Longwood Homes with Courtyard Exterior Features

Longwood Homes with Courtyard Exterior Features

Welcome to Longwood, Florida – a hidden gem nestled in the heart of Seminole County. This charming city is not just a place to live; it’s a vibrant community brimming with Southern hospitality, rich history, and an abundance of recreational opportunities. With its lush landscapes, serene parks, and friendly neighborhoods, Longwood offers a perfect blend of suburban tranquility and urban convenience. Residents enjoy easy access to major highways, making commutes to nearby Orlando and other attractions a breeze.

One of the standout features of homes in Longwood is their stunning courtyard exterior designs. Imagine stepping into your own private oasis, where the hustle and bustle of daily life melts away. Homes with courtyard features are designed to maximize outdoor living, providing a serene space for relaxation, entertaining, or simply enjoying the beautiful Florida sunshine. These courtyards often serve as a focal point of the home, seamlessly blending indoor and outdoor spaces, creating an inviting atmosphere for family gatherings or quiet evenings under the stars.

In Longwood, you’ll find a variety of architectural styles that cater to diverse tastes, but the allure of courtyard homes is undeniable. With ample space for lush gardens, outdoor furniture, and even water features, these homes offer a unique lifestyle that emphasizes connection with nature and community.

Whether you’re a first-time homebuyer or looking to upgrade, Longwood’s courtyard homes provide an idyllic setting to call home. Experience the charm of this delightful city and discover your perfect sanctuary in Longwood, where every day feels like a vacation.

Newest Longwood Homes with Courtyard Exterior Features

8209 Olympia Court Unit 8209, Longwood
$215,000
2 Beds ⋅ 3 Baths ⋅ Clubside At Sabal Point A Condo SubDv. ⋅ 32779 Zip Code
Enjoy a convenient Central Florida lifestyle in the desirable Clubside at Sabal Point community in Longwood, Florida! This inviting condo offers two spacious primary bedrooms, each with its own ensuite bathroom, an open living and dining area, a large kitchen, and a private balcony and laundry room inside the unit. This condo community is established with plenty of parking, a tropical pool and tennis courts just steps away from this unit Ideally located near highly regarded Seminole County schools, popular shopping destinations, grocery stores, local restaurants, and everyday conveniences. With easy access to major roadways like I4, enjoy a convenient 15 minute commute to downtown Orlando and nearby world-famous theme parks, including Walt Disney World and Universal Orlando Resort. This location offers an appealing combination of comfort, low maintenance, convenience, and access to the best of the Orlando area, making it a wonderful opportunity for homeowners and investors alike.

8209 Olympia Court Unit 8209, Longwood
558 Shining Armor Lane, Longwood
$470,000
4 Beds ⋅ 4 Baths ⋅ Highcroft Pointe Twnhms SubDv. ⋅ 32779 Zip Code
Are you excited for the holiday season, but just don't know what to do with your home? Well, I have the perfect solution! The minute you walk into this 4/3.5/2 bedroom home, you'd swear you were walking into a new build model home! Anything you've ever envisioned for the holidays are now about to be reality! As soon as you walk in the door, you enter a beautiful open room with high ceilings and beautiful open windows. Perfect for any size tree to show off to your neighbors! Walk down the hall through beautiful arched openings which makes this such an extraordinary showing! Off to the right is an amazing open and updated kitchen and living room area! The kitchen countertops are a beautiful granite and the entire kitchen is worry free! Just imagine the aromas and memories you could make! The dishwasher is only a year old, and the stove and dishwasher are only approximately 5 years old. You will enjoy lots of entertaining in this kitchen area to come. Conveniently located downstairs is the master bedroom and bathroom. The bedroom can easily hold any size bedroom set you can imagine and wait till you see the master bathroom! It is dream come true! It also has granite countertops with a glass walk-shower and a garden tub! Outside the master area is a beautiful lanai. Perfect for that morning coffee. Not sold yet, let's go upstairs and check out the amazing view! While the downstairs is completely tiled, the upstairs is carpeted. Upstairs offers luxuries that are rarely found! Both designated bedrooms also come with full bathrooms! Your guest will not need to share. Have a few more guests than planned. The additional room upstairs can also be a bedroom with a closet! You have more than enough room for everyone. If you haven't noticed by now, there are amazing plantation shutters all throughout this home. Something else very unique with this home is that the 2 car garage is located on the other side of a beautiful breezeway! It provides more peace for those still sleeping in the home for those mornings you want to sleep in. What else could you ask for? Well how about the fact that the roof is only 2 years old, the water heater is only 3 years old and the a/c is only 8 years old! This truly is a move in and enjoy home for you! The 4th bedroom can be used as a flex room, its an open space but is classified as 4 bedroom because it has a closet.

558 Shining Armor Lane, Longwood
221 Pine Cone Lane, Longwood
$525,000
3 Beds ⋅ 3 Baths ⋅ The Springs Whispering Pines Sec 2 SubDv. ⋅ 32779 Zip Code
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
615 Cambridge Court, Longwood
$499,900
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
1940 Deerview Place, Longwood
$869,000
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. Seller offers $5000 credit towards closing costs.

1940 Deerview Place, Longwood
116 Golf Club Drive, Longwood
$359,900
3 Beds ⋅ 2 Baths ⋅ Wekiva Country Club Villas SubDv. ⋅ 32779 Zip Code
Virtually Staged. *WELCOME HOME* 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. The Wekiva Gold Club, a public course, is right in your backyard. This home offers an opportunity to enjoy a comfortable, low-maintenance lifestyle in a very desirable Longwood location.

116 Golf Club Drive, Longwood
136 Glendale Drive, Longwood
$560,000
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
150 Tollgate Trail, 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
230 Bay Meadow Road, 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
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
128 Woodmill Road, Longwood
$949,900
4 Beds ⋅ 3 Baths ⋅ Springs Whispering Pines Sec 1 SubDv. ⋅ 32779 Zip Code
Virtually Staged. **SOME PHOTOS ARE VIRTUALLY STAGED** DETACHED. TURNKEY. LOCK & LEAVE. A rare freestanding 4-bedroom, 3-bath home with no shared walls, extensively redesigned in 2025 with meticulous attention to detail, architect involvement and structural engineering consultation. The Signature Gourmet Kitchen features custom solid-maple cabinetry with extensive built-in storage, quartz countertops, a waterfall island, GE Monogram professional-grade appliances, a Bosch Platinum Glass refrigerator with a built-in wine drawer and a pot-filler faucet. Integrated under cabinet lighting illuminates the work surfaces. A dramatic glass atrium, spa-inspired primary bath, wet bar and wood-burning fireplace bring distinctive character throughout. The guest bathroom is just as beautifully appointed as the primary bath, with spa-inspired finishes, James Martin floating vanities and mirrors with integrated defoggers and vanity lighting. Enjoy a private gated courtyard, three composite decks, upgraded irrigation, landscape lighting and professionally designed landscaping. The attached 2-car garage features professionally coated flooring and an added electrical sub-panel to accommodate future EV charger installation. Improvements include a 2023 tile roof, hurricane-rated impact-glass skylights, new gutters with gutter guards, an updated main electrical panel and replaced subfloors and new flooring throughout. Durable finishes and composite decking support an easy-care, lock-and-leave lifestyle. Enjoy life in guard-gated The Springs, with its private natural swimming spring, wooded trails, recreation facilities and vibrant calendar of community events. Convenient access to I-4 connects you to Winter Park, Downtown Orlando, shopping and theme parks, with Florida beaches within reach. Turnkey living. Private outdoor spaces. Thoughtful storage. Spa-inspired baths. A home best appreciated in person. ** furnishings may be available separately.**

128 Woodmill Road, Longwood
104 Juniper Lane, Longwood
$379,999
3 Beds ⋅ 2 Baths ⋅ Springs Glenwood Village Sec 1 Rev The SubDv. ⋅ 32779 Zip Code
** Exceptional Opportunity in The Springs: Bring Your Vision to Life! Rarely available, this spacious 3-bedroom, 2-bathroom townhome offers the perfect canvas to create your dream space in one of Longwood’s most coveted, spring-fed communities. *** Why You’ll Love This Home: * **Prime Potential:** A fantastic opportunity to build immediate equity. Bring your vision and custom touches to this well-loved property. * **Ideal Layout:** Featuring a spacious, functional floor plan designed for effortless entertaining. * **Classic Charm:** Highlights include a beautiful fireplace in the formal living room, perfect for cozy evenings. * **Legendary Lifestyle:** Enjoy the unparalleled amenities and serene atmosphere that make living in The Springs so highly sought after. **Property Details:** * **Bedrooms:** 3 * **Bathrooms:** 2 * **Condition:** Offered **AS-IS**. * **Note:** All room measurements are to be verified by the buyer. This home is priced to move and offers an incredible foundation for your next chapter. Don't miss out on this prime Longwood gem—contact us today to schedule your private tour!

104 Juniper Lane, Longwood
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