Longwood Homes with Waterfront

Longwood Homes with Waterfront

Longwood, located in Seminole County, Florida, is a charming city known for its picturesque landscapes and vibrant community. Situated in the heart of the Sunshine State, Longwood offers residents the perfect blend of suburban tranquility and urban convenience.

One of the city's standout features is its abundance of homes with waterfront views. Whether you're seeking a serene lakefront property or a home nestled along the banks of the Wekiva River, Longwood has a variety of options to suit every taste and lifestyle.

Living in a waterfront home in Longwood comes with a host of benefits. Imagine waking up to breathtaking sunrises over the water, enjoying a peaceful afternoon fishing or boating, or simply relaxing in your backyard oasis, surrounded by nature's beauty. Waterfront properties in Longwood offer a unique opportunity to enjoy a tranquil lifestyle while still being close to all the amenities the city has to offer.

In addition to the stunning waterfront properties, Longwood boasts a thriving downtown area, complete with a variety of shops, restaurants, and entertainment options. The city is also known for its excellent schools, making it an ideal place for families to settle down.

With its idyllic waterfront homes, vibrant community, and convenient location, Longwood is a city that truly has it all. Whether you're looking for a peaceful retreat or a place to raise a family, Longwood offers the perfect blend of natural beauty and modern conveniences.

Newest Longwood Homes with Waterfront

$1,750,000
5 Beds ⋅ 4 Baths ⋅ TB8530020 MLS
Welcome to Paradise: A Rare Lakefront Opportunity Location, Location, Location. This isn't just a home, it's a lifestyle. Waterfront living on beautiful Lake Brantley, one of Central Florida’s premier Private ski lakes. Nestled on the water with resort style living at every turn, this beautiful lakefront property offers 5 bedrooms plus a home office and 3.5 bathrooms.  Designed for both everyday living and effortless entertaining. Step outside to your own backyard oasis, complete with a sparkling pool, relaxing spa, and a fully equipped summer kitchen, perfect for hosting or unwinding after a long day. Boating enthusiasts will love the boat lift and floating jet ski ramp, offering direct, hassle-free access to the water. And when the day winds down, nothing compares to sunset happy hour on your own patio, offering breathtaking sunsets you simply can't beat. Set in a highly sought after neighborhood known for friendly neighbors, top “A” rated schools, private beach, boat ramp and tennis court this home delivers the complete package. Only one mile to shopping and dining and two miles to I-4 make it a highly desirable location. Luxury, Lifestyle, and Location.

236 S Shadowbay Boulevard, Longwood
$1,350,000
5 Beds ⋅ 6 Baths ⋅ O6423982 MLS
Welcome to an exceptional lakefront residence in the highly sought-after Sweetwater Oaks community of Longwood, where thoughtfully designed upgrades, resort-style outdoor living, and direct access to Lake Brantley create a distinctive Central Florida lifestyle. Extensively renovated with over $230,000 in luxury improvements, this impressive residence offers five bedrooms, four full bathrooms, two half bathrooms, a private screened pool and spa, an expansive outdoor kitchen, and a redesigned private dock—all thoughtfully designed for comfortable everyday living and effortless entertaining. At the heart of the home, the open-concept kitchen is surrounded by windows showcasing picturesque pool and lake views while filling the space with natural light. The kitchen features granite countertops, a stone backsplash, stainless steel appliances, a convection oven with glass cooktop, generous cabinetry, and flows seamlessly into the oversized family room highlighted by a classic brick wood-burning fireplace. The expansive primary suite serves as a private retreat with vaulted ceilings, tranquil lake views, French doors opening to the screened pool, and an impressive custom-built walk-in closet with premium organization. The beautifully renovated primary bath features granite countertops, a spacious walk-in shower with rainfall showerhead, and a stunning freestanding soaking tub that creates a true spa-inspired retreat. A private in-law suite offers exceptional flexibility for multigenerational living, extended guests, or a home office. Complete with its own entrance from the driveway, the suite now includes a beautifully finished full bathroom, providing added comfort and privacy. Designed for Florida living, the impressive 40-foot covered lanai overlooks the screened pool, spa, and peaceful lakefront setting. The fully equipped outdoor kitchen includes a built-in grill, vented hood, refrigerator, granite countertops, and serving bar, making it ideal for entertaining. The pool and spa were updated in 2019, and a dedicated pool bath offers convenient access from the outdoor living area. Beyond the lanai, enjoy a redesigned private dock, fire pit, dedicated garden, chicken coop, and enclosed storage for recreational equipment and water toys. Additional improvements include two new A/C systems, providing enhanced comfort and efficiency. Residents of Sweetwater Oaks enjoy private access to Lake Brantley, community parks, playgrounds, tennis and basketball courts, and top-rated Seminole County schools. Conveniently located near Wekiwa Springs State Park, Interstate 4, premier shopping, dining, and entertainment. Experience luxury lakefront living where thoughtful renovations, exceptional outdoor spaces, and timeless design come together in one of Longwood's most desirable communities.

306 N Sweetwater Cove Boulevard, Longwood
$1,388,000
5 Beds ⋅ 6 Baths ⋅ TB8522474 MLS
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
$1,250,000
O6404698 MLS
Set along the scenic Wekiva River, these two exceptional, side-by-side waterfront homesites spanning 5.13 acres (Parcel # 7-20-29-300-004A-0000) and 4.64 acres (Parcel # 27-20-29-300-0040-0000) present a rare and compelling opportunity within the prestigious Markham Woods Corridor. Offered individually or together, this unique pairing provides flexibility for a singular private estate or two distinct residences. Offering a refined balance of privacy, natural beauty and long-term value, the properties are surrounded by established multimillion-dollar estates and accessed by paved roads, creating a setting that feels exclusive and effortlessly connected. Both parcels span flood zones X and AE, with the AE portion closer to the river, allowing for thoughtful site planning that maximizes usability and the enjoyment of their serene riverfront setting. Their generous scale and proportions provide an ideal canvas for a custom estate designed to capture tranquil water views while maintaining a heightened sense of seclusion. Zoned A-1, the homesites support a variety of residential possibilities, including construction of a custom single-family residence, while preserving the open, pastoral character that defines this desired corridor. Ideally, within highly regarded school zones and just moments from major roadways, shopping, dining and everyday conveniences, the properties offer a seamless blend of peaceful retreat and modern accessibility. Opportunities of this scale and setting along the Wekiva River are increasingly rare. Whether envisioned as a private sanctuary or a legacy estate, this remarkable offering invites the creation of something exceptional in one of Seminole County’s sought-after enclaves.

Delk Road, Longwood
$3,100,000
5 Beds ⋅ 6 Baths ⋅ O6399898 MLS
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
$625,000
O6399090 MLS
Set along the scenic Wekiva River, this rare 4.64-acre estate homesite presents an exceptional opportunity in the desired Markham Woods Corridor. This expansive waterfront offering reflects a refined balance of privacy, natural splendor and enduring value, surrounded by distinguished multimillion-dollar estates and accessed by quiet paved roads that enhance its sense of exclusivity. The property reveals a graceful interplay of upland and riverfront terrain, inviting a bespoke approach to site planning that fully embraces the beauty and serenity of its surroundings. With its generous scale and captivating waterfront backdrop, this homesite offers an extraordinary canvas upon which to create a custom residence of architectural distinction, thoughtfully designed to complement the landscape. Zoned A-1, the parcel supports a range of residential possibilities, including creation of a grand single-family estate, while preserving the open estate character that defines this prestigious corridor. Ideally positioned in highly regarded school zones and offering effortless access to major roadways, fine dining and premier shopping destinations, the location provides a seamless blend of seclusion and convenience. Whether envisioned as a private sanctuary or a legacy property to be enjoyed for generations, opportunities of this caliber along the Wekiva River are increasingly rare. This is a compelling offering for those seeking to craft a residence of enduring elegance in one of Seminole County’s distinguished and sought-after settings.

Delk Road, Longwood
$625,000
O6399140 MLS
Along the winding expanse of the Wekiva River, this exceptional 5.13-acre waterfront homesite presents a rare opportunity in the prestigious Markham Woods Corridor. Offering a refined balance of privacy, natural beauty and long term value, the property is surrounded by established multimillion dollar estates and accessed by paved roads, creating a setting that feels exclusive and effortlessly connected. The parcel spans flood zones X and AE, with the AE portion closer to the river, allowing for thoughtful site planning that maximizes usability and the enjoyment of its serene riverfront setting. Its generous scale and proportions provide an ideal canvas for a custom estate designed to capture tranquil water views while maintaining a heightened sense of seclusion. Zoned A-1, the homesite supports a variety of residential possibilities, including construction of a custom single-family residence, while preserving the open, pastoral character that defines this coveted corridor. Ideally within highly regarded school zones and just moments from major roadways, shopping, dining and everyday conveniences, the property offers a seamless blend of peaceful retreat and modern accessibility. Opportunities of this scale and setting along the Wekiva River are increasingly rare. Whether envisioned as a private sanctuary or a legacy estate, this remarkable 5.13-acre parcel invites creation of something exceptional in one of Seminole County’s sought after enclaves.

Delk Road, Longwood
$7,250,000
9 Beds ⋅ 13 Baths ⋅ O6370385 MLS
One or more photo(s) has been virtually staged. REINTRODUCING The Fortress, with APPRAISAL in hand, available for review by qualified buyers. Set on nearly 12 acres, a one-of-a-kind architectural masterpiece created for those who understand that true luxury is not merely styled, but built to endure, remain irreplaceable, and stand the test of time. Designed and constructed over seven years by the world-renowned architectural firm HHCP for Harold Mertz, billionaire founder of Publishers Clearing House, this nearly 20,000-private compound, has hosted presidents, global dignitaries, private concerts, and philanthropic gatherings of the highest caliber. Approached by a quarter-mile, tree-lined driveway, the fully walled estate is centered around a 5-acre private lake, spring-fed by the Wekiva Springs State Park area, and surrounded by museum-quality grounds featuring imported European fountains, life-size bronze sculptures, curated statuary throughout the gardens, and ornamental ponds suitable for koi fish. The main residence spans approximately 14,623 sf and offers 7 bedrooms, each with its own full bathroom, along with an elegant powder room near the main entrance, formal living and dining rooms, a breakfast room, a main kitchen, and a separate staff kitchen. Constructed of solid poured concrete, the residence reflects permanence, privacy, and security with bulletproof glass, hand-plastered walls, soaring 25-foot ceilings, graceful arches, and signature fluted architectural textures expressed through curved, nonlinear walls. A massive custom bronze door opens to interiors finished with polished marble and terrazzo flooring, including brand-new floors in the main living room and kitchen. The kitchen showcases panoramic lake views, an oversized island, an oversized pantry, a private service entrance, and a fully equipped staff kitchen with its own dining area. Four bedrooms are located upstairs, offering some of the estate’s most impressive lake views, while three bedrooms are located downstairs. A monumental round atrium crowns the sculptural marble staircase, a remarkable architectural feature that took two full years to complete. Additional highlights include a dramatic two-story library that converts into a home theater, a glass conservatory with a Murano chandelier designed for a grand piano, an elevator near the foyer, two authentic wood-burning fireplaces, custom Sherle Wagner bathrooms, hidden closets throughout, and a bar near the piano room. The West Wing principal suite features a private Italian-inspired alfresco patio and an adjacent private gym with a full bathroom, sauna, and walk-in closet, creating a self-contained wellness retreat. The East Wing suite also enjoys its own Italian-inspired patio, adding symmetry, privacy, and elegance to the estate’s layout. The property is further enhanced by an approximately 2,500sf guest and pool house with 2 bedrooms and 3 full bathrooms, staff quarters of approximately 1,000 sf, and a 2,300-sf, 8-car garage with a full bathroom, laundry, and storage. Resort-style amenities include a pool and spa, a professional court lined for tennis and pickleball, a hot tub, sandy beach access, and multiple alfresco entertaining areas designed for unforgettable gatherings. With countless custom and invaluable features, this is a true legacy estate, built to stand for the next century and beyond. Conveniently located near top-rated schools, just approximately 2 miles from Wekiva Springs State Park, Private appointments available.

812 Sweetwater Club Boulevard, Longwood
$709,000
4 Beds ⋅ 4 Baths ⋅ S5140226 MLS
Virtually Staged. This 4 bedroom, 3.5 bathroom pool home is the kind of home that makes outdoor lovers feel like they finally found their place. Set on over half an acre with peaceful pond frontage and wide-open water views, this property delivers the serenity of lake living with the convenience of Seminole County’s most coveted amenities. Whether your ideal afternoon is launching a boat, paddling the Wekiva River, or unwinding while deer stroll through the yard, this address puts nature at your doorstep. The home has been thoughtfully updated to support a low-maintenance lifestyle. Fresh 2025 interior and exterior paint, a newer roof 2022, upgraded windows and doors installed in 2024, and a paver driveway and pool deck added in 2020 create a clean, modern feel. Inside, newer appliances and a 2019 AC system support comfort year-round. Two master suites provide flexibility, including the option for a mother-in-law suite or multi-generational living. A massive picture window frames the water perfectly, giving the living spaces a tranquil, postcard-worthy backdrop. Your oversized pool comes heated, with a pool heater installed 2024. The neighborhood is a rare gem for active residents. Enjoy three community parks, private Wekiva River access, members-only Lake Brantley beach and boat ramp, and more than ten tennis and pickleball courts. With Wekiva Springs State Park just moments away, adventure comes standard. For buyers who crave space, privacy, and a lifestyle built around the outdoors, this home is the invitation you have been waiting for.

204 Blue Lake Drive, Longwood
$10,000,000
O6294158 MLS
Offered exclusively as a combined 9.53-acre lakefront opportunity, this property consists of two contiguous residential parcels along Central Florida’s highly sought-after Markham Woods corridor. The parcels are being offered together only and feature approximately 846 feet of frontage on Rice Lake, creating a remarkable setting for a private lakefront estate or legacy family compound. The scale of the property, substantial lake frontage and established Markham Woods location provide an increasingly difficult-to-replicate combination of acreage, privacy and convenience. Currently zoned RC-1, the property offers a peaceful natural setting while remaining convenient to Lake Mary, Longwood, major transportation corridors, shopping, dining and surrounding amenities. For buyers interested in uses beyond a single private estate, additional residential possibilities may exist subject to zoning, subdivision requirements, site conditions and all applicable governmental approvals. Buyers are encouraged to conduct independent due diligence regarding their intended use. The offering includes two contiguous parcels totaling approximately 9.53 acres and will be sold together only. Serious inquiries are welcomed. Contact the listing agent for additional property information or to arrange a private tour.

Markham Woods Road, Longwood
$229,900
2 Beds ⋅ 2 Baths ⋅ V4941609 MLS ⋅ Wekiva Condos BLDG.
True Florida Paradise ! Possible owner financing is just an added bonus True gated and guarded Community. Enjoy your ground level 2 bedroom, 2 bath home with many community features. new CARPETS, STOVE, flooring and lighting. Home has nice fireplace in Living room that overlooks the private courtyard. Master has New carpet new lighting and over look private courtyard! Community features of the beautiful Wekiva to include large community building, playgrounds, walking paths, tennis courts and horse barn, The Springs' is a guarded gated community that offers guarded security but also a ton of amenities for the residents to enjoy. From the beach and clubhouse to tennis courts, basketball courts, and even a horse barn, there's something for everyone. Also, the proximity to over 100 acres of preserved land and access to natural wonders like the Palm and Sanlando Springs and the Little Wekiva River makes it an ideal location for nature lovers seeking tranquility and outdoor adventures. And with its convenient access to I-4, commuting to downtown Orlando, international airports, beaches, and amusement parks is a breeze. Right off S.R. 434 and I-4 in Longwood you’re close to diverse restaurants, groceries, Sunrail, and more. The Springs features a natural wonderland as the entire area is dedicated as a wildlife sanctuary.

123 Tomoka Trail Unit 123, Longwood
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