Featured Property Listings
12.8 Acre hunting preserve and recreation area on River Rd. in Bascom, FL.
12.8± wooded acres on River Rd. in Bascom, FL. This private, North Florida hunting preserve is loaded with mature oaks, trails, and game sign—perfect for hunting, recreation, or a quiet country retreat. No HOA, no restrictions. A solid spot for your cabin, camper, or homestead dreams. Peaceful, wild, and full of potential. Includes a ready-to-go hog trap and pen—set up and staying with the property.
https://www.flexmls.com/share/CZLnQ/0-River-Rd.-Road-Bascom-FL-32423
Custom-built in 2004 on 9′ pilings with 4′ of fill, this 2,172 sq ft, 3-bed, 2.5-bath home sits on the southeast corner of Fanning Oaks Peninsula with 50′ of frontage on Fanning Bayou/North Bay. Hardie board siding, 2020 metal roof, 2023 gutters, Rinnai tankless water heater, updated septic, and HVAC replaced in 2020. Open living with LVP flooring, built-ins, and bay views from every angle. Kitchen includes gas range, downdraft oven, double sinks, beverage fridge, under-counter fridge drawers, ice machine, pantry, and built-in hutch. Primary suite has dual baths, walk-ins, and office space. Extras include chair lift, dumbwaiter, screened porch, open deck, heated lap pool, and private dock and Gulf access. Lot is 0.47 acres, landscaped, fenced, and gated. Flood insurance approx. $990/yr. Assumable mortgage available.
Rare 99-year leasehold on Black's Island - Unit 20 offers a one-of-a-kind private island retreat in St. Joseph's Bay. Accessible only by boat, this fully appointed bungalow enjoys resort-style amenities, breathtaking bay views, and the serenity of a natural Gulf Coast sanctuary. Ownership includes use of the island's boardwalks, beaches, docks, pool, and gathering spaces. A perfect escape for those seeking privacy, adventure, and unmatched waterfront beauty.
1 Story units available. 2 Bed 2 Bath $1,250,000
2 Story unit, 2 Bed 2 Bath $1,350,000
Contact Matthew Grimsley for a private showing. (850) 890-6832
I’m Matthew Grimsley — a real estate agent, outdoorsman, father, and cinematic photographer based in Northwest Florida.
My work blends southern grit with quiet emotional honesty. Whether I’m shooting a rattlesnake on an empty highway, a family at the farm, or a $2M waterfront listing, I look for the same thing: mood, meaning, and story.
Outlaw Land & Flight Co. is where those worlds meet — photography, land, family, and the wild Florida landscapes that shaped me.
Be Human. Stay Wild.
Services we offer
Our Outlaw Land Listing Package includes:
Custom Branding & Storytelling – Your property gets a name, a vibe, and a purpose
Drone + Ground-Level Media – Shot by a licensed pilot, edited for impact
Mapped & Marketed Right – GIS overlays, boundary lines, and the best angles
Powerful Digital Exposure – MLS + Zillow + social channels that actually sell
Boots-on-Ground Service – Real conversations, real buyers, real results
Cinematic • Outdoor • Unscripted • Real
I create portraits that feel alive—images with depth, mood, and presence.
No stiff poses. No forced smiles. Just honest moments captured with intention.
My signature style.
Shot in natural light, with shadows, atmosphere, and a sense of story behind every frame.
Perfect for:
Personal portraits
Lifestyle images
Creative concepts
Artists, musicians, and entrepreneurs
Branding headshots with edge
• Moody, Editorial-Style Headshots
Not your typical realtor headshots.
I capture people in their element—working, thinking, creating.
Natural expressions. Real emotion. A portrait that says something.
Great for:
Realtors
Business professionals
Creatives & makers
Social profiles
Actor/Model portfolio updates
• Golden Hour & Twilight Sessions
Your best look.
The kind of light people don’t forget.
Available sunrise or sunset—whichever your story calls for.
Great for:
couples
portraits with movement
dramatic silhouettes
landscapes with a human element
• Outdoor Family & Parent-Child Sessions
Raw, simple, natural.
No stiff posing—just you and the people you love in a moment that feels like you.
Perfect for:
parents + kids
small families
documentary-style sessions at home, the farm, or your favorite outdoor spot
Every Portrait Session Includes
Guided posing (so you never feel lost)
My signature cinematic editing
High-resolution digital gallery
Print-ready downloads
Optional fine-art prints
Location guidance anywhere in Northwest Florida
Up to 90 minutes of shooting (extended sessions available)
Eyes in the sky. Precision on the ground.
Services include:
Aerial Photography & Cinematic Video – High-res drone content shot by licensed FAA Part 107 pilot
Property Flyovers & Boundary Overlays – Showcase land from above with GIS-accurate mapping
Site Scouting & Project Monitoring – Track progress, inspect terrain, or document improvements
Marketing Media for Listings & Brands – Compelling visuals that sell land, homes, and lifestyle
Custom Shoots & Specialty Content – From sunrise ranch flyovers to off-road adventure reels