Longwood Homes under $500,000

Longwood Homes under $500,000

Welcome to Longwood, Florida—a hidden gem nestled in the heart of Seminole County. This charming city is known for its picturesque landscapes, family-friendly atmosphere, and a strong sense of community. With a rich history dating back to the 19th century, Longwood seamlessly blends small-town charm with modern conveniences, making it an ideal place to call home.

Longwood boasts a variety of parks and recreational areas, perfect for outdoor enthusiasts and families alike. Enjoy leisurely strolls through the beautiful trails at Wekiva Springs State Park, or take the kids to the local playgrounds and sports fields. The city also offers a vibrant downtown area with unique shops, delightful eateries, and community events that foster a strong sense of belonging.

For those looking to settle down in Longwood, you’ll be pleased to discover a diverse selection of homes available for under $500,000. Whether you're a first-time buyer, a growing family, or looking to downsize, Longwood has something for everyone. From charming single-family homes to modern townhouses, these properties offer excellent value without compromising on quality or comfort.

With its convenient access to major highways, Longwood is just a short drive away from the bustling cities of Orlando and Sanford, providing easy access to shopping, dining, and entertainment options. Experience the perfect blend of tranquility and convenience in Longwood, where your dream home awaits! Come explore the possibilities in this delightful city and discover why so many are proud to call Longwood home.

Newest Longwood Homes under $500,000

827 Daybreak Place, Longwood
$499,900
3 Beds ⋅ 4 Baths ⋅ Oakmont Reserve Ph 2 SubDv. ⋅ 32750 Zip Code
Welcome home to this 2018-built, single-story 3-bedroom, 2-bath home in Oakmont Reserve, a gated community in the heart of Longwood. Inside, the home has been freshly painted throughout in a clean two-tone neutral palette, with new carpet. The kitchen features an island with seating and opens directly to the living room, creating a great flow for everyday living and entertaining. A separate dining area provides additional space for meals and gatherings. Residents enjoy the privacy of gated living along with a community playground and sidewalk-lined streets. Just minutes from historic downtown Longwood, the Longwood SunRail station, shopping, dining, and parks, with convenient access to SR 434 and I-4 for an easy commute throughout the Orlando area.

827 Daybreak Place, Longwood
107 Sunset Drive, Longwood
$449,900
4 Beds ⋅ 2 Baths ⋅ Shadow Hill SubDv. ⋅ 32750 Zip Code
POOL HOME+PAID-OFF SOLAR PANELS! Welcome to this spacious 4-Bedroom. 2-Bathroom home featuring an excellent floor plan, generous llvlng areas. and Inviting outdoor spaces. Enjoy the Florida lifestyle wllh a private pool and expansive porch. perfect for relaxing. entertaining. and creating memorable moments with family and friends. The thoughtfully designed layout provides bolh comfort and functionality. offering plenty of space for everyday Jiving. Fully paid-off solar panels add an attractive energy-conscious benefit for the next homeowner A wonderful opportunity to own a spacious home with desirable indoor and outdoor features.

107 Sunset Drive, Longwood
1417 Noble Street, Longwood
$460,000
4 Beds ⋅ 2 Baths ⋅ Sanlando Spgs SubDv. ⋅ 32750 Zip Code
Virtually Staged. Home sweet home!This well loved 4 bedroom 2 bath house has a split floor plan with 3 large sized bedrooms on one side of the house and the primary suite on the other side allowing privacy and quietness when needed. The kitchen has been updated and opens to the family room that overlooks the screened in porch. There also is a living room and dining room which could easily be converted to an office if needed.The entire house has just been repainted inside, and outside where needed. Brand new updates include luxury vinyl flooring throughout the living areas, new carpet in all of the bedrooms, new refrigerator, faucets have been replaced in both bath rooms and HVAC was replaced in 2025.There also is a large laundry/utility room inside. This is truly MOVE IN ready. The oversized lot (.29 acre) gives you space for outdoor play and or gardening. When you want to take a break, relax and enjoy hearing the birds chirp while sitting in the covered screened in porch overlooking the shaded back yard. This location is conveniently located to I-4, shopping, schools, restaurants, bike/walking paths, historic Longwood and Rolling Hills Community Park. There is no HOA. Call me today before it goes away!

1417 Noble Street, Longwood
1641 Stanley Street, Longwood
$419,900
3 Beds ⋅ 2 Baths ⋅ Sanlando Spgs SubDv. ⋅ 32750 Zip Code
Welcome to 1641 Stanley St in Longwood! This 3-bedroom, 2-bath single-family home offers approximately 1,897 square feet of living space and sits on a spacious 0.37-acre lot in the established Sanlando Springs area. The property offers a generous homesite with plenty of room for outdoor living, entertaining, gardening, recreation or future customization. The convenient Longwood location provides easy access to major roadways, shopping, dining, parks and surrounding Seminole County communities. With no HOA, this property offers additional flexibility for homeowners. Don't miss the opportunity to make this Longwood property your own!

1641 Stanley Street, Longwood
206 Duncan Trail, Longwood
$479,900
4 Beds ⋅ 3 Baths ⋅ Wekiva Hills Sec 08 SubDv. ⋅ 32779 Zip Code
Virtually Staged. Wekiva Hills — Well-Maintained 4-Bedroom Home Near Duncan Park. Located in the heart of the highly desirable Wekiva Hills community, just steps from Duncan Park, this beautifully maintained 4-bedroom, 2-bath residence offers a wonderful combination of comfort, functionality, and location.The thoughtfully designed split-bedroom floor plan features four bedrooms, two full bathrooms, a well-appointed kitchen, separate living and family rooms, and a convenient interior laundry area. A standout feature of the home is the spacious 30' x 15' covered and screened porch, overlooking the private, fenced backyard. The generous outdoor space provides an ideal setting for entertaining, relaxing, and enjoying Florida's year-round lifestyle, with ample room to add a future pool. Additional highlights include: New roof installed in 2022. Excellent location within Wekiva Hills, one of Central Florida's established residential communities and offers an exceptional array of amenities and recreational opportunities. Residents enjoy miles of scenic walking and biking trails, parks, playgrounds, tennis courts, sports facilities, a community library, and nearby golf. The property is conveniently located near Lake Brantley High School, local shopping and dining, and major roadways. Outdoor enthusiasts will appreciate the close proximity to Wekiwa Springs State Park, Wekiva Island, and Rock Springs Run. With its desirable location, spacious floor plan, private outdoor setting, and access to an outstanding array of community amenities, this home presents an excellent opportunity to become part of the Wekiva Hills community.

206 Duncan Trail, Longwood
1901 Glen Mist Cove, Longwood
$345,000
3 Beds ⋅ 3 Baths ⋅ Hanover Pointe Rep - Rep SubDv. ⋅ 32750 Zip Code
Welcome to this beautifully maintained two-story corner residence, offering added privacy, abundant natural light, and inviting indoor and outdoor living spaces. The bright, open-concept floor plan creates a comfortable, welcoming atmosphere, while the updated kitchen features stainless steel appliances and a clean, modern design—perfect for everyday living and entertaining. A true highlight of the property is the private, beautifully landscaped garden, offering a peaceful outdoor retreat. Whether you're enjoying morning coffee, relaxing after a long day, or entertaining family and friends, this charming outdoor space sets this home apart. Meticulously maintained and move-in ready, the home offers an ideal combination of comfort, style, and convenience. Its desirable corner location provides additional outdoor space and a greater sense of privacy. Located within a gated community featuring security and a community swimming pool, residents can enjoy a relaxed lifestyle with attractive amenities close at hand. With its prime corner location, updated interior, private garden, and move-in-ready condition, this exceptional property is ready to welcome its next owner. Schedule your private showing and experience everything this home has to offer!

1901 Glen Mist Cove, Longwood
258 Capulet Cove, Longwood
$349,900
3 Beds ⋅ 4 Baths ⋅ Monterey North SubDv. ⋅ 32750 Zip Code
Short Sale. CENTRALLY LOCATED 3 BED 2.5 BATH TOWNHOUSE IN A GREAT COMMUNITY. OPEN FLOOR PLAN WITH ALL GRANITE COUNTERS AND STAINLESS-STEEL APPLIANCES, LARGE PANTRY IN KITCHEN, LARGE LIVING AND DINING AREA PERFECT FOR YOUR FAMILY OR ENTERTAINING. PRIMARY BEDROOM HAS LARGE WALK IN CLOSET AND SPACIOUS BATH, OTHER TWO BEDROOMS ARE SPACIOUS WITH A DOUBLE SINK BATHROOM, LAUNDRY ROOM UPSTAIRS FOR ADDITIONAL CONVENIENCE. MANY RESTAURANTS AND STORES WITHIN EASY WALKING DISTANCE. CALL TO SET YOUR APPOINTMENT.

258 Capulet Cove, Longwood
228 S Fox Chase Point, Longwood
$475,000
3 Beds ⋅ 3 Baths ⋅ Hunters Glen SubDv. ⋅ 32779 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 228 S Fox Chase Point in Longwood, a spacious 3-bedroom, 2.5-bathroom home in the established Wekiva Hunt Club community. The two-story layout offers a comfortable balance of gathering spaces and private retreats, along with a dedicated office that can accommodate working from home, studying, or other flexible uses. Inside, the home features inviting living areas filled with natural light, complemented by vaulted ceilings and a fireplace that add character and warmth to the interior. Three bedrooms provide comfortable accommodations, while two full bathrooms and a convenient half bath offer functionality for both residents and guests. The outdoor setting is well suited for enjoying the Florida lifestyle. A private in-ground pool with a surrounding deck creates a relaxing centerpiece for the backyard, with plenty of room for lounging and entertaining. The covered and screened patio provides a shaded spot for outdoor dining or unwinding, while the private yard offers additional space to enjoy the outdoors. Set in Wekiva Hunt Club, the home is surrounded by mature landscaping and an established residential setting. The community offers access to parks, playgrounds, tennis courts, a clubhouse, and walking trails, with golf and additional outdoor recreation nearby. Shopping, dining, and everyday conveniences are also within easy reach, along with SR 434 and other major roadways connecting Longwood to Altamonte Springs and surrounding Seminole County destinations.

228 S Fox Chase Point, Longwood
205 W Cumberland Circle, Longwood
$440,000
3 Beds ⋅ 2 Baths ⋅ Wekiva Hunt Club 3 Fox Hunt Sec 3 SubDv. ⋅ 32779 Zip Code
Virtually Staged. Welcome to Hunt Club! This tastefully updated and meticulously maintained home offers the perfect blend of comfort, convenience, and an active community lifestyle. The open kitchen and family room create a wonderful gathering space, with the family room overlooking the beautifully renovated kitchen featuring quartz countertops and stainless-steel appliances. The split-bedroom floor plan offers added privacy, with the primary suite separated from the additional bedrooms—ideal for families, guests, or a home office. Major updates provide peace of mind, including roof replacement in 2017, replumbing in 2021, hot water heater in 2022, HVAC in 2023, and windows in 2024. Step outside to the spacious screened porch, perfect for enjoying your morning coffee, relaxing in the evening, or entertaining friends and family. The fenced backyard provides a private outdoor space for play, entertaining, gardening, or simply letting your furry friends enjoy some fresh air and room to roam. And there's even more to love! The garage workbenches, lawnmower, and garden tools convey with the property, giving the new owners everything they need to get started right away and making this home truly turnkey ready. Located in the highly sought-after Lake Brantley school district, this home is also part of a community with an impressively low HOA of just $275 per year. Residents enjoy an array of amenities, including basketball, racquetball, tennis, pickleball, parks, and a community center. Golf enthusiasts will appreciate the nearby public golf course. Nature lovers will enjoy easy access to community trails and nearby Wekiwa Springs State Park, with opportunities to explore the outdoors and catch occasional glimpses of local wildlife. Conveniently located near Wekiva Springs, SR 436, SR 434, major thoroughfares, shopping, dining, and everyday conveniences. Updated, well maintained, great schools, wonderful amenities, a fenced backyard, and a location that puts it all within easy reach—this Hunt Club home is truly ready to welcome its new owners!

205 W Cumberland Circle, Longwood
526 E Jessup Avenue, Longwood
$299,900
3 Beds ⋅ 2 Baths ⋅ Wildmere SubDv. ⋅ 32750 Zip Code
NO HOA Move-in ready and full of value, this updated Longwood home features a 2020 roof, 2021 A/C, 2022 water heater and a security system that conveys with the property. This 3-bedroom, 2-bath home offers a comfortable layout and a great opportunity to step into homeownership. Major improvements are already in place, including a 2021 roof and A/C, giving buyers added peace of mind. The beautiful and modern kitchen has stone countertops and stainless steel appliances. The security system stays with the property, adding convenience from day one. The backyard has a lot of potential and has a shed. The location is a standout, with convenient access to shopping, dining, schools, major roadways, and everything Longwood and the surrounding Orlando area have to offer. Schedule your tour today.

526 E Jessup Avenue, Longwood
441 Black Knight Way, Longwood
$337,500
3 Beds ⋅ 3 Baths ⋅ Highcroft Pointe Twnhms SubDv. ⋅ 32779 Zip Code
Virtually Staged. Turnkey living meets everyday convenience in this beautifully maintained Longwood townhome! Located in a gated community, this inviting 3-bedroom, 2.5-bath home offers a bright, open-concept layout designed for easy everyday living and entertaining. RECENT UPDATES INCLUDE A NEW ROOF (3 yrs old), NEW HVAC SYSTEM, NEW WATER HEATER, AND NEW DISHWASHER, PROVIDING ADDED PEACE OF MIND FOR THE NEW HOMEOWNER. The spacious kitchen features wood cabinetry, stainless steel appliances, a stylish backsplash, generous counter space, and a convenient pantry, with an eat-in area that provides the perfect spot for casual meals. The comfortable living area is filled with natural light and opens to a private patio, creating your own outdoor space to enjoy your morning coffee, dine al fresco, relax, or soak up the sun. The patio leads directly to the attached two-car garage, adding everyday convenience and functionality. The entire main living area is conveniently located on the first floor, while all three bedrooms are privately situated upstairs, creating a comfortable separation between living and sleeping spaces. The spacious primary suite offers a relaxing retreat with a walk-in closet and a private bath featuring double vanities, a relaxing garden tub, and a separate stall shower. Two additional bedrooms share a second full bath, and an upstairs laundry closet adds everyday convenience. Enjoy carefree, low-maintenance living along with the added appeal of a gated community featuring a scenic nature walk surrounding a charming gazebo, creating a peaceful place to take a stroll or enjoy the outdoors. The location puts everyday necessities close by, with a supermarket and drug store close by, plus nearby restaurants, shopping, and convenient access to major highways. With three bedrooms, 2.5 baths, a two-car garage, private outdoor space, gated-community living, and a convenient location, this move-in-ready townhome offers the space, updates, and lifestyle you've been looking for. Simply move in, unpack, and enjoy!

441 Black Knight Way, Longwood
1051 Alameda Drive, Longwood
$394,900
3 Beds ⋅ 2 Baths ⋅ Windtree West Unit 2 SubDv. ⋅ 32750 Zip Code
Location , location!! 3/2 HOME in the highly desired Windtree West subdivision! Enjoy SOARING HIGH CEILINGS in the living room, a COZY FIREPLACE, and a spacious KITCHEN ISLAND. The entire home features beautiful tile flooring throughout no carpet to replace, offering clean, low maintenance and move in ready feel. Major upgrades include a NEWER 2024 AC, 2018 WINDOWS, STAINLESS STEEL APPLIANCES plus a dedicated laundry room with modern washer and dryer, the home also offers a 2 CAR GARAGE with wide driveway for extra parking. Sitting on a 0.21 ACRE LOT, this property has a generous backyard and plenty of side space perfect for outdoor activities, gardening or creating your own relaxing retreat. Located close to TOP RATED SCHOOLS, parks, shopping, and dining AND have quick access to I-4 for easy commuting. Downtown Orlando, major employers, and popular attractions are all a short drive away, giving you convenience without sacrificing that peaceful Longwood feel. Make your appointment today!

1051 Alameda Drive, Longwood
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