Longwood Real Estate

Longwood Real Estate

Welcome to Longwood, Florida – a charming gem nestled in the heart of Seminole County. Known for its picturesque landscapes and friendly community, Longwood offers a perfect blend of suburban tranquility and urban convenience. With its roots dating back to the late 1800s, this vibrant city is steeped in history while embracing modern living.

Longwood boasts a diverse array of parks and recreational facilities, making it an ideal destination for families and outdoor enthusiasts alike. The scenic Lake Mary and the lush Longwood Historic District provide ample opportunities for leisurely strolls, picnics, and community events. Residents can enjoy the beauty of nature with walking trails, playgrounds, and sports facilities that cater to all ages.

In addition to its natural beauty, Longwood is strategically located just a short drive from the bustling city of Orlando, providing easy access to world-renowned attractions, shopping, and dining options. The city is well-connected by major roadways, ensuring that residents can enjoy the excitement of the city while returning to their peaceful suburban oasis.

Longwood is also home to a tight-knit community that values education and family. The city features highly-rated schools and various educational opportunities, making it an attractive choice for families looking to settle down.

Whether you’re drawn to its historical charm, outdoor adventures, or the welcoming community spirit, Longwood, Florida, is a place where you can truly feel at home. Discover the allure of this delightful city and envision your future in Longwood, where life is as vibrant as the beautiful Florida sunshine.

Newest Listings in Longwood

4 Beds ⋅ 2 Baths ⋅ O6430959 MLS

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

3 Beds ⋅ 2 Baths ⋅ O6430760 MLS

Stunning Remodeled Home in the Heart of Longwood — No HOA. Please visit our 3D tour. Don’t miss this exceptional opportunity to own a beautifully updated, move-in-ready home in the highly desirable city of Longwood. Featuring a brand-new roof, modern upgrades throughout, and no HOA restrictions, this residence offers comfort, style, and flexibility—ideal for families, professionals, and those who enjoy entertaining. 3 Bedrooms, 2 Bathrooms, No HOA. Open-concept floor plan, perfect for entertaining, Tile flooring throughout for easy maintenance, Remodeled bathrooms with sleek, modern finishes. Large windows providing abundant natural light. Spacious living areas that blend comfort and elegance. Chef’s Kitchen, Exotic granite countertops, Stainless steel appliances, Rich wood cabinetry Major Updates, Brand-new roof, A/C unit installed in 2019, New interior and exterior paint. Outdoor Living, Screened porch ideal for relaxing or outdoor dining, Large backyard with ample space for gatherings, Expansive front yard offering additional outdoor enjoyment. Prime Location, Located within an excellent school district, Close to shopping, dining, and Altamonte Mall, Near hospitals and medical centers, Easy access to I-4, SR-434, Ronald Reagan Boulevard, and US-17-92, Just minutes from Downtown Orlando. Enjoy the freedom of no HOA and the convenience of a central location. Schedule your private showing today.

790 Silhouette Court, Longwood

3 Beds ⋅ 2 Baths ⋅ G5116020 MLS

Professional photos will be available 08/15/2026. Now more than ever, owning a home offers true peace of mind. Step into this mid-century modern masterpiece, extensively revitalized and expanded into a bright, airy, boutique-style retreat. Take advantage of an incredible financial opportunity with a VERY LOW assumable mortgage, offering massive monthly savings! Rare opportunity to assume the seller's low INTEREST mortgage (subject to lender approval and qualification) Perched on an elevated, nearly half-acre corner lot, this 3-bedroom, 2-bathroom residence seamlessly combines private, peaceful living with top-rated Seminole County schools right at your doorstep. From the moment you enter, you are greeted by light-filled spaces and a cozy feature fireplace that unites the open-concept kitchen, dining, and living areas. The primary suite is an exceptional retreat in itself—featuring a expansive layout, a private exterior entrance, and a versatile flex space ideal for an executive home office, lounge, or in-law suite. Major updates bring long-term confidence, including a custom kitchen, solid concrete block construction, a newer roof (2017), new windows (2021), and updated electrical—all with NO HOA. Outside, the massive, fully fenced backyard offers endless possibilities with ample space for a pool, workshop, or garden. Move-in ready, effortlessly stylish, and built for modern living!

428 Ruth St, Longwood

4 Beds ⋅ 2 Baths ⋅ O6430138 MLS

Back on the Market. New Improved Price!! Your new pool home in the desirable Wekiva Hills community is waiting for you. This 4 bedroom, 2 bathroom home sits on a spacious corner lot with a fenced backyard. The Kitchen recently updated with granite countertops, stainless steel appliances, ample cabinetry, and a breakfast. Inviting Family room with cozy fireplace, vaulted ceilings, and expansive windows fill the space with natural light. Primary Suite is generously sized with walk-in customized closet. This property requires repairs and is being sold As Is. Location is perfect just minutes from everything including shopping, entertainment, schools, major streets and expressways. This property may qualify for Seller Financing (Vendee). Call today for your private showing.

210 Banbury Court, Longwood

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

4 Beds ⋅ 3 Baths ⋅ O6429951 MLS

Welcome to this spacious and beautifully maintained family home in the highly desirable Wekiva Hills community, where comfort, functionality, and location come together. Offering 4 bedrooms, 3 full bathrooms, and an abundance of versatile living space, this home is designed to accommodate today's busy lifestyle. Roof (2022), new windows (2022), Water Heater (2023), Pool re-surfaced and tiled (2022), fence (2023). Freshly painted inside and featuring hard-surface flooring throughout with no carpet, the interior offers a clean, modern feel that's both stylish and easy to maintain. Multiple living areas include formal living and dining rooms, wood-burning fireplace, a generous bonus space, and an oversized family room centered around a classic wood-burning fireplace. The formal dining room is currently used as a home office, showcasing the flexibility of the floor plan to fit your needs. The spacious family room opens to a covered lanai and private screened swimming pool, creating the perfect setting for entertaining or relaxing year-round. The large fenced backyard is beautifully landscaped with mature fruit and flowering trees, providing plenty of room for outdoor activities and gardening. Additional features include an inside laundry/utility room, updated bathrooms, tile flooring in all wet areas, a whole-home water filtration system, AC system (2015), and all major appliances convey with the home, making it truly move-in ready. Located in the heart of Wekiva, residents enjoy miles of scenic walking and biking trails, parks, playgrounds, sports courts, and a vibrant community atmosphere. Zoned for highly sought-after Brantley High School and conveniently located near shopping, dining, Wekiva Springs State Park, and major roadways, this home offers the perfect balance of peaceful living and everyday convenience. This is a wonderful opportunity to own a spacious pool home in one of Central Florida's most established and sought-after communities. Schedule your private showing today.

165 Duncan Trail, Longwood

2 Beds ⋅ 2 Baths ⋅ O6429515 MLS ⋅ 163 BLDG.

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 ⋅ 4 Baths ⋅ O6425076 MLS

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 ⋅ S5154698 MLS

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

5 Beds ⋅ 4 Baths ⋅ O6429108 MLS

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 ⋅ 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

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

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