Location: Longwood
Do Not Show Listings
421 E BAY AVE, LONGWOOD, FL 32750
$339,0007 Days on yellowkey MLS ID: O6415931
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1048 Built: 1979 Tax: $1,311 (2025)Community: LongwoodSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,311
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: From modern finishes to classic comfort, this move-in-ready 3-bedroom, 2-bathroom Longwood gem has it all. Inside, the beautifully updated kitchen shines with granite countertops and stainless steel appliances, while both bathrooms have been thoughtfully refreshed. Enjoy ultimate peace of mind with major structural updates, including a brand-new AC installed in 2024 and roof replaced in 2022. An exceptional highlight of the property is the climate-controlled, multi-purpose bonus suite. Equipped with its own dedicated cooling system, this versatile space offers endless possibilities; it is currently curated as the ultimate game-day lounge, but easily adapts into a quiet executive home office, a private fitness sanctuary, or an inspiring creative studio for art and music. Step outside to find an oversized, fully fenced backyard—the perfect oasis for your pets to roam freely— as well as enhanced landscaping that provides incredible curb appeal. Perfectly positioned just moments from shopping, dining, the SunRail station, and the vibrant weekly farmer's market, this home blends contemporary charm with ultimate convenience!
Listing is courtesy of: PLATINUM REAL ESTATE (888-974-7253)
Listing Agent: Abby Chitty (407-766-5046)
1653 WINDY BLUFF PT, LONGWOOD, FL 32750
$580,000Listed 06/17/2026 3:37PM MLS ID: O6417754
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2061 Built: 1985Monthly Fee: $45 Tax: $2,686 (2025)Community: NorthridgeSpa: YesSingle Family
Taxes:$2,686
Elementary School: Woodlands Elementary
High School: Lake Mary High
Middle School: Rock Lake Middle
Remarks: Absolutely stunning, fully updated 3-bedroom, 2.5-bath pool home located in the highly sought-after Northridge community of Longwood! From the moment you enter, you'll be impressed by the abundance of natural light, beautiful hardwood floors, and soaring cathedral ceilings that create an inviting and spacious atmosphere. The heart of the home is the beautifully remodeled kitchen, featuring granite countertops, custom cabinetry, stylish tile backsplash, a large center island, newer stainless steel appliances, and a picturesque window overlooking the sparkling pool. The adjacent family room boasts cathedral ceilings, a cozy wood-burning fireplace, and expansive views of the backyard oasis. The spacious primary suite with walk in closet, offers a beautifully updated en-suite bathroom with dual vanities, a bidet and walk in shower. The private office with entrance to the primary bedroom could easily serve as a nursery, sitting room, or flex space. Bedrooms two and three are conveniently located near the updated secondary bathroom. An interior laundry room and half bath with direct pool access add functionality and convenience. Designed for year-round Florida living, the fully fenced backyard is an entertainer's dream, featuring a large refinished pool, ample space for grilling, gatherings, and outdoor relaxation with no rear neighbors. The community amenities include a playground, pickle ball, tennis, and basketball courts. This is truly Florida living at it's finest! Major updates provide peace of mind, including: Roof (2022), Windows & Doors (2022), Gutters (2022), HVAC (2023), Exterior Paint (2023), Vinyl Fence (2023), Kitchen Appliances (2024), Water Heater (2021), Pool Refinish (2017), Pool Pump (2025), and Pool Deck Paint (2026).
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Randy Adams Pa (321-438-1027)
200 CROOKED OAK CT, LONGWOOD, FL 32779
$790,00015 Days on yellowkey MLS ID: O6412046
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3007 Built: 1974Monthly Fee: $54 Tax: $4,878 (2025)Community: Sweetwater Oaks Sec 03Single Family
Taxes:$4,878
Remarks: Are you looking for an affordable Multi-Generational home? This beautiful pool home offers the flexibility to have up to 5 bedrooms and 3 living spaces. There is a main living space and 3 bedrooms upstairs, a flex space in the basement with a living room and separate room that can be used as an office/bedroom, and a detached Guest House with 1 bedroom and 1 bath. The detached guest house has its own private entrance and full kitchen, ideal for multigenerational living, a private office, or potential income-producing use. You will love the size of the property, where you can enjoy the private pool and have plenty of green space for entertaining. Enjoy the convenience of a three-car garage and room for boat parking. Plenty of upgrades including Brazilian wood flooring & Butcher block countertops. Located close to Wekiwa Springs State Park in one of Longwood's most sought-after neighborhoods, this home has the beauty and flexibility that is rare to find. *All information is intended to be accurate but is not guaranteed.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ryan Minadie (407-765-9990)
2644 BENT HICKORY CIR, LONGWOOD, FL 32779
$429,000Listed 06/17/2026 3:06PM MLS ID: O6417103
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1833 Built: 1985Monthly Fee: $86 Tax: $4,445 (2025)Community: Sabal Point At Sabal GreenSingle Family
Taxes:$4,445
Elementary School: Sabal Point Elementary
High School: Lyman High
Remarks: Architectural Charm Reimagined for Modern Living! Tucked away on a quiet cul-de-sac and surrounded by lush greenery, this beautifully renovated residence offers a rare combination of architectural character, modern updates, and privacy. From the moment you arrive, the home's inviting courtyard entry, manicured landscaping, and distinctive rooflines create a memorable first impression. Upon entering, the dramatic sense of space is undeniable, with soaring smooth-finish ceilings, clerestory-style windows that fill the home with natural light, and wide-plank luxury vinyl flooring enhancing the spacious open-concept design. The expansive living and dining areas are anchored by a double-sided fireplace and framed by walls of French doors and oversized windows that draw the outdoors in, creating a bright and welcoming atmosphere throughout. Whether hosting friends or enjoying a quiet evening at home, the seamless flow between the living spaces makes everyday living effortless. The kitchen has been carefully crafted with a fresh design that blends style and functionality. All-new custom cabinetry in a sophisticated sage hue is paired with quartz countertops, brushed brass hardware, and stainless appliances, creating a warm yet refined aesthetic. Abundant cabinetry, generous prep space, and a dedicated pantry cabinet provide impressive storage, while the open connection to the great room and views of the surrounding greenery enhance the home's airy atmosphere, making everyday living and entertaining equally enjoyable. The generously sized primary suite is a true retreat, offering peaceful wooded views and a stunning reimagined bath complete with an oversized walk-in shower, furniture-style dual vanity, designer lighting, and a large picture window overlooking a private garden courtyard that fills the space with natural light. Bedroom 2 is both bright and versatile, featuring a skylight, ample closet storage, and plenty of room. Designed for productivity and organization, Bedroom 3 features vaulted ceilings and double French doors that provide both privacy and connection to the rest of the home. An ideal space for working from home, pursuing hobbies, or accommodating overnight guests. Guests will appreciate the beautifully remodeled 2nd bath featuring dual sinks, abundant storage, quartz surfaces, and a striking blue herringbone tile surround. Crisp finishes and thoughtful details create a fresh, inviting space that feels straight out of a design magazine. Outdoor living is a true highlight, with a newly installed wraparound brick-paver patio, creating a series of inviting outdoor vignettes designed for both intimate gatherings and larger-scale entertaining. Surrounded by mature landscaping and a lush, wooded backdrop, the setting offers an exceptional sense of privacy and seclusion. Whether enjoying morning coffee, dining al fresco with friends, or unwinding beneath the trees at day's end, the outdoor spaces feel like a peaceful extension of the home. Additional improvements include smooth-finish walls and ceilings throughout, a new HVAC (2025), roof (2020), updated electrical (2024), and a whole-house replumb (2025), providing peace of mind for years to come. Situated within desirable Sabal Green in Sabal Point, this home combines stylish renovations, impressive volume ceilings, architectural character, thoughtful improvements, abundant natural light, and a tranquil natural setting to create the ideal lifestyle.
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Lisa Shear (407-721-9375)
814 MIAMI SPRINGS DR, LONGWOOD, FL 32779
$1,050,00097 Days on yellowkey MLS ID: O6390329
REDUCED by $35,000 (3.2%) on 05/15/2026
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3706 Built: 2002 Tax: $5,468 (2024)Community: Highland EstatesSpa: YesSingle Family
Taxes:$5,468
Tax Year: 2024
Remarks: Welcome to 814 Miami Springs Drive, an exceptional private estate nestled in one of Longwood’s most desirable locations near the Wekiva River and Wekiva Island. Positioned on a beautifully landscaped homesite backing to a tranquil natural preserve, this residence offers a rare blend of elegance, privacy, and resort-style living with no HOA restrictions. This impressive five-bedroom, five-bathroom residence with a loft was thoughtfully designed with both comfort and sophistication in mind. From the moment you enter, the home showcases soaring ceilings, expansive living spaces, and refined architectural details that create an inviting yet grand atmosphere. The main living areas flow effortlessly, providing an ideal setting for both everyday living and entertaining. The spacious chef’s kitchen features a large center island, generous cabinetry, and seamless connection to the surrounding living and dining areas, allowing gatherings to feel both open and intimate. The primary suite serves as a private retreat, offering a luxurious bathroom complete with dual vanities, a soaking tub, walk-in shower, and generous closet space designed for comfort and functionality. Upstairs, a versatile loft space provides endless possibilities and could function beautifully as a media room, executive home office, or additional lounge area. Outside, the home transforms into a private outdoor sanctuary. A screen-enclosed resort-style pool and spa are framed by an expansive covered lanai, creating a perfect setting for relaxation and entertaining while overlooking the lush preserve beyond. With no rear neighbors, the backyard delivers a level of privacy that is increasingly rare while still being moments from everyday conveniences. The home offers five spacious bedrooms, five bathrooms, and a flexible loft layout, all complemented by grand ceiling heights, elegant architectural detailing, and thoughtfully designed living areas. The preserve backdrop enhances the sense of tranquility, while the screened pool and outdoor living space allow you to fully embrace the Florida lifestyle. Located just minutes from Wekiva Island, Wekiva Springs State Park, scenic trails, dining, and shopping, this property offers a lifestyle centered around nature, privacy, and refined living. A rare opportunity to own a luxury estate near the Wekiva River where space, tranquility, and convenience come together seamlessly.
Listing is courtesy of: PRIMEFIT PROPERTIES LLC (407-305-2284)
Listing Agent: Nick Vaseloff (407-305-2284)
901 CUTLER RD, LONGWOOD, FL 32779
$538,50012 Days on yellowkey MLS ID: O6414587
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2226 Built: 1979Monthly Fee: $54 Tax: $5,799 (2025)Community: Cutler CoveSingle Family
Taxes:$5,799
Remarks: Pull over HONEY! This home is move it ready. Roof. 2023. AC 1 2020, AC 2 2022. Look at the cute swing in the front yard. That looks like a great home to relax in. Let's take a look. As you walk up to the home you are greeted by double doors making it feel like a grand entrance. Enchanted ivy grows to the left of the entrance. Immediately upon entering the home you can access the updated kitchen. To the right of the entry you have the huge living room which can take you to the laundry room and garage. The living room features a wood burning fireplace as well as being open to the kitchen. There is a nice spot for stools so you can eat a quick breakfast without going to the dining room. The kitchen is nicely appointed with white shaker cabinets and subway tile. Also off of the living room is a HUGE family room with vaulted ceilings and plenty of natural light from large sliding doors that leads to the back yard. Off of the family room is a nice area that would make a great little office space. Back through the kitchen and down the hall you will find all three bedrooms. The master is plenty spacious and the ensuite bathroom has lots of space. There is currently a nice long double vanity and large shower. The master bath has been updated! Quartz counters, double vanity with a spot for a stool to do you facial maintenance regimen. There is a door that leads to the back yard making it easy to clean up after playing or working in the back yard. The home has fresh paint inside and out. Luxury vinyl plank throughout the home makes maintenance a breeze. Come add your personal touches to really make this home shine! Lake Brantley Beach park with all amenities including boat ramp, volleyball sand court, playground, grills, basketball court and ability to rent pavilion. The same for Riverside park which also has tennis courts, ball fields, larger covered pavilion and nature trails. The clubhouse playground and tennis courts across Wekiva Springs Rd. Maintenance of all common areas including the path to the beach by our house. Several family events throughout the yr incl Halloween costume parade, egg hunts, Christmas parade, and parties with games, bounce houses, etc. Don't miss out. Contact us today!
Listing is courtesy of: TC ORLANDO HOMES LLC (407-960-6145)
Listing Agent: Eric Soto (407-394-5651)
210 W TIMBERCOVE CIR, LONGWOOD, FL 32779
$820,0001 Day on yellowkey MLS ID: O6417465
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3328 Built: 1971Monthly Fee: $54 Tax: $3,355 (2025)Community: Sweetwater OaksSpa: YesSingle Family
Taxes:$3,355
High School: Lake Brantley High
Remarks: Sweetwater Oaks Executive Pool Home, Open Floor Plan, Most Rooms have Pool Views, Beautifully Landscaped Pool Area, 6 Bed Rooms Split Floor Plan including a 2 Bed Room 1 Bath Guest House/Pool House ADU, Massive Beautiful Screened Pool, 80' x 49' Pool Deck and 40' Covered Porch all Screened in, Large Florida Room with Dining Table Seating 14, Massive Bar, Huge Fully Fenced Back Yard Plenty of Room for the Dogs, New Roof 12/2025, New PGT Casement Low E Double Pane Tinted Windows and 12' x 7-6" Sliding Stacking Doors 4/2023, New Plumbing Re-Pipe 10/2024, Beautiful Wood Plank Tile Flooring Throughout, Old Chicago Brick Wood Burning Fireplace, Huge Primary Suite has a Huge Walk in Closet with Custom Built ins, Primary Bath with His and Hers Vanities and Solarium for Yoga, Bed Rm 2 has Built in Book Shelves, Bed Rm 3 has a walk in closet, Bed Rm 4 has En Suite Bath 3 Pool Bath and Opens to the Pool, Bed Room 5 and 6 are in the ADU with Bath 4 all Open to the Pool, Circular Driveway with Front Porto Cochere. Pebble Tech Pool Interior Finish, Pool Sweep, Separate Whirlpool Spa, Large Garage 23' Wide x 23'-6" Deep, Sweetwater Oaks Lake Brantley Park, dock and boat launch. Some of the Best Seminole County Schools. Convenience to I-4, Schools, Shopping, Hospitals and Restaurants. A beautiful home ready for a new family to enjoy.
Listing is courtesy of: RCI REAL ESTATE INC. (407-256-0123)
Listing Agent: Devin Greene (407-236-2380)
375 BRENTWOOD CLUB CV, LONGWOOD, FL 32750
$668,00074 Days on yellowkey MLS ID: O6396065
INCREASED by $19,000 (2.9%) on 06/17/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2997 Built: 2006Monthly Fee: $148 Tax: $4,171 (2024)Community: Brentwood ClubSingle Family
Taxes:$4,171
Elementary School: Longwood Elementary
Middle School: Greenwood Lakes Middle
Remarks: Price REDUCED for a quick sale! Welcome to 375 Brentwood Club Cove, a beautifully maintained residence tucked within the gated community of Brentwood Cove in desirable Longwood. This immaculate five-bedroom (one is an ideal office), three-bath home offers 3,000 square feet of thoughtfully designed living space, blending comfort, style, and true move in readiness. From the moment you arrive, the home makes a striking impression with its brick paver driveway and pristine presentation. Every detail has been meticulously cared for, with the exterior freshly pressure washed and the carpets professionally cleaned, the space is spotless and inviting. Inside, expansive living areas flow effortlessly, offering both functionality and elegance for everyday living and entertaining. Outside is your private outdoor retreat, where a sparkling blue pool is surrounded by a beautiful brick paver deck and enclosed within a screened lanai, delivering the ultimate Florida lifestyle. The large yard with perimeter vinyl fencing provides exceptional space for recreation, pets and outdoor enjoyment. Additional highlights include a spacious two car garage, a newer roof installed in 2019, kitchen exhaust to exterior behind microwave, fans and light fixtures in all rooms including garage, blinds for all windows and sliding doors, separate irrigation line and faucets in front and rear, plus a termite bond already paid for the year, offering valuable peace of mind. Ideally located, Brentwood Cove places you just moments from major highways, premier shopping, dining and leading regional hospitals. The property is also zoned for some of the most sought-after schools serving both Longwood and nearby Lake Mary, adding exceptional long-term value and appeal. This is a turnkey opportunity to enjoy refined Florida living in a home that is as impressive as it is welcoming.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Mel Bernstein (407-810-4726)
1351 N CLASSIC CT, LONGWOOD, FL 32779
$3,400,00055 Days on yellowkey MLS ID: O6399898
REDUCED by $100,000 (2.9%) on 06/17/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5012 Built: 1989Monthly Fee: $167 Tax: $11,952 (2024)Community: Brantley Cove NorthSpa: YesSingle Family
Taxes:$11,952
Remarks: CRUISING THE WATERWAYS of the MAJESTIC SPRING FED LAKE BRANTLEY await you. Stroll around your sculptured & manicured gardens. Elegant entry features include PORTE-COCHERE. Biltmore GAS LANTERNS, SHUTTERS, BALCONIES & TOWERING tree canopies as you approach this MEDITERRANEAN-RIVIERA style estate. The cultivated beauty of this "one-owner home". Impressive CUSTOM-BUILT SHOWPLACE is nestled back on a LUSH, PRIVATE ENCLAVE, oversized *4-Acre lot. *Over 1+ acre for residence. WATERFRONT LIVING at its' finest. 4/5 Bedrooms, 5.5 baths, pool home, 3 car garage, porte-cochere, pool/ spa, and dock with BONUS/FLEX space in the basement, perfect for a workout room. Over $380,000+ in updates & renovations. Majestic MAHOGANY entry doors welcome you, and once inside the seamless floor plan is OPEN w/ VOLUMINOUS ceilings (10-foot ceiling throughout, Primary bedroom 12 ft, other rooms 20 ft.). EXPANSIVE living/dining/kitchen/ family rm w/ PANORAMIC, BREATHTAKING WATER, VIEWS that engulf most rooms. SUN DRENCHED lighting pours in as it illuminates the CUSTOM-BUILT with HIGH-QUALITY finishes and fixtures that enhance the architectural elegance. Tongue & Groove Cedar ceilings in fam & breakfast rm, & porch. Interior solid core 4 panel wood doors throughout. Generous use of ST. LOUIS BRICK, WOOD flooring, WROUGHT IRON accents and 2 palatial wood burning fireplaces. EXCITE the CHEF with this dream kitchen while overlooking expansive water views! Create culinary masterpieces in style. An abundance of cabinetry, storage, island, massive dinette and a snack bar. STAINLESS STEEL appliances, GRANITE prep space & HIGH-END fixtures make this functional & impressive. Wet bar w/ GRANITE snack bar/cabinets sit under the upstairs LOFT area. 3-way split bedrooms with private baths, are perfectly situated around the living / family rm and dining space. All the bedrooms are roomy with large closet space; one even has a window seat. All bathrooms are situated near bedrooms which make it perfect for privacy and versatility. Library/ office with solid CHERRY WOOD finishes line the walls & solid wood beamed ceiling can be used for the 5th bedroom or nursery. Regal Master bedroom DOWNSTAIRS, with 12' ceilings, sitting room space & ensuite bath SPA like retreat. MARBLE galore! Step into the Roman tub, or roomy walk-in shower with private atrium. Dual sink cabinets, MARBLE counters & a BIDET and don't forget the enormous walk-in closet. Spiral wood and wrought iron staircase lead to LOFT with additional flex space & bathroom. Peak into the basement for additional BONUS space, with its own bathroom. So many possibles for this area. OPULENT OUTDOOR RESORT living OASIS w/ OUTDOOR KITCHEN, and your own private SANDY BEACH to build your own sand sculptures on. This is the perfect space for entertaining and making memories. Ride the waves, ski or boating & relax & watch the incredible SUNSETS over the lake. Wood dock leads to your private lift & covered space. Brand new Kohler Generator too! Relax and enjoy the ambiance. the sights and sounds of the rippling waters lapping around you and the tranquility of this one-of-a-kind residence. Spend a LAZY afternoon fishing/skiing the 288-acre Lk. with its PRISTINE waters & SANDY BEACH bottom. RELAX with a glass of wine, as you have reserved SUNSET seating as you watch the MOONLIGHT dance the night away. Desirable location that is close to all shopping, major roadways, restaurants and top schools.
Listing Agent: Suzanne Crudo (407-489-8953)
1890 LONG POND DR, LONGWOOD, FL 32779
$615,0007 Days on yellowkey MLS ID: O6415503
0 Days Off yellowkey (back on 6/17/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2448 Built: 1987 Tax: $6,777 (2025)Community: Mandarin Sec 7Spa: NoSingle Family
Taxes:$6,777
Middle School: Markham Woods Middle
Remarks: Move-In Ready 4 Bedroom 3 Bathroom Pool Home Located on an Oversized 1 Acre Corner Lot in the Quiet Mandarin Community with NO HOA. Home has a wonderful open floorplan with a formal living room, a separate dining room plus a family room with a wood burning fireplace as the centerpiece. The kitchen has plenty of countertop and cabinet space with a full set of stainless-steel appliances and features a breakfast room. Primary bedroom suite features a walk-in closet with a private bathroom. Home also features 3 additional bedrooms, a 2-car side entry garage, an interior laundry room w/washer & dryer, ceiling fans, blinds, plenty of storage, and pool views throughout the home. Exterior has a screened in pool with baby safety fence, covered lanai area perfect for cookouts or entertaining family and friends while the backyard is fenced perfect for the pets to play. Location is excellent just minutes from all daily necessities including shopping, grocery, restaurants, entertainment, excellent schools, SR-436, I-4 and 429. Please call to schedule a showing today!
Listing is courtesy of: MIGHTY REALTY INC (407-403-6540)
Listing Agent: Joann Bonilla (317-435-5235)
207 LONESOME PINE DR, LONGWOOD, FL 32779
$559,9006 Days on yellowkey MLS ID: O6416580
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1908 Built: 1977Monthly Fee: $54 Tax: $5,568 (2025)Community: Sweetwater Oaks Sec 08Spa: NoSingle Family
Taxes:$5,568
Remarks: FANTASTIC OPPORTUNITY IN SWEETWATER OAKS! Nestled under a canopy of mature trees in one of Longwood’s premier neighborhoods, this pristine 4-bedroom, 2-bathroom pool residence flawlessly showcases true pride of ownership! Exceptionally maintained: ROOF 2016, REPIPED w/PEX, NEWER ELECTRICAL PANEL & OUTLETS, REMODELED KITCHEN AND BATHS, NEWER GARAGE DOOR and Freshly Painted Pool Decking! PERFECT for both everyday living and grand-scale entertaining, the traditional floor plan offers a seamless flow, featuring spacious living areas, neutral decor throughout, soaring ceilings, a welcoming atmosphere, inviting wood burning fireplace and beautiful architectural touches! GOURMET kitchen with granite counters, convenient pass through window to patio, ample cabinets and SS appliance package (3 yrs new!). The heart of the home effortlessly transitions to a private backyard oasis with spacious covered patio and sparkling screen-enclosed pool serving as your personal Florida retreat. Enjoy the fenced in dog run/pet area with your 4 leg best friend(s). Home boasts a generous size corner lot at .32 acres with definite curb appeal along with convenient side facing garage and utility door access to garage! Beyond the property line lies the unparalleled lifestyle of Sweetwater Oaks, giving you exclusive access to the private Sweetwater Beach on Lake Brantley (for boating and skiing), tennis, playground/picnic area and Riverbend Park’s kayak launches onto the Wekiva River. Complete with top-tier Seminole County schools including Sabal Point Elementary, Rock Lake Middle, and Lake Brantley High, this MOVE-IN-READY gem offers the ultimate blend of timeless comfort and luxury community living. Incredible Longwood location with easy access to 434, 436, I4 plus close to multiple Publix, schools, shopping, dining, Wekiva Island, Wekiwa Springs Park, Uptown Altamonte, Orlando Health, Advent Health and so MUCH MORE!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Laura Toppin (407-489-0415)
1715 SUNSET DR, LONGWOOD, FL 32750
$329,900Listed 06/17/2026 2:48PM MLS ID: O6412253
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1957 Tax: $2,814 (2025)Community: Pine ViewSingle Family
Taxes:$2,814
Remarks: Virtually Staged. Welcome to this inviting single-story home in Longwood, offering a bright layout, spacious rooms, and a large yard surrounded by mature trees. The HVAC was replaced in 2020 and the water heater was replaced in 2021, adding practical updates for peace of mind. From the moment you arrive, the fresh exterior, extended driveway, and peaceful setting create a sense of privacy and possibility. Inside, the home features tile flooring throughout the main living areas, neutral finishes, updated baseboards, arched entryways, ceiling fans, and abundant natural light. The living room offers a comfortable gathering space with large windows and an easy flow into the kitchen and bedroom areas. The kitchen features shaker-style cabinetry, granite countertops, generous storage, a built-in microwave, range, refrigerator, and a window over the sink that brings in natural light. The primary bedroom offers excellent space, a private bath, closet, ceiling fan, and flexible layout, while the additional bedrooms provide natural light, closet space, and options for guests, family, or a home office. Both bathrooms feature tiled finishes, with the primary bath offering a walk-in shower and the secondary bath offering a clean, functional layout. A standout feature is the oversized laundry room, offering impressive bonus space for storage, hobbies, utility needs, or future customization. Step outside and imagine the potential of the expansive backyard, with plenty of room to relax, entertain, garden, or create the outdoor space you have been wanting. Mature trees provide shade and character, while the large lot gives the home a sense of openness that is hard to find. Conveniently located near shopping, dining, schools, parks, and major roadways, this home offers comfort, flexibility, and everyday convenience in an established Longwood setting. Once you walk through it, you can easily see how this home could fit the way you want to live.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Carlos German (888-883-8509)
1833 CROWLEY CIR, LONGWOOD, FL 32779
$550,000154 Days on yellowkey MLS ID: O6369834
REDUCED by $10,000 (1.8%) on 06/15/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2742 Built: 1985 Tax: $5,474 (2024)Community: Mandarin Sec 5Single Family
Taxes:$5,474
Remarks: Virtually Staged. Welcome to 1833 Crowley Circle, a beautifully maintained POOL home offering comfort, freedom, and an unbeatable location — with NO HOA! This inviting property features a private backyard oasis with a lovely pool, perfect for Florida living and entertaining year-round. Enjoy peace of mind knowing the home has been thoughtfully updated, including a full replumb completed 4 years ago, new breaker boxes 4 years, a new pool pump 4 years, and an AC compressor replaced approximately 5 years ago. Stunning fireplace featured in living room to keep the whole family cozy. Enjoy the amazing kitchen in the heart of the home with serving window, breakfast bar area, and extra pull out pantry space! Ideally situated just one mile from the Seminole Wekiva Trail, this home is perfect for outdoor enthusiasts who love biking, walking, and nature, while still being close to everyday conveniences. Near major roadways including I4 making commute to theme parks, downtown, Orlando or Sandford International airports, beaches, and so much more! Whether you’re relaxing poolside, hosting friends, or enjoying nearby trails, 1833 Crowley Circle delivers the perfect blend of lifestyle, location, and long-term value. Don’t miss this opportunity to own a move-in-ready pool home! Easy to show so come see today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Christina Rampersad (407-995-6788)
3591 TERRA OAKS CT, LONGWOOD, FL 32779
$1,200,00027 Days on yellowkey MLS ID: NS1088208
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3810 Built: 2002Monthly Fee: $169 Tax: $5,617 (2024)Community: Terra OaksSpa: YesSingle Family
Taxes:$5,617
Elementary School: Forest City Elementary
Middle School: Teague Middle
Remarks: Tucked behind the gates of one of Longwood’s most desirable communities, this beautifully maintained four-bedroom, five-bath estate blends timeless elegance with modern luxury. From the moment you enter, soaring elevated ceilings, refined architectural details, and expansive living spaces create an immediate sense of sophistication and comfort. Designed for both everyday living and exceptional entertaining, the home features a thoughtfully crafted floor plan, upscale finishes throughout, and a stunning chef’s kitchen appointed with high-end appliances, custom cabinetry, and generous gathering space at the heart of the home. Includes a whole house generator and security system. The spacious primary suite offers a private retreat with spa-inspired amenities, while each additional bedroom provides comfort, privacy, and its own distinctive character. Multiple living and entertaining areas flow seamlessly to the outdoor oasis, where a sparkling pool and beautifully maintained surroundings invite year-round Florida living at its finest. Set within a secure gated neighborhood in the heart of Longwood, this exceptional residence delivers luxury, privacy, and convenience in one extraordinary offering.
Listing is courtesy of: ENGEL & VOLKERS NEW SMYRNA (386-213-6899)
Listing Agent: David Dell'Olio (407-228-4613)
342 COBLE DR, LONGWOOD, FL 32779
$530,000135 Days on yellowkey MLS ID: O6379074
REDUCED by $5,000 (0.9%) on 06/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2596 Built: 1978Monthly Fee: $23 Tax: $2,766 (2024)Community: Wekiva Hills Sec 04Spa: NoSingle Family
Taxes:$2,766
Elementary School: Wekiva Elementary
Remarks: One or more photo(s) has been virtually staged. Major price appeal meets lifestyle living in Wekiva Hills! This three-bedroom, two-bath pool home stands out with dramatic ceilings, skylights, and a stunning stone fireplace that anchors the bright and open living space. Entertain with ease in the elevated dining area overlooking the living room, while the updated kitchen offers modern finishes, a large walk-in pantry, and a cheerful breakfast nook. The upstairs primary suite is filled with natural light and features a bonus sitting area, spacious closet, and refreshed bath. Out back, enjoy a screened patio and your private pool surrounded by mature landscaping. A rear gate opens directly to a peaceful walking trail—perfect for morning walks or evening relaxation. Light-filled, updated, and priced to move—don’t miss this Wekiva Hills opportunity.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Veronica Parker (407-718-6983)
2201 COVE CT, LONGWOOD, FL 32779
$1,695,0001 Day on yellowkey MLS ID: O6417257
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3805 Built: 1959 Tax: $15,741 (2025)Community: Lake Brantley Isles AmdSingle Family
Taxes:$15,741
Remarks: Set behind a private gated entrance on over four acres along the shores of Lake Brantley, this exceptional waterfront estate offers a lifestyle that few properties in Central Florida can replicate. Here, mornings begin with coffee overlooking the water as paddleboarders glide across the lake, afternoons are spent boating, waterskiing, kayaking or fishing from your shoreline, and evenings conclude with breathtaking sunsets reflected across one of the region's most sought-after lakes. Encompassing over 3,800 square feet of living space, the residence is designed to keep the lake at the center of daily life. From the moment of entry, sweeping water views immediately capture attention, drawing the eye through the great room and beyond to the shoreline. Vaulted ceilings and expansive windows fill the home with natural light while creating a constant connection to the outdoors. The open-concept floor plan brings family and guests together with effortless flow between the living spaces, dining area and a beautifully appointed kitchen featuring Sub-Zero refrigeration, Wolf gas cooking and generous gathering space. Two primary suites, additional guest bedrooms, three-and-a-half baths and a dedicated game room provide flexibility for everyday living and extended stays with family and friends. Outdoor living is where this property shines. A sprawling brick-paver terrace surrounds the pool, creating multiple spaces for entertaining, relaxing and enjoying panoramic lake views. Beyond, an expansive wooden deck stretches toward the water and private boathouse, inviting spontaneous afternoons on the lake and sunset cruises just moments from home. Designed for serious lake enthusiasts, the boathouse features a 15,000-pound lift capable of accommodating a 24-foot boat along with three dedicated Jet Ski lifts. With over 190 feet of direct Lake Brantley frontage and a side canal, the property offers a level of privacy and waterfront access rarely found. A private beach and summer kitchen centered around a handcrafted tiled pizza oven create the perfect setting for lakeside gatherings long after the sun goes down. Adding to the appeal is a level of freedom increasingly difficult to find. Private well and septic systems, no HOA, a metal roof, double-insulated windows and doors and a whole-house standby generator provide independence, efficiency and peace of mind. Despite its secluded atmosphere, the property remains just minutes from Orlando, major airports, world-renowned attractions and Florida's beaches. Combining acreage, privacy and one of Central Florida's premier lakefront settings, this is more than a home. It is a waterfront lifestyle built around recreation, connection and unforgettable days on the water.
309 HICKORY DR, LONGWOOD, FL 32779
$520,00013 Days on yellowkey MLS ID: O6413953
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1852 Built: 1976Monthly Fee: $54 Tax: $3,232 (2025)Community: Sweetwater Oaks Sec 06Single Family
Taxes:$3,232
Remarks: One or more photo(s) has been virtually staged. NEW ROOF Prior to closing on this Move-In Ready Pool Home in Sweetwater Oaks and with the SELLERS WILLING TO CONTRIBUTE TOWARDS BUYER'S CLOSING COSTS, it provides added flexibility and value for purchasers! Welcome to highly desirable Sweetwater Oaks, where this beautifully maintained 4-bedroom, 2-bathroom home offers the perfect blend of space, and comfort, with RECENT UPGRADES. The functional floor plan features separate living, dining, and family rooms, an eat-in kitchen, utility room, and walk-in pantry. Enjoy Florida living at its best with a large screened pool and covered lanai, ideal for relaxing or entertaining. The fully fenced backyard also features a new storage shed added in 2024. Major recent updates, all within the last year, provide peace of mind, including a new HVAC system, electrical panel, water heater, and microwave, plus a new dishwasher, flooring and baseboards in the living and dining rooms, fresh interior paint, painted pool deck, new blinds, updated lighting, and new electrical outlets and switches throughout. Additional improvements include a new pool patio roof and pool light (2020). With the new roof being installed prior to closing, this home offers peace of mind with all the recent improvements. Sweetwater Oaks residents enjoy deeded access to skiable Lake Brantley with a boat ramp, tennis and pickleball courts, picnic pavilion, and access to the Wekiva River, parks, and playgrounds. Conveniently located near top-rated Seminole County schools, shopping, dining, and major highways, this move-in-ready home is one you won't want to miss.
Listing is courtesy of: CHAMBERLAIN REALTY LLC (407-542-3033)
Listing Agent: Carol Pennington (407-335-0907)
1652 RUTLEDGE RD, LONGWOOD, FL 32779
$699,99954 Days on yellowkey MLS ID: V4948735
REDUCED by $9,001 (1.3%) on 06/17/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2760 Built: 1982 Tax: $2,994 (2024)Community: Mandarin Sec 2Single Family
Taxes:$2,994
Remarks: Making its debut on the market in the sought-after Markham Woods area, 1652 Rutledge Road in Longwood is a charming one-owner home with much to offer. Sitting on one full acre, this spacious 5-bedroom, 3-bath pool home welcomes you with gorgeous pool views as you step through the front double doors. Sunlight fills the rooms and the family room’s stone-front wood-burning fireplace offers a cozy touch. It also overlooks the kitchen which is ideal for entertaining. The kitchen features stainless steel appliances, generous counter space, and a closet pantry. Large sliders in both the family room and living room lead to the fully fenced yard, a screen-enclosed porch, and a paver-lined pool area. Other perks include an indoor laundry room with washer and dryer, a storage shed, and a freshly paved driveway with ample parking. Roof replaced in April 2026. AC (Del-Air) replaced in 2021. No HOA. Horses welcome, and the property borders the Seminole Wekiva Bike Trail. Another bonus feature is that there is a whole house generator offering additional peace of mind during those Florida storms. Zoned for Lake Mary High School—Go Rams!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Melissa Stalzer (386-405-3457)
820 GEORGIA AVE, LONGWOOD, FL 32750
$300,00077 Days on yellowkey MLS ID: O6395730
0 Days Off yellowkey (back on 6/16/2026)
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1422 Built: 1972 Tax: $2,000 (2024)Community: Lake Wayman Heights Lake AddSingle Family
Taxes:$2,000
Remarks: Under contract-accepting backup offers. Perfect for first-time home buyers, this charming Longwood home offers the ideal blend of comfort, convenience, and lifestyle. More than just a place to live, it's a place where memories are made, neighbors become friends, and every day feels a little more enjoyable. Imagine starting your mornings with a cup of coffee overlooking the peaceful lake view across the street before taking a stroll along the sidewalk-lined neighborhood. Inside, you'll find bright, open living spaces designed for gathering, relaxing, and creating lasting memories. Beautiful new flooring flows throughout the home, while the updated kitchen featuring granite countertops and stainless steel appliances serves as the heart of the home—perfect for everything from busy weekday mornings to hosting family and friends. One of the home's standout features is the spacious bonus room, offering the flexibility today's buyers are looking for. Whether you envision a playroom for the kids, a home office, media room, game room, library, fitness space, or the ultimate spot to watch the big game, this room can grow and change with your lifestyle. The thoughtfully designed split floor plan creates the perfect balance of privacy and connection, with the primary suite tucked away from the additional bedrooms. Whether you're starting a family, working from home, or simply enjoying extra space, this layout offers comfort and functionality for years to come. Step outside and embrace the Florida lifestyle. Situated on a generous quarter-acre lot, there's plenty of room for backyard barbecues, outdoor games, gardening, entertaining, or simply soaking up the sunshine. When the afternoon heat sets in, relax under the covered patio and enjoy your own private outdoor retreat. Location is where this home truly shines. Take a quick bike ride to the nearby SunRail station for an easy commute, or hop on I-4 and be just minutes from Orlando's attractions, major employers, shopping, dining, and Florida's beautiful beaches. On weekends, experience the charm of Historic Downtown Longwood, where you'll enjoy farmers markets, live music, local restaurants, seasonal festivals, and community events that make this area such a special place to call home. For buyers looking to put down roots in a welcoming community while enjoying everything Central Florida has to offer, this home delivers the lifestyle you've been searching for. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: David Miller (407-323-4210)
714 WEST CT, LONGWOOD, FL 32750
$324,30083 Days on yellowkey MLS ID: O6394329
REDUCED by $100 (0.0%) on 06/17/2026
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1413 Built: 1972 Tax: $3,448 (2024)Community: Longwood NorthSingle Family
Taxes:$3,448
Remarks: Just reduced!!! Charming and beautifully maintained 4-bedroom, 3-bath home offering both comfort and efficiency. Enjoy significant energy savings with a fully installed solar system, while major upgrades—including a complete home re-pipe and conversion from septic to city sewer—provide peace of mind for years to come. The property features a spacious corner lot with a partially fenced backyard, perfect for both privacy and outdoor enjoyment. A well-maintained irrigation system keeps the yard lush and green, and a large, high-quality shed offers excellent additional storage. Relax year-round on the inviting screened porch, ideal for entertaining or unwinding in comfort. This thoughtfully updated, move-in-ready home combines modern improvements with everyday convenience—an exceptional opportunity you won’t want to miss.
Listing is courtesy of: PARK PLACE REAL ESTATE (407-504-1110)
Listing Agent: Pat Glenn (407-504-1110)
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