Longwood Homes with Gated Community - Guard Community Features

Longwood Homes with Gated Community - Guard Community Features

Welcome to Longwood, Florida – a charming city nestled in the heart of Seminole County, known for its serene landscapes, friendly neighborhoods, and vibrant community spirit. With its lush greenery and picturesque parks, Longwood offers a perfect blend of suburban tranquility and easy access to the bustling city life of nearby Orlando. This delightful locale is rich in history, featuring beautiful historic architecture and a variety of local shops and dining options that reflect the unique character of the area.

For those seeking a secure and exclusive living environment, Longwood boasts several gated communities with guard features, ensuring peace of mind for residents. These communities are designed to provide not just safety but also a sense of community and belonging. Imagine waking up each day in a beautifully landscaped neighborhood where friendly neighbors greet you, and children play freely.

The homes within these gated communities are often thoughtfully designed, offering modern amenities and spacious layouts that cater to a variety of lifestyles. Whether you’re looking for a cozy family home or a luxurious retreat, Longwood’s gated neighborhoods provide a range of options, all set against the backdrop of Florida’s stunning natural beauty.

Living in Longwood means enjoying not only the security of a guard-gated community but also the convenience of nearby shopping, dining, and recreational activities. With top-rated schools and easy access to major highways, this city is an ideal place for families, retirees, and everyone in between. Discover the charm of Longwood and find your dream home in a community that truly feels like a sanctuary.

Newest Longwood Homes with Gated Community - Guard Community Features

94 Wisteria Drive, Longwood
$529,900
4 Beds ⋅ 3 Baths ⋅ V4952184 MLS
Virtually Staged. AN OPPORTUNITY TO MAKE YOUR MARK IN THE SPRINGS—WHERE NATURAL BEAUTY, PRIVACY, AND POSSIBILITIES COME TOGETHER! BRING YOUR VISION AND UNLOCK THE POTENTIAL! Discover the potential of this distinctive residence in The Springs, one of Longwood's most established guard-gated communities, celebrated for its majestic trees, natural freshwater spring, and exceptional recreational amenities. Set on approximately three-quarters of an acre, this sprawling single-story home offers 4 bedrooms, 3 bathrooms, and over 2,600 square feet of living space, a private screened pool, and an expansive backyard surrounded by mature landscaping. From the moment you arrive, the winding driveway, towering trees, and generous homesite set the stage for something special. Inside, soaring vaulted ceilings, abundant natural light, and spacious living areas showcase the home's architectural character and possibilities. A dramatic floor-to-ceiling stone fireplace anchors the family room, while oversized sliding glass doors connect the interior to the outdoor living areas and pool. The thoughtfully designed floor plan features multiple living and dining spaces, offering flexibility for entertaining, everyday living, or creating spaces that reflect your personal style. The kitchen offers wood cabinetry, generous storage, and a casual dining area overlooking the backyard. Two spacious primary suites provide added versatility, while two additional bedrooms offer room for guests, a home office, or other uses. OUTDOOR LIVING IS WHERE THE POSSIBILITIES REALLY SHINE! The expansive screened pool enclosure, covered patio with vaulted wood ceiling, and generously sized backyard provide the foundation for a wonderful outdoor retreat. Imagine transforming this space into your own private oasis, with areas for poolside gatherings, outdoor dining, gardening, and relaxation beneath the surrounding canopy of mature trees. This home is ready for its next chapter and offers an opportunity for buyers who appreciate established neighborhoods, generous homesites, and the ability to create a space uniquely their own. While the property needs some TLC, repairs, and updating, its spacious layout, distinctive architectural features, private pool, and beautiful setting provide an excellent starting point for renovation and restoration. THE SPRINGS OFFERS A LIFESTYLE ALL ITS OWN! Residents enjoy a remarkable collection of community amenities, including 24-hour guard-gated access, a private natural freshwater spring and swimming area, community pool, clubhouse, tennis and pickleball courts, basketball courts, playgrounds, and equestrian stables. Scenic walking trails, preserved green spaces, and the Little Wekiva River contribute to the community's unique natural setting. Beyond the gates, enjoy nearby Wekiwa Springs State Park, Wekiva Island, and the Seminole Wekiva Trail, with opportunities for kayaking, hiking, cycling, and outdoor recreation. Shopping, dining, and everyday conveniences are nearby, while access to SR 434 and I-4 provides connections to Lake Mary, Altamonte Springs, Winter Park, downtown Orlando, and beyond. Whether you're looking to restore its original charm or reimagine the interiors with your own design vision, 94 Wisteria Drive offers a unique opportunity to invest in a generous homesite within one of Longwood's most distinctive communities. Bring your imagination, explore the possibilities, and discover what this property could become!

94 Wisteria Drive, Longwood
3375 Regal Crest Drive, Longwood
$1,445,000
5 Beds ⋅ 4 Baths ⋅ O6454668 MLS
Welcome to an exceptional golf-front residence in the sought-after, guard-gated community of Alaqua Lakes, ideally positioned along the 7th fairway with sweeping golf course views. Thoughtfully designed to embrace both elegant entertaining and comfortable everyday living, this beautifully appointed home offers an inviting open floor plan, abundant natural light, and seamless indoor-outdoor living. New glass entry doors create a striking first impression, opening to light-filled interiors framed by expansive sliding glass doors and tranquil outdoor vistas. The formal dining room provides an elegant setting for entertaining, while a private executive office features California Closets custom built-ins, generous storage, and additional workspace. At the heart of the home, a brand-new, completely remodeled kitchen showcases beautiful new cabinetry, luxurious quartzite countertops and backlit island, and high-end stainless-steel appliances, creating a cultivated space that seamlessly connects to the spacious family room and living areas. A desirable three-way split-bedroom floor plan offers exceptional privacy and flexibility. The luxurious owner's retreat is privately situated and features a comfortable sitting area and dual custom-built walk-in closets. The spa-inspired ensuite bath is beautifully appointed with a walk-in shower and freestanding soaking tub, creating a peaceful retreat at the end of the day. Designed for exceptional indoor-outdoor entertaining, the living room, family room, and versatile bonus room open directly to the expansive lanai. The outdoor living experience is further elevated by a Paradise Grills summer kitchen, complete with a refrigerator, Bluetooth stereo system, seating, umbrella, integrated lighting, and a natural gas connection—creating the perfect setting for entertaining while enjoying picturesque golf course and pool views. An additional bedroom is privately situated at the rear of the home, accompanied by two versatile bonus spaces. One bonus room features a custom Murphy bed, offering the flexibility to serve as a comfortable guest retreat, while the second provides additional space for a media room, playroom, fitness area, or hobby space. An updated full bath conveniently serves this area of the home. On the opposite side of the kitchen, two additional bedrooms share a convenient Jack-and-Jill bath, complemented by a separate powder room and dedicated laundry room. A three-car garage with new garage doors completes the home's functional appeal. Additional recent improvements include a brand-new tankless water heater and a new sprinkler system, adding to the home's appeal and convenience. Residents of Alaqua Lakes enjoy an exceptional lifestyle with resort-style amenities, including a community pool, covered pavilion, clay tennis courts, playground, sports field, and more. Ideally located near premier shopping, dining, and recreational destinations, the home is zoned for highly regarded Seminole County schools and offers convenient access to Orlando's world-class attractions, international airport, and Florida's beautiful beaches. An exceptional opportunity to experience refined golf-front living, thoughtfully enhanced with impressive interior upgrades and outdoor amenities, in one of Central Florida's most sought-after communities. This property may be under video/audio surveillance.

3375 Regal Crest Drive, Longwood
501 Sweetwater Club Boulevard, Longwood
$1,300,000
6 Beds ⋅ 5 Baths ⋅ O6454152 MLS
Virtually Staged. Welcome to an extraordinary estate in the prestigious, guard-gated community of Sweetwater Club! Nestled on 1.43 acres of lush, beautifully private grounds, this exceptional residence offers an impressive combination of elegance, space, and resort-style living. As you arrive, the beautifully designed circular driveway leads to a beautiful custom wood double doors. Step through the front doors and be greeted by soaring cathedral ceilings, abundant natural light, and an impressive sense of openness. Thoughtfully designed for both entertaining and everyday living, the home features a desirable split floor plan that provides comfort and privacy for the entire family. A stunning spiral staircase leads to an expansive upstairs loft, complete with double doors overlooking the grand family room below. Adding exceptional versatility, a private in-law suite is tucked away at the rear of the home, offering a separate private entrance and an ideal setup for guests or multigenerational living. This impressive space includes its own living room, bedroom, office, kitchen, and two sets of sliding glass doors overlooking the pool, filling the space with natural light while providing a beautiful view of the outdoor setting. Numerous major updates add peace of mind, including a new roof in 2021. The home's living experience extends outdoors to a resort-style swimming pool and an expansive backyard surrounded by mature trees, creating a peaceful, private retreat perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Sweetwater Club offers an exceptional lifestyle with 24-hour guard-gated security, tennis and pickleball courts, and a welcoming community filled with family-friendly events throughout the year. With homesites ranging from approximately one to eleven acres, residents enjoy a rare combination of estate-sized properties, privacy, and community connection. An especially desirable feature is the community's deeded access to Lake Brantley, complete with a private boat ramp, making boating, fishing, and lakeside recreation part of everyday living. Conveniently located within highly regarded Seminole County school zones and just minutes from shopping, dining, golf courses, and major roadways, this remarkable property offers both privacy and accessibility, with convenient access to Orlando and surrounding destinations. More than a home, this is an opportunity to experience the best of Florida estate living — where luxury, privacy, space, and lifestyle come together. Don't miss your opportunity to own this exceptional Sweetwater Club estate. Schedule your private showing today!

501 Sweetwater Club Boulevard, Longwood
269 Crown Oaks Way Unit 202, Longwood
$190,000
2 Beds ⋅ 2 Baths ⋅ O6448644 MLS ⋅ Bldg V BLDG.
Welcome to this beautifully updated condominium, offering modern finishes, a thoughtfully designed layout, and access to an exceptional array of community amenities. Located on the second floor, this inviting home features stylish vinyl plank flooring throughout, an upgraded kitchen, and renovated bathrooms that bring a fresh, contemporary feel to the space. Vaulted ceilings enhance the open, airy atmosphere of the living area, while a separate laundry room adds convenience and functionality. Additional updates include a new A/C system in 2021, a new refrigerator and microwave in 2019, and a new dishwasher in 2026. Enjoy the unique lifestyle offered by this highly sought-after, 24-hour guard-gated community, renowned for its beautiful private natural freshwater spring, complete with a swimming area and sandy beach. Residents enjoy access to tennis, pickleball, and basketball courts, a community pool, clubhouse, and playground. Conveniently located just over a mile from I-4, this community offers an excellent central location close to shopping centers, restaurants, and everyday conveniences, making it easy to enjoy both the peaceful natural surroundings and the accessibility of nearby amenities. A great long-term tenant currently occupies the property on a month-to-month lease and would love to stay, making this an attractive opportunity for investors seeking an established tenant. For owner-occupants, a flexible arrangement is possible, with the tenant's move-out coordinated through appropriate notice. With its appealing interior upgrades, desirable community amenities, convenient location, and flexible occupancy options, this condo offers a wonderful opportunity to enjoy a unique lifestyle or add a promising property to your investment portfolio!

269 Crown Oaks Way Unit 202, Longwood
2124 Woodbridge Road, Longwood
$169,000
1 Beds ⋅ 1 Baths ⋅ O6443578 MLS ⋅ 2124 BLDG.
Welcome Home! This updated one-bedroom, one-bath condo features high ceilings and an open-concept layout that feels warm and spacious for relaxing or entertaining. The property features recent updates throughout, including a new HVAC, new kitchen appliances, new carpet in the bedroom, and fresh interior paint. The living room is large and includes a wood-burning fireplace for cozy evenings, with sliding glass doors that open onto a private patio. Interior features include a spacious closet in the bedroom, a separate dining area, and inside laundry. You will also have a private garage for your car and additional storage. Enjoy living in The Springs with a 24-hour guard gate and top-tier amenities. Features include nearby tennis courts, a swimming pool, basketball and Pickleball courts, horse stables, a playground, a clubhouse, RV and boat storage, nearby jogging trails, nature trails along the Little Wekiva River, picnic and barbecue areas, and the natural spring. Shopping, restaurants, and public transportation are all nearby with access to Interstate 4. This is a Fannie Mae HomePath Property. Contact us today before this is gone.

2124 Woodbridge Road, Longwood
221 Pine Cone Lane, Longwood
$525,000
3 Beds ⋅ 3 Baths ⋅ O6444033 MLS ⋅ 221 BLDG.
Virtually Staged. Outstanding opportunity to own a very large, detached townhome in The Springs, Longwood. Picture splashing at the community pool, racing to the playground, or strolling to the spring - all just a short walk from your door. With great schools and a vibrant, fun-filled community, it's the perfect lifestyle, and why so many who grew up here return to raise their families. Located on a quiet cul-de-sac in the 24-hour, guard-gated Springs community, this brick home features 3 generously sized bedrooms and 3 baths, including two primary suites - one on the main floor with attached OFFICE and another primary suite and loft space upstairs. It’s perfect for multi-generational living and offers plenty of room for everyone. With soaring ceilings and lots of windows, this home is filled with natural light, while the screened-in patio extends the living space to the outdoors. Surrounded by lush greenery, winding trails, and natural springs, living here feels like stepping into the country. Residents enjoy exclusive access to Whispering Pines’ community pool and tennis courts, along with The Springs’ amenities: a private spring, river, horse stables, walking and jogging paths, food trucks, movie nights, and a vibrant calendar of community events. With Longwood’s rich history, top-rated Seminole County schools, and an unbeatable location just under a mile from I-4, this home makes it so easy to get toPublix, schools, gyms, Altamonte Springs, Costco, Whole Foods, Lake Mary, Winter Park, downtown Orlando, the attractions, farmer’s markets, and the beach. Everything you need is close by! Scheduling a showing is easy, just reach out!

221 Pine Cone Lane, Longwood
1901 Glen Mist Cove, Longwood
$330,000
3 Beds ⋅ 3 Baths ⋅ S5158695 MLS ⋅ - BLDG.
"Motivated seller! All reasonable offers will be considered."Welcome to this beautifully maintained two-story corner residence, offering added privacy, abundant natural light, and inviting indoor and outdoor living spaces. The bright, open-concept floor plan creates a comfortable, welcoming atmosphere, while the updated kitchen features stainless steel appliances and a clean, modern design—perfect for everyday living and entertaining. A true highlight of the property is the private, beautifully landscaped garden, offering a peaceful outdoor retreat. Whether you're enjoying morning coffee, relaxing after a long day, or entertaining family and friends, this charming outdoor space sets this home apart. Meticulously maintained and move-in ready, the home offers an ideal combination of comfort, style, and convenience. Its desirable corner location offers additional outdoor space and greater privacy. Located in a gated community with security and a community swimming pool, residents can enjoy a relaxed lifestyle with attractive amenities nearby. With its prime corner location, updated interior, private garden, and move-in-ready condition, this exceptional property is ready to welcome its next owner. Schedule your private showing.

1901 Glen Mist Cove, Longwood
209 Jasmine Lane, Longwood
$399,900
O6445575 MLS
HIGH AND DRY BUILDABLE LOT in THE SPRINGS! A true Hidden Gem! Located in a Col-de-sac, the pie-shaped lot fans out in rear, allowing fore a HUGE back yard. Geotechnical report completed, confirming the dirt is good to go! Survey available includes boundary, topo and trees. Preliminary site work should be minimal. A few trees may need to go for building, but otherwise the lot is mostly clear. Purchase the lot as-is or discuss a build-to-suit with the owner, who is a locally established, award-winning custom-home builder. Great fortunes come to those who TAKE IMMEDIATE ACTION when opportunity presents itself. Come

209 Jasmine Lane, Longwood
104 Wild Fern Drive, Longwood
$997,000
4 Beds ⋅ 3 Baths ⋅ O6440568 MLS
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 ⋅ O6439484 MLS
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 ⋅ O6435091 MLS ⋅ 2184 BLDG.
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
$2,299,000
5 Beds ⋅ 6 Baths ⋅ O6436456 MLS
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 cultured 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 refined 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 highly sought-after 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
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