Longwood Homes with Gated Community - Guard Community Features

Longwood Homes with Gated Community - Guard Community Features

Welcome to Longwood, Florida – a hidden gem nestled in the heart of Seminole County. Known for its lush greenery and friendly atmosphere, Longwood offers a perfect blend of suburban tranquility and urban convenience. With its charming historic district, excellent schools, and vibrant community events, it's no wonder that families and professionals alike are drawn to this delightful city.

One of the standout features of Longwood is its array of gated communities, providing residents with an added layer of security and exclusivity. These guard-gated neighborhoods are designed to foster a sense of community while ensuring peace of mind. Imagine returning home to your beautifully landscaped property, knowing that your family is safe and secure behind the walls of a well-maintained community.

Homes in these gated communities are often characterized by spacious layouts, modern amenities, and stunning architectural designs. Whether you’re looking for a cozy single-family home or a luxurious estate, Longwood’s gated communities offer a variety of options to suit your lifestyle. Residents enjoy access to resort-style amenities, including sparkling pools, fitness centers, and tennis courts, perfect for those seeking an active lifestyle.

Living in Longwood means embracing a lifestyle rich in outdoor activities, with nearby parks and nature trails that invite exploration. The city’s strategic location also provides easy access to major highways, making commuting to Orlando and beyond a breeze.

If you’re searching for a place that combines safety, community spirit, and beautiful homes, Longwood’s gated communities are waiting to welcome you home. Come discover the charm of Longwood, where your dream home awaits!

Newest Longwood Homes with Gated Community - Guard Community Features

$1,300,000
5 Beds ⋅ 5 Baths ⋅ Wingfield North 2 SubDv. ⋅ 32779 Zip Code
Welcome to an exceptional estate in the prestigious guard gated community of Wingfield North, ideally positioned along Lake Mary’s renowned Markham Woods Corridor. Set on a private cul-de-sac surrounded by distinguished one-acre homes, this custom residence offers an extraordinary combination of privacy, sophistication, and natural beauty. A circular driveway welcomes you to the home, framed by mature landscaping and towering trees, with a private pond and the Wekiva Springs Conservation Area creating a serene backdrop with no rear neighbors—only peaceful views and the occasional passing deer. Step through the stately covered entry and leaded-glass front door into a dramatic, light-filled interior where soaring 20-foot ceilings and expansive windows immediately set the tone. The first floor is beautifully finished with ceramic tile designed to replicate the warmth and character of wood, offering an elegant look with exceptional durability. At the heart of the home is the stunning kitchen, completely renovated in 2025, featuring sophisticated quartz countertops, generous workspace, and a seamless connection to the expansive great room. Designed for effortless entertaining, the indoor living spaces open through hidden sliding glass doors to the screened lanai, enclosed pool, and summer kitchen, creating a true indoor-outdoor Florida lifestyle. The private primary suite encompasses the entire left wing of the first floor and opens directly to the lanai. Its spacious spa-inspired bath features a double vanity and walk-in closet, creating a tranquil retreat separate from the home’s additional bedrooms. A grand staircase leads to the second level, where a spacious bonus loft provides an additional gathering or entertainment space alongside two bedrooms and a full bath. Beyond its impressive design, the home has been thoughtfully enhanced with significant recent improvements, including a 2025 kitchen renovation, exterior paint in 2025, all three A/C systems replaced in 2025, and a new water heater installed in 2026. Surrounded by conservation views, mature landscaping, and remarkable privacy, this Wingfield North residence offers the rare opportunity to enjoy gracious luxury living in one of Lake Mary’s most desirable settings—where elegant interiors, expansive entertaining spaces, and the beauty of nature come together seamlessly.

359 Vista Oak Drive, Longwood
$429,900
4 Beds ⋅ 4 Baths ⋅ Reserve At Lake Wildmere - Ph 1 SubDv. ⋅ 32750 Zip Code
Move-In-Ready Luxury End-Unit Townhome Welcome to 534 Lake Wildmere Cove, a beautifully designed end-unit townhome offering 4 bedrooms, 3.5 bathrooms, approximately 2,316 square feet, and an attached two-car garage in the Reserve at Lake Wildmere community. Built in 2019, the home features a bright, open layout with abundant natural light and generous living and dining spaces. The spacious kitchen is highlighted by quartz countertops, an oversized center island, stainless-steel appliances, ample cabinetry, and plenty of room for entertaining. Upstairs, you’ll find spacious bedrooms, private en-suite bathrooms, a versatile loft and office area, and a private balcony. Additional outdoor living areas include a covered front porch and rear patio. Community amenities include a swimming pool, clubhouse, gated entrance, and access to the community lake dock. Conveniently located near Downtown Longwood, Lake Mary, Sanford, Altamonte Springs, shopping, dining, major roadways, and everything Central Florida! move-in ready Property highlights: End-unit location with only one shared wall 4 bedrooms and 3.5 bathrooms Approximately 2,316 square feet Quartz countertops and oversized kitchen island Stainless-steel appliances Two-car garage Upstairs loft and office space Private balcony and covered patio Gated community Community pool, clubhouse, and lake dock Built in 2019 Move-in ready

534 Lake Wildmere Cove, Longwood
$2,000,000
4 Beds ⋅ 4 Baths ⋅ Springs The Deerwood Estates SubDv. ⋅ 32779 Zip Code
Back on the market — buyers never funded their deposit. A rare second chance at a Gene Leedy original. For the first time in 28 years, the most coveted mid-century home in Orlando is available. Your private compound. A piece of art you live inside. The Strasberg Residence, designed by award-winning architect Gene Leedy. He built only three private homes in the Orlando area, and this is his Masterpiece. Beyond the 8-foot concrete stucco wall wrapped in ivy, the world disappears from view, and yours begins. Trees, gardens, and a pool the color of dark glass lie behind your private wall. At its center, a breathtaking atrium and courtyard: a reflecting pool with twin fountains and a tree rising from the water, framed by glass on every side. Inside, Leedy's design language of clean lines and subtle, important details is everywhere. Eleven-foot doors, warm wood trim throughout, and expansive glass in every room harmonize nature with the interior, bringing together privacy, gardens, and water features. The social center of the home is the soaring great room with fireplace and wet bar. Formal dining. All wired for sound. Two separate entrances serve the east and west wings, each with its own foyer. The primary suite occupies an entire wing: a bedroom sitting room with its own bar, a dressing room, an enormous custom-built closet, a dual-sink countertop with a separate vanity, a separate WC with bidet, a tub that overlooks the pool, a steam shower that feels like a spa, and its own private walled patio and another patio that leads to the pool. Nearly every room opens to its own patio and garden. And then the rarest amenity of all: a fully detached in-law suite with its own private entrance through the second decorative iron door, a full en-suite bath, and two patios of its own, one overlooking the backyard and one fully private behind its own 8-foot wall, just like the primary. A complete home within the home, for extended family, guests, or total independence. 4 bedrooms, 4 baths, 3,885 SF. The grounds are one with the architecture: a dark-water pool with jacuzzi among specimen trees and sculptures, an outdoor kitchen, and a richly planted .67-acre lot of total walled seclusion. All in The Springs, a guarded, gated sanctuary of natural springs, stables, and trails, minutes from Greater Orlando. This is the home everyone wants, held closely for a generation. Now, rarely, it's yours to claim.

111 Sand Pine Lane, Longwood
$1,750,000
5 Beds ⋅ 5 Baths ⋅ Alaqua Lakes Ph 5 SubDv. ⋅ 32779 Zip Code
Custom estate home on an oversized lot in the 24-hour guard-gated community of Alaqua Lakes, with water and golf course views and beautiful sunsets from the living room. This five-bedroom, four-and-one-half-bath residence features a private office, three-car garage, soaring ceilings, and a thoughtfully designed floor plan with the primary living areas on the main level. The renovated kitchen features quartz countertops, a large center island, custom cabinetry, a Wolf range, Bosch dishwasher, built-in microwave drawer, and opens seamlessly to the family room and breakfast area. Recent updates include designer-painted custom cabinetry with premium hardware, beautifully renovated bathrooms, a modern fireplace surround, solid wood shaker-style interior doors with Emtek hardware, custom baseboards and trim, updated LED recessed lighting throughout, and carefully selected designer light fixtures that create a warm, refined atmosphere. Custom built-in cabinetry in both the living room and family room adds architectural character while providing exceptional style and functionality. Designed for both everyday living and effortless entertaining, the outdoor living space features a heated screened pool, an expansive patio and pool deck, a covered lanai with an outdoor grill, and tranquil water and golf course views. Additional features include a whole-house generator and a private upstairs guest suite. Residents of Alaqua Lakes enjoy a 24-hour guarded entrance, a seven-acre community park, tennis courts, a playground, pavilion, and convenient access to shopping, dining, and major highways.

3450 Foxmeadow Court, Longwood
$429,000
3 Beds ⋅ 2 Baths ⋅ Springs Glenwood Village Sec 1 Rev The SubDv. ⋅ 32779 Zip Code
Beautiful 3 Bedroom, 2 Bath End Unit Town Home in the Glenwood Village area of the Springs (Once a Public Park) This Guard Gated Community is a Wildlife Lovers Paradise Where You Will Have the Opportunity to Enjoy Mother Nature at Her Finest Living Amongst the Peacocks, Deer, Raccoons, Opossums, Bears, Squirrels and Many Species of Birds. The Home Features Fresh Paint, Newer Roof and Window Treatments, Upgraded Kitchen, Hardie Board Siding, Double Courtyards, Front and Back, Privacy Fenced for Little Ones and Pets, Extended Paver Driveway, Huge Laundry Room, Oversized Two Car Garage With Lots of Storage. It is Light, Bright, and Open With Floor to Ceiling Windows, Natural Light, 20 Foot Ceilings in the Primary Suite and Great Room, Fantastic Floor to Ceiling Fireplace. Glenwood Village has it's Own Large Pool and Bathhouse Which Has Recently Been Renovated. Tennis and Pickleball Courts Have Been Renovated. The Springs Pool, Clubhouse and Bathhouses Will Be Renovated Next, And All Assessments Have Already Been Paid For By the Seller! There Are Also Horse Stables and RV Parking Available for Residents. You have Access to a Private Natural Spring With a Sandy Beach, Walking and Biking Trails. Truly a Nature Lover's Paradise Offering Privacy, Yet Conveniently Located Minutes From I-4, Shopping, Restaurants, Schools, Hospitals. Call Today To See This Exceptional Home! The Home May be Under Audio/Video Surveillance. All Information Believed Correct but Not Guaranteed, Buyer and Buyer's Agent to Verify.

111 Juniper Lane, Longwood
$3,600,000
6 Beds ⋅ 9 Baths ⋅ Sweetwater Club Estates SubDv. ⋅ 32779 Zip Code
Nestled behind wrought-iron privacy gates on 2.89 acres in Sweetwater Club Estates, this magnificent 10,623-square-foot residence offers an unparalleled blend of timeless architecture, grand-scale entertaining, and resort-inspired living. A sweeping circular driveway leads to a breathtaking arrival framed by soaring cathedral ceilings, dramatic sandstone feature walls, and handcrafted wood details throughout. Designed for both elegant entertaining and multi-generational living, this six-bedroom estate offers seven full bathrooms and two half bathrooms with exceptional privacy for family and guests alike. The home's spectacular great room is nothing short of impressive, showcasing two-story wood-clad ceilings, a magnificent stone fireplace, a full entertaining bar, and dramatic sandstone accents that create an unforgettable gathering space. From intimate evenings to grand celebrations, this home was designed to host life's most memorable moments. Movie nights become an experience in the dedicated theater room, while the richly appointed wood-clad parlor offers the perfect setting for a game room, bourbon lounge, or sophisticated retreat complete with its own stone fireplace. Executives and entrepreneurs will appreciate the expansive private office featuring custom wood finishes, a cedar-lined walk-in closet, and its own full bath—ideal as an executive suite, private study, or additional guest accommodations. Five luxurious bedroom suites are conveniently located downstairs, each offering cedar-lined walk-in closets and private en-suite baths. The secondary primary suite on the main level is thoughtfully positioned, providing exceptional flexibility for multi-generational living or long-term guests. Ascending the grand wooden staircase—worthy of a Scarlett O'Hara entrance—you'll discover the home's most exclusive retreat. Occupying the entire second floor, the primary owner's sanctuary features a stunning stone fireplace, spacious sitting room currently utilized as an additional bedroom, a private office, and an extraordinary sense of privacy seldom found in luxury homes. Step outside to your private resort where sandstone patios surround the sparkling pool, spa, and cascading waterfall. The gazebo provides the perfect backdrop for outdoor entertaining, while the expansive grounds offer ample space to build your own basketball court, tennis court, putting green, or other recreational amenities. Car enthusiasts will appreciate the detached six-car garage and generous parking, while boat owners will love the private neighborhood access to Lake Brantley, with available boat parking at the clubhouse. Recent improvements include a newer roof and six recently replaced air conditioning systems, offering peace of mind for years to come. Residents of Sweetwater Club Estates enjoy exclusive access to Sweetwater Beach and Lake Brantley's private boat ramp, picnic facilities, basketball and tennis courts, creating an exceptional Florida lifestyle just minutes from home. Conveniently located only minutes from Wekiva Springs State Park and major thoroughfares including I-4, SR 434, and SR 436, this remarkable estate offers both privacy and accessibility in one of Central Florida's most sought-after luxury communities. This is more than a home—it is a legacy estate designed to be enjoyed for generations.

1041 Sweetwater Club Boulevard, Longwood
$3,000,000
8 Beds ⋅ 10 Baths ⋅ Sweetwater Club Unit 4 SubDv. ⋅ 32779 Zip Code
Welcome to this exceptional executive estate located within the 24-hour manned, gated community of Sweetwater Club. Privately positioned on an elevated 1.27-acre corner lot, this impressive residence offers a four-car garage, circular driveway, and striking curb appeal. Step through the oversized front entry into a thoughtfully designed open-concept floor plan where spacious living areas blend seamlessly for everyday living and entertaining. The foyer flows into the formal dining room, living room, sitting area, wet bar, and den, all overlooking the stunning courtyard-style pool to create exceptional indoor-outdoor living. The chef's kitchen is beautifully appointed with solid wood cabinetry, premium granite countertops, pendant lighting, dual dishwashers, double convection ovens, a spacious walk-in pantry, and recently updated appliances, including a refrigerator, freezer, double ovens, and built-in microwave.Conveniently located just minutes from Wekiva Springs State Park, Sweetwater Golf & Country Club, shopping, dining, and everyday conveniences, this extraordinary property combines luxury, privacy, and convenience in one exceptional offering. Schedule your private showing today.

1040 Sweetwater Club Boulevard, Longwood
$1,200,000
6 Beds ⋅ 5 Baths ⋅ Retreat At Lake Brantley SubDv. ⋅ 32779 Zip Code
Welcome to this exceptional residence in Retreat at Lake Brantley, one of Longwood’s most sought-after gated communities, celebrated for its private boat ramp access to Lake Brantley, highly rated Seminole County schools, convenient location, and enduring desirability. Built in 2021 and thoughtfully enhanced beyond the original builder plan, this Casabella floor plan by Pulte Homes offers over 5,200 square feet of living space, six bedrooms, and four-and-a-half bathrooms, seamlessly blending elevated design elements with the versatility and functionality today’s lifestyles demand. A paver driveway and covered entry welcome you into interiors enriched by extensive millwork, statement lighting, tile flooring, and new carpeting. The foyer opens to beautifully proportioned living spaces designed to accommodate both gracious entertaining and everyday living. The kitchen is both stylish and functional, featuring quartz countertops, a generous center island with seating, built-in wall ovens, stainless steel appliances, gray cabinetry, abundant storage, and an open layout that flows effortlessly into the dining area and great room. Anchoring the main living space is a striking linear gas fireplace framed by custom built-ins, while oversized sliding glass doors invite natural light and create a seamless connection to the outdoor living areas. A dedicated flex room on the main level provides an ideal setting for a home office, study, library, or sitting room. The expanded owner’s retreat, thoughtfully enlarged beyond the original floor plan, serves as a private sanctuary with ample room for a sitting area or lounge space. The oversized custom walk-in closet is complemented by integrated laundry with a stackable washer and dryer—an elevated convenience rarely found in comparable homes. Upstairs, over 2,000 square feet of additional living space creates a true second-level retreat. An expansive loft functions as a spacious secondary family room and gathering space, while the adjoining flex room offers exceptional versatility as a playroom, media room, theater, game room, teen lounge, or potential additional bedroom with the addition of a closet. Generously sized secondary bedrooms and bathrooms further enhance the home’s ability to accommodate evolving lifestyles, guests, or multi-generational living. Additional highlights include a thoughtfully organized pantry, extensive storage throughout, solar panels for enhanced energy efficiency, and a covered brick-paver lanai designed for year-round enjoyment. Equipped with remote-controlled retractable screens and dual ceiling fans, this inviting outdoor space provides comfort, airflow, and protection from the elements while serving as a natural extension of the home’s interior living areas. The fully fenced backyard offers ample space for recreation, entertaining, and future outdoor enhancements. Combining elevated design details, exceptional flexibility, over 5,200 square feet of living space, private Lake Brantley access, and a setting within one of Seminole County’s premier gated communities, this thoughtfully enhanced residence presents a rare opportunity to enjoy a lifestyle defined by comfort, convenience, and connection. Schedule your private showing today and experience all this remarkable home has to offer.

3367 Canyon Grand Point, Longwood
$1,175,000
6 Beds ⋅ 5 Baths ⋅ Bella Vista SubDv. ⋅ 32779 Zip Code
Lot size is approximately 9,324 sq/ft or .21 acre

1442 Vivaldi Place, Longwood
$1,388,000
5 Beds ⋅ 6 Baths ⋅ Sweetwater Club Unit 1 SubDv. ⋅ 32779 Zip Code
Welcome home to this stunning, fully renovated home sitting on 1.51 acres in the coveted Sweetwater Club neighborhood. The home has been professionally remodeled from top to bottom with marble tile flooring and walls throughout most of the first floor. Pull into the lot by way of the wrap around driveway that leads to a massive three car garage, with extra exterior parking space as well. Upon entry, you'll be greeted by a gorgeous luxury vinyl plank staircase with a luxury glass railing. To your left is the show-stopping kitchen with brushed-gold accents throughout, and new high-end appliances to match. You'll be amazed by the honeycomb-inspired mosaic backsplash and the gorgeous premium light fixtures above the island and in the attached dining room. The kitchen also features a massive walk-in pantry, a smaller bonus pantry, a convenient half bath, and a hidden protracting charging station for all of your wireless needs. From the dining room, step down into the family room with a gorgeous built in electric fireplace that also connects to the expansive living room, both with massive ceiling fans. Also conveniently located on the first floor is a bonus room with an exterior door that's perfect for an office. From there, step into the massive 3 car garage that has also been finished with marble tile flooring. Connected to the garage is the 5th bedroom with exterior access and a full ensuite bathroom, perfect to convert to an in-law suite, or even a gym or tool room. From the living room, step out to the back patio area that is made for entertaining. It has been set up with a bar, wine cooler, built in grill, and a large fan to create the perfect space that is just begging to watch your favorite sports team with friends and family. Then of course is the pool and built in hot tub, a convenient half bath, and also includes a sauna that comfortably accommodates three guests. Upstairs you'll find the four main bedrooms, with two of the guest rooms having full ensuite baths with exterior access to the upstairs patio overlooking the pond. The laundry room is conveniently located upstairs as well, so no worrying about running back and forth downstairs for your laundry duties. The primary bedroom is massive, and includes a built in vanity desk with custom shelving, additional built in shelving, a massive walk in closet, and exterior access to a covered outdoor hallway that connects to the second bedroom. The primary bathroom is truly show-stopping with a massive frameless shower, floating custom vanities, brushed gold hardware, and an architectural wood-slat feature wall creating a true resort-style ambiance. EVERY major system (roof, HVAC, electrical, and plumbing) has been updated and is less than two years old, and the home also features a tankless hot water heater. The septic tank was also cleaned/inspected in September of 2025. Every window and sliding door has been upgraded to double-pane, giving you energy efficient peace of mind that is a must-have in the Florida heat. With designer finishes throughout, luxurious living spaces, and attention to detail from top to bottom, the only thing missing is you! Schedule your private showing today before someone else calls it home.

305 Sweetwater Club Circle, Longwood
$698,800
4 Beds ⋅ 3 Baths ⋅ Springs The Deerwood Estates SubDv. ⋅ 32779 Zip Code
Welcome to The Springs, one of Central Florida’s most sought-after guard-gated communities, where towering oak canopies, winding roads, and unmatched natural beauty create a lifestyle unlike anything else in Seminole County. With 24/7 guarded entry and an extraordinary park-like setting, The Springs offers a rare blend of privacy, serenity, and convenience. Situated on a premium oversized homesite with no rear neighbors, this beautifully maintained one-story home enjoys exceptional curb appeal enhanced by mature landscaping that seamlessly blends into the surrounding natural environment. The private backyard and expansive screened lanai provide the perfect setting for relaxing, entertaining, or simply enjoying peaceful Florida living. Inside, the timeless floor plan features soaring ceilings, abundant natural light, and generous living spaces designed for both everyday comfort and entertaining. A rare and highly desirable feature, the home offers two primary suites, making it ideal for multigenerational living, guests, or anyone seeking additional flexibility. Steam shower in 2nd primary is great feature as well. Spacious formal living and dining rooms complement the inviting family room and bright open kitchen, creating a layout that lives beautifully. Ample storage throughout this well designed floor plan is another huge plus. Major updates have already been completed, offering peace of mind for years to come. A new roof and HVAC system were installed in 2020, while the home was completely replumbed and received a new water heater in 2019, providing true move-in-ready convenience and low-maintenance ownership. Residents of The Springs enjoy an unmatched lifestyle centered around nature and community. Century-old live oaks, scenic walking and jogging trails, horse stables, a clubhouse, community pool, THE ONLY PRIVATELY OWNED SPRING IN FLORIDA and year-round events create an atmosphere that feels more like a private retreat than a neighborhood. Native Florida woodlands and abundant wildlife are part of everyday life. Families appreciate access to highly rated Seminole County schools, while commuters enjoy exceptional convenience with I-4 less than one mile away. Downtown Lake Mary, Altamonte Springs, Winter Park, Cranes Roost Park, farmers markets, shopping, dining, and entertainment are all within easy reach. Orlando’s world-famous attractions and Florida’s east coast beaches are also just a short drive away. Rarely does an opportunity present itself to own a spacious one-story home with two primary suites, no rear neighbors, major system updates, and the unmatched lifestyle offered by The Springs. Experience the privacy, beauty, and timeless charm that make this exceptional Longwood community one of Central Florida’s hidden gems.

148 Wisteria Drive, Longwood
$155,000
2 Beds ⋅ 1 Baths ⋅ Fairway Villas SubDv. ⋅ 32779 Zip Code
The Springs lifestyle at an exceptional value. Discover the perfect blend of comfort, character, and convenience in this ground-floor end-unit condo located in the highly sought-after gated community of Fairway Villas in Longwood. More than just a place to live, this home offers a lifestyle defined by privacy, security, and resort-style amenities. Inside, the open-concept layout is highlighted by soaring wood-beamed ceilings that bring warmth and architectural charm, blending rustic character with modern appeal. Sliding glass doors open to an expansive private deck surrounded by mature trees - an ideal setting for morning coffee, quiet evenings, or entertaining guests. Thoughtful updates include refreshed counters, solid-surface finishes, and the ease of a primary suite conveniently located on the main floor. As an end unit, the home enjoys extra natural light and a greater sense of privacy than many other units. Living in The Springs means enjoying 24-hour gated security along with access to an impressive collection of amenities, including a private clubhouse, fitness center, tennis courts, community stables, and a natural spring for swimming. With all-inclusive maintenance fees covering water, exterior upkeep, 24/7 security, and recreational facilities, this property delivers outstanding value in one of Longwood’s most desirable communities. Opportunities like this in The Springs are rare - schedule your private showing and experience it for yourself.

100 Fairway Drive Unit 100, Longwood
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