Homes for Sale Between $500,000 to $600,000 in Longwood, FL

4 Beds ⋅ 3 Baths ⋅ Sec 26 Twp 20s Rge 29e Beg 831 Ft S & 25 Ft E Of N SubDv. ⋅ 32779 Zip Code

Virtually Staged. This home can be purchased with NO INCOME VERIFICATION needed, plus receive 1% back from the seller’s preferred lender! Enjoy the added benefit of NO HOA, meaning no homeowners association fees, no monthly or annual HOA dues, and no HOA-related restrictions. Enjoy greater flexibility and freedom to make this property your own without the added expense of association fees! Discover the possibilities at 1351 Markham Woods Road in Longwood, Florida! This property has seen numerous renovations and thoughtful updates, offering a refreshed space with room to make it your own. The kitchen has been fully renovated, the living and dining room ceilings updated, additional electrical work completed in the living room, and the interior freshly painted. Other improvements include updated flooring throughout and a refreshed fireplace. Outside, enjoy a revitalized pool area featuring a completely redone pool interior finish and a replaced pool screen enclosure, creating an inviting setting for relaxing and entertaining. Additional planned improvements include two new hallway closets—a coat closet and a linen closet—along with bathroom upgrades featuring a new vanity, toilets, faucets, a glass-enclosed shower, and a new exhaust fan, plus additional interior painting. Conveniently positioned along Markham Woods Road, the property offers access to State Road 434, Interstate 4, and Lake Mary Boulevard, making travel throughout Longwood, Lake Mary, and the greater Orlando area convenient. Nearby shopping, dining, everyday essentials, and local amenities add to the appeal of this location. Whether you're looking for a property to personalize or a home with significant improvements already underway, this is an opportunity to explore. With no HOA fees to factor into your budget, attractive financing options through the seller’s preferred lender, and a refreshed pool area, this Longwood property offers plenty of possibilities. Schedule your private showing today and discover its potential!

1351 Markham Woods Road, Longwood

$599,900

4 Beds ⋅ 3 Baths ⋅ Hidden Oak Estates SubDv. ⋅ 32750 Zip Code

Welcome to 1043 Bucksaw Place—a beautifully reimagined pool home where thoughtful design, extensive renovations, and water views come together in the heart of Longwood. Situated on a .28-acre corner lot in Hidden Oak Estates, this fully renovated 4-bedroom, 2.5-bath home offers 2,149 square feet of stylish, move-in-ready living space. Step inside to a bright, inviting interior that has been transformed with new flooring, designer lighting, fresh finishes, and a completely renovated kitchen featuring new cabinetry, quartz countertops, new appliances, backsplash, and fixtures. The kitchen flows into the main living areas, where a wood-burning fireplace creates a warm focal point for gathering and entertaining. All bathrooms have been beautifully renovated with updated tile, vanities, fixtures, and finishes. Beyond the cosmetic transformation, major improvements include a BRAND NEW ROOF, NEW HVAC system, and NEW WATER HEATER, offering added peace of mind for the next owner. The outdoor living space is equally impressive. Step through to the screened pool overlooking the pond and enjoy the newly resurfaced and retiled pool and refreshed outdoor space. With peaceful pond frontage in the backyard and an additional lake view from the front of the home, water views can be enjoyed from both sides of the property. Located in an established Longwood neighborhood with convenient access to shopping, dining, parks, and major roadways, 1043 Bucksaw Place combines the character of an established community with the finishes and major updates of a newly renovated home. Move-in ready, beautifully designed, and made for Florida living—schedule your showing today.

1043 Bucksaw Place, Longwood

$599,900

4 Beds ⋅ 3 Baths ⋅ North Cove SubDv. ⋅ 32750 Zip Code

Stunning 4-bedroom, 3-bathroom home featuring fresh exterior and interior paint, along with new LVP flooring and new carpet throughout. The dramatic living room impresses with soaring vaulted wood-paneled ceilings, a striking floor-to-ceiling brick fireplace, and walls of windows and French doors that flood the space with natural light. The beautifully updated kitchen boasts crisp white cabinetry, sleek black countertops, and stainless steel appliances, opening to a bright breakfast area. Bathrooms feature stylish black-framed mirrors and modern fixtures for a fresh, updated feel. Step outside to a true backyard oasis, complete with a sparkling pool, covered patio with wood-beamed ceiling, and a fully fenced yard, perfect for entertaining or relaxing in privacy. With its blend of character, space, and resort-style outdoor living, this home is a must-see.

1539 Grace Lake Circle, Longwood

$599,000

4 Beds ⋅ 2 Baths ⋅ Sweetwater Oaks Sec 04 SubDv. ⋅ 32779 Zip Code

DEEDED ACCESS TO BOATABLE & SKIABLE LAKE BRANTLEY AND THE SCENIC WEKIVA RIVER! LIVE THE WATERFRONT LIFESTYLE AT A STUNNING VALUE! Discover an exceptional opportunity to experience the coveted SWEETWATER OAKS LIFESTYLE in the heart of LONGWOOD, FLORIDA, where RESORT-STYLE AMENITIES, WATERFRONT RECREATION, and the natural beauty of Central Florida come together in one of SEMINOLE COUNTY'S most desirable established communities. Located JUST ONE BLOCK FROM BEAUTIFUL LAKE BRANTLEY, this inviting 4 BEDROOM, 2 BATHROOM POOL HOME offers an extraordinary combination of comfort, convenience, and access to a lifestyle typically associated with much higher-priced waterfront properties. Surrounded by mature landscaping and timeless Florida charm, this residence features a thoughtfully designed SPLIT FLOOR PLAN with spacious OPEN LIVING AREAS ideal for both everyday living and effortless entertaining. The beautifully appointed KITCHEN showcases GRANITE COUNTERTOPS, rich cabinetry, STAINLESS STEEL APPLIANCES, and generous preparation space, seamlessly complementing the home's inviting interior. Stylish WOOD-LOOK FLOORING, a distinctive ACCENT WALL, and comfortable gathering spaces create an atmosphere of warmth and understated elegance. Step outside to your PRIVATE SCREENED-IN POOL, where Florida's beautiful climate can be enjoyed year-round. Whether hosting weekend gatherings, relaxing poolside, or enjoying a peaceful afternoon, this private outdoor retreat provides the perfect extension of the home's living and entertaining spaces. THE TRUE LUXURY OF SWEETWATER OAKS EXTENDS FAR BEYOND YOUR FRONT DOOR! Residents enjoy DEEDED ACCESS TO LAKE BRANTLEY, a BOATABLE AND SKIABLE LAKE, complete with a PRIVATE WHITE-SAND BEACH, BOAT RAMP, and FISHING DOCK, offering exceptional opportunities for boating, waterskiing, fishing, and lakeside relaxation. For those who appreciate Florida's natural waterways, the community also provides ACCESS TO THE SCENIC WEKIVA RIVER with KAYAK AND CANOE LAUNCHING opportunities. An extraordinary collection of COMMUNITY RECREATIONAL AMENITIES further elevates the experience, including 8 TENNIS COURTS, 8 PICKLEBALL COURTS, 2 BASKETBALL COURTS, a VOLLEYBALL COURT, SOCCER AND BASEBALL FIELDS, a COMMUNITY CLUBHOUSE, PARKS, PLAYGROUNDS, and beautifully maintained outdoor gathering spaces. From active recreation to peaceful afternoons along the water, SWEETWATER OAKS delivers a lifestyle that truly embraces the best of CENTRAL FLORIDA LIVING. Ideally positioned in the highly desirable LONGWOOD area, this established community offers convenient access to shopping, dining, major transportation corridors, and SEMINOLE COUNTY SCHOOLS, all while maintaining the peaceful character of a neighborhood celebrated for its mature trees, natural surroundings, and exceptional recreational opportunities. WHY PAY WATERFRONT PRICES WHEN YOU CAN ENJOY THE WATERFRONT LIFESTYLE? With DEEDED LAKE BRANTLEY ACCESS, WEKIVA RIVER RECREATION, an extraordinary collection of COMMUNITY AMENITIES, and your very own PRIVATE SCREENED POOL, this SWEETWATER OAKS residence presents a remarkable opportunity to enjoy the very best of FLORIDA LIVING AT AN EXCEPTIONAL VALUE!

207 Royal Oaks Circle, Longwood

$589,900

4 Beds ⋅ 2 Baths ⋅ Sanlando Spgs SubDv. ⋅ 32750 Zip Code

Virtually Staged. WELCOME HOME TO THIS SPACIOUS 4-BEDROOM, 2-BATH POOL HOME OFFERING THE PERFECT BLEND OF CHARACTER, UPDATES, AND FLORIDA LIVING! Situated on a fully fenced lot with RV parking, this solid block home offers exceptional space, thoughtful updates, and plenty of room to entertain. Step through the hardwood entryway into the inviting living room, where you'll find a cozy fireplace that also connects to the primary bedroom, creating warmth and charm throughout the home. Just beyond is the beautifully remodeled kitchen featuring a large center island, farmhouse sink, ample cabinetry, pantry, and generous prep space—perfect for everyday living and entertaining. The adjoining family room flows seamlessly into the incredible climate-controlled Florida room, complete with heating, air conditioning, and its own stunning stone fireplace, making it the perfect year-round gathering space overlooking the backyard and pool. The spacious primary suite offers private access to the Florida room, a large walk-in shower, dual vanities, and generous closet space. The secondary bathroom has been beautifully remodeled with dual sinks and an updated shower. The additional bedrooms are all generously sized, including one with a walk-in closet and another featuring French doors leading to the backyard along with its own walk-in closet. The dining room includes custom built-in storage, while additional linen, utility, and pantry storage provide functionality throughout the home. Outside, you'll enjoy your own private backyard retreat featuring a sparkling pool with a new pool pump (2026), a fully fenced yard, RV parking, and plenty of space for entertaining, pets, or gardening. The climate-controlled two-car garage features a new electrical panel, laundry area, and is complemented by an additional carport. A generator transfer switch is also already installed for added peace of mind. Major updates include a new addition completed in 2024, new septic system and drain field installed in 2024, repiped plumbing, new HVAC system, roof replaced in 2017, flat roof replaced in 2021, and a new electrical panel. The home is on septic, and while a well is present, it is not currently in use. Conveniently located just minutes from Historic Downtown Longwood, SunRail, I-4, shopping, dining, top-rated Seminole County schools, Big Tree Park, and Wekiwa Springs State Park, this home offers the perfect combination of space, comfort, and convenience. Don't miss your opportunity to own this one-of-a-kind Longwood home. Schedule your private showing today!

442 Homer Avenue, Longwood

$587,000

4 Beds ⋅ 3 Baths ⋅ Knollwood 3rd Add Amd SubDv. ⋅ 32750 Zip Code

Your Dream Home Awaits! Discover the perfect combination of space, comfort, and endless possibilities in this charming ranch-style home, ideally positioned on an impressive 0.71-acre corner lot in the highly sought-after Knollwood community of Seminole County. Offering 4 spacious bedrooms, 2.5 bathrooms, and 2,416 square feet of living space, this home is designed for growing families, entertaining, and creating memories that will last a lifetime. From the moment you arrive, you'll appreciate the oversized driveway with abundant parking and the expansive yard that provides limitless opportunities to design your own private retreat—whether you envision a sparkling pool, outdoor kitchen, garden, playground, or the ultimate backyard entertainment space. Step inside to a warm and welcoming interior where timeless charm meets modern comfort. The inviting living room features elegant crown molding, a cozy wood-burning fireplace, and beautiful rustic barn doors that lead into the heart of the home—an updated kitchen complete with stainless steel appliances, sleek countertops, generous cabinetry, and abundant natural light, making it the perfect place to gather with family and friends. Built with the quality and craftsmanship of a classic 1974 ranch, this home offers solid construction, spacious living areas, and incredible potential to personalize and make it uniquely yours while enjoying its timeless character. Perfectly located within one of Seminole County's most desirable school districts, you'll enjoy convenient access to premier shopping, dining, parks, major highways, and everything Central Florida has to offer. Homes with this much land, this much living space, and this prime location rarely become available. Whether you're searching for your forever home or an exceptional investment, this property offers a rare opportunity to own one of Knollwood's most desirable homes. Don't miss your chance to make this incredible property yours—schedule your private showing today before it's gone!

1200 Waverly Way, Longwood

$575,000

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

$575,000

4 Beds ⋅ 3 Baths ⋅ Woodlands Sec 4 SubDv. ⋅ 32750 Zip Code

Back on the Market! Buyer financing last minute fell through. VA appraisal was done and approved. Second chance for you to grab this fabulous house with in-law suite. Absolutely Everything You’ve Been Looking For — in the Sought-After Woodlands Community of Longwood! This lovingly maintained home has been cherished by the same owners for 39 years and is now ready to welcome new memories. With an ideal multigenerational floor plan, in-law suite, sparkling pool with natural gas heater, and huge yard, this home truly has it all. Key Features Spacious Layout: Bright, open floor plan with flexible living spaces — perfect for entertaining or quiet family living. Gourmet Kitchen: A chef’s dream with an abundance of rich wood cabinetry featuring 42" cabinets, soft-close drawers, granite countertops and backsplash, stainless appliances featuring double ovens with convection, 5 burner gas cooktop 2024, microwave, and ample amounts of counter space. A large window overlooks the pool, and the breakfast bar is ideal for casual meals. Comfortable Gathering Spaces: The kitchen opens to a large family room with French doors leading to a massive 30-foot screened lanai with gorgeous wood ceiling and huge paddle fans, perfect for summer barbecues and poolside relaxation. A separate dining area features elegant built-in cabinetry. Versatile Living Room: A huge formal living room (or flex space) features a gorgeous gas fireplace surrounded by beautiful stone and framed by custom shelving—ideal for a game room, home theater, or play area. Private Primary Suite: The spacious primary retreat includes French doors overlooking the pool, dual closets, and an ensuite bath with double sinks and walk-in shower. Large Bedrooms: Spacious secondary bedrooms with large closets and conveniently located near full bath with pool access. In-Law Suite: Thoughtfully designed newer addition with its own private entrance, full bath, dual sinks, walk-in shower, and a generous 23’ x 12’ living space—perfect for guests or multigenerational living. Outdoor Oasis: Enjoy the 8-foot-deep screened pool and spa with heater for year-round swimming. The 30’ x 17’ lanai has a natural gas hookup for grilling and entertaining. Despite the large pool, there’s still ample green space on your .29-acre yard for gardening. Seller added a separate Well for Irrigation System to keep your plants lush and green and watering costs low!. Bonus size indoor laundry room, extra storage closets throughout and large two car garage. Updates include: Brand-new plumbing, new electrical panels, 2020 roof, replaced windows, Kitchen update, bathroom showers retiled, pool resurfaced within last 10 years, exterior paint and freshly painted living areas. Four-point inspection available. Location & Lifestyle In the heart of Seminole County, zoned for top-rated schools and just minutes from I-4, world-famous attractions, dining, and shopping. This home blends classic character with modern comfort in one of Longwood’s most desirable neighborhoods. Come see why this home truly has everything you’ve been searching for—and more!

105 Cedar Oak Trail, Longwood

$569,999

4 Beds ⋅ 2 Baths ⋅ Winsor Manor 1st Add SubDv. ⋅ 32750 Zip Code

Welcome to 219 Sheridan Avenue in Longwood! This beautifully remodeled pool home features a spacious open floor plan with light LVP flooring, recessed lighting, and a stunning custom wood-slat fireplace accent wall. The updated kitchen offers shaker cabinets, quartz countertops, stainless steel appliances, modern fixtures, and a large peninsula perfect for entertaining. The spacious primary suite features a luxurious bathroom with a freestanding soaking tub, oversized walk-in shower, double vanity, and elegant gold finishes. Step outside to enjoy the covered patio and screened-in swimming pool, perfect for Florida living. Additional upgrades include a 2022 roof and fully paid-off solar panels for added energy efficiency and savings. Conveniently located near shopping, dining, and major highways. This move-in-ready home offers modern finishes, spacious living, and exceptional outdoor entertainment space. Schedule your showing today!

219 Sheridan Avenue, Longwood

$565,000

3 Beds ⋅ 2 Baths ⋅ Sanlando Spgs SubDv. ⋅ 32750 Zip Code

Welcome home! This beautiful 3 bedroom, 2 bath is a place to call your personal retreat! Enjoy a location close to shopping, restaurants, easy access to I-4 and state roads and yet, it is quiet and boasts a country feel. Step into a totally renovated home that reflects lots of pride in every detail. Enjoy one of 2 patios and welcome the leisure lifestyle of friends and neighbors or enjoy the privacy of your fenced in backyard. Your gourmet kitchen is perfect for someone who enjoys cooking and also being part of the family activities or entertainment. This bright, sunny home offers not only an open feeling with the renovations, but a modern feel to a well built foundation. The primary bedroom has a special flex space which can be used as an office, exercise room, sitting area or nursery. This spectacular find has has a/c, some plumbing and window changes made to afford you the best possible easy to maintain lifestyle. Come visit and get ready to step into a perfect move-ibn experience!

1701 Carlton Street, Longwood

$560,000

3 Beds ⋅ 3 Baths ⋅ Springs Whispering Pines Sec 2 SubDv. ⋅ 32779 Zip Code

Virtually Staged. A rare detached brick townhome on a private, quiet cul de sac in Longwood's guard gated Springs community. Step through 9 foot custom European style double doors into a foyer opening to the great room, where dramatic 14 foot ceilings and walls of transom windows bathe the space in natural light. Recessed lighting keeps it glowing after dark, and a wood burning fireplace anchors the living area. The kitchen has a gas range and two large pantries, secluded yet connected to the main living space. The main floor primary suite is a true highlight, with automated blackout shades, a large 10x10 walk in closet, and an adjoining private room designed with an executive office in mind, equally perfect as a nursery or study, closed off by French doors. The ensuite bath features a steam shower and separate water closet. The three way split floor plan places a second main floor bedroom, ideal as a guest room or office, on the opposite side of the home for privacy, with a full bath featuring a cleverly hidden shower. Upstairs is its own private retreat with a bonus flex space, game closet with additional storage, and a second primary suite with full bath, ideal for multigenerational living. A lovely screened lanai with courtyard extends your living space outdoors. Designed with distinction, this home has incredible bones and awaits your personal updates. Recent updates: full replumb December 2025 and brand new AC May 2026. Exclusive to the Whispering Pines village: community pool and clay tennis courts. The Springs is a community like no other, an immersive natural sanctuary where residents stroll beneath century old Live Oaks, walking and jogging paths, horse stables, a clubhouse, pool, and a full calendar of community events. Wildlife and native Florida woodlands are part of daily life here. The Springs is also prized for its highly desired top rated schools, and is conveniently located less than 1 mile from I-4, with easy access to Altamonte Springs, Lake Mary, Winter Park, farmer's markets, Crane's Roost, shopping, dining, vibrant restaurants, the beaches and attractions. Longwood offers a small town vibe while being just a short drive from all that Orlando is known for. A rare opportunity to enjoy space, privacy, and true Florida living. Schedule your private showing today!

221 Pine Cone Lane, Longwood

$557,000

4 Beds ⋅ 2 Baths ⋅ Sabal Point Amd SubDv. ⋅ 32779 Zip Code

Virtually Staged. Welcome to 326 W Hornbeam in the exclusive community of Sabal Point. Not many homes come up for sale in this beautiful neighborhood, don't miss your opportunity to take advantage of this property! Property features include a new roof (2026), newer A/C, updated electric panel, whole home re-pipe, and newer water heater. Upon arrival a round-about driveway with mature landscaping welcomes you to the front door, with additional parking in front of the garage. Inside you are greeted by an open concept living area with dining and private office or media room. This home has a split floorplan with oversized secondary bedrooms and a pool bathroom featuring double showers for large families. On the other side of the home is the primary suite with walk-in closet an en-suite bathroom. Enjoy an updated kitchen that has a great view of the pool and outdoor kitchen. The community features miles of walking trails, two playgrounds, basketball courts, and gorgeous trees that provide a beautiful view while you drive. Shopping and dining are only minutes away with quick access to I-4. This home is ready for its new owner, so book your appt today!

326 W Hornbeam Drive, Longwood

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