Freeport Homes with Short Term Rental Allowed Community Features

Freeport Homes with Short Term Rental Allowed Community Features

Welcome to Freeport, Florida – a hidden gem nestled in the heart of Walton County! Known for its charming small-town atmosphere and breathtaking natural scenery, Freeport offers a delightful blend of tranquility and adventure, making it the perfect destination for those seeking a serene lifestyle or an investment opportunity.

Freeport is ideally located just a short drive from the stunning beaches of South Walton, where sugar-white sands meet the sparkling emerald waters of the Gulf of Mexico. The city is surrounded by lush forests, scenic lakes, and an array of outdoor recreational activities, including fishing, hiking, and biking. With a rich history and a friendly community, Freeport embodies the warmth of southern hospitality.

For those interested in real estate, Freeport boasts a vibrant housing market with homes that allow short-term rentals. This feature is particularly appealing for investors looking to capitalize on the booming vacation rental market. Imagine owning a charming home that not only serves as your personal retreat but also generates income when you're not enjoying it! Many properties in this community come equipped with modern amenities, spacious layouts, and outdoor spaces perfect for entertaining guests.

The community features in Freeport enhance the living experience, offering residents access to parks, walking trails, and community events that foster a strong sense of belonging. With a growing population and a commitment to preserving its natural beauty, Freeport is not just a place to live; it’s a lifestyle filled with opportunity and adventure. Discover your dream home in Freeport, where every day feels like a vacation!

Newest Freeport Homes with Short Term Rental Allowed Community Features

6 Beds ⋅ 8 Baths ⋅ 1010280 MLS

Turnkey Freeport duplex with both units currently leased, strong rental history, and a potentially assumable VA loan at 5.99%, subject to lender approval and buyer qualification. 182 Madison Street includes Units A and B together on one parcel, offering two mirrored townhome-style residences in a convenient Freeport location. Built in 2023, each unit features 3 bedrooms, 2.5 baths, an open-concept living and kitchen area, kitchen island, stainless-steel appliances, LVP flooring, generous storage, and an attached one-car garage. Both sides are currently occupied by long-term tenants, and the property has historically produced gross rental income of approximately $60,000 per year. Rent rolls are available to qualified buyers. This is an excellent opportunity for an investor seeking a newer, income-producing property with established tenancy and the flexibility of two separate residences under one ownership. Photos shown are of Unit B; Unit A is substantially identical in finishes and layout, but mirrored. Property may also offer potential for short-term or furnished rental use. 182 Madison Street presents a unique opportunity to acquire both sides of a newer duplex together as one investment property. Units A and B feature mirrored floor plans and are currently operated as long-term rentals, providing immediate income without the need to locate tenants after closing. Each residence offers three bedrooms, two and one-half bathrooms, an attached one-car garage, and a modern open-concept layout designed for comfortable everyday living. Interior features include luxury vinyl plank flooring, stainless-steel appliances, kitchen islands, ample cabinetry and storage, and spacious living areas. The property has demonstrated strong rental performance, with historical gross rental income reaching approximately $60,000 annually. Both units are currently leased, and rent rolls and additional rental information are available for review by qualified buyers. An additional potential benefit is the existing VA loan carrying a 5.99% interest rate, which may be assumable by a qualified buyer subject to approval by the lender/loan servicer and applicable VA requirements. Buyers should independently verify assumption eligibility, remaining loan balance, required equity or cash contribution, and all financing terms. Located in Freeport with convenient access to Highway 20, schools, shopping, dining, and South Walton, the property is positioned in one of Walton County's growing residential areas while remaining within convenient reach of the beaches and communities along the Emerald Coast. Property is being sold as a single duplex consisting of Units A and B on one parcel. Photos shown are primarily of Unit B. Unit A is substantially identical in design and finishes but features a mirrored floor plan. Tenant occupancy should be considered when scheduling showings.

182 Madison St Unit A & B, Freeport

3 Beds ⋅ 3 Baths ⋅ 1009426 MLS

Experience 30A-inspired style without the 30A price tag at 236 N Marsh Landing in LaGrange Landing. Ideally positioned near Highway 331, this custom-built, new-construction home offers convenient access to the beaches, dining, and activities along Scenic Highway 30A, as well as Publix and the new Walmart development now underway. As Freeport continues to grow and welcome new businesses, this centrally located community offers an exceptional opportunity to own a high-end home near the area's expanding commercial corridor and the Emerald Coast lifestyle. Inside, the home features 3 bedrooms, 2.5 bathrooms, 1,958 square feet of refined living space, an open-concept floor plan, and an attached garage. The designer kitchen showcases quartz countertops, a waterfall island, and premium Bosch appliances, combining everyday functionality with polished, coastal-inspired style. Quality upgrades include solid-wood interior doors, 6-inch baseboards, custom closet systems, tile flooring in the bathrooms and laundry room, 2x6 exterior framing, and enhanced roofing underlayment. Residents can also enjoy the community pool and playground. Thoughtfully crafted with upscale finishes and quality construction, this home delivers the elevated look and feel associated with 30A at a more attainable Freeport price point. The seller is providing a one-year builder warranty and a 10-year structural warranty.

236 N Marsh Lndg, Freeport

4 Beds ⋅ 2 Baths ⋅ 1007990 MLS

Welcome to your private waterfront escape in the heart of Freeport. Situated on two oversized lots with approximately 210 feet of creek frontage and direct access to Choctawhatchee Bay, this 2020-built home offers the perfect blend of space, comfort, and outdoor lifestyle. Inside, you'll find over 2,200 square feet of thoughtfully designed living space featuring 4 bedrooms and 2 full bathrooms. The open layout includes both a formal living room and a spacious great room complete with a fireplace and built-in entertainment center--ideal for hosting family and friends. The kitchen is a standout, featuring granite countertops, stainless steel appliances, a farmhouse sink, kitchen island, and a barn-door pantry for added character and functionality.

748 Phillips Dr, Freeport

3 Beds ⋅ 2 Baths ⋅ 1004766 MLS

Hammock Bay Living at Its Best - Resort-Style Amenities, Low-Maintenance Living & Unmatched Value. Welcome to Firefly, the premier gated neighborhood within the highly desirable Hammock Bay community in Freeport. Offering a true resort-style lifestyle, Firefly residents enjoy exclusive amenities while also having full access to Hammock Bay's incredible collection of recreation, fitness, and social offerings. Built in 2020, this beautifully maintained 3-bedroom, 2-bath home combines modern comfort, thoughtful upgrades, and easy, low-maintenance living. Inside, you'll find an open and inviting floor plan enhanced with custom blinds, ceiling fans, a stylish kitchen backsplash, a tiled walk-in shower with glass enclosure, and an upgraded heated bidet toilet in the primary suite. Step outside to your private backyard retreat featuring no rear neighbors, brand-new sod, a fully fenced yard, and an extended patio with a custom privacy curtain--perfect for entertaining, morning coffee, or relaxing after a day at the pool. What truly sets this home apart is the exceptional lifestyle and value provided through the Firefly HOA. Residents enjoy a private neighborhood pool, clubhouse, and lighted pickleball and tennis courts, all reserved exclusively for Firefly homeowners. In addition, owners have full access to Hammock Bay's resort-style amenities, including multiple swimming pools, an Olympic-sized pool, a state-of-the-art fitness center, sports courts, walking and biking trails, pla ygrounds, parks, and year-round community events. The HOA also handles many of the time-consuming responsibilities of homeownership, making this an ideal primary residence, vacation home, or investment property. HOA services include cable TV, front and backyard lawn maintenance, fertilization, annual pine straw installation, irrigation from a community well-water system, shrub trimming, and common area maintenance. Beyond the amenities, Hammock Bay offers a vibrant community atmosphere with a General Store, brewery, live entertainment, and convenient access to the beautiful beaches of South Walton and the Emerald Coast. Enjoy the security of a planned community, the convenience of maintenance-free living, and the lifestyle of a year-round resort--all in one exceptional home. For buyer's convenience washer, dryer, murphy bed, ADT security equipment and Blink doorbell remain! Termite Bond with Tru North as well.

451 Lightning Bug Ln, Freeport

5 Beds ⋅ 5 Baths ⋅ 1004433 MLS

Some properties are built. Others are discovered. Hidden beneath the sweeping canopy of century-old live oaks where sunlight filters through draping branches and water views peek through the trees, this extraordinary 1.34-acre waterfront estate offers an experience that feels increasingly impossible to find along the Emerald Coast. Spanning nearly 6,000 square feet across three levels, this impressive brick residence combines scale, flexibility, and waterfront living in a way few properties can. Offering five bedrooms, four-and-a-half bathrooms, elevator access to all levels, hardwood flooring throughout, and private en-suites for every bedroom, this home was designed for buyers who need more than space--they need options. The thoughtful floor plan creates exceptional opportunities for multi-generational living, large households, guest accommodations, or those seeking a property capable of adapting alongside changing needs. Whether housing multiple generations under one roof or creating separate spaces for long-term guests, the layout provides both connection and privacy. At the center of the home, the gourmet kitchen opens into expansive gathering spaces designed for entertaining on every scale. Multiple screened porches create natural extensions of the living spaces, offering peaceful mornings beneath the oaks, sunset dinners overlooking the water, and spaces large enough to host celebrations, holidays, and unforgettable gatherings. The second level creates one of the home's most remarkable living spaces with walls of windows stretching across the home, flooding interiors with natural light while showcasing stunning basin bayou views that shift beautifully throughout the day. Storage, recreation, and flexibility were clearly part of the vision behind this property. The third floor is finished and a blank canvas that could be used for 2000 sqft of storage or creative options that fit your vision. Two oversized drive-through bay garages create extraordinary opportunities for RV storage, boats, workshops, recreational vehicles, watercraft, or collections that require more than traditional garage space can offer. Outside, the possibilities expand even further. Launch a kayak or paddleboard directly from your property and explore the waterways leading toward the bay. Spend the day fishing in the lake or head toward the bay by way of the low bridge near the locals' favorite, Nick's Seafood Restaurant. Bring the boat, the RV, the jet skis, and all the water toys because this property offers one luxury that has become increasingly rare--freedom. No HOA. No restrictive covenants. Located along Highway 20 with convenient access to Destin, marinas, dining, shopping, and the white sand beaches of the Emerald Coast, this property offers the rare combination of waterfront privacy while remaining connected to everything that makes coastal living desirable. Luxury homes exist, Waterfront homes exist, Large homes exist. However, properties that combine all three with acreage, unrestricted use, multi-generational functionality, income potential, and a setting this remarkable are extraordinarily uncommon. There is simply not another property like this. Waterfront living without compromise. Unlimited potential with room to create whatever comes next. Call for your private tour today.

7348 W St Hwy 20, Freeport

Experience the beauty of bayfront living with this exceptional 0.48-acre waterfront lot on the serene shores of Choctawhatchee Bay. Offering breathtaking views and direct access to the water, this property is a rare opportunity to build your dream home or vacation retreat in one of the most sought-after coastal areas. Property has permits already to build a dock on water, expands towards the water with a curve shoreline, mostly flat with existing tree coverage, strong feasibility. Whether you're drawn to boating, fishing, or simply enjoying peaceful sunsets over the bay, this lot delivers the perfect blend of natural beauty and lifestyle potential.

Lot 25 Bayou Forest, Freeport

2 Beds ⋅ 1 Baths ⋅ 972538 MLS

Extraordinary Views!!! A Waterfront Dream on Choctawhatchee Bay As the morning sun rises over Choctawhatchee Bay, golden light dances across the water, painting the sky in shades of pink and orange. The soft sounds of waves gently lapping against the shore create a peaceful rhythm—this is the kind of serenity that awaits you every single day. Nestled along 147 feet (approx.) of pristine waterfront, this rare, cleared, and level lot is a true hidden gem. A quaint 2-bedroom, 1-bath cabin sits on the property, waiting for the right vision to bring it back to life. Whether you dream of restoring its charm or building something entirely new, the opportunity to create your own bayfront sanctuary is here. Step outside, and the possibilities are endless. The seawall and dock pilings are already in place, inviting you to rebuild a dock designed for memorable days on the water. Imagine launching your boat just steps from your door, setting out for a morning of fishing where Speckled Trout, Redfish, and Flounder await. In the afternoon, take a paddleboard or kayak across the bay, letting the salty breeze guide you toward adventure. And when the day winds down, there's no better way to end it than with a front-row seat to the most breathtaking sunsets. Pour a glass of wine, settle in on the porch, and watch as the sky turns brilliant shades of crimson and gold, reflecting off the water in a mesmerizing display. Just 200 feet away, Grady Brown Park offers even more to love about this location. With a sandy beach, a large boat ramp, a handicap-accessible kayak launch, picnic areas, and open green space, it's like having a private retreat right next door. But the magic of this property extends beyond its beauty - it's also incredibly convenient. Located in a peaceful, welcoming community, you're just a short boat ride from North Beach Social and The Bay Restaurant, perfect for a waterfront dinner with friends. Freeport is minutes away, offering shopping and essentials, while the stunning beaches of 30A are only 15-20 minutes from your doorstep. And with quick access to Interstate 10 and the VPS & ECP airports, travel is effortless. This is more than just a piece of land. It's a lifestyle, a retreat, a dream waiting to be realized. Whether you're looking for a weekend getaway, a permanent waterfront home, or an investment in a slice of paradise, this property offers everything you could want. Why wait? The sunrises are calling, the bay breeze is whispering, and the chance to live your dream is right here. Come see it for yourself--your waterfront story begins today!

2894 Bay Grove Rd, Freeport

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