Leeward Real Estate

Welcome to Leeward, a picturesque subdivision nestled in the heart of Pensacola, Florida. This charming community offers a perfect blend of tranquility and convenience, making it an ideal place for families, retirees, and anyone seeking a serene lifestyle with easy access to urban amenities.

Leeward boasts beautifully designed homes that reflect modern aesthetics while maintaining a warm, inviting atmosphere. The subdivision is characterized by tree-lined streets, manicured lawns, and a friendly neighborhood vibe, making it a perfect retreat from the hustle and bustle of city life. Residents enjoy spacious yards, perfect for family gatherings or peaceful evenings under the stars.

One of the standout features of Leeward is its proximity to some of the best attractions Pensacola has to offer. Just a short drive away, you’ll find stunning beaches, vibrant downtown areas, and a rich array of dining and shopping options. The renowned Pensacola Naval Air Station and the historic sites of the city are also within easy reach, providing endless opportunities for exploration and recreation.

For families, Leeward is conveniently located near top-rated schools, parks, and community centers, ensuring that children have access to quality education and plenty of outdoor activities. The neighborhood fosters a sense of community with regular events and gatherings, allowing residents to connect and build lasting friendships.

In Leeward, you’re not just buying a home; you’re investing in a lifestyle. Discover the charm and convenience of this delightful subdivision, where every day feels like a vacation in paradise. Come and experience the warmth of Leeward—your new home awaits!

Newest Listings in Leeward

$699,000

5 Beds ⋅ 686354 MLS

Experience refined coastal living in the highly sought-after Leeward community, where timeless elegance meets resort-style comfort. Perfectly situated on an impeccably landscaped lot, this meticulously maintained home offers premium finishes, thoughtful upgrades, and exceptional indoor-outdoor living. The chef-inspired kitchen is the heart of the home, featuring custom cabinetry with accent lighting, granite countertops, top-of-the-line appliances, a gas cooktop, built-in oven and microwave, soaring ceilings, recessed lighting, and an oversized walk-in pantry. The open layout flows seamlessly into the formal dining room and spacious living area, where custom built-ins and walls of windows fill the home with natural light. Step outside to your private backyard oasis with a screened lanai overlooking a sparkling custom in-ground pool with a new liner and lighting. A fully fenced yard provides the perfect setting for relaxing or entertaining. The flexible main-level office can easily serve as a fifth bedroom with access to a full bath. Upstairs, you'll find new flooring throughout, an oversized laundry room with custom cabinetry and utility sink, spacious guest bedrooms, and a luxurious primary suite featuring high ceilings, a spa-inspired bath with a soaking tub, walk-in shower, dual granite vanities, private water closet, and an expansive walk-in closet. Above the oversized two-car garage, a private guest suite with new flooring, custom cabinetry, and stone countertops provides the perfect retreat for guests or multigenerational living. Major updates include a new roof (2021), tankless water heater (2022), and upgraded garage doors (2025). Residents enjoy underground utilities, beautifully maintained parks, a volleyball court, and a community pool—all just minutes from the area's pristine beaches, boating, dining, and shopping. Move-in ready and designed for effortless coastal luxury.

10690 Close Hauled Rd, Pensacola

Listing courtesy of LPT Realty.

$53,900

685580 MLS

Build your dream home on Lot 55 in the highly sought-after coastal community of Leeward! Recognized as one of Florida's premier neighborhoods, Leeward is a private, master-planned community known for its beautiful custom homes inspired by classic Florida architecture. Residents enjoy exceptional amenities, including a community pool, parks, sand volleyball court, picnic area, and a welcoming neighborhood atmosphere. Ideally located just minutes from Perdido Key's white-sand beaches, multiple marinas, waterfront dining, Big Lagoon State Park, Johnson Beach, and NAS Pensacola, this homesite offers the perfect blend of coastal living and everyday convenience. An added bonus: the adjacent Lot 54 is also available for purchase separately, providing a rare opportunity to own side-by-side lots and create a larger homesite with additional privacy and flexibility - see MLS 685578. Explore the possibilities this beautiful homesite has to offer.

10691 Close Hauled Rd, Pensacola

Listing courtesy of Levin Rinke Realty.

$49,900

685578 MLS

Build your dream home on Lot 54 in the highly sought-after coastal community of Leeward! Recognized as one of Florida's premier neighborhoods, Leeward is a private, master-planned community known for its beautiful custom homes inspired by classic Florida architecture. Residents enjoy exceptional amenities, including a community pool, parks, sand volleyball court, picnic area, and a welcoming neighborhood atmosphere. Ideally located just minutes from Perdido Key's white-sand beaches, multiple marinas, waterfront dining, Big Lagoon State Park, Johnson Beach, and NAS Pensacola, this homesite offers the perfect blend of coastal living and everyday convenience. An added bonus: the adjacent Lot 55 is also available for purchase separately, providing a rare opportunity to own side-by-side lots and create a larger homesite with additional privacy and flexibility - see MLS 685580. Explore the possibilities this beautiful homesite has to offer.

10687 Close Hauled Rd, Pensacola

Listing courtesy of Levin Rinke Realty.

$58,000

684334 MLS

An exceptional opportunity awaits in the highly desirable Leeward neighborhood. This 0.16-acre homesite offers the perfect setting to create the custom home you've always envisioned in one of the area's most convenient and sought-after communities. The current owners have already explored the possibilities for this lot by working with a local architect on a thoughtfully designed 2-story bungalow-style residence. While the architectural plans remain the property of the architect and are not included in the sale, they showcase one potential vision for maximizing the homesite. The proposed design features nearly 1,800 square feet on the main level, including a primary suite, guest bedroom, and additional full bath, with approximately 950 square feet on the second floor offering two additional bedrooms and a shared bathroom. The concept also includes a detached two-car garage with an approximately 450-square-foot guest suite above, providing additional flexibility for guests, a home office, or private living space. Of course, you're not obligated to use the existing architect or pursue the proposed plans. This lot presents the opportunity to bring your own vision to life and design a home that perfectly fits your lifestyle, subject to Leeward's Architectural Control Committee (ACC) approval. Ideally located, Leeward offers easy access to everything the Gulf Coast has to offer. You'll be just minutes from shopping, dining, grocery stores, the back gate of NAS Pensacola, beautiful Gulf beaches, and the Florida-Alabama state line. Downtown Pensacola's vibrant restaurants, boutique shopping, entertainment, and nightlife are only about 20 minutes away, making this location ideal for both full-time residents and second-home owners. Whether you're dreaming of a coastal cottage, a custom luxury retreat, or an investment opportunity, this homesite provides the perfect foundation to make it a reality. Don't miss your chance to secure a prime lot in Leeward.

4884 Leeward Dr, Pensacola

Listing courtesy of POINTE SOUTH.

$85,000

679563 MLS

Two wooded lots just a few home sites West of the community pool and park. Many owners have purchased two sites together to accommodate a nice size dwelling, garage, and private pool area. Possible two more sites available adjacent to the East of these.

500 & 504 Downhaul Dr, Pensacola

Listing courtesy of Connell & Company Realty Inc..

$1,149,000

5 Beds ⋅ 6 Baths ⋅ 677398 MLS

Welcome to luxury living in this NEW CONSTRUCTION home with 5 bedrooms, 5 full bathrooms, 1 half bath, and almost 5,000square feet in the sought after Leeward Subdivision. Leeward is located near the beautiful beaches of Perdido Key, Big LagoonState Park, and just minutes from the Pensacola Naval Aviation Museum. As you arrive into the cul-de-sac, you will notice the beautiful construction, and the thought and time that has been put into this home. Privacy awaits as common areas surround the home, and you will only have one direct neighbor. Tongue and groove ceilings, on the beautifully stained porch, greet you as you step into the home. As you enter, you are greeted with a large entryway that opens up to the open concept living, kitchen, and dining area. You will immediately notice the details of this home from the high ceilings, crown molding, tongue and groove, beautiful stone countertops, Thor appliances, coffered ceilings in the dining area, and the custom wine room perfect for entertaining. Upstairs, you will find 3 bedrooms (including the master), and 3 full bathrooms with a large sitting area. The master bedroom has a fireplace and walk-in closet, and the master bathroom boasts a double vanity, separate garden tub and walk-in tile shower perfect for a night of relaxation after a long day. The fifth bedroom with a full bath is located above the garage and would be the perfect mother-in-law suite, game room, or guest room. The oversized 2.5 car garage is 27 ft deep, and provides plenty of room for large vehicles, lawn equipment, and storage. Additionally, the community has a community pool, park and volleyball courts to use at your leisure. The home is located near everything Pensacola has to offer. Do not wait, your dream home awaits!

10520 Squall Line Rd, Pensacola

Listing courtesy of Wellhouse Real Estate.

$115,000

669465 MLS

Lot 140 in the beautiful community of Leeward is ready for you to build your home and enjoy this charming coastal community and all it has to offer. Leeward is a private community known for its custom-built homes in the traditional Florida style. Amenities include a community pool, sidewalks, underground utilities, park, and sand volleyball court. Located close to NAS Pensacola, Perdido Key, Johnson's Beach, Big Lagoon State Park, shopping and downtown Pensacola. This exceptional CUL-DE-SAC lot and is one of the bigger lots in the subdivision. Does need to be cleared. Please see the Documents section for all documents related to the neighborhood, building, and disclosures. 2025 taxes: $1178.78 and 2026 HOA fees $1475 plus $200 annual fee for "right of way" maintenance for vacant lots.

10550 Squall Line Rd, Pensacola

Listing courtesy of Levin Rinke Realty.

$58,000

654378 MLS

Build your Dream Home on Lot 50 in the beautiful community of Leeward! Voted one of the BEST neighborhoods in Florida, Leeward is a private community known for its custom-built homes in the traditional Florida style. Amenities include sidewalks, underground utilities, parks, a pool and sand volleyball court. It is a charming coastal community! Located close to Perdido Key, Johnson's Beach, Big Lagoon State Park, NAS Pensacola and downtown Pensacola. Lot 50 is an exceptional corner lot and is being sold with partially developed architectural plans for a Victorian style home. A rendering (photo) is provided in the Documents section.

4972 Leeward Dr, Pensacola

Listing courtesy of Levin Rinke Realty.

$119,900

412073 MLS

Lot 132 is the largest corner lot in Leeward; over 1/2 acre and located on the corner of Downhaul DR at the back gate of the Leeward development. This large corner lot gives you plenty of space to design your dream home and the option of a side entry garage. Leeward is a private development of beautiful custom homes featuring the "Old Florida" style. Located minutes from the back gate to NAS Pensacola, Leeward is a former Parade of Homes site and includes many elements of the Traditional Neighborhood Design. The development features beautifully landscaped common areas, picnic area, pet park, sand volley ball and community pool/bath house. The traditional "Old Florida Style" home features turn-of-the-century residential architecture with large deep porches, raised foundations, tall windows and detached garages attached by breezeways. Strict architectural guidelines ensure that each home is unique.

577 Downhaul Dr, Pensacola

Listing courtesy of VISION INVESTMENTS, INC..

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