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$474,900

The ONLY inground POOL HOME in Freeport under $500,000! If a private pool is on your wish list, 330 Gray Owl Drive deserves your attention. Located in the popular Owl's Head Farms neighborhood, this immaculate, owner-occupied home offers 2,053 square feet of living space across a spacious single-story floor plan, complete with 5 bedrooms and 3 full baths. The backyard is the true showstopper, centered around a sparkling inground pool completed in 2025 featuring customizable LED lighting and an upgraded ozone aeration filtration system for clean, low-maintenance swimming. A premium screen enclosure protects the entire pool area, connecting directly to the covered porch for seamless indoor-outdoor living. A dedicated paved BBQ patio and a fully privacy-fenced backyard create a relaxing outdoor oasis ready for immediate enjoyment. Inside, the open-concept layout features a light-filled kitchen with granite countertops, an expansive center island, a corner walk-in pantry, and a dining area that flows seamlessly into the main family room. The spacious primary suite is situated at the back of the home overlooking the pool and features dual vanities, a large walk-in shower, a linen closet, and an oversized walk-in closet. Four additional bedrooms and two full guest bathrooms provide exceptional flexibility for guests, dedicated home offices, or hobby spaces. Meticulously cared for from day one, the home's interior is in pristine condition and completely pet-free. Valuable home enhancements provide everyday efficiency and peace of mind, including added ceiling insulation to help keep utility bills low, an active termite bond with protective attic spray treatment, a SimpliSafe security system with a video doorbell camera, and smart home technology featuring keyless entry, a smart thermostat, and automated garage controls. Owl's Head Farms features low HOA fees of just $80 per month alongside fantastic neighborhood amenities, including a community pool with a covered gathering area, pickleball courts, a playground, and sidewalks throughout. Conveniently located near the US-331 corridor, you are only minutes from Freeport shopping and dining, Choctawhatchee Bay boat launches, and a straight drive to the sugar-white beaches of South Walton and 30A. Schedule your private tour today to experience this rare Freeport pool home! A video tour is also available.

5 Beds ⋅ 3 Baths ⋅ 1010771 MLS

The ONLY inground POOL HOME in Freeport under $500,000! If a private pool is on your wish list, 330 Gray Owl Drive deserves your attention. Located in the popular Owl's Head Farms neighborhood, this immaculate, owner-occupied home offers 2,053 square feet of living space across a spacious single-story floor plan, complete with 5 bedrooms and 3 full baths. The backyard is the true showstopper, centered around a sparkling inground pool completed in 2025 featuring customizable LED lighting and an upgraded ozone aeration filtration system for clean, low-maintenance swimming. A premium screen enclosure protects the entire pool area, connecting directly to the covered porch for seamless indoor-outdoor living. A dedicated paved BBQ patio and a fully privacy-fenced backyard create a relaxing outdoor oasis ready for immediate enjoyment. Inside, the open-concept layout features a light-filled kitchen with granite countertops, an expansive center island, a corner walk-in pantry, and a dining area that flows seamlessly into the main family room. The spacious primary suite is situated at the back of the home overlooking the pool and features dual vanities, a large walk-in shower, a linen closet, and an oversized walk-in closet. Four additional bedrooms and two full guest bathrooms provide exceptional flexibility for guests, dedicated home offices, or hobby spaces. Meticulously cared for from day one, the home's interior is in pristine condition and completely pet-free. Valuable home enhancements provide everyday efficiency and peace of mind, including added ceiling insulation to help keep utility bills low, an active termite bond with protective attic spray treatment, a SimpliSafe security system with a video doorbell camera, and smart home technology featuring keyless entry, a smart thermostat, and automated garage controls. Owl's Head Farms features low HOA fees of just $80 per month alongside fantastic neighborhood amenities, including a community pool with a covered gathering area, pickleball courts, a playground, and sidewalks throughout. Conveniently located near the US-331 corridor, you are only minutes from Freeport shopping and dining, Choctawhatchee Bay boat launches, and a straight drive to the sugar-white beaches of South Walton and 30A. Schedule your private tour today to experience this rare Freeport pool home! A video tour is also available.

330 Gray Owl Dr, Freeport

$1,595,000

Welcome to an extraordinary Randy Wise custom home in the exclusive Vineyards at Hammock Bay, where timeless elegance meets exceptional Florida living. Thoughtfully designed with impeccable craftsmanship and refined finishes throughout, this stunning residence offers the perfect blend of sophistication, comfort, and resort-style luxury. Step inside to discover an open, light-filled floor plan with soaring ceilings, designer details, and seamless indoor-outdoor living. Every space has been carefully curated to create an atmosphere of effortless elegance with stunning Cambria countertops that will make every event feel magical and elegant. The true showpiece awaits outdoors. This spectacular backyard retreat is nothing short of spectacular featuring a fireplace, sparkling resort-style, gunite, saltwater and heated pool, expansive screened covered living areas, and an incredible outdoor kitchen entertaining space designed for unforgettable gatherings. Whether you're hosting friends for sunset cocktails, enjoying family celebrations, or simply unwinding in your own private oasis, this outdoor sanctuary delivers the ultimate Florida lifestyle. Nestled within the prestigious Vineyards neighborhood of Hammock Bay, this exceptional residence offers privacy, luxury, and access to one of Freeport's most sought-after communities. Combining Randy Wise's renowned quality and craftsmanship with unparalleled outdoor living, this is more than a home--it's a lifestyle unlike any other. *There is also a whole house generator. *There is a three car garage with epoxy flooring and a generous sized storage closet.

5 Beds ⋅ 5 Baths ⋅ 1008633 MLS

Welcome to an extraordinary Randy Wise custom home in the exclusive Vineyards at Hammock Bay, where timeless elegance meets exceptional Florida living. Thoughtfully designed with impeccable craftsmanship and refined finishes throughout, this stunning residence offers the perfect blend of sophistication, comfort, and resort-style luxury. Step inside to discover an open, light-filled floor plan with soaring ceilings, designer details, and seamless indoor-outdoor living. Every space has been carefully curated to create an atmosphere of effortless elegance with stunning Cambria countertops that will make every event feel magical and elegant. The true showpiece awaits outdoors. This spectacular backyard retreat is nothing short of spectacular featuring a fireplace, sparkling resort-style, gunite, saltwater and heated pool, expansive screened covered living areas, and an incredible outdoor kitchen entertaining space designed for unforgettable gatherings. Whether you're hosting friends for sunset cocktails, enjoying family celebrations, or simply unwinding in your own private oasis, this outdoor sanctuary delivers the ultimate Florida lifestyle. Nestled within the prestigious Vineyards neighborhood of Hammock Bay, this exceptional residence offers privacy, luxury, and access to one of Freeport's most sought-after communities. Combining Randy Wise's renowned quality and craftsmanship with unparalleled outdoor living, this is more than a home--it's a lifestyle unlike any other. *There is also a whole house generator. *There is a three car garage with epoxy flooring and a generous sized storage closet.

121 Revana Way, Freeport

$1,500,000

**MAJOR PRICE CORRECTION** Waterfront multigenerational dream home on half an acre, all on one level and fully fenced for privacy, security, and fun. This rare property offers two separate homes, a covered pool, private dock, and tons of parking--perfect for a large family, multi-gen living, or a primary residence with incredible Airbnb/short-term rental potential. The main home is a spacious 3 bedroom, 2 bathroom layout with easy, single-level living, water views and includes a true mother-in-law suite with its own full kitchen, bathroom, and private access that leads directly out to the covered pool area--ideal for extended family, guests, or income-producing space. The second home is also a 3 bedroom, 2 bathroom layout. Multiple living areas, split bedrooms, and separate entrances give everyone room to spread out while still feeling connected. Step outside to your own private resort: a screened/covered pool just steps from both homes, a private dock for boating, fishing, or paddleboarding, and a fully fenced yard with privacy fence and gated entry. The oversized lot (approximately half an acre) offers room for kids, pets, toys, and gatherings, with ample driveway space and parking for cars, RV, or boat. This is an entertainer's paradise and a true lifestyle property--waterfront living, no stairs, multiple kitchens, and flexible spaces that can adapt as your needs change.

7 Beds ⋅ 5 Baths ⋅ 1006674 MLS

**MAJOR PRICE CORRECTION** Waterfront multigenerational dream home on half an acre, all on one level and fully fenced for privacy, security, and fun. This rare property offers two separate homes, a covered pool, private dock, and tons of parking--perfect for a large family, multi-gen living, or a primary residence with incredible Airbnb/short-term rental potential. The main home is a spacious 3 bedroom, 2 bathroom layout with easy, single-level living, water views and includes a true mother-in-law suite with its own full kitchen, bathroom, and private access that leads directly out to the covered pool area--ideal for extended family, guests, or income-producing space. The second home is also a 3 bedroom, 2 bathroom layout. Multiple living areas, split bedrooms, and separate entrances give everyone room to spread out while still feeling connected. Step outside to your own private resort: a screened/covered pool just steps from both homes, a private dock for boating, fishing, or paddleboarding, and a fully fenced yard with privacy fence and gated entry. The oversized lot (approximately half an acre) offers room for kids, pets, toys, and gatherings, with ample driveway space and parking for cars, RV, or boat. This is an entertainer's paradise and a true lifestyle property--waterfront living, no stairs, multiple kitchens, and flexible spaces that can adapt as your needs change.

4374 W County Highway 83a, Freeport

$519,900

Price improvement..$10k off price..Located in the gated golf community of Windswept Estates, this beautiful 3-bedroom, 2-bath home on a rare .73-acre corner lot. This property offers a rare opportunity to add a detached 2-car garage, due to expansion of this lot size. Designed for comfortable living, the home features a spacious floor plan with a cozy fireplace, large primary suite with walk-in closet, garden tub, and separate shower, plus a convenient mudroom and walk-in laundry room. Enjoy Florida living at its best with an in-ground fiberglass pool, screened lanai, soothing fountain, covered porches, quiet space for relaxing with nature or entertaining. Storage and parking are abundant with an oversized 2-car garage, enclosed golf cart garage, covered portico, and extra parking for boats, RVs, or guests. Current updates include a new roof and HVAC (2023). This well built home is four-sided brick and includes a Generac whole-home generator for added peace of mind. Residents of the Estates enjoy pickle ball, tennis, a community pool, playground, golf course (pay to play) & gated security. Located within a 30 minute drive of the white-sand beaches, dining, shopping, and entertainment on 30A, Destin, Panama City Beach, NW Florida Airports & Niceville. A quick call to schedule your private viewing & begin your new Florida Adventure. Virtual staging has been used and identified in select photos. RESTATING DETAILS The Survey shows the additional layout of the extra garage build should you decide. THE ARC will require an update of docs to finalize approval. The Review board approved (new owner to re-qualify approval)..Survey and ARC Drawings. Roof and HVAC updated in 2023. Parking attached two-car garage, additional driveway space with room for recreational vehicles.Time limits apply to parking Motor homes.Coaches, recreational vehicles. See the C & Rs /Rules attached to listing. Covered portico connects the golf cart garage directly to the home through the mudroom, offering added convenience. As mentioned the home is constructed of brick siding and 2023 composite shingle roof. Energy features include central electric air conditioning updated 2023, high-efficiency heating, ceiling fans, and an electric water heater. A Generac whole-home generator provides added reliability during power outages. Installed and turns off with a power outage instantly. The original cost $9000. Windswept offers a range of amenities including gated entry, golf course for a fee, see (windsweptdunes.com), pickleball and tennis courts, a community pool, playground, fishing pond and a pet-friendly environment. Windswept Dunes Golf Club operates primarily as a daily-fee, public golf course. They do not offer traditional annual equity or full-week golf memberships. Instead, the course utilizes a pay-to-play model featuring public green fees.Standard Green Fees: Usually range from $130 to $140 (including a cart) depending on the season and time of day.Men's Golf League: If you want regular play and a structured community, you can join their Men's Golf League. This requires an annual one-time $25 sign-up fee, and members receive discounted $95 green fees (cart included) during league events. The Gulf Coast's beaches are approximately 30 minutes away, along with the attractions and events throughout Walton County and the scenic Highway 30A area. This property offers a combination of space, comfort, and community in a well-established neighborhood. The Neighbors Boast of the Peace and Quiet in Windswept yet convenient to shopping and daily services. Centrally located approximately a half hour to the NW Florida Beaches Airport. Tired of the Bustle, just Schedule a showing to see if this is the next place you call home.

3 Beds ⋅ 2 Baths ⋅ 1001834 MLS

Price improvement..$10k off price..Located in the gated golf community of Windswept Estates, this beautiful 3-bedroom, 2-bath home on a rare .73-acre corner lot. This property offers a rare opportunity to add a detached 2-car garage, due to expansion of this lot size. Designed for comfortable living, the home features a spacious floor plan with a cozy fireplace, large primary suite with walk-in closet, garden tub, and separate shower, plus a convenient mudroom and walk-in laundry room. Enjoy Florida living at its best with an in-ground fiberglass pool, screened lanai, soothing fountain, covered porches, quiet space for relaxing with nature or entertaining. Storage and parking are abundant with an oversized 2-car garage, enclosed golf cart garage, covered portico, and extra parking for boats, RVs, or guests. Current updates include a new roof and HVAC (2023). This well built home is four-sided brick and includes a Generac whole-home generator for added peace of mind. Residents of the Estates enjoy pickle ball, tennis, a community pool, playground, golf course (pay to play) & gated security. Located within a 30 minute drive of the white-sand beaches, dining, shopping, and entertainment on 30A, Destin, Panama City Beach, NW Florida Airports & Niceville. A quick call to schedule your private viewing & begin your new Florida Adventure. Virtual staging has been used and identified in select photos. RESTATING DETAILS The Survey shows the additional layout of the extra garage build should you decide. THE ARC will require an update of docs to finalize approval. The Review board approved (new owner to re-qualify approval)..Survey and ARC Drawings. Roof and HVAC updated in 2023. Parking attached two-car garage, additional driveway space with room for recreational vehicles.Time limits apply to parking Motor homes.Coaches, recreational vehicles. See the C & Rs /Rules attached to listing. Covered portico connects the golf cart garage directly to the home through the mudroom, offering added convenience. As mentioned the home is constructed of brick siding and 2023 composite shingle roof. Energy features include central electric air conditioning updated 2023, high-efficiency heating, ceiling fans, and an electric water heater. A Generac whole-home generator provides added reliability during power outages. Installed and turns off with a power outage instantly. The original cost $9000. Windswept offers a range of amenities including gated entry, golf course for a fee, see (windsweptdunes.com), pickleball and tennis courts, a community pool, playground, fishing pond and a pet-friendly environment. Windswept Dunes Golf Club operates primarily as a daily-fee, public golf course. They do not offer traditional annual equity or full-week golf memberships. Instead, the course utilizes a pay-to-play model featuring public green fees.Standard Green Fees: Usually range from $130 to $140 (including a cart) depending on the season and time of day.Men's Golf League: If you want regular play and a structured community, you can join their Men's Golf League. This requires an annual one-time $25 sign-up fee, and members receive discounted $95 green fees (cart included) during league events. The Gulf Coast's beaches are approximately 30 minutes away, along with the attractions and events throughout Walton County and the scenic Highway 30A area. This property offers a combination of space, comfort, and community in a well-established neighborhood. The Neighbors Boast of the Peace and Quiet in Windswept yet convenient to shopping and daily services. Centrally located approximately a half hour to the NW Florida Beaches Airport. Tired of the Bustle, just Schedule a showing to see if this is the next place you call home.

51 Tournament Ln, Freeport