Leeward Real Estate

Welcome to Leeward, a vibrant subdivision nestled in the heart of Pensacola, Florida, in the picturesque Escambia County. This charming community is a hidden gem, offering a perfect blend of tranquility and accessibility, making it an ideal place for families, retirees, and everyone in between.

Leeward is characterized by its beautifully designed homes, many of which feature modern amenities and spacious layouts that cater to today’s lifestyle. The tree-lined streets and well-maintained landscaping create an inviting atmosphere, encouraging evening strolls and friendly neighborly interactions. With a variety of home styles available, from cozy single-family residences to more expansive properties, there’s something to suit every taste and budget.

One of the standout features of Leeward is its proximity to some of the best attractions that Pensacola has to offer. Residents enjoy easy access to stunning beaches, where you can soak up the sun or indulge in water sports. The vibrant downtown area is just a short drive away, offering a plethora of dining, shopping, and entertainment options. Additionally, families will appreciate the nearby schools, parks, and recreational facilities that provide ample opportunities for outdoor activities.

As a community that values connection and comfort, Leeward is not just a place to live; it’s a place to thrive. Whether you're looking for a peaceful retreat or a lively neighborhood atmosphere, Leeward welcomes you with open arms. Discover your dream home in this delightful subdivision and experience the best of Pensacola living!

Newest Listings in Leeward

$42,000

687093 MLS

Build on the lowest-priced lot on the market in Leeward. This 0.18-acre interior homesite sits in one of Pensacola's most established private neighborhoods — sidewalks, underground utilities, a gas-lamp entrance and landscaped medians, with a community pool, sand volleyball court, parks and a pet park. Leeward is known for custom homes in traditional coastal Florida style, and an Architectural Review Committee keeps it that way, so no two houses look alike. The Nature Conservancy's Perdido Pitcher Plant Prairie borders the neighborhood, and you're minutes from Big Lagoon State Park, the white sand of Perdido Key, NAS Pensacola and downtown. Zoned LDR. Bring your own builder and your own plans, subject to ARC approval — CC&Rs and ARC guidelines are in the listing documents. Eight lots for sale in Leeward and this is the cheapest one.

4921 Leeward Dr, Pensacola

$699,000

5 Beds ⋅ 5 Baths ⋅ 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

$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

$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

$58,000

398038 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. Buyer to verify all inform

4884 Leeward Dr, Pensacola

$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

$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

$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

$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

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© Baldwin County Association of Realtors, Inc. Information deemed to be reliable but not guaranteed. The data relating to real estate for sale on this website comes in part from the Broker Reciprocitysm Program. Listing broker has attempted to offer accurate data, but buyers are advised to confirm all items. Information last updated on .