Longwood Homes with Two Story Style

Longwood Homes with Two Story Style

Welcome to Longwood, a charming city located in Seminole County, Florida. Known for its picturesque landscapes, friendly community, and convenient location, Longwood offers the perfect blend of suburban tranquility and urban amenities.

If you are in the market for a home with a two-story style, Longwood has a variety of options to choose from. Whether you are looking for a cozy two-story cottage or a spacious two-story estate, you are sure to find the perfect home to suit your needs in this vibrant city.

With its tree-lined streets, top-rated schools, and abundance of parks and recreational facilities, Longwood is a great place to raise a family or enjoy a peaceful retirement. Residents can also take advantage of the city's proximity to major highways, shopping centers, and dining options, making it easy to explore all that Central Florida has to offer.

If you are looking to make Longwood your new home, now is the perfect time to start your search for a two-story home in this beautiful city. Contact a local real estate agent today to learn more about the available properties and find your dream home in Longwood, Florida.

Newest Longwood Homes with Two Story Style

$1,899,000
5 Beds ⋅ 6 Baths ⋅ O6435662 MLS
Welcome to an exceptional luxury estate in the prestigious, 24-hour guard-gated community of Wingfield North, ideally located along the highly sought-after Markham Woods Road corridor. Situated on a private 1.23-acre cul-de-sac lot, this remarkable residence offers an impressive combination of scale, luxury, privacy, and resort-style outdoor living. This five-bedroom, six-bathroom home features spacious bedrooms, each with its own en-suite bathroom and walk-in closet. The first-floor primary suite offers a private retreat with French doors opening directly to the patio and pool. Custom walk-in closet design, dual vanity & a walk in shower with multiple shower heads and features. One bedroom features French doors leading to its own private screened porch. Two bedrooms share a private study at the entrance of the dedicated space. Throughout the living areas and bedrooms, engineered hardwood flooring adds warmth and sophistication. Designed for both elegant entertaining and everyday living, the home includes a formal living room overlooking the pool and patio, a formal dining room ideal for large gatherings, and a private office complete with a walk-in closet. The brand-new chef's kitchen is a true centerpiece, with custom cabinetry, marble countertops, an oversized island with seating, gas cooktop, Thermador appliances, and a dedicated eating area overlooking the living room, pool, and outdoor living spaces. Upstairs, the loft provides flexible living space along with an additional bedroom, walk-in closet, and full bathroom. Abundant storage is thoughtfully incorporated throughout the home. The four-car garage offers ample room for a boat or other toys along with a dedicated golf simulation area and an approximately 8' x 17' air-conditioned room perfect for a workshop, hobby space, or additional storage. Outdoor living is equally impressive. The backyard features a screened in pool and spa, covered patio, pool house with storage, and space designed for a future summer kitchen. A creek runs along the rear of the property, while mature wooded areas along the perimeter provide exceptional privacy. A brick-paver circular driveway, covered front porch and cul-de-sac location further enhance the estate's curb appeal and setting. Extensive recent improvements include a recently inspected tile roof with substantial remaining life, whole-home sound system, Control4 smart-home technology, security system, two tankless gas water heaters, new filtration system, front landscaping and irrigation, interior painting, pool equipment, interior lighting and fixtures, garage door openers, screened enclosure upgrades, and exterior pressure washing. A 1,000-gallon propane tank serves the home. Great opportunity to own a substantial luxury estate in one of the Markham Woods area's most desirable guard-gated communities, offering privacy, generous indoor and outdoor spaces, amenities, and a location convenient to top-rated schools, shopping, dining, and major roadways.

334 Vista Oak Drive, Longwood
$649,900
4 Beds ⋅ 3 Baths ⋅ O6429571 MLS
Virtually Staged. Welcome to 401 Woodview Drive, a spacious 4-bedroom, 2.5-bath home nestled in the desirable Sabal Point area of Longwood. Situated on an oversized corner lot, this two-story residence offers an inviting floor plan with soaring ceilings, abundant living space, and a cozy wood-burning fireplace that creates a natural focal point for gatherings. The home features approximately 2,392 square feet of living space, a two-car garage, balcony/deck areas, and a screened porch overlooking the private yard. The kitchen offers ample cabinetry and counter space, while the generously sized bedrooms provide flexibility for family, guests, a home office, or additional living needs. Conveniently located near parks, shopping, dining, major roadways, and highly regarded Seminole County schools, this home combines space, comfort, and an excellent Longwood location. A wonderful opportunity to make this established Sabal Point property your own. Home features a 2020 ROOF and 2020 WATER HEATER.

401 Woodview Drive, Longwood
$1,300,000
4 Beds ⋅ 4 Baths ⋅ O6431642 MLS
The time is NOW! Rare opportunity to live the waterfront lifestyle on a wide canal leading to idyllic Lake Brantley. This amazing home is situated on an exceptionally beautiful, half-acre lot with a dock and boathouse (with lift) Step into the wide-open floor plan with soaring tongue and groove ceilings, dramatic transom windows and an impressive floor-to-ceiling wood burning fireplace. This home is made for entertaining as the sprawling great room, dining room and kitchen flow seamlessly together with the captivating view out back as the backdrop. You'll appreciate the beautiful and durable groutless travertine floors throughout the main level. The dining area features stylish built-in cabinetry. The kitchen has a built-in oven, cooktop, spacious breakfast bar and eat-in area overlooking the scenic yard. All secondary bedrooms are downstairs. The million dollar view is reserved for the upstairs primary retreat, with it's own private terrace looking out to the gorgeous yard and water. The generously sized primary bath has a large jetted tub, dual vanities, walk-in shower and spacious walk-in closet with plenty of room for your accoutrements. Also upstairs, you'll find a very large bonus room/game room with a wet bar and it's own bath! The focal point of this amazing home is the outdoor area. Step into the backyard oasis which includes a large covered porch with room enough for a seating area and an al fresco dining area. Just beyond this, you'll find a stunning pavered pool area and fire pit surrounded by adirondack chairs. There is plenty of yard beyond, with a winding path leading down to the boathouse and dock. The private canal is a short ride to Lake Brantley, a spectacular sought-after 287 acre private ski lake. Roof replaced in 2021. This home has it all! A waterfront retreat, A-rated schools & just minutes to a plethora of wonderful dining and shopping!

1336 Classic Drive, Longwood
$795,000
5 Beds ⋅ 4 Baths ⋅ O6430546 MLS
Welcome to 351 E Wildmere Ave, a brand-new construction home in one of Longwood, Florida's established legacy neighborhoods where new builds are still the exception, not the rule. This is a rare chance to get in early as this pocket of Longwood redevelops, without sacrificing the mature trees, larger lots, and settled character that new subdivisions can't offer. You also have the benefit of no HOA, saving you hundreds. Everything about this home is new — the roof, systems, finishes, and fixtures giving buyers the peace of mind of a builder-fresh home with none of the deferred maintenance of an older property. Inside, the home offers just under 3,000 square feet of living space across 5 bedrooms and 4 full bathrooms, filled throughout with an abundance of natural light that gives every room an open, airy feel. Highlights include a bonus loft ideal for a second living area, playroom, or media space, and a large walk-in pantry built for real-life kitchen storage. The primary suite is designed to feel like a private spa retreat. It features a modern, open-concept bathroom layout with a freestanding soaking tub and walk-in shower positioned together for a serene, resort-style feel, along with an oversized walk-in closet with room to spare. It's the kind of end-of-day escape that's hard to find in this price range. One of the home's biggest differentiators is the attached in-law suite with its own private entrance, a flexible space suited to multigenerational households, adult children, long-term guests, a private home office, or even rental income potential, all without sacrificing privacy for either party. Outside, the home sits on an oversized lot with ample green space and room for a pool, a garden, play space, or simply more breathing room between neighbors, which is increasingly hard to find in new construction. Zoned for Lyman High School, a well-regarded school in the area, this location is a strong fit for families prioritizing both a brand-new home and school quality. Priced below $800,000, this home offers new-construction quality at a price point that's competitive with resale homes in the area, in a neighborhood that's just beginning its redevelopment story.

351 E Wildmere Avenue, Longwood
$414,900
3 Beds ⋅ 2 Baths ⋅ S5155274 MLS
POOL HOME + LARGE FENCED YARD + NO CARPET! NEW ROOF! This 3-bedroom, 2-bath Longwood home in the sought-after Sandalwood community offers the perfect combination of comfort, style, and location. Step inside to an open-concept floor plan featuring granite countertops, espresso cabinetry, a tiled backsplash, stainless steel appliances, and easy-care laminate and tile flooring throughout. The inviting living space is highlighted by a wood-burning fireplace, creating a cozy gathering spot. Outside is where this home truly shines—a generous, fenced backyard with a sparkling pool provides plenty of room for weekend gatherings, play, or simply enjoying the Florida sunshine. A utility shed offers convenient additional storage. Located in the highly rated Seminole County school district with easy access to schools, parks, dining, shopping, SunRail, major roads, and I-4. If you’ve been waiting for a Longwood pool home in a great location, this one is worth seeing!

103 Cashew Court, Longwood
$419,900
4 Beds ⋅ 4 Baths ⋅ O6431308 MLS ⋅ Lake Wildmere BLDG.
RARE 4 BEDROOM END UNIT WITH TWO EN SUITE BEDROOMS, LOFT AND 2 CAR GARAGE Built in 2019, this move in ready end unit includes approximately 2,300 square feet, four bedrooms, 3.5 bathrooms, two bedrooms with en suite bathrooms, an upstairs loft, a separate workspace nook, and an attached two car garage. Windows on three sides fill the home with natural light. The end unit location has only one shared wall. The main level includes generous living and dining areas plus a spacious kitchen with quartz countertops, an oversized island with breakfast seating, stainless steel appliances, and plentiful cabinet storage. All four bedrooms are upstairs, together with the loft, workspace nook, dedicated laundry room, and balcony. A covered front porch and rear patio add low maintenance outdoor living space. Reserve at Lake Wildmere includes controlled access, a swimming pool, clubhouse, and community lake dock. The home is near Downtown Longwood, Lake Mary, Sanford, Altamonte Springs, shopping, dining, and Interstate 4. PROPERTY HIGHLIGHTS Four bedrooms and 3.5 bathrooms Approximately 2,300 square feet Two bedrooms with en suite bathrooms End unit with windows on three sides Only one shared wall Upstairs loft and workspace nook Attached two car garage Quartz countertops and oversized kitchen island Stainless steel appliances Dedicated laundry room Balcony, covered front porch, and rear patio Community pool, clubhouse, and lake dock Built in 2019 Move in ready

534 Lake Wildmere Cove, Longwood
$619,999
3 Beds ⋅ 3 Baths ⋅ O6430346 MLS
Fully renovated on nearly half an acre with no HOA and private Lake Brantley access, 2261 Charlotte Drive offers 3 bedrooms, 3 full bathrooms, and 2,202 square feet of living space. Updates include new tile and vinyl plank flooring, a completely remodeled kitchen, three fully renovated bathrooms, and all-new lighting throughout. The kitchen features shaker cabinetry, stainless-steel appliances, quartz countertops, and a matching full-height quartz backsplash. Under-cabinet lighting provides additional task and accent lighting. The home has two separate living areas, including a front living room with double-height ceilings and a large wood-burning fireplace. LED accent lighting along the staircase and living-room ceiling adds a modern finish. All three bedrooms are located upstairs. The Florida room provides flexible additional space for an office, den, game room, playroom, or hobby room. A dedicated laundry closet provides convenience without taking away from the main living areas. The fully fenced backyard offers plenty of room for entertaining and includes mature trees, a garden area, and a large deck with a pergola. Water and electrical connections are already installed at the pergola for a future outdoor kitchen, bar, or entertaining setup. A gated entrance provides additional backyard access and storage space for boats, RVs, trailers, and other recreational equipment. The 24-by-24-foot garage includes a temperature-controlled storage room. There is a Tesla Charger installed in the garage. The water heater was replaced in 2024, while the roof, windows, and air-conditioning system were replaced in November 2017. The AC air handler is located indoors to protect it from the elements and help extend the system’s service life. Private access to the Lake Brantley neighborhood park is available for $39 annually and includes a playground and small-boat launch. The home is approximately five minutes from two grocery stores, Lake Brantley High School, and Forest Lake Elementary, with I-4 about 10 minutes away.

2261 Charlotte Drive, Longwood
$1,750,000
5 Beds ⋅ 5 Baths ⋅ O6429109 MLS
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
$400,000
4 Beds ⋅ 3 Baths ⋅ O6429050 MLS ⋅ 114 BLDG.
Blank Canvas in The Springs waiting for you to bring your vision and ideas to reality! Rarely available, this spacious two story 4-bedroom, 2.5-bathroom townhome offers a blank canvas. You can create your dream space in this Longwood community. This property has tremendous upside and immediate equity. This house has a functional floor plan, great for families. Contact listing agent today to schedule your private tour!

114 Hidden Oak Drive, Longwood
$1,299,000
4 Beds ⋅ 4 Baths ⋅ O6426765 MLS
Nestled on a quiet cul-de-sac within the exclusive enclave of Sandy Lane Reserve, a private community of just 24 custom-built estate homes, this exceptional Signature Homes residence offers timeless architecture, refined finishes, and an ideal floor plan designed for both everyday living and effortless entertaining. Boasting 4 bedrooms, 3.5 bathrooms, a private office, bonus room, and 3,757 square feet of thoughtfully designed living space, this custom home combines elegance with modern comfort. A grand foyer welcomes you with soaring ceilings, abundant natural light, and easy-to-maintain wood-look tile flooring that flows throughout the main living areas. The beautifully updated gourmet kitchen is truly the heart of the home, featuring custom cabinetry, quartz countertops, a decorative tile backsplash, top-of-the-line GE Monogram stainless steel appliances, a built-in desk area, dry bar, a large center island with seating, a built-in wine refrigerator, and a spacious dinette overlooking the living spaces. Tongue-and-groove ceilings throughout the main living areas and covered lanai add warmth, character, and architectural charm. The thoughtfully designed floor plan offers a luxurious first-floor primary suite with brand-new carpeting, a spa-inspired bath with a soaking tub, separate shower, and spacious walk-in closets. A first-floor guest suite with its own ensuite bath and new carpeting provides ideal accommodations for visitors or multigenerational living. Upstairs, two additional bedrooms, each with walk-in closets, share access to a full bath and a generously sized bonus room, offering flexible space for a media room, playroom, or home gym. Step outside to your private Florida retreat, where a screened lanai overlooks the heated resort-style pool and spa, creating the perfect setting for year-round outdoor living and entertaining. Mature landscaping and the home's cul-de-sac location provide exceptional privacy and a peaceful setting. Located in one of Longwood's most desirable custom home communities, residents enjoy convenient access to top-rated Seminole County schools, Wekiva Springs, premier shopping, dining, golf, and major roadways. This is a rare opportunity to own a beautifully crafted custom home that seamlessly blends luxury, comfort, and an exceptional location.

3318 Sunset View Court, Longwood
$459,900
3 Beds ⋅ 3 Baths ⋅ O6426601 MLS
Nestled at the end of a quiet cul-de-sac in Longwood's Crystal Creek community, this waterfront residence offers the rare combination of tranquil water views behind the home and a picturesque wooded setting across the street, creating a sense of privacy and natural beauty from every direction. Inside, soaring ceilings and a dramatic two-story great room set the tone for the home's open and inviting design. A fireplace anchors the living space while expansive windows frame peaceful views of the water beyond the oversized screened porch, creating a seamless connection between indoor and outdoor living. The beautifully renovated kitchen serves as the heart of the home, featuring solid wood cabinetry with abundant drawer storage, generous granite countertops and an open layout designed for everyday living and effortless entertaining. Luxury vinyl plank flooring extends throughout the kitchen and every bedroom, while tile flooring enhances the foyer, dining room and great room with durability and timeless appeal. The first-floor primary suite provides a private retreat overlooking the backyard, complete with a spacious walk-in closet and an ensuite bath. A conveniently located powder bath serves guests on the main level. Upstairs, a generous loft offers flexible space for a media room, home office or play area, accompanied by two well-proportioned bedrooms and a full bath. Crystal Creek is a welcoming community with a low HOA fee and amenities including a neighborhood park, playground, tennis courts and basketball court. Ideally positioned near the best shopping, dining and entertainment found in Longwood, Lake Mary and Sanford, with convenient access to major roadways, this exceptional waterfront home places all of Central Florida comfortably within reach while offering a peaceful setting to come home to each day.

416 Sand Pebble Cove, Longwood
$1,739,000
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
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