the same standard to every client. Whether you're a veteran using your VA benefits, a family looking for land, or a property owner who needs reliable management — you're in good hands.

10 Must-Knows Before Buying Rural San Diego Land

Water, septic, power, access, fire zones, zoning, VA-loan quirks — the ten things Starlene wishes every backcountry buyer knew before they made an offer. Written from 15+ years of rural San Diego transactions.

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