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

$385,000

4 Beds ⋅ 4 Baths ⋅ 1012629 MLS

Welcome to 299 Marsh Landing S! Built in 2023, this spacious 4-bedroom, 3.5-bath home offers approximately 2,348 square feet and a versatile floor plan highlighted by an in-law suite and two living spaces--perfect for multi-generational living, extended family, guests, or anyone looking for additional privacy and flexibility under one roof. The open-concept main living area provides plenty of space for everyday living and entertaining, while the additional living space and in-law suite make this floor plan especially versatile. With four bedrooms and three and a half bathrooms, there's room to spread out while still giving everyone their own space. Step outside and enjoy the deck and outdoor living area, perfect for grilling, entertaining, or relaxing at the end of the day. The neighborhood adds even more to enjoy with a community pool, playground, and open greenspace--giving you plenty of options to enjoy the outdoors without leaving the community. Conveniently located in Freeport with easy access to schools, shopping, dining, and the bay, while the beaches, dining, and entertainment of South Walton and 30A are just a short drive away. Built in 2023, a flexible 4-bedroom layout, 3.5 bathrooms, in-law suite, multiple living spaces, first floor primary bedroom and neighborhood amenities all come together to make 299 Marsh Landing S a home worth seeing. Schedule your private showing today!

299 S Marsh Lndg, Freeport

$145,000

1010588 MLS

Build your ideal home on this fully cleared lot featuring beautiful views of Choctawhatchee Bay. With no HOA and no required build-out timeframe, you'll have the flexibility to build when and how you choose. Located just minutes from the heart of Freeport, the property offers convenient access to shopping, dining, and everyday essentials, while the sugar-white beaches of 30A are only a short drive away. Grady Brown Park is just down the street and features boat and kayak launches for easy access to the bay. Don't miss this opportunity to own a cleared homesite near the bay with the freedom to build on your own timeline.

Lot 18 Bay Grove, Freeport

$359,000

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

$379,900

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

$1,250,000

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

$345,000

988691 MLS

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

Start Your Search

Copyright© 2016 by the Multiple Listing Service of the Pensacola Association of REALTORS® This information is believed to be accurate but is not guaranteed. Subject to verification by all parties. This data is copyrighted and may not be transmitted, retransmitted, copied, framed, repurposed, or altered in any way for any other site, individual and/or purpose without the express written permission of the Multiple Listing Service of the Pensacola Association of REALTORS®. Florida recognizes single and transaction agency relationships. Information Deemed Reliable But Not Guaranteed. Any use of search facilities of data on this site, other than by a consumer looking to purchase real estate, is prohibited.

Vendor Member Number : 28166