Longleaf Real Estate

Longleaf Real Estate

Welcome to Longleaf, a charming subdivision nestled in the heart of Winter Garden, Florida, located in picturesque Orange County. This vibrant community offers a perfect blend of suburban tranquility and modern convenience, making it an ideal place for families, retirees, and everyone in between.

Longleaf is characterized by its beautifully designed homes, meticulously landscaped gardens, and friendly neighbors who foster a close-knit community atmosphere. The subdivision features a variety of architectural styles, ensuring that every homeowner can find their perfect match. Whether you’re drawn to cozy single-family homes or spacious modern designs, Longleaf has something for everyone.

Residents of Longleaf enjoy access to a wealth of amenities that enhance the quality of life. Stroll through scenic walking trails, relax in well-maintained parks, or take a dip in the community pool on warm Florida days. The subdivision is also home to playgrounds and recreational areas, providing ample opportunities for outdoor fun and family gatherings.

Location is key, and Longleaf shines in this regard. Situated just minutes from the bustling downtown Winter Garden, residents can easily access a variety of shopping, dining, and entertainment options. The area is known for its vibrant farmers’ market, charming boutiques, and delectable eateries, ensuring there’s always something new to explore.

With excellent schools, nearby healthcare facilities, and quick access to major highways, Longleaf is not just a place to live; it’s a place to thrive. Discover the warmth and charm of Longleaf, where community spirit meets modern living in the heart of sunny Florida!

Newest Listings in Longleaf

3 Beds ⋅ 2 Baths ⋅ Longleaf SubDv.

Virtually Staged. Move-in ready impeccably maintained one story 3-bedroom 2-bath home with TWO flex rooms in Longleaf Village neighborhood! This thoughtfully designed open-concept floor plan offers a spacious family room, dining area, and kitchen—perfect for both everyday living and entertaining plus a study and flex room that can double as a den, formal living or dining room. Gorgeous light laminate wood flooring flows throughout the main living areas, while the bedrooms feature comfortable carpeting. The kitchen showcases wood cabinetry, stainless steel appliances, and ample prep and storage space. The spacious primary suite features a large walk-in closet and an en-suite bathroom complete with a soaking tub, walk-in shower, and expansive vanity. Step outside to an impressive screened lanai designed for outdoor living. The oversized patio includes a fully equipped outdoor kitchen with a built-in grill connected to natural gas, sink, beverage fridge, generous counter space, and solar screening—ideal for year-round entertaining and enjoying Florida living.This home has been meticulously maintained with numerous recent upgrades, including a new HVAC and AC system with UV lights installed in 2024 and serviced every six months, new roof, skylight, and gutters in 2024 with transferable warranty, exterior paint and shutter replacement in 2024, lanai screen replacement with solar screens in 2024, and a new water heater installed in 2023. Additional features include a 2-car garage. Enjoy the wonderful community ammenities icluding a large pool, clubhouse with full gym, tennins courts, basketball courts and playground. Conveniently located within 4 miles of shopping and dining at Celebration Pointe or Bulter Plaza, parks, and within 7.5 miles of the University of Florida and UF Health Shands hospital, this move-in ready home combines comfort, style, and peace of mind with major system updates already completed!

8632 Sw 76th Place, Gainesville

4 Beds ⋅ 4 Baths ⋅ Longleaf SubDv.

Just reduced to $349./per square foot. Owner will include GOLD COMMONS CLUB membership for newly built Beach Club!! Brand new HVAC system (2 units) is being installed which will include a 12-year warranty. Exterior painting was completed mid-May…thanks to the Longleaf HOA. Whether scaling down from a larger custom home or moving-up from a condo you will love the living space provided by the Kingfisher floor plan- and this one particularly on the cul-de-sac gives you extra privacy with a extra long drive-way and front yard plus LAKE & ISLAND from the lanai. Rare to find 2 FULL BATHS on the 2nd floor which accommodates your guests. A large 1st floor Master Suite offers walk-in closets, a large bathroom space with separate vanities and separate walk-in shower and corner bathtub. Kitchen offers GE Profile Refrigerator, Dishwasher, Microwave and GAS range. Pantry. and there is an extra storage closet in Laundry room. Washer and Dryer are Samsung. Also on the first floor is the office/den has wood flooring and a walk-in closet. 4 BATHROOMS TOTAL as one is a powder room by the foyer/Great Room. There is also a Rinnai GAS Water heater and GAS POOL HEATER. Electric hurricane shutters are on the lanai. electric shutters over the from Door. The home also has hurricane sliding doors off the lanai!!!! A new tile ROOF as of 2020. Homeowners only used the home for a few weeks each year / it was never rented. Shadow Wood Country Club offers 54 holes of championship golf, 2 clubhouses, 9 Har Tru tennis. 2 Bocce courts. Shadow Wood is in the process of building a Brand new Lifestyle Centering opening Fall-2026 with 6 new Indoor Pickleball Courts, Brand new Resort Pool with poolside dining and bar, a dedicated kids pool and pool with lap lanes. This 26 Million dollar world class facility comes with NO assessment to Members.

21780 Longleaf Trail Drive, Estero

3 Beds ⋅ 2 Baths ⋅ Longleaf SubDv.

Exclusive, Shadow Woods at the Brooks, waterfront home. Enjoy spectacular sunsets as you lounge on your private, poolside lanai. Featuring an open floor plan with plenty of natural light. Perfect for entertaining. or just quiet enjoyment. Shadow Wood Country Club memberships are available and offer a spectacular clubhouse, 3 championship golf courses and a top rated tennis program. Additional membership to The Commons Club at the Brooks offers a private beach club, fitness club, social activities and swimming pool. NEW amenity of the Lifestyle Center construction and expansion are underway and will include: indoor Pickleball courts, new tennis courts, a resort-style pool with poolside seating, a firepit lounge, poolside restaurant with full kitchen and a brand-new racquets pro shop (projected completion is Fall 2026. this project will be done with no assessment to the Members.)

22140 Long Leaf Trail Drive, Estero

4 Beds ⋅ 3 Baths ⋅ Longleaf SubDv.

This stunning home features a spacious screened lanai with south exposure, offering breathtaking lake and preserve views, complemented by a gas-heated pool—creating an ideal outdoor sanctuary for morning coffee or relaxing during the day. An 3 bedroom plus den Kingfisher model home located in the highly desirable Shadow Wood at The Brooks community, it offers the perfect balance of comfort, style, and Florida lifestyle living. The open-concept Great Room design on the first floor features soaring ceilings, abundant natural light, and spacious living and dining areas—perfect for relaxing and entertaining. The updated kitchen boasts new granite countertops, a pantry, breakfast bar, and ample storage, seamlessly flowing into the dining area and out to the outdoor oasis. The primary suite and den are conveniently located on the first floor, while upstairs offers two guest bedrooms and a versatile loft space, ideal for family or visitors. The Shadow Wood Club has been completely renovated, providing world-class amenities, and there is no current assessment for the community. Residents enjoy optional golf and country club memberships, tennis, pickleball, fitness, and access to The Commons Club with a private beach club, spa, and dining. This home truly captures the essence of luxury Florida living—a peaceful retreat surrounded by nature and community, where every day feels like a getaway.

21900 Longleaf Trail Drive, Estero

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