Longwood Real Estate

Longwood Real Estate

Welcome to Longwood, Florida—a hidden gem in Seminole County that combines the charm of small-town living with the conveniences of modern life. Nestled just north of Orlando, Longwood offers residents a serene environment surrounded by lush landscapes and tranquil lakes, making it an ideal place for families, professionals, and retirees alike.

Longwood is rich in history, with its roots dating back to the 1800s. Today, it boasts a vibrant community that celebrates its heritage through various local events and festivals. The picturesque downtown area is lined with quaint shops, delightful cafes, and a variety of dining options, ensuring that there’s always something to explore. The Longwood Historic District features beautiful architecture and is a testament to the city’s storied past.

For outdoor enthusiasts, Longwood is a paradise. With numerous parks, including the expansive Candyland Park and the scenic Lake Mary Jane, residents can enjoy picnics, hiking, and recreational activities year-round. The city is also conveniently located near the stunning Wekiva River, perfect for kayaking and nature walks.

Families will find that Longwood is served by excellent schools and a strong sense of community, making it an ideal place to raise children. The city also offers easy access to major highways, allowing for quick commutes to nearby Orlando and its world-famous attractions.

Whether you’re looking to buy your first home, relocate, or invest in a property, Longwood has something for everyone. Discover the charm and warmth of this beautiful city—your new home awaits!

Newest Listings in Longwood

2 Beds ⋅ 2 Baths ⋅ Springwood Village SubDv. ⋅ 32750 Zip Code

Welcome to easy Condo living in Springwood Village! This Condo has it ALL AND MORE! As soon as you enter you'll be wowed by how open the Kitchen & Living Room areas are. The Kitchen is a SHOW STOPPER featuring a LARGE ISLAND, Real Wood Cabinets that Soft Close with Granite Countertops, Stainless Steel Appliances including Fridge, Stove and Built-In Microwave. The Bedroons are both a Great Size and the Primary Bedroom Features an En-Suite Bathroom with an updated Shower. The AC and Water Heater are NEWER from 2025 and the Windows are NEWER. The community has Two Pools, Tennis Courts, Clubhouse with Fitness Center, Billiards Room and Kitchen. This location is very close to I-4 and SR 434 as well as Sanlando Park if you like nature and bike trails or go a short drive up the road to Wekiwa Springs. If you're a foodie, there are LOTS of spots close by to check out including Starbucks, 4 Rivers Smokehouse BBQ, Bonefish Grill, Kobe's Japanese Steakhouse and more! Scheudle your private showing today!

163 Springwood Circle Unit B, Longwood

4 Beds ⋅ 3 Baths ⋅ Springs The Deerwood Estates SubDv. ⋅ 32779 Zip Code

For the first time in 28 years, the most coveted mid-century home in Orlando is available. Your private compound. A piece of art you live inside. The Strasberg Residence, designed by award-winning architect Gene Leedy. He built only three private homes in the Orlando area, and this is his Masterpiece. Beyond the 8-foot concrete stucco wall wrapped in ivy, the world disappears from view, and yours begins. Trees, gardens, and a pool the color of dark glass lie behind your private wall. At its center, a breathtaking atrium and courtyard: a reflecting pool with twin fountains and a tree rising from the water, framed by glass on every side. Inside, Leedy's design language of clean lines and subtle, important details is everywhere. Eleven-foot doors, warm wood trim throughout, and expansive glass in every room harmonize nature with the interior, bringing together privacy, gardens, and water features. The social center of the home is the soaring great room with fireplace and wet bar. Formal dining. All wired for sound. Two separate entrances serve the east and west wings, each with its own foyer. The primary suite occupies an entire wing: a bedroom sitting room with its own bar, a dressing room, an enormous custom-built closet, a dual-sink countertop with a separate vanity, a separate WC with bidet, a tub that overlooks the pool, a steam shower that feels like a spa, and its own private walled patio and another patio that leads to the pool. Nearly every room opens to its own patio and garden. And then the rarest amenity of all: a fully detached in-law suite with its own private entrance through the second decorative iron door, a full en-suite bath, and two patios of its own, one overlooking the backyard and one fully private behind its own 8-foot wall, just like the primary. A complete home within the home, for extended family, guests, or total independence. 4 bedrooms, 4 baths, 3,885 SF. The grounds are one with the architecture: a dark-water pool with jacuzzi among specimen trees and sculptures, an outdoor kitchen, and a richly planted .67-acre lot of total walled seclusion. All in The Springs, a guarded, gated sanctuary of natural springs, stables, and trails, minutes from Greater Orlando. This is the home everyone wants, held closely for a generation. Now, rarely, it's yours to claim.

111 Sand Pine Lane, Longwood

3 Beds ⋅ 2 Baths ⋅ Wekiva Hunt Club 1 Fox Hunt Sec 1 SubDv. ⋅ 32779 Zip Code

Welcome to 108 Kilkenny Court, a beautifully updated 4-bedroom, 2-bath pool home in the sought-after Wekiva Hunt Club community. Offering 1,979 square feet of single-story living on an oversized 0.26-acre lot, this home combines modern updates, inviting indoor spaces, and the Florida lifestyle buyers are searching for. The bright, open layout features a cozy living-room fireplace, updated light fixtures, and ceiling fans throughout. At the center of the home, the renovated kitchen impresses with new cabinetry, a spacious island, new 2026 countertops, brand-new Samsung stainless-steel appliances, and a new sliding glass door that opens to the outdoor living area. Both bathrooms have also been renovated with fresh, contemporary finishes, while a second new sliding door in the primary bedroom provides direct access to the backyard. Step outside to your private retreat, complete with a sparkling screen-enclosed pool, covered patio, and fully fenced yard—perfect for relaxing, entertaining, or enjoying year-round Florida sunshine. Additional highlights include a 2-car garage, roof replaced in 2018, A/C replaced approximately two years ago, pool pump replaced last year, and vinyl fencing installed in 2023. Located just minutes from Publix at Springs Plaza, Wekiva Golf Club, parks, walking trails, and community tennis, pickleball, racquetball, basketball, baseball, and soccer facilities. Outdoor enthusiasts will also appreciate being approximately 10 minutes from Wekiwa Springs State Park, offering spring swimming, kayaking, hiking, and scenic natural beauty. Updated, spacious, and perfectly positioned for convenience and recreation, this Longwood pool home is ready to impress. Schedule your private showing today!

108 Kilkenny Court, Longwood

4 Beds ⋅ 3 Baths ⋅ Sweetwater Oaks Sec 07 SubDv. ⋅ 32779 Zip Code

Welcome to 102 Stonebridge Drive, a beautifully reimagined 4-bedroom, 3-bathroom pool home tucked beneath the canopy of majestic oak trees in one of Longwood's most beloved communities, Sweetwater Oaks. Thoughtfully renovated from top to bottom, this home seamlessly blends timeless character with today's modern design, creating a space that is as beautiful as it is functional. From the moment you walk inside, soaring ceilings, abundant natural light, and wide-open living spaces immediately make you feel at home. Designed with entertaining in mind, the current owners transformed the main living area by removing the original fireplace and creating a stunning, open sightline between the kitchen and family room. The result is a home that feels bright, connected, and perfectly suited for gathering with family and friends. The heart of the home is the spectacular chef's kitchen, where a dramatic oversized island serves as both a beautiful centerpiece and the ultimate gathering place. Complete with custom soft-close cabinetry, quartz countertops, designer tile backsplash, stainless steel appliances, built-in microwave, range hood, and abundant storage, this space was designed for everything from casual breakfasts to holiday entertaining. A spacious flex room at the front of the home offers endless possibilities as a home office, formal living room, playroom, or additional lounge space, while the split-bedroom floor plan provides comfort and privacy for family and guests alike. Every bathroom has been beautifully renovated with elegant tile, updated vanities, quartz countertops, modern fixtures, and designer finishes. The spacious primary suite offers direct access to the lanai and pool, a generous walk-in closet, and a spa-inspired en-suite bath with dual vanities and an oversized walk-in shower. Step outside to your own private backyard retreat. Situated on over one-third of an acre, the fully fenced backyard is surrounded by mature landscaping and enhanced with new paver hardscaping, creating multiple spaces to relax or entertain. The screened swimming pool has been upgraded to a saltwater system and features a new pool pump, making maintenance simple while creating the perfect place to enjoy Florida's year-round sunshine. No detail has been overlooked. Additional improvements include a 2020 roof, luxury vinyl plank flooring throughout, fresh interior and exterior paint, beautifully renovated bathrooms, new ceiling fans and designer light fixtures, an epoxy-coated garage floor, a new water heater, and countless thoughtful updates that make this home truly move-in ready. Life in Sweetwater Oaks offers so much more than just a beautiful home. Residents enjoy exclusive access to Lake Brantley, including a private beach park and boat ramp, along with tennis and pickleball courts, parks, playgrounds, basketball and volleyball courts, and easy access to the Wekiva River for kayaking and paddleboarding. All of this is located within one of Seminole County's most desirable school districts, featuring Sabal Point Elementary, Rock Lake Middle, and Lake Brantley High School. Completely renovated, thoughtfully redesigned, and located in one of Central Florida's most sought-after communities, 102 Stonebridge Drive offers the perfect combination of luxury, comfort, and lifestyle. This is more than just a home—it's a place you'll love coming home to. Schedule your private showing today!

102 Stonebridge Drive, Longwood

5 Beds ⋅ 4 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32779 Zip Code

Virtually Staged. ONE-OF-A-KIND ESTATE ON NEARLY AN ACRE | ATTACHED IN-LAW SUITE + DETACHED 2-BEDROOM GUEST HOUSE | ZONED AGRICULTURAL | NO HOA Nestled on nearly an acre in the coveted Markham Woods corridor, this exceptional estate offers luxury, privacy, and unmatched flexibility. Featuring a FULLY RENOVATED MAIN RESIDENCE, an ATTACHED PRIVATE IN-LAW SUITE, and a DETACHED 2-BEDROOM GUEST HOME, this property is ideal for adult children living at home, extended guests, multi-purpose living, a home office, or hobby space. With NO HOA, you'll also enjoy the freedom to park your RV, boat, ATV, trailer, or other recreational vehicles right on your property. The MAIN RESIDENCE offers over 3,750 SQUARE FEET with 5 BEDROOMS AND 4 FULL BATHROOMS, highlighted by a stunning 2024 kitchen featuring custom cabinetry, quartz countertops, farmhouse sink, induction cooktop, double oven with air fryer, and an oversized island perfect for gathering. The PRIMARY SUITE offers a spa-inspired bath with a concrete soaking tub, frameless glass shower, bidet, and custom walk-in closet. Every bedroom includes custom closet systems. Major updates include TWO NEW HVAC SYSTEMS, full repipe replacing polybutylene plumbing, 80-GALLON WATER HEATER, updated electrical panel, and whole-home surge protection. An attached PRIVATE IN-LAW SUITE with its own entrance, kitchenette, full bath, and living area offers endless possibilities for guests or flexible living. Outside, enjoy your own private resort featuring a HEATED SALTWATER POOL, covered lanai with eucalyptus ceiling, stacked stone accents, slate flooring, koi pond with waterfall, pergola, fire pit, and beach-style lounge area. Over the past several years, the property has undergone an extensive landscape transformation with new sod, irrigation, refreshed landscaping, mature trees, and a new backyard fence, while many of the custom outdoor entertaining features were added within the last two years. The 2,550-SQUARE-FOOT DETACHED GUEST HOME (built in 2014) includes hardwood floors, gas fireplace, tankless water heater, Generac generator, new HVAC (2023), and an expansive second floor with two spacious bedrooms and private balcony—perfect for guests, adult children, a home gym, office, or recreation space. The location is just as impressive. You're minutes from the Seminole Wekiva Trail and beautiful Wekiwa Island, where you can spend weekends kayaking, canoeing, paddleboarding, swimming in the spring-fed Wekiva River, or simply relaxing with live music and waterfront dining. Enjoy quick access to the shops, restaurants, and entertainment of Lake Mary, nearby golf courses, top-rated Seminole County schools, Orlando Sanford International Airport, I-4, and SR 434, making it easy to enjoy both outdoor adventure and everyday convenience. This is more than a home—it's a rare opportunity to own a private estate offering luxury, flexibility, space for all your toys, and an exceptional Central Florida lifestyle. Schedule your private showing today.

113 Sandy Oaks Place, Longwood

5 Beds ⋅ 5 Baths ⋅ Alaqua Lakes Ph 5 SubDv. ⋅ 32779 Zip Code

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

4 Beds ⋅ 3 Baths ⋅ The Spgs Glenwood Village Sec 2 SubDv. ⋅ 32779 Zip Code

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

4 Beds ⋅ 2 Baths ⋅ Wekiva Hills Sec 02 SubDv. ⋅ 32779 Zip Code

Welcome home to this beautifully maintained 4-bedroom, 2-bathroom pool home tucked away on a quiet cul-de-sac in the heart of Wekiva. Situated on an oversized, private lot, this property offers the space and privacy today's buyers are searching for—perfect for entertaining, relaxing by the pool, or simply enjoying your own backyard retreat. Located in the highly desirable Seminole County school district, this home is zoned for top-rated Lake Brantley schools, with sought-after Wekiva Elementary just moments away, making it an exceptional choice for those seeking both outstanding schools and an unbeatable location. Enjoy the best of Central Florida living with convenient access to premier shopping, dining, golf courses, and the natural beauty of nearby state parks. Whether you're spending the day exploring local trails or enjoying everything the area has to offer, you'll love the balance of convenience and outdoor lifestyle. For added peace of mind, the home's major systems have already been updated, including a 2018 roof, 2018 HVAC system, and a brand-new 2026 water heater—allowing you to move in with confidence. Rarely do homes with this combination of privacy, updates, location, and outdoor living become available. Don't miss your opportunity to own this move-in-ready Wekiva pool home. Schedule your private showing today!

260 Queensberry Court, Longwood

3 Beds ⋅ 2 Baths ⋅ Lake Wayman Heights Hwy Add SubDv. ⋅ 32750 Zip Code

Welcome home to this beautifully updated 3-bedroom, 2-bath pool home in the heart of Longwood! Step inside to find luxury vinyl plank flooring throughout the main living areas and bedrooms, creating a modern, low-maintenance living space. The kitchen, breakfast area, and bathrooms feature tile flooring, offering durability where it matters most. The true highlight of this home is the backyard oasis. Enjoy Florida living year-round in your private pool featuring a beautiful waterfall, surrounded by an expansive paver patio that's perfect for entertaining, relaxing, or hosting family and friends. Conveniently located near shopping, dining, parks, SunRail, and major roadways, this home combines comfort, style, and an outstanding location. Don't miss your opportunity to own this move-in-ready Longwood pool home! Windows 2006, FPE 2026, Roof 2023, AC 2021, Water Heater 2014 Septic drain field 2005

430 Georgia Avenue, Longwood

2 Beds ⋅ 3 Baths ⋅ Clubside At Sabal Point A Condo SubDv. ⋅ 32779 Zip Code

Welcome to Clubside at Sabal Point, one of Longwood's most desirable communities in the heart of the Wekiva Springs area. This spacious 2-bedroom, 2.5-bath condominium offers approximately 1,365 square feet of comfortable living space with a functional floor plan designed for both everyday living and entertaining. The home features dual primary suites, generous walk-in closets, an updated kitchen with granite countertops, a bright dining area, and a large screened patio overlooking the community tennis courts. Residents enjoy access to resort-style amenities including a community pool, clubhouse, fitness center, and tennis courts, all within the highly sought-after Seminole County school district. Conveniently located near shopping, dining, major roadways, and outdoor recreation, this property offers the perfect combination of comfort, convenience, and low-maintenance living

1203 Clubside Drive Unit 1203, Longwood

Lake Brantley Terrace SubDv. ⋅ 32779 Zip Code

Rare Opportunity in LongWood! Build your future on this exceptional parcel located at 1292 Hickory Dr. Whether you're looking to create a custom residence or add a valuable asset to your portfolio, this lot provides endless possibilities in a highly desirable Seminole County location. Conveniently located near premier amenities, major roadways, and everything Longwood has. Come explore the potential of this property today!

1292 Hickory Drive, Longwood

4 Beds ⋅ 3 Baths ⋅ Wekiva Hills Sec 08 SubDv. ⋅ 32779 Zip Code

NEW ROOF TO BE INSTALLED PRIOR TO CLOSING Welcome to this graceful, one-of-a-kind 4 Bed, 2.5 Bath with Den split-level executive home, perfectly positioned on a picturesque cul-de-sac lot spanning nearly 3/4 of an acre in a highly sought-after golf course community. Surrounded by mature trees and lush landscaping, this contemporary residence offers exceptional privacy, generous living spaces, and timeless architectural character. Fresh exterior paint and a charming wood walkway create a warm and inviting first impression. Inside, abundant natural light fills the home through expansive windows, highlighting the neutral décor and thoughtfully designed floor plan. New AC, Fresh exterior paint, The beautifully updated chef's kitchen is the heart of the home, featuring stainless steel appliances, a massive center island, breakfast bar, and seamless flow into the main living areas—perfect for everyday living and effortless entertaining. The unique split-level design offers multiple spacious gathering areas, including formal living and dining rooms, a cozy family room with a wood-burning fireplace, and attractive laminate flooring, large tile throughout the main living spaces. The versatile lower-level bonus room provides endless possibilities as a home office, media room, game room, or optional fifth bedroom. A convenient guest half bath and inside utility room, complete with washer and dryer, add to the home's functionality. Upstairs, all primary bedrooms are thoughtfully situated for added privacy. The bathrooms offer modern finishes and style, while the spacious primary suite features a private balcony overlooking the peaceful, fully fenced backyard—an ideal place to enjoy your morning coffee or unwind at the end of the day. Outdoor living is equally impressive with a covered, screened porch and an expansive backyard oasis offering ample room for recreation, gardening, a future pool, or additional outdoor amenities. The property also includes dedicated space for RV or boat parking, with plenty of room for entertaining family and friends. With a new roof being installed prior to closing, a prime location in a golf course community, and a rare combination of privacy, space, and versatility, this exceptional property offers a lifestyle that's truly hard to find. Set up your showing today!!

1215 Duncan Court, Longwood

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