Longwood Homes with Gated Community - Guard Community Features

Longwood Homes with Gated Community - Guard Community Features

Welcome to Longwood, a charming city located in Seminole County, Florida. Known for its serene neighborhoods and friendly atmosphere, Longwood offers a wonderful blend of suburban living with easy access to urban amenities.

For those seeking a secure and exclusive living experience, Longwood boasts a variety of homes within gated communities with guard features. These communities provide residents with an added layer of security and privacy, giving homeowners peace of mind and a sense of comfort.

Living in a gated community in Longwood not only offers security benefits but also provides a strong sense of community. Residents often enjoy shared amenities such as swimming pools, fitness centers, walking trails, and more. It's a great way to connect with neighbors and foster a tight-knit community spirit.

Whether you're looking for a luxurious estate or a cozy townhome, Longwood's gated communities offer a range of housing options to suit your lifestyle and preferences. With well-maintained grounds and a focus on safety, these neighborhoods provide a tranquil retreat from the hustle and bustle of city life.

Experience the best of both worlds in Longwood – a peaceful retreat nestled in the heart of Seminole County, with the added security and convenience of a gated community. Find your dream home in Longwood today and enjoy the comfort and luxury of guard-gated living.

Newest Longwood Homes with Gated Community - Guard Community Features

104 Crown Oaks Way Unit 104, Longwood
$140,000
2 Beds ⋅ 2 Baths ⋅ Crown Oaks SubDv. ⋅ 32779 Zip Code
WELCOME TO THE SPRINGS | FULLY REMODELED FIRST-FLOOR CONDO | PRIVATE DECK | GUARDED-GATED COMMUNITY | NATURAL SPRING Imagine coming home to a beautifully remodeled retreat surrounded by towering trees, lush landscaping, and the natural beauty of one of Longwood's most treasured communities. Nestled within the sought-after, guarded-gated community of The Springs, this exceptional first-floor, 2-bedroom, 2-bath condominium combines designer finishes, effortless living, and resort-style amenities that make every day feel like a getaway. Beautifully renovated with style and functionality in mind, this light-filled home showcases luxury wood-plank vinyl flooring throughout with no carpet, elegant plantation shutters, custom lighting, and thoughtfully selected finishes. The inviting living and dining spaces offer a comfortable setting for everyday living and entertaining. The stunning remodeled kitchen steals the show, featuring granite countertops, custom cabinetry and hardware, stainless steel appliances, a farmhouse sink, and generous workspace. The spacious owner's suite offers a peaceful escape with a custom-built closet organization system, beautifully remodeled en-suite bathroom, and charming sitting area overlooking a private patio. Both bathrooms have been completely renovated with updated cabinetry, fixtures, and lighting. Additional improvements include updated plumbing, and an upgraded electrical panel. Interior laundry adds everyday convenience and storage. Step outside to your expansive private deck, an inviting extension of your living space perfect for morning coffee, outdoor dining, entertaining, or relaxing beneath the surrounding greenery. Ground-floor living means easy access without stairs. Additional highlights include a dedicated lighted carport with lockable storage, low electric bills, and water and trash included in the HOA dues. But the real magic of this home extends far beyond its walls. The Springs offers a lifestyle unlike any ordinary condominium community. At its heart lies a breathtaking, crystal-clear natural spring with a private sandy beach, surrounded by lush tropical beauty. Swim in the spring, explore scenic trails along the Little Wekiva River, or enjoy the community pool, sauna, fitness center, tennis courts, pickle-ball courts, basketball court, playgrounds, picnic areas, clubhouse, horse stables, and RV storage. An active social calendar featuring food trucks, outdoor movie nights, and holiday celebrations creates a wonderful sense of community. Enjoy the privacy and peace of mind of 24-hour guard-gated security, all just minutes from shopping, dining, I-4, SR 434, and everything greater Orlando has to offer. It's the rare combination of a peaceful natural sanctuary and exceptional everyday convenience. Beautifully remodeled. Effortlessly livable. Surrounded by nature. At 104 Crown Oaks Way, you're not simply buying a condominium—you're embracing a lifestyle where every day offers something extraordinary. Come experience the magic of The Springs. Schedule your private showing today!

104 Crown Oaks Way Unit 104, Longwood

221 Pine Cone Lane, Longwood
$560,000
3 Beds ⋅ 3 Baths ⋅ Springs Whispering Pines Sec 2 SubDv. ⋅ 32779 Zip Code
Virtually Staged. A rare detached brick townhome on a private, quiet cul de sac in Longwood's guard gated Springs community. Step through 9 foot custom European style double doors into a foyer opening to the great room, where dramatic 14 foot ceilings and walls of transom windows bathe the space in natural light. Recessed lighting keeps it glowing after dark, and a wood burning fireplace anchors the living area. The kitchen has a gas range and two large pantries, secluded yet connected to the main living space. The main floor primary suite is a true highlight, with automated blackout shades, a large 10x10 walk in closet, and an adjoining private room designed with an executive office in mind, equally perfect as a nursery or study, closed off by French doors. The ensuite bath features a steam shower and separate water closet. The three way split floor plan places a second main floor bedroom, ideal as a guest room or office, on the opposite side of the home for privacy, with a full bath featuring a cleverly hidden shower. Upstairs is its own private retreat with a bonus flex space, game closet with additional storage, and a second primary suite with full bath, ideal for multigenerational living. A lovely screened lanai with courtyard extends your living space outdoors. Designed with distinction, this home has incredible bones and awaits your personal updates. Recent updates: full replumb December 2025 and brand new AC May 2026. Exclusive to the Whispering Pines village: community pool and clay tennis courts. The Springs is a community like no other, an immersive natural sanctuary where residents stroll beneath century old Live Oaks, walking and jogging paths, horse stables, a clubhouse, pool, and a full calendar of community events. Wildlife and native Florida woodlands are part of daily life here. The Springs is also prized for its highly desired top rated schools, and is conveniently located less than 1 mile from I-4, with easy access to Altamonte Springs, Lake Mary, Winter Park, farmer's markets, Crane's Roost, shopping, dining, vibrant restaurants, the beaches and attractions. Longwood offers a small town vibe while being just a short drive from all that Orlando is known for. A rare opportunity to enjoy space, privacy, and true Florida living. Schedule your private showing today!

221 Pine Cone Lane, Longwood

2405 Alaqua Drive, Longwood
$3,995,000
6 Beds ⋅ 10 Baths ⋅ Alaqua Ph 3 SubDv. ⋅ 32779 Zip Code
Alaqua's flagship estate: an unparalleled custom residence set on a rare 2.31-acre double homesite, the widest within Seminole County's premier luxury neighborhood, the 24-hour guard-gated community of Alaqua. Surrounded by sweeping golf course, conservation, and water views, this remarkable property offers an extraordinary combination of privacy, scale, architectural presence, and resort-style living. A stately porte-cochère creates an impressive arrival and introduces an interior defined by soaring ceilings, intricate millwork, abundant natural light, and a dramatic grand dual staircase. At the heart of the residence, the formal living room makes a striking statement with coffered 23' ceilings, expansive two-level windows taking advantage of vistas behind, custom built-ins, and an elegant fireplace. Generous proportions and a seamless connection to the surrounding living spaces make the home equally suited for intimate gatherings and grand-scale entertaining. The gourmet kitchen is designed for both beauty and function, featuring premium appliances, extensive custom cabinetry, and an oversized center island with abundant workspace and seating. Opening directly to the spacious family room, the kitchen creates an inviting environment for everyday living while maintaining the sophistication expected of an estate of this caliber. A gracious formal dining room provides an elegant setting for memorable dinners and special occasions. The upper-level primary suite is a private retreat unto itself, showcasing picturesque golf and water views along with beautifully designed custom walk-in closets. The spa-inspired bath features dual vanities, polished marble finishes, an oversized frameless-glass shower, and a freestanding soaking tub. A private kitchenette and dedicated laundry further enhance the suite’s exceptional comfort and convenience. Adjacent to the primary suite, a distinctive glass-enclosed room overlooks the dramatic living space below and offers remarkable versatility as a private office, fitness studio, sitting room, or additional retreat. Multiple ensuite bedrooms provide privacy and comfort for family and guests, while a dedicated theater is designed for an immersive entertainment experience, featuring custom wood detailing, cove lighting, a convenient minibar, surround sound, and a sophisticated cinematic atmosphere. Outdoors, the estate transforms into a private resort. The expansive pool and raised spa are complemented by dramatic water features and lush tropical landscaping, creating an atmosphere of serenity and seclusion. A fully equipped outdoor kitchen with built-in grill, hood, generous preparation areas, and service space makes year-round entertaining effortless. Expansive pool decking provides abundant room for lounging and entertaining, while the covered lanai—with decorative beams and multiple ceiling fans—offers a sophisticated extension of the home’s interior living spaces. Beyond, panoramic golf course and water views create a spectacular backdrop from morning through evening. From quiet mornings overlooking the water to unforgettable gatherings beneath the covered lanai, 2405 Alaqua Drive represents a rare opportunity to own a truly exceptional estate on one of Alaqua’s most distinctive double homesites. This property may be under audio/visual surveillance.

2405 Alaqua Drive, Longwood

104 Wild Fern Drive, Longwood
$997,000
4 Beds ⋅ 3 Baths ⋅ Springs The Deerwood Estates SubDv. ⋅ 32779 Zip Code
Welcome to a home where iconic 1970s character, thoughtful modernization, and an extraordinary resort-style setting come together behind the guarded gates of The Springs. This distinctive 4-bedroom, 3-bathroom residence has been beautifully preserved while evolving for modern living. Soaring ceilings, walls of natural light, polished concrete slab floors, and an open-concept floor plan create an atmosphere that feels sophisticated, organic, and unmistakably unique. Even better, fully paid-off solar panels add energy efficiency without sacrificing style, and the garage features a Tesla auto charger and solar wall. The home unfolds with dramatic architectural character and effortless indoor-outdoor living. Upstairs, the private primary suite feels like its own retreat, complete with an ensuite bath featuring double vanities and a private balcony overlooking the spectacular backyard. Throughout the home, original design influences remain celebrated rather than erased, creating a rare combination of warmth, personality, and modern functionality. Outside is where this property becomes truly unforgettable. Designed for enjoying the Florida lifestyle year-round, the backyard is its own private resort featuring a large saltwater swimming pool, raised hot tub, putting green, fire pit, and outdoor sauna. The impressive outdoor kitchen is equipped with a wood-fire pizza oven, grill, bar seating, keg setup, and TVs. Tucked away from the main entertaining areas is an entirely separate private garden & koi pond, creating a quiet escape surrounded by lush greenery. With the smart irrigation and well system included, keeping up with the lawncare is a breeze. Whether hosting a crowd, watching the game from the outdoor bar, or enjoying an evening around the fire pit, this outdoor environment is exceptional. The lifestyle continues beyond the property in The Springs, one of Longwood's most distinctive 24-hour guard-gated communities. Surrounded by natural Florida beauty, residents enjoy exclusive access to historic Sanlando Springs, with its crystal-clear natural spring and sandy beach, along with tennis and pickleball courts, recreation facilities, clubhouse, trails, and private horse stables and equestrian facilities. Few Central Florida communities combine privacy, recreation, and nature quite like this. Ideally positioned in the sought-after Longwood/Wekiva Springs corridor, the home offers convenient access to SR-434 and I-4, connecting you quickly to the dining, shopping, and lifestyle destinations of Longwood, Altamonte Springs, and the Markham Woods corridor. This is not simply a beautifully updated home. It is a property with character, architecture, privacy, and an incredible sense of fun, set within a community unlike anything else in Central Florida. Welcome to 104 Wild Fern Drive and a lifestyle that feels like a getaway every day.

104 Wild Fern Drive, Longwood

3387 Regal Crest Drive, Longwood
$1,199,000
4 Beds ⋅ 3 Baths ⋅ Alaqua Lakes Ph 4 SubDv. ⋅ 32779 Zip Code
Welcome to 3387 Regal Crest Drive-an elegant golf front residence ideally positioned along the 7th fairway of the Legacy Club within the prestigious guard-gated community of Alaqua Lakes. Offering 3,038 square feet of beautifully designed living space, this home features 3 bedrooms, 3 full baths and a dedicated over-sized office that can easily be converted to a 4th bedroom. A refined interior showcases timeless architectural details including crown molding and coffered ceilings throughout. The formal living room is anchored by a fireplace and enhanced by a wet bar with a wine refrigerator creating a sophisticated setting for entertaining. A separate formal dining room provides an elegant space for hosting family and guests. At the heart of the home, the kitchen opens naturally to the spacious family room creating an inviting and functional layout for everyday living. Custom built-ins add both character and style to the family room while providing a beautiful focal point and additional display and storage space. Designed to embrace the Florida lifestyle, the living areas flow effortlessly to the expansive lanai, outdoor summer kitchen, screened sparkling pool and spa offering a private oasis for relaxing and entertaining. With its desirable golf-course setting, gracious formal spaces, custom architectural details, versatile floor plan and resort-style outdoor living, this residence offers an exceptional opportunity to enjoy the privacy, elegance and lifestyle of Alaqua Lakes. This home is covered by a whole home warranty to also cover the pool/spa and is transferable to the new owner. Alaqua Lakes is set within a premier golf course community where residents enjoy world-class amenities including clay tennis courts, a resort-style pool, playground and sports field, a 24-hour guard-gated entrance and enhanced community security. Located near A-rated schools, Central Florida’s best attractions, upscale shopping and dining, major highways and international airports.

3387 Regal Crest Drive, Longwood

2184 Woodbridge Road Unit 2184, Longwood
$260,000
3 Beds ⋅ 3 Baths ⋅ Palm Spgs Condo At The Spgs SubDv. ⋅ 32779 Zip Code
Welcome to The Springs! This beautiful 3-bedroom, 3-bathroom condo is ideally located in one of the community’s most desirable areas. Surrounded by nature and nestled among the trees, this home has a true treehouse feel, offering a peaceful and private setting with beautiful views of the surrounding greenery, tennis courts, and The Springs from the living room and porch. Meticulously maintained, this home is bright, inviting, and thoughtfully designed, with an abundance of natural light throughout. High ceilings and an open-concept floor plan create a warm and spacious atmosphere, perfect for relaxing or entertaining. There is plenty of storage space throughout the home, making it easy to keep everything organized. A wood-burning fireplace adds a cozy touch during the cooler months. The oversized primary suite is tucked away in a private loft on the second floor and features beautiful wooded views, creating a peaceful and serene retreat. The spacious bathroom includes a walk-in closet, separate shower and soaking tub, and dual vanities. The second bedroom is also located upstairs and has its own private bathroom with a shower/tub combination. The third bedroom is conveniently located on the first floor and includes its own private bathroom with a shower. Additional features include plantation shutters, a convenient laundry area just off the kitchen, a one-car garage, and additional storage space conveniently located next to the garage. The home also features a newer A/C system installed in July 2024, new plumbing in April 2026, and a new water heater in April 2026. Enjoy the best of The Springs lifestyle with the river, community pool, tennis and pickleball courts, playground, and basketball courts all just steps from your door. With its elevated setting among the trees, peaceful surroundings, meticulous upkeep, and incredible location, this home truly feels like your own private treehouse retreat—while still being close to all the amenities of The Springs. Residents of The Springs enjoy exclusive access to the community's natural crystal-clear spring and river, along with an impressive collection of resort-style amenities. The Springs is a spectacular 24-hour guard-gated community with hourly patrols and resort-style amenities, including tennis courts, pickleball courts, a swimming pool, basketball court, horse stables, playground, clubhouse, RV and boat storage, walking and jogging trails, nature trails along the Little Wekiva River, picnic and barbecue areas, and the stunning natural spring. This vibrant community hosts year-round events and activities, including movie nights under the stars, holiday celebrations, food truck nights, and more. Located within a top-rated school district and offering convenient access to I-4, shopping, dining, major highways, amusement parks, outlet malls, and Florida's beautiful beaches, this home combines comfort, convenience, and an exceptional lifestyle. Schedule your private tour today!

2184 Woodbridge Road Unit 2184, Longwood

3355 Lakeview Oaks Drive, Longwood
$2,399,000
5 Beds ⋅ 6 Baths ⋅ Alaqua Lakes Ph 1 SubDv. ⋅ 32779 Zip Code
Virtually Staged. A bespoke Dave Brewer masterpiece in Alaqua lakes — where exceptional architecture, refined craftsmanship and extraordinary indoor-outdoor living converge. This distinguished custom residence offers five ensuite bedrooms, six baths and a dedicated office that can easily transition to a sixth bedroom, creating an exceptional blend of elegance, comfort and versatility. A brand-new roof further enhances the home's appeal and peace of mind. Created with sophisticated entertaining in mind, the residence unfolds into an extraordinary outdoor retreat. The custom architectural screened lanai is a true extension of the home, featuring a resort-style pool and spa, a full summer kitchen, generous gathering spaces and surrounding misting fans for effortless comfort. A private putting green adds a distinctive touch, framed by natural-gas tiki torches that create an unforgettable ambiance after sunset. At the edge of the lanai, a beautifully positioned fire pit invites intimate evenings while overlooking sweeping golf course vistas and tranquil water views. Inside, the gourmet kitchen was completely reimagined in 2021 and showcases a gas range with professional exhaust, a built-in oven, a steam oven, a microwave and a dedicated ice maker. The expansive family room is enhanced by automated shades programmed on timers, seamlessly combining convenience with sophisticated design. Thoughtfully engineered for efficiency and comfort, the home features two zoned HVAC systems, allowing individual areas to be conditioned according to daily use. Set within the prestigious guard-gated community of Alaqua Lakes, residents enjoy an exceptional collection of amenities, including a resort-style pool, a wading pool, five clay Har-Tru tennis courts with two full-time pros available for lessons, a basketball court, a playground, a sand volleyball court and a multi-purpose field. The community's lush natural surroundings and picturesque lakes provide a serene backdrop, while the Tom Fazio-designed golf course creates a coveted setting for this exceptional residence. A truly remarkable custom home offering elevated Florida living, extraordinary entertaining spaces and a level of privacy, craftsmanship and design rarely found in Alaqua Lakes.

3355 Lakeview Oaks Drive, Longwood

334 Vista Oak Drive, Longwood
$1,775,000
5 Beds ⋅ 6 Baths ⋅ Wingfield North 2 SubDv. ⋅ 32779 Zip Code
Welcome to an exceptional luxury estate in the prestigious, 24-hour guard-gated community of Wingfield North, ideally located along the highly sought-after Markham Woods Road corridor. Situated on a private 1.23-acre cul-de-sac lot, this remarkable residence offers an impressive combination of scale, luxury, privacy, and resort-style outdoor living. This five-bedroom, six-bathroom home features spacious bedrooms, each with its own en-suite bathroom and walk-in closet. The first-floor primary suite offers a private retreat with French doors opening directly to the patio and pool. Custom walk-in closet design, dual vanity & a walk in shower with multiple shower heads and features. One bedroom features French doors leading to its own private screened porch. Two bedrooms share a private study at the entrance of the dedicated space. Throughout the living areas and bedrooms, engineered hardwood flooring adds warmth and sophistication. Designed for both elegant entertaining and everyday living, the home includes a formal living room overlooking the pool and patio, a formal dining room ideal for large gatherings, and a private office complete with a walk-in closet. The brand-new chef's kitchen is a true centerpiece, with custom cabinetry, marble countertops, an oversized island with seating, gas cooktop, Thermador appliances, and a dedicated eating area overlooking the living room, pool, and outdoor living spaces. Upstairs, the loft provides flexible living space along with an additional bedroom, walk-in closet, and full bathroom. Abundant storage is thoughtfully incorporated throughout the home. The four-car garage offers ample room for a boat or other toys along with a dedicated golf simulation area and an approximately 8' x 17' air-conditioned room perfect for a workshop, hobby space, or additional storage. Outdoor living is equally impressive. The backyard features a screened in pool and spa, covered patio, pool house with storage, and space designed for a future summer kitchen. A creek runs along the rear of the property, while mature wooded areas along the perimeter provide exceptional privacy. A brick-paver circular driveway, covered front porch and cul-de-sac location further enhance the estate's curb appeal and setting. Extensive recent improvements include a recently inspected tile roof with substantial remaining life, whole-home sound system, Control4 smart-home technology, security system, two tankless gas water heaters, new filtration system, front landscaping and irrigation, interior painting, pool equipment, interior lighting and fixtures, garage door openers, screened enclosure upgrades, and exterior pressure washing. A 1,000-gallon propane tank serves the home. Great opportunity to own a substantial luxury estate in one of the Markham Woods area's most desirable guard-gated communities, offering privacy, generous indoor and outdoor spaces, amenities, and a location convenient to top-rated schools, shopping, dining, and major roadways.

334 Vista Oak Drive, Longwood

Start Your Search