Longwood Homes with Courtyard Exterior Features

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

$520,000

4 Beds ⋅ 3 Baths ⋅ Devonshire SubDv. ⋅ 32750 Zip Code

Welcome to Devonshire, a quiet and inviting community neighboring The Woodlands and zoned for highly rated Seminole County schools. This spacious home features a desirable split floor plan with a generously sized primary suite, offering privacy and comfort. Designed with Florida living in mind, the expansive Florida room provides additional living and entertaining space while opening directly to the oversized pool and backyard. Whether hosting friends and family, enjoying a weekend barbecue, or simply relaxing poolside, this home offers plenty of space to enjoy both indoors and out. Additional features include ample parking, a two-car garage, and a spacious yard with room to make it your own. The owner is relocating, creating a great opportunity for the next owner to add their personal touches and call this home. All furniture is also available for purchase separately.

615 Cambridge Court, Longwood

$875,000

4 Beds ⋅ 3 Baths ⋅ Hidden Cove SubDv. ⋅ 32750 Zip Code

Virtually Staged. Stunning Lakefront Pool Home in Gated Community, in Longwood, Florida. This residence offers the perfect combination of space, privacy, comfort, and Florida living. Located in the desirable gated Hidden Cove community, it features 3,104 square feet of open floor plan living space, 4 bedrooms, and a studio room, plus a large second floor bonus room, 3 bathrooms, the kitchen has a nook, and an oversized 3-car garage. Conveniently located in Longwood, with easy access to Lake Mary, shopping, dining, major highways, and everything Central Florida has to offer. The generous lot of approximately 0.41 acres provides a wonderful sense of openness, while mature landscaping complements the home’s attractive Mediterranean-inspired architecture and tile roof. The home has a spacious, light-filled floor plan and beautiful views to Lake Myrtle, that make this home special. The primary suite and all bedrooms are located on the first floor, while multiple living and dining areas provide plenty of room for entertaining, relaxing, or working from home. A versatile 2nd floor large bonus room adds even more flexibility for a home office, media room, game room, or guest space. The heart of the home opens toward an exceptional outdoor living area: Step outside to your screened lanai, private pool and heated spa, where you can enjoy Florida living throughout the year. Beyond the pool is one of the property’s most appealing features: peaceful Lake Myrtle views, creating a beautiful backdrop for morning coffee, afternoon relaxation, and spectacular Florida sunsets. Canoeing and fishing, and walking or jogging along the shores are part of the nature activities the community offers. Additional highlights include a spacious kitchen with island, breakfast bar and adjacent nook, formal living and dining areas, family room, interior laundry, ample storage, and a split-bedroom layout designed for both privacy and functionality. A 3-car garage has beautiful epoxy flooring, and an EV electric car port. Take the rare opportunity to enjoy a pool home on a lake, inside the privacy of a gated community, and enjoy the relaxation in your own pool and spa. You will especially enjoy how the home combines indoor and outdoor living. Whether having morning coffee overlooking the lake, relaxing by the pool, entertaining family and friends on the lanai, or simply enjoying the sunset, there is always a special place to unwind.

1940 Deerview Place, Longwood

$364,900

3 Beds ⋅ 2 Baths ⋅ Wekiva Country Club Villas SubDv. ⋅ 32779 Zip Code

Enjoy golf course living in this charming townhome-style condominium at Wekiva Golf Club Villas. Situated along the 9th hole of the Wekiva Golf Course, this two-story home offers beautiful views, abundant natural light, an oversized garage, and a FIRST-FLOOR PRIMARY SUITE. The main level features VAULTED CEILINGS, a spacious living area, and a floor-to-ceiling fireplace that creates a warm and inviting focal point. The first-floor primary suite includes a WALK-IN-CLOSET, while the second floor offers two additional bedrooms, a full bathroom, and an open loft overlooking the living space, ideal for a home office, sitting area, or additional flex space. The ENCLOSED FLORIDA ROOM lanai extends the living space and provides a peaceful spot to enjoy the views year-round. A front patio and courtyard provide additional outdoor space, while luxury vinyl and tile flooring provide easy maintenance throughout the home. NEW ROOF AND GUTTERS- 2025. NEW EXTERIOR PAINT- 2026. NEW AC UNIT- 2020. Residents of Wekiva Golf Club Villas also enjoy access to a community pool. Conveniently located near Wekiwa Springs State Park, the Seminole County Public Library, shopping, dining, and everyday conveniences. This home offers an opportunity to enjoy a comfortable, low-maintenance lifestyle in a very desirable Longwood location.

116 Golf Club Drive, Longwood

$575,000

4 Beds ⋅ 3 Baths ⋅ Winsor Manor SubDv. ⋅ 32750 Zip Code

A beautifully renovated, move-in ready family home with over 2,600 square feet of living space is now available in the established Winsor Manor community of Longwood. This 4-bedroom, 3-bathroom, single-story property offers the space, fresh modern finishes and long-term peace of mind every growing family deserves. Step inside to a bright, open layout featuring vaulted ceilings, plenty of natural light, brand new flooring, fresh paint and modern fixtures throughout. The fully renovated kitchen takes center stage with solid wood shaker cabinets featuring soft-close hinges, elegant Quartz countertops and brand new appliances. All bathrooms have been completely renovated with a fresh modern feel, while major improvements including a brand new roof installed just weeks ago, a newer and fully serviced AC and new water heater offer the kind of worry-free ownership that lets you focus on what really matters - making everlasting memories with your family. One of the home's most impressive features is the oversized enclosed rear porch, creating a massive additional gathering area where the entire family can come together for holidays, birthdays and weekend get-togethers without ever feeling cramped. Outside, a large backyard and spacious two-car garage provide even more room to enjoy everyday family life. Set on a 0.28-acre lot within the well-established Winsor Manor neighborhood, you'll enjoy mature surroundings and welcoming neighbors in a community that has stood the test of time. Conveniently located just minutes from SR 434, I-4, the Seminole-Wekiva Trail, shopping, dining and everyday necessities, with easy access to Altamonte Springs, Lake Mary, Maitland and the greater Orlando area, this home truly offers the ideal combination of space, comfort and location. At $575,000, this is a fantastic opportunity to plant roots in Longwood in a home that's already been completely refreshed for its next family. Reach out to your preferred real estate professional today to schedule your private showing before it's gone.

136 Glendale Drive, Longwood

$450,000

4 Beds ⋅ 2 Baths ⋅ Meadows Unit 1 SubDv. ⋅ 32750 Zip Code

Welcome home to 150 Tollgate Trail, a beautifully maintained single-story retreat shaded by mature trees in The Woodlands, one of Longwood's most established communities. Major systems have already been taken care of, with a 2022 roof, HVAC system, and water heater offering years of worry-free living. Step inside to a thoughtfully designed floor plan that flows effortlessly between everyday comfort and elegant entertaining. Formal living and dining rooms set the stage for gatherings, while the spacious family room anchored by a cozy wood-burning fireplace invites relaxed evenings at home. Generously sized bedrooms and an enclosed rear porch add flexible living space for however you need it, and the fully fenced backyard delivers privacy and room to unwind outdoors. Set in the sought-after Woodlands neighborhood, residents enjoy an optional HOA along with community amenities including a park, playground, pavilion, and recreational areas. You're also just minutes from the Seminole Wekiva Trail, Wekiwa Springs, everyday shopping and dining, and quick access to I-4 and SR 434. With major updates already complete, versatile living spaces, and timeless charm throughout, 150 Tollgate Trail is ready to welcome its next owner. Schedule your private showing today. This one won't last long. With major systems already updated, abundant living space, and a beautiful established setting, 150 Tollgate Trail offers the space and lifestyle today's buyers are looking for. Schedule your private showing today!

150 Tollgate Trail, Longwood

$549,900

6 Beds ⋅ 4 Baths ⋅ Hensons Acres SubDv. ⋅ 32750 Zip Code

Your chance to own a 2.25 acre property well under market value. The house needs TLC but bones are in great shape. The main house features 5 bedrooms and 3 bathrooms, and the in-law suite is 1 bedroom 1 bathroom. A large pool awaits it's new owner to bring it back to its former glory. The home features a brand new water filtration system. Bring your toys, your cars, your plants, your animals, and your creative eye and make this property yours. Cash-only offers Buyer to verify square footage.

230 Bay Meadow Road, Longwood

$470,000

4 Beds ⋅ 2 Baths ⋅ Devonshire SubDv. ⋅ 32750 Zip Code

Virtually Staged. Welcome to 580 Devonshire Boulevard, a beautifully updated four-bedroom, two-bath pool home located in the Devonshire community of Longwood. The welcoming single-story exterior features a modern neutral color palette, covered two-car carport, fresh landscaping, updated exterior lighting, mature trees, and clean architectural lines. A private gated entry leads to the front entrance, creating a secure and inviting arrival. Access to the spacious courtyard patio from the carport features freshly finished concrete, decorative rock landscaping, privacy walls, and expansive sliding glass doors that create a seamless indoor-outdoor connection. Inside, the bright foyer opens into an airy living room featuring wide-plank wood-look flooring, recessed lighting, neutral finishes, overhead skylights, and abundant natural light. The updated kitchen showcases bright shaker cabinetry, quartz-style countertops, a full subway tile backsplash, stainless steel appliances, sleek hardware, and an oversized center island with pendant lighting, storage, prep space, and casual seating. The adjoining dining area features a modern statement light fixture and sliding glass doors overlooking the courtyard, creating an ideal setting for everyday meals and entertaining. The spacious primary bedroom offers wood-look flooring, neutral finishes, expansive sliding glass doors, courtyard views, and convenient access to the private en-suite bathroom. The updated primary bath features shaker-style vanity, solid-surface countertop, modern fixtures, a framed mirror, and a walk-in shower with marble-look tile, rainfall showerhead, built-in shelving, and contemporary accents. Bedrooms two through four feature wood-look flooring, modern lighting, ample closet space, and natural light. One secondary bedroom also provides sliding glass doors with direct access to the outdoor living area, offering flexible use as a guest room, office, or additional living space. The updated guest bathroom includes a spacious dual-sink vanity, solid-surface countertops, modern fixtures, an oversized mirror, and a tub-and-shower combination surrounded by full-height subway tile. Step outside to the spacious screened pool area featuring a covered patio, expansive deck space, privacy walls, and a refreshing in-ground pool. This enclosed outdoor retreat offers plenty of room for lounging, dining, and entertaining while enjoying Florida living throughout the year. A functional laundry and storage room provides washer and dryer connections, a utility sink, built-in shelving, and generous space for household supplies, tools, and additional storage. Conveniently located near shopping, dining, parks, schools, and major roadways, this thoughtfully updated Devonshire home combines modern finishes, flexible living spaces, private outdoor areas, and an exceptional Longwood lifestyle.

580 Devonshire Boulevard, Longwood

$425,000

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

1041 Sweetwater Club Boulevard, Longwood

$3,399,000

6 Beds ⋅ 9 Baths ⋅ Sweetwater Club Estates SubDv. ⋅ 32779 Zip Code

Beyond private wrought-iron gates on 2.89 acres in prestigious Sweetwater Club Estates, this extraordinary 10,623-square-foot residence offers impressive scale, privacy, and resort-style living. Designed for grand entertaining and multigenerational living, the estate features six bedrooms, seven full and two half baths, soaring cathedral ceilings, handcrafted woodwork, dramatic sandstone accents, and multiple fireplaces. The spectacular two-story great room features wood-clad ceilings, a stone fireplace, and full entertaining bar, complemented by a dedicated theater, richly appointed parlor, and expansive executive office with a full bath. Five bedrooms and eight bathrooms are located on the main level, including a secondary primary suite ideal for extended family or guests. Upstairs, the entire second floor becomes the private owner's retreat with a stone fireplace, sitting room, and private office. Outside, sandstone patios surround a resort-style pool, spa, and cascading waterfall, while a gazebo and expansive grounds provide exceptional space for entertaining and future recreational amenities. A detached six-car garage offers outstanding capacity for collectors and enthusiasts. Recent improvements include a newer roof and six replaced HVAC systems. Residents enjoy private access to Sweetwater Beach and Lake Brantley, including the community boat ramp, plus tennis and basketball courts and picnic facilities. Convenient to Wekiwa Springs State Park, I-4, SR 434, and SR 436. Nearly three private acres, more than 10,600 square feet, six-car garaging, flexible multigenerational living, and exceptional entertaining spaces create a rare opportunity to personalize a true Central Florida legacy estate. Schedule your private showing today.

1041 Sweetwater Club Boulevard, Longwood

$949,900

4 Beds ⋅ 3 Baths ⋅ Springs Whispering Pines Sec 1 SubDv. ⋅ 32779 Zip Code

Virtually Staged. **The Springs Lifestyle. The Privacy of a RARE FREESTANDING HOME.** Some places are defined by the home. Others by the life that surrounds it, this is the best of both worlds! Welcome to **The Springs**, one of Central Florida’s most distinctive guard-gated communities, where an authentic natural freshwater spring lies at the heart of mature trees, winding roads and preserved natural beauty—an amenity other developments simply cannot recreate. Life here extends beyond your front door. Residents enjoy the natural spring, clubhouse and recreation facilities, tennis, pickleball, equestrian stables, trails and beautifully preserved common areas, all conveniently located near Maitland, Winter Park, Altamonte Springs, dining, shopping, major roadways and Central Florida destinations. There is a sense of arrival here—a quieter pace, greater privacy and a connection to nature that has become increasingly difficult to find. Mornings here often begin with birdsong and glimpses of native wildlife among the mature trees and lush surroundings—a daily reminder that life in The Springs feels connected to nature in a way newer communities simply cannot replicate. Within this remarkable setting, **128 Woodmill Road is a rare freestanding townhome with no shared walls**, combining the privacy and separation of a freestanding residence with the convenience of an easy **lock-and-leave lifestyle**. Its outdoor setting is equally distinctive, with **front, side and backyard areas**, lush landscaping, a private gated courtyard and an expansive rear deck that creates a natural extension of the living space. Multiple outdoor areas provide room to entertain, dine, relax or simply enjoy the surrounding greenery. Inside, the residence was **extensively redesigned in 2025** with professional oversight, architect involvement and structural engineering consultation. The result is a refined, contemporary home filled with natural light and thoughtfully designed for modern living. At its center is the **Signature Gourmet Kitchen**, featuring custom solid maple cabinetry, quartz surfaces, a waterfall island, workstation sink and professional-grade appliances. Carefully selected materials, designer finishes and extensive improvements continue throughout the residence, inside and out. The **spa-inspired baths** continue the same attention to design, featuring **solid-wood James Martin floating vanities**, refined finishes and a clean contemporary aesthetic that feels polished and relaxing. **Turnkey and move-in ready**, this property brings together qualities rarely found in one place: the natural lifestyle of The Springs, the privacy of a detached residence, meaningful outdoor space and the ease of a lock-and-leave home. ** furnishings may be available separately.**

128 Woodmill Road, Longwood

$2,895,000

5 Beds ⋅ 6 Baths ⋅ Brantley Cove North SubDv. ⋅ 32779 Zip Code

CRUISING THE WATERWAYS of the MAJESTIC SPRING FED LAKE BRANTLEY await you. Stroll around your sculptured & manicured gardens. Elegant entry features include PORTE-COCHERE. Biltmore GAS LANTERNS, SHUTTERS, BALCONIES & TOWERING tree canopies as you approach this MEDITERRANEAN-RIVIERA style estate. The cultivated beauty of this "one-owner home". Impressive CUSTOM-BUILT SHOWPLACE is nestled back on a LUSH, PRIVATE ENCLAVE, oversized *4-Acre lot. *Over 1+ acre for residence. WATERFRONT LIVING at its' finest. 4/5 Bedrooms, 5.5 baths, pool home, 3 car garage, porte-cochere, pool/ spa, and dock with BONUS/FLEX space in the basement, perfect for a workout room. Over $380,000+ in updates & renovations. Majestic MAHOGANY entry doors welcome you, and once inside the seamless floor plan is OPEN w/ VOLUMINOUS ceilings (10-foot ceiling throughout, Primary bedroom 12 ft, other rooms 20 ft.). EXPANSIVE living/dining/kitchen/ family rm w/ PANORAMIC, BREATHTAKING WATER, VIEWS that engulf most rooms. SUN DRENCHED lighting pours in as it illuminates the CUSTOM-BUILT with HIGH-QUALITY finishes and fixtures that enhance the architectural elegance. Tongue & Groove Cedar ceilings in fam & breakfast rm, & porch. Interior solid core 4 panel wood doors throughout. Generous use of ST. LOUIS BRICK, WOOD flooring, WROUGHT IRON accents and 2 palatial wood burning fireplaces. EXCITE the CHEF with this dream kitchen while overlooking expansive water views! Create culinary masterpieces in style. An abundance of cabinetry, storage, island, massive dinette and a snack bar. STAINLESS STEEL appliances, GRANITE prep space & HIGH-END fixtures make this functional & impressive. Wet bar w/ GRANITE snack bar/cabinets sit under the upstairs LOFT area. 3-way split bedrooms with private baths, are perfectly situated around the living / family rm and dining space. All the bedrooms are roomy with large closet space; one even has a window seat. All bathrooms are situated near bedrooms which make it perfect for privacy and versatility. Library/ office with solid CHERRY WOOD finishes line the walls & solid wood beamed ceiling can be used for the 5th bedroom or nursery. Regal Master bedroom DOWNSTAIRS, with 12' ceilings, sitting room space & ensuite bath SPA like retreat. MARBLE galore! Step into the Roman tub, or roomy walk-in shower with private atrium. Dual sink cabinets, MARBLE counters & a BIDET and don't forget the enormous walk-in closet. Spiral wood and wrought iron staircase lead to LOFT with additional flex space & bathroom. Peak into the basement for additional BONUS space, with its own bathroom. So many possibles for this area. OPULENT OUTDOOR RESORT living OASIS w/ OUTDOOR KITCHEN, and your own private SANDY BEACH to build your own sand sculptures on. This is the perfect space for entertaining and making memories. Ride the waves, ski or boating & relax & watch the incredible SUNSETS over the lake. Wood dock leads to your private lift & covered space. Brand new Kohler Generator too! Relax and enjoy the ambiance. the sights and sounds of the rippling waters lapping around you and the tranquility of this one-of-a-kind residence. Spend a LAZY afternoon fishing/skiing the 288-acre Lk. with its PRISTINE waters & SANDY BEACH bottom. RELAX with a glass of wine, as you have reserved SUNSET seating as you watch the MOONLIGHT dance the night away. Desirable location that is close to all shopping, major roadways, restaurants and top schools.

1351 N Classic Court, Longwood

Longwood Homes with Courtyard Exterior Features

Newest Longwood Homes with Courtyard Exterior Features