Leeward Real Estate

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

10663 Heavy Weather Way, Pensacola
$56,000
690462 MLS
Build the custom home you've always dreamed of in Leeward, one of Pensacola's most desirable residential communities! Whether you're envisioning a full-time residence or a coastal retreat, this homesite offers the perfect opportunity to build a home that complements your lifestyle while enjoying all that the Leeward community and beautiful Gulf Coast have to offer. Leeward amenities include a swimming pool, neighborhood parks, pet park, volleyball, and picnic area. Location is another outstanding advantage! Ideally located, Leeward offers convenient access to shopping, dining, NAS Pensacola, and the beautiful beaches of Perdido Key. Just a short 20-minute drive away, vibrant Downtown Pensacola offers an exciting mix of exceptional dining, boutique shopping, entertainment, and local events. Your dream home starts with the perfect homesite. Discover the possibilities in Leeward! Seller also owns lot 89 behind this one, so a back-to-back combination could also be accommodated if interested.

10663 Heavy Weather Way, Pensacola

Listing courtesy of Levin Rinke Realty.

10683 Noreaster Way, Pensacola
$589,000
3 Beds ⋅ 3 Baths ⋅ 689410 MLS
Enjoy the charm of coastal living in Leeward, a beautiful, planned neighborhood near the beaches of Perdido Key, with quick access to the NAS Pensacola back gate and an easy commute to Downtown Pensacola. Known for its custom homes, inviting front porches, sidewalks, neighborhood parks and community pool, Leeward offers a true neighborhood feel with Old Florida character. This custom Craftsman-style home welcomes you with a wide covered front porch and porch swing, setting the tone for relaxed evenings and coastal breezes. Inside, oak hardwood floors, high ceilings, abundant natural light and detailed millwork create a warm, polished interior. The spacious kitchen features a large island, granite countertops, breakfast bar, walk-in pantry, wall oven and microwave, with an open connection to the great room and formal dining area accented by wainscoting. French doors lead to the private backyard and deck, providing plenty of room for outdoor dining, entertaining or simply unwinding at home. A dedicated office or flex space, utility room & oversized two-car garage round out the home’s impressive features. The primary suite offers a spacious retreat with a large walk-in closet with built-ins and an ensuite bath featuring dual vanities, granite countertops, a separate tiled shower and soaking tub. Additional built-ins and custom details can be found throughout the home. Major improvements completed in 2022 include the roof, HVAC, water heater and siding, providing added peace of mind. Just minutes from the beautiful beaches of Perdido Key, Big Lagoon State Park, boating, dining & endless outdoor recreation, this home puts the best of coastal living right at your fingertips. Schedule your showing today & start imagining yourself at home here!

10683 Noreaster Way, Pensacola

Listing courtesy of POINTE SOUTH.

4921 Leeward Dr, Pensacola
$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

Listing courtesy of Warner Realty Inc..

10690 Close Hauled Rd, Pensacola
$675,000
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

Listing courtesy of LPT Realty.

10691 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

Listing courtesy of Levin Rinke Realty.

10687 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

Listing courtesy of Levin Rinke Realty.

500 & 504 Downhaul 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

Listing courtesy of Connell & Company Realty Inc..

4972 Leeward 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

Listing courtesy of Levin Rinke Realty.

577 Downhaul 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

Listing courtesy of VISION INVESTMENTS, INC..

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