Longwood Homes for Sale

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

$1,495,000

4 Beds ⋅ 4 Baths ⋅ Lake Brantley Isles Amd SubDv. ⋅ 32779 Zip Code

Welcome to this luxurious 4 BR/3.5 BA Lake Brantley canal home complete with pool, hot tub, expansive paver patio w/firepit, screened in 2nd patio and private boat dock on the canal leading to Lake Brantley! A peaceful and serene vibe can be found in this lush and beautiful backyard; perfect setting for relaxing or entertaining. Bring your ski boat, kayaks, and paddleboards as well as fishing poles & enjoy this incredible waterfront living! This is a private spring fed lake with no public access. Inside the home offers four spacious bedrooms, including a distinctive primary suite that has a unique flare incorporated into the octagonal style architecture with high ceilings, lots of windows, French doors leading to the 2nd story balcony, & a separate seating area currently being used as a massage room! The primary closet has a generous amount of space with ample shelving. The primary ensuite bathroom includes a separate soaking tub, an oversized decorative walk-in shower, & a private water closet with bidet. Two additional bedrooms share a Jack n Jill bathroom, one with French doors leading to 2nd story balcony. (Relax with the ambiance of a cozy fireplace in that same bedroom which also has a vaulted high ceiling & additional high windows that bring in plenty of natural light.) Both bedrooms have a large amount of closet space. The fourth bedroom has a nice view of the beautiful old oak trees along with ensuite bath that is accessible through the upstairs hallway as well. This spacious kitchen is designed for both everyday living and holiday entertaining with a double oven, gas cooktop & sizeable island. More than just a walk-in pantry, an entire 11x5 pantry/storage room is conveniently located immediately upon entering home from the garage and features shelving with additional refrigerator. Just around the corner, you’ll find a dedicated office with built-in desk and shelving, a comfortable sitting room, a dining room with French doors and wet bar, plus a spacious family room showcasing a wood fireplace & French doors overlooking the backyard and pool. The wrap around 2nd floor balcony off the back of the home details an intricate wrought iron railing and spiral staircase that can access the rooftop as well. You will also enjoy amazing 4th of July fireworks views off the roof top balcony! Additional features and updates include: Private boat dock approximately 2 years old, roof approximately 8 years old, rwo AC units with compressors were replaced in 2018 and 2023, pool pump approximately 5 years old, home is on septic and well; well features a new pressure tank and new filtration-system mechanicals, balcony was recently remodeled with Trex Decking. With its beautiful waterfront/canal setting, spacious interior, and thoughtful features throughout, this Seminole County Lake Brantley canal home offers a truly one of a kind opportunity to enjoy a relaxed Florida lifestyle with plenty of space for entertaining, recreation, and everyday living.

2261 Poinsettia Drive, Longwood

$449,900

3 Beds ⋅ 2 Baths ⋅ Columbus Harbor SubDv. ⋅ 32750 Zip Code

LAKE ACCESS, a top-to-bottom remodel and a tucked-away cul-de-sac location—this Longwood home checks all the boxes! Enjoy access to beautiful Lake Fairy, including a private community boat ramp, gazebo and picnic area, plus a tennis and pickleball court. Inside, professional contractors have completely transformed the home, and the quality shows in every room. The gorgeous kitchen is ready for everything from pancake breakfasts to holiday parties, featuring granite countertops, wood cabinetry, a pantry, ceramic tile flooring, a stylish backsplash and an oversized breakfast bar with seating for four. Open to the dinette and living areas, the cook never has to miss the conversation! Skylights fill the living room with natural light, while the fireplace adds the perfect touch for cozy evenings. The flexible living and dining combination offers plenty of possibilities for entertaining, a home office, playroom or additional lounge space. The split-bedroom floor plan provides privacy, with spacious secondary bedrooms and an additional walk-in closet. The beautifully remodeled bathrooms shine with granite countertops, tile flooring, updated fixtures and dual-sink vanities. Beautifully updated, full of personality and offered at $449,900—just unpack and start enjoying the Florida lifestyle!

711 Columbus Way, Longwood

$220,000

2 Beds ⋅ 2 Baths ⋅ Evergreen Place SubDv. ⋅ 32750 Zip Code

Virtually Staged. Welcome to this charming 2-bedroom, 2-bathroom half-duplex in the heart of Longwood! Offering approximately 990 square feet of living space, this home features an upgraded kitchen with modern finishes and ample cabinet storage, creating a functional and inviting space for everyday living and entertaining. The home offers a spacious living and dining area, two comfortable bedrooms, and two full bathrooms with convenient shower/tub combinations. Step outside to enjoy a fully fenced backyard, perfect for outdoor enjoyment, along with a covered one-car carport. With NO HOA, this property provides flexibility for homeowners and investors alike. Conveniently located near SR 434, I-4, shopping, dining, schools, and major roadways, with easy access to Downtown Orlando and surrounding Central Florida communities. Whether you're looking for a primary residence or an investment opportunity, this Longwood property offers convenience, functionality, and an excellent location.

330 E Evergreen Avenue, Longwood

$230,000

2 Beds ⋅ 2 Baths ⋅ Evergreen Place SubDv. ⋅ 32750 Zip Code

Virtually Staged. Welcome to this charming 2-bedroom, 2-bathroom half-duplex in the heart of Longwood! Offering approximately 990 square feet of living space, this home features an upgraded kitchen with modern finishes and ample cabinet storage, creating a functional and inviting space for everyday living and entertaining. The home offers a spacious living and dining area, two comfortable bedrooms, and two full bathrooms with convenient shower/tub combinations. Step outside to enjoy a fully fenced backyard, perfect for outdoor enjoyment, along with a covered one-car carport. With NO HOA, this property provides flexibility for homeowners and investors alike. Conveniently located near SR 434, I-4, shopping, dining, schools, and major roadways, with easy access to Downtown Orlando and surrounding Central Florida communities. Whether you're looking for a primary residence or an investment opportunity, this Longwood property offers convenience, functionality, and an excellent location.

328 E Evergreen Avenue, Longwood

$395,000

3 Beds ⋅ 2 Baths ⋅ Windtree West Unit 2 SubDv. ⋅ 32750 Zip Code

WELCOME HOME! Don’t miss this beautifully maintained 3-bedroom, 2-bath home featuring a renovated kitchen, spacious living areas, and a large fully fenced backyard with NO REAR NEIGHBORS! Step through the inviting foyer into the comfortable living room, where a central wood-burning fireplace creates a warm and welcoming focal point. A separate dining area provides the perfect space for entertaining. Upgraded tile flooring flows throughout the main living areas, offering both style and easy maintenance. The spacious family room is filled with natural light and opens through sliding glass doors to the expansive backyard, creating an ideal indoor-outdoor living space. The renovated kitchen features newer cabinetry, granite countertops, stainless steel appliances, a generous eat-in area, and its own sliding glass doors leading directly to the backyard. The convenient laundry area is located just off the kitchen and leads to the oversized 2-car garage, providing plenty of storage and parking space. Major updates include a 2022 roof, 2022 A/C, 2022 gas water heater, and 2022 stove, microwave, and dishwasher, offering valuable peace of mind for the next owner. Outside, the large fully fenced backyard—with no rear neighbor—provides plenty of room for barbecues, gatherings, pets, play, or simply relaxing and enjoying your own private outdoor space. With its inviting layout, renovated kitchen, numerous 2022 updates, oversized garage, and private backyard, this home offers the space, comfort, and convenience you’ve been looking for. Come see it before it’s gone!

990 Waverly Drive, Longwood

$460,000

3 Beds ⋅ 2 Baths ⋅ Wekiva Hills Sec 01 SubDv. ⋅ 32779 Zip Code

Welcome to this move-in ready 3 bedroom, 2 bathroom home in Longwood, offering a great combination of comfort, character, outdoor living, and a convenient Central Florida location. Inside, the spacious family room immediately stands out with cathedral ceilings and a wood-burning fireplace, creating a warm and inviting space for everyday living and entertaining. One of the best features of the home is the screened back porch, complete with a ceiling fan and patio furniture that stays with the home. It’s the perfect extension of the living space for morning coffee, relaxing in the evenings, or entertaining while overlooking the nicely fenced backyard. The home also comes with some great extras, including a 90-inch TV in the TV room, a 52-inch TV on the back porch, and the TV in the office. The neighborhood offers even more to enjoy with a low HOA fee and a community park, playground, and small fishing lake within walking distance. And when location matters, this one delivers. You’ll be conveniently located near I-4 with easy access to Orlando, shopping, dining, and everything Central Florida has to offer. With its cathedral ceilings, fireplace, screened outdoor living space, fenced backyard, included furniture and TVs, and desirable Longwood location, this home has plenty to offer and is ready for its next owner. Schedule your private showing and come see it for yourself!

207 Harrogate Place, Longwood

$399,900

3 Beds ⋅ 3 Baths ⋅ The Landings SubDv. ⋅ 32750 Zip Code

Virtually Staged. Beautiful West Lake views from this 3-bedroom, 2.5-bath home in The Landings, a gated community in Longwood, Florida! From the moment you step inside, the open living area draws your eye toward the water, with vaulted ceilings, a wood-burning fireplace and a split bedroom floor plan creating a comfortable and inviting space. The updated kitchen also enjoys views toward West Lake, bringing the peaceful setting right into the home. Step outside onto the updated Trex deck and enjoy beautiful water views and a relaxing outdoor space for morning coffee, entertaining or simply unwinding. The home offers 1,442 square feet of living space and a 2-car attached garage, along with several recent updates including a 2024 roof, two new patio doors in 2025, exterior paint in 2026, refrigerator in 2026 and garbage disposal in 2023. The Landings offers a gated community setting with a community pool, tennis and pickleball courts, plus jogging and biking trails. Enjoy the combination of beautiful West Lake views and community amenities, all conveniently located in historic Longwood, Florida, near shopping, dining, parks and major roadways.

624 Fallsmead Circle, Longwood

$375,000

3 Beds ⋅ 3 Baths ⋅ Meusers Sub SubDv. ⋅ 32750 Zip Code

CASH COW | This versatile property offers a unique opportunity to receive 3 rental incomes | either a high-cash-flow investment or conversion into a spacious 4-bedroom, 3-bathroom single-family home. Featuring an open floor plan, independent entrances for maximum privacy, modern tile flooring, and bright living spaces, it is perfect for an investor seeking high returns or a homeowner looking to offset their mortgage with rental income. Some of the pictures have been virtually enhanced.

520 E Magnolia Avenue, Longwood

$499,000

3 Beds ⋅ 2 Baths ⋅ Shadowbay, Lake Vista At SubDv. ⋅ 32779 Zip Code

Welcome Home to this beautifully maintained three bedroom, two bathroom home with a spacious two car garage, nestled in the sought-after Lake Vista at Shadowbay, a desirable lakefront community offering an exceptional Central Florida lifestyle. From the moment you step inside, you'll appreciate the home's open, airy design, abundant natural light, and soaring vaulted ceilings. Rich wood flooring and tile flow throughout, complemented by unique architectural details and thoughtfully designed built-in niches that add warmth, character, and charm. The home offers a wonderful blend of formal and casual living spaces, including an elegant dining room, inviting living room, and additional flexible areas that seamlessly connect throughout the home. Whether you're hosting friends, enjoying family time, or simply relaxing at the end of the day, this thoughtfully designed floor plan offers both comfort and versatility. But the true showstopper may be waiting just outside. Step into the oversized, tranquil screened-in lanai, where vaulted ceilings create an expansive outdoor retreat. Two wood ceiling fans, each featuring three lighting options and remote controls, allow you to create just the right atmosphere for any occasion. With plenty of space for outdoor dining, entertaining, or simply unwinding, this peaceful setting overlooks a beautiful wooded conservation area and serene pond, creating a private backdrop you'll enjoy year-round. And then there's the lifestyle. Located in the lakefront community of Shadowbay, residents enjoy private access to the highly desirable Ski Lake Brantley, along with community amenities including a tennis court, boat ramp, and more. Whether you're looking to spend the day on the water, enjoy outdoor recreation, entertain friends, or simply take in the peaceful surroundings, this community offers something truly special. Conveniently located near top-rated Seminole County schools, shopping, dining, major roadways, and everything Longwood and Central Florida have to offer, this home perfectly combines comfort, convenience, and an exceptional location. Best of all, there is NO HOA and NO restrictions, providing a level of freedom and flexibility that's becoming increasingly difficult to find. This is more than a house—it's an opportunity to enjoy a peaceful home, beautiful outdoor living, and the sought-after Florida lake lifestyle all in one remarkable setting. Don't miss your opportunity to make this wonderful home your own. Schedule your private showing today and come experience the lifestyle of Lake Vista at Shadowbay for yourself!

322 N Shadowbay Boulevard, Longwood

$820,000

4 Beds ⋅ 4 Baths ⋅ Knollwood 2nd Add SubDv. ⋅ 32750 Zip Code

This magnificent home rests on 3/4 of an acre in the much desired community of Knollwood in Longwood. Close to shopping, dining, I-4 access and yet maintains a quiet and peaceful atmosphere. Large and spacious is definitely the key to this house. It boasts 4 bedrooms, 2 full baths and 2 half baths. The kitchen is a cooks delight. Cabinets and storage for everything! The gas fireplace adds true warmth to the family room, a place for family & friends to gather. Step out into your large patio, perfect for entertaining and then out to your oversized pool. A dream home to make memories that will last forever.

1550 Warwick Place, Longwood

$2,577,421

5 Beds ⋅ 6 Baths ⋅ Sweetwater Club Unit 2 SubDv. ⋅ 32779 Zip Code

Welcome to this impressive estate in the exclusive, guard-gated Sweetwater Club community. Situated on approximately 1.4 acres, this 7,231-square-foot residence offers grand-scale living, beautifully updated interiors, generous outdoor spaces, and remarkable privacy. A dramatic two-story foyer sets the tone with soaring ceilings, floating dual staircases, abundant natural light, and elegant architectural details. Throughout the home, you’ll find substantial crown molding, custom baseboards, solid wood doors, beautifully renovated baths, custom cabinetry, designer lighting, and thoughtfully selected finishes. The chef-inspired gourmet kitchen is truly the heart of the home, featuring rich custom cabinetry, expansive granite countertops, premium stainless-steel appliances, a custom wood vent enclosure, exposed ceiling beams, and an impressive oversized center island complemented by a second island with generous bar seating. The open layout flows effortlessly into adjoining living and dining areas, creating a wonderful setting for both everyday living and larger gatherings. The spacious primary suite is a private retreat featuring its own sitting room, fireplace, and outdoor balcony—a peaceful space to relax and unwind. Adding tremendous versatility is a large game room that can also serve as an in-law or guest suite, complete with a bedroom and full bathroom, providing an ideal arrangement for extended family or overnight guests. One of the home’s most distinctive features is the private whiskey cellar, offering a unique space for displaying a collection and gathering with family and friends. Outdoors, mature landscaping and expansive grounds create a private, resort-like atmosphere. Enjoy the pool, spacious patio areas, fire-pit gathering space, and lush backyard, with plenty of room to take advantage of Florida’s indoor-outdoor lifestyle. A rare four-car garage provides ample room for vehicles, storage, or a car collection. Beyond the property, Sweetwater Club offers pickleball courts and a beautiful park-like setting with inviting areas for community gatherings, adding to the neighborhood’s distinctive lifestyle and sense of community. With its impressive scale, flexible living spaces, distinctive amenities, privacy, and highly desirable Sweetwater Club location, this beautifully appointed estate presents a rare opportunity to enjoy luxury living with space to gather, relax, and entertain.

1303 Sweetwater Club Boulevard, Longwood

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