Location: Longwood
Do Not Show Listings
1781 OAKBROOK DR, LONGWOOD, FL 32779
$2,050,0003 Days on yellowkey MLS ID: O6415988
0 Days Off yellowkey (back on 6/15/2026)
Bed: 4 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5160 Built: 2001Monthly Fee: $353 Tax: $14,738 (2025)Community: Alaqua LakesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,738
Elementary School: Heathrow Elementary
High School: Lake Mary High
Tax Year: 2025
Middle School: Markham Woods Middle
Remarks: Under contract-accepting backup offers. Welcome to an extraordinary custom estate in sought-after Alaqua Lakes, masterfully built by renowned luxury builder Dave Brewer and extensively renovated in 2013. Ideally on a fully fenced, over half-acre homesite, this exceptional residence showcases breathtaking golf course and pond views, along with spectacular sunset vistas. Designed for luxurious everyday living and effortless entertaining, the home features four spacious bedrooms, a private office, and two versatile bonus rooms, providing incredible flexibility for work, recreation, fitness, media or guest accommodations. The gourmet kitchen is appointed with premium Wolf and Sub-Zero appliances, while a dedicated bar area includes a Sub-Zero wine refrigerator for the discerning collector. The expansive bonus room elevates entertaining with its full-service bar, complete with an ice machine, dual tap kegerator, dishwasher and refrigerator. Throughout the home, thoughtful upgrades and high-end finishes create a seamless blend of elegance and comfort. Major system improvements provide peace of mind, including HVAC replacements in 2017, 2022 and 2023, a new tank water heater in 2021, a tankless water heater serving the primary suite, a whole-home generator installed in 2022 and a whole-home water filtration system. Triple reverse osmosis drinking water systems serve the kitchen and bar areas. Outdoor living is equally impressive, featuring a signature Dave Brewer outdoor shower, expansive outdoor spaces, and stunning views of the golf course and tranquil pond beyond. Residents of Alaqua Lakes enjoy a premier gated lifestyle with a seven-acre community park, resort-style swimming pool, tennis and basketball courts, sand volleyball, playground and scenic recreational paths. The community surrounds a championship golf course, creating a beautiful setting throughout the neighborhood. This home is also zoned for highly regarded Seminole County schools, making it an exceptional choice for those seeking luxury living and access to top-rated educational opportunities. This rare offering combines timeless craftsmanship, extensive modern updates, exceptional entertaining amenities and one of Central Florida's desirable locations. A remarkable opportunity in Alaqua Lakes.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Kristen Wenderfer (973-868-9745)
96 HICKORY TREE RD, LONGWOOD, FL 32750
$450,00073 Days on yellowkey MLS ID: O6396626
0 Days Off yellowkey (back on 6/16/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1668 Built: 1975Monthly Fee: $8 Tax: $4,535 (2024)Community: Woodlands Sec 5 Rep Of Blk DSpa: NoSingle Family
Taxes:$4,535
Elementary School: Woodlands Elementary
High School: Lyman High
Tax Year: 2024
Middle School: Rock Lake Middle
Remarks: Under contract-accepting backup offers. FANTASTIC OPPORTUNITY IN THE HEART OF LONGWOOD! THIS 3/2 IMPECCABLE UPDATED HOME IN THE WOODLANDS IS MOVE-IN-READY! NEW ROOF 2026, PATIO 2016, HVAC 2011, WATER HEATER 2011, ELECTRICAL PANEL 2011, AND UPDATED PLUMBING! Plenty of space to make this home your own with generous size bedrooms ALL with walk-in closets! Neutral decor throughout with a newer modern feel and fresh laminate floors! REMODELED KITCHEN with granite counters, breakfast bar, ample cabinets, and appliance package! Inviting family room off kitchen with a wood burning fireplace and glass sliders that access the patio area! Relax in the evenings after a long day or entertain on your oversized covered screened in patio! Enjoy the HUGE LUSH fenced in backyard including a separate dog run and/or utility vehicle storage area along with a shed for added convenience! This oversized lot has tremendous potential! Exterior extras include: Garden bed, large 2 car garage with utility room and side access door, exterior lighting, rain gutters, and a transferable Termite Bond serviced by Massey! This home has been meticulously maintained! OTHER NOTABLE MENTIONS INCLUDE: NEW BLINDS AND GARAGE FLOOR PAINTED. Expect to be Impressed! Excellent area close to major highways, shopping, dining and ONLY 30 min to most major attractions! Amazing mature established neighborhood currently zoned for Woodlands Elementary, Rock Lake Middle and Lyman High! The OPTIONAL HOA makes this lovely home very affordable! Don't miss out on the chance to own this special home!
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Laura Toppin (407-489-0415)
808 SWEETWATER CLUB BLVD, LONGWOOD, FL 32779
$3,799,000265 Days on yellowkey MLS ID: O6339805
Bed: 7 Bath: 8.0 Gar: 6 Liv Area Sq Ft: 14801 Built: 1977Monthly Fee: $370 Tax: $29,413 (2024)Community: Sweetwater Club Unit 1-ASpa: NoSingle Family
Taxes:$29,413
Elementary School: Sabal Point Elementary
High School: Lake Brantley High
Remarks: Behind the guarded gates of the prestigious Sweetwater Club, on over three acres of manicured grounds, lies an extraordinary fully remodeled 14,000+ square foot estate that redefines grandeur and sophistication. A sweeping double-entry driveway framed by mature, curated landscaping guides you to the stately façade, where timeless architecture meets meticulous design, including a new roof (2022) and freshly refined exterior finishes. At the heart of the home, the grand family room captivates with its soaring ceilings, bespoke millwork, and custom illuminated built-ins with LED underlighting. Expansive windows invite natural light while framing serene views of the pool courtyard, ensuring every moment feels cinematic. The chef’s kitchen is a true culinary masterpiece. Exquisite quartz countertops and professional-grade stainless appliances stand ready for both intimate family dinners and grand-scale entertaining. A generous island doubles as a culinary stage and social hub, while the adjoining formal dining room, finished with refined detailing and natural light, offers the perfect backdrop for soirées and celebratory dinners. The primary is truly a room of palatial scale; the suite is wrapped in floor-to-ceiling glass overlooking the shimmering courtyard pool. The spa-inspired bath rivals the finest resorts, featuring an expansive walk-in shower with multiple rain showerheads, a freestanding soaking tub, and a spacious dressing walk-in closet. Each secondary bedroom has been designed with equal attention to luxury, spacious in proportion, each with its own walk-in closet. This estate was created for living large and entertaining even larger. The bar and lounge area, complete with its own island, is perfect for entertaining. Outdoor living unfolds as a true resort with a screened courtyard pool, expansive travertine decking for grand entertaining, and a fully appointed summer kitchen pavilion complete with a pizza oven, built-in seating, and shaded dining space that create an atmosphere of Mediterranean resort living. Steps away, your newly resurfaced private tennis courts extend the estate’s leisure amenities, providing the perfect stage for recreation. For the automobile enthusiast, the five-car garage and sprawling motor court make a dramatic statement seamlessly integrated into the estate’s unrivaled design. Fully gated and meticulously upgraded, this estate is not just a home but an irreplaceable lifestyle, offering unparalleled privacy, scale, and elegance in one of Central Florida’s most distinguished communities. Beyond the estate, life in Sweetwater Club offers unparalleled exclusivity, you have access to tennis/pickleball courts, a basketball court, and your in a secure, guard-gated setting. Opportunities like this rarely come along, don’t miss the chance to make this estate yours.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Christopher Christensen (407-312-8003)
910 PARSON BROWN WAY, LONGWOOD, FL 32750
$364,900128 Days on yellowkey MLS ID: O6380478
0 Days Off yellowkey (back on 5/8/2026)
REDUCED by $13,100 (3.5%) on 05/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1407 Built: 1977 Tax: $4,167 (2025)Community: Lake Searcy ShoresSingle Family
Taxes:$4,167
Elementary School: Longwood Elementary
Middle School: Greenwood Lakes Middle
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully maintained 3-bedroom split floorplan residence offering privacy, space, and modern comfort—all with NO HOA. Situated on a nearly ¼-acre fully fenced lot, this property is a rare find both inside and out. Step inside to discover all solid-surface flooring throughout—no carpet, complemented by fresh, updated interior paint and two fully renovated bathrooms. The galley-style kitchen features granite countertops, stainless steel appliance package, and efficient design, perfect for everyday living and entertaining alike. Outdoors is where this home truly shines. The gorgeous backyard oasis includes a gazebo, fire pit, pavered walkways, storage shed, and even a chicken run, offering endless possibilities for relaxation, hobbies, or entertaining guests. Ideally located near historic Longwood, Orlando Health, shopping, and dining, this home blends convenience with charm. Reiter Park—with its splash pad, playground, food trucks, and vibrant community events—is just a pleasant walk or bike ride away. This move-in-ready home delivers space, upgrades, and a lifestyle you’ll love—schedule your showing today.
Listing is courtesy of: WATSON REALTY CORP (407-359-2300)
Listing Agent: Virginia Bellhorn (407-580-7235)
102 EASTERN FRK, LONGWOOD, FL 32750
$389,0007 Days on yellowkey MLS ID: O6412608
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1666 Built: 1972 Tax: $4,433 (2025)Community: Woodlands Sec 3Single Family
Taxes:$4,433
Remarks: Under contract-accepting backup offers. WELCOME TO THE WOODLANDS, one of Longwood’s most established and desirable neighborhoods known for its mature trees, spacious homesites, and convenient Seminole County location. Offered for the first time since it was built, this original-owner home has been cared for by the same family for more than five decades and is ready for its next chapter. This 3-bedroom, 2-bath home offers 1,667 square feet of living space, a desirable single-story floor plan, and a spacious 2-car garage. Even better, the sellers will install a NEW ROOF prior to closing, helping provide peace of mind for years to come. Inside, you'll find a functional layout with generously sized rooms, including three bedrooms with walk-in closets and flexible living spaces that can accommodate everyday living, entertaining, hobbies, or a home office. The kitchen offers abundant cabinet and counter space and overlooks the main living areas, creating a comfortable flow throughout the home. Step outside to the covered and screened patio overlooking the fenced backyard. Whether you enjoy gardening, entertaining, spending time with pets, or simply relaxing outdoors, the backyard offers plenty of room to enjoy Florida living. A storage shed and additional utility area provide added convenience and functionality. For buyers looking to build equity through cosmetic improvements rather than paying a premium for someone else's renovations, this property presents a unique opportunity. With the roof being replaced prior to closing, one of the largest future expenses is already being addressed, allowing the next owner to focus on updates and personal touches that fit their own style and budget. Located just minutes from shopping, dining, parks, major highways, and everyday conveniences, this home offers the combination of location, space, and potential that is becoming increasingly difficult to find. Zoned for Woodlands Elementary, Rock Lake Middle School, and Lyman High School, and with an optional HOA, this is an outstanding opportunity to own a home in one of Longwood’s most sought-after established communities. Priced under $390,000, this is a rare chance to own an original-owner home in The Woodlands and create your own vision in a neighborhood where homes are often held for generations.
Listing is courtesy of: RE/MAX 200 REALTY (407-629-6330)
Listing Agent: Will Lavalle (407-620-7785)
486 N PIN OAK PL #308, LONGWOOD, FL 32779
$179,900129 Days on yellowkey MLS ID: O6381034
REDUCED by $5,000 (2.7%) on 05/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1110 Built: 1991 Tax: $2,066 (2025)Community: Windsor At Sabal Walk A CondoCondo
Taxes:$2,066
Remarks: Recently remodeled 2-bedroom, 2-bath condo in Longwood with over $20,000 in upgrades. This move-in-ready home features a brand-new HVAC system, luxury vinyl plank flooring throughout (no carpet), fresh interior paint, and newly reglazed tubs and showers. Located in the desirable Windsor at Sabal Walk community, this Longwood condo offers a bright, open floor plan with a spacious living room, dining area, and sliding glass doors leading to a screened-in balcony. The split-bedroom floor plan provides privacy, with two generously sized bedrooms, each featuring walk-in closets and its own full bathroom. The kitchen includes ample cabinet storage, a breakfast bar, and open views into the main living space. A full-size laundry room adds everyday convenience rarely found in condo living. Residents of this amenity-rich condo community enjoy a resort-style swimming pool, fitness center, clubhouse, and beautifully maintained walking paths. The location is just minutes from Wekiva Springs, Uptown Altamonte, Lake Mary, and I-4. Ideal for a first-time buyer, downsizing, or a low-maintenance investment property. Call today to schedule a private tour.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
2208 COVE CT, LONGWOOD, FL 32779
$1,500,000258 Days on yellowkey MLS ID: O6348378
2 Days Off yellowkey (back on 1/30/2026)
Bed: 5 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3404 Built: 2020 Tax: $11,004 (2024)Community: Lake Brantley Isles AmdSpa: YesSingle Family
Taxes:$11,004
Middle School: Teague Middle
Remarks: Under contract-accepting backup offers. This stunning Lake Brantley estate combines timeless design, cutting-edge systems, and a thoughtful layout ideal for both everyday living and entertaining. Built by Dakota Homes on nearly half an acre with 106 feet of private canal frontage, the residence offers seamless access to Lake Brantley, one of Central Florida’s most desirable private ski lakes. Inside, every detail reflects quality and craftsmanship. The home features two primary suites, one on the main level with spa-inspired bath and patio access, and a second upstairs with its own covered balcony and expansive rooftop terrace overlooking the water. The chef’s kitchen showcases solid maple cabinetry, GE Café appliances, granite countertops, and a large island that flows naturally into the open-concept living and dining areas. Upgraded systems include a Generac whole-house generator with 500-gallon buried propane tank, a private well with advanced filtration and softening, dual HVAC systems, and a natural gas tankless water heater. Thoughtful enhancements like motorized screens and shades, Closets by Design storage, and integrated smart home controls add modern convenience. Outdoor living shines with a resort-style pool and spa, travertine pavers, tropical landscaping, and permanent Gemstone LED lighting. The built-in outdoor kitchen, lighted patio, and upper-level terrace provide endless space to unwind or entertain. Zoned for top-rated Seminole County schools and minutes from Winter Park, Maitland, and Downtown Orlando, this property offers the perfect blend of privacy, luxury, and lakeside lifestyle.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Brandon Geers (941-928-5152)
289 WILMA ST, LONGWOOD, FL 32750
$274,9003 Days on yellowkey MLS ID: O6417204
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1277 Built: 1964 Tax: $4,247 (2025)Community: LongwoodSingle Family
Taxes:$4,247
Remarks: Property is zoned Urban for residential or commercial office space. In the heart of Downtown Longwood, this property is a clean slate for the potential vision you may have. Highly desirable area with plenty of parking for office space OR easily converted back to a Single Family Residence. Property is vacant and ready to be built out to your dreams. Roll down roof was replaced in 2021. Electrical Panel upgraded in 2024. Plumbing upgraded in 2025. Fully treated and Bonded termite treatment in 2025. Some interior drywall and painting in 2025. HVAC is 2010
Listing is courtesy of: KONA REALTY SERVICES LLC (407-960-6844)
Listing Agent: Alex Bogumil (407-616-0942)
1126 BROWNSHIRE CT, LONGWOOD, FL 32779
$2,598,0003 Days on yellowkey MLS ID: O6415357
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 8100 Built: 1984Monthly Fee: $367 Tax: $11,452 (2025)Community: Sweetwater Club Unit 3Single Family
Taxes:$11,452
Remarks: This majestic estate is a true masterpiece of elegance and timeless architecture, gracefully set among mature oak trees and lush, manicured gardens, blending clasic design with modern luxury, this residence offers an exceptional lifestyle defined by confort, sophistication and privacy. Featuring 5 spacious bedrooms, 7 bathrooms and a private mother-in-law suite. The home was thoughtfully designed with generous spaces and refined finishes throughout. The soaring high ceilings flood every room with natural light, creating a bright and airy atmosphere. Designed for both entertaining and relaxation, the property boast a custom-designed bar, a private home theater, a luxury sauna , and a fully equipped summer kitchen for outdoor gatherings. The sparkling saltwater pool is surrounded by lush landscaping, offering the perfect setting for tranquil retreats or elegant celebrations. Every detail reflects meticulous craftsmanship and timeless style, making this estate a true sanctuary of luxury living in a serene natural setting.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Gustavo Vargas (407-854-2161)
3382 FERNLAKE PL, LONGWOOD, FL 32779
$1,699,0003 Days on yellowkey MLS ID: O6413702
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4001 Built: 2004Monthly Fee: $340 Tax: $9,779 (2024)Community: Alaqua LakesSpa: YesSingle Family
Taxes:$9,779
Elementary School: None
High School: None
Middle School: None
Remarks: RENOVATED IN 2024 INCLUDING NEW TILE ROOF IN ALAQUA LAKES!! Discover this one level turn key home needs absolutely nothing! Nestled on a nearly half-acre homesite in sought-after 24-hour guard-gated Alaqua Lakes featuring tranquil water views, this home has it all. Arrive at a fully brick paver courtyard driveway, enter through double glass doors, and jaws will immediately drop upon first glance at the evident updates throughout. Boasting porcelain tile and wood throughout, a fully remodeled and renovated kitchen, master bath, family room built-in, and bonus room built-in! The primary suite is worthy of a 5-star hotel and showcases a MASSIVE ADDED-ON, extended walk-in closet, and a spa-quality brand new primary bath; all tucked privately away to one side of the home. Professional chefs and home cooks alike will appreciate the brand new kitchen with dramatic center island, new custom pendant lighting, and soft-close cabinetry. An open and airy floorplan is ideal for entertaining friends and family alike with a split bedroom plan, and extended rear covered patio area with summer kitchen. Never have a worry with storage at this home with its massively extended owner's suite closet and exterior pool-area storage; ALL 4 bedrooms feature a walk-in closet as well. Seemingly endless upgrades include custom built-ins nearly throughout, including a hallway full-size refrigerator built-in near the laundry room, Generac back-up generator(2021), resurfaced pool with new gas heater, replaced water heater for the home (2019), and much more; too much to list!! Residents of Alaqua Lakes can enjoy the amenities of a unique 7-acre community park, including an open-air pavilion, a multi-purpose field, tennis courts, and much more. All minutes from shopping, dining, business districts, and major highways. This property may be under audio/visual surveillance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Frank Benevento (407-492-5153)
478 SABAL TRAIL CIR, LONGWOOD, FL 32779
$599,50051 Days on yellowkey MLS ID: O6403175
REDUCED by $10,500 (1.7%) on 06/15/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2529 Built: 1984Monthly Fee: $85 Tax: $6,601 (2025)Community: Sabal Point Sabal Trail AtSpa: NoSingle Family
Taxes:$6,601
Remarks: NEW PRICE: As Of 6/15 : Welcome to the desirable Sabal Point community! Located at 478 Sabal Trail Circle in Longwood, this well-maintained home sits on a nearly one-third acre lot, offering a spacious front yard and one of the larger rear yards in the neighborhood. The home features a split-bedroom floor plan and an open layout with both a large living room and separate family room, providing flexibility for everyday living or entertaining. The living room can easily be utilized as a spacious home office. The expansive covered rear porch overlooks a screened-in pool and deck, along with a large open patio area—ideal for enjoying Florida outdoor living. Interior features include solid wood cabinetry in the kitchen and bathrooms, solid surface countertops, and quality laminate flooring throughout the main living areas and bedrooms. Major updates include a full re-plumb with PEX piping, an upgraded HVAC system, a new roof installed in 2024, and a new pool heat pump added in 2022. Electric vehicle charging hookup in garage. Conveniently located near major roadways, shopping, dining, and zoned for great schools, this property offers space, functionality, and key upgrades within an established Longwood community.
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Daniel Araque (321-276-0747)
1562 DOWNY BIRCH LN, LONGWOOD, FL 32750
$310,00064 Days on yellowkey MLS ID: O6396660
REDUCED by $4,900 (1.6%) on 06/15/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1369 Built: 2013Monthly Fee: $194 Tax: $2,266 (2025)Community: Hanover PointeTownhouse
Taxes:$2,266
Remarks: New Price! Welcome home to this beautifully maintained END-UNIT townhome in Longwood, zoned for highly desirable Lake Mary High School. Backing to a peaceful wooded setting, this 3-bedroom, 2.5-bath home offers added privacy, extra windows, and the natural light that makes end units so appealing. The gated community provides low-maintenance living with HOA coverage that includes lawn and shrub care, building exterior maintenance, roof, and community amenities. Residents also enjoy access to a sparkling community pool—perfect for cooling off and relaxing on warm Florida afternoons. Inside, the open-concept layout creates an easy flow between the kitchen, dining, and living areas, making the home feel both comfortable and functional. The kitchen features GRANITE countertops, STAINLESS STEEL appliances, and a newer refrigerator replaced just two years ago. Unwind on the screened back porch overlooking the wooded backdrop, where you can enjoy morning coffee, evening conversations, or simply a little extra peace and quiet. The backyard fencing on both sides enhances the sense of privacy rarely found in townhome living. Additional highlights include GUTTERS, an in-wall pest control system, and a fire sprinkler system for added convenience and peace of mind. With its move-in ready condition, private setting, low-maintenance lifestyle, and sought-after Longwood location, this home offers the perfect blend of comfort and convenience.
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Susan Smith (352-745-9435)
450 E WARREN AVE, LONGWOOD, FL 32750
$265,0007 Days on yellowkey MLS ID: O6415957
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 888 Built: 1958 Tax: $3,920 (2025)Community: LongwoodSingle Family
Taxes:$3,920
High School: Winter Springs High
Middle School: Milwee Middle
Remarks: Under contract-accepting backup offers. Situated on an oversized double lot in the heart of Longwood, this 2-bedroom, 1-bath home offers endless potential for homeowners and investors alike. Offering a spacious living room, a functional kitchen, and an updated bathroom with walk-in shower, the home also features tile flooring throughout the main living areas and carpet in the bedrooms, making it ready for someone to move in and make it their own. Just off the kitchen and dining area, a recently installed patio creates the perfect outdoor entertaining space, complete with corner posts ready for shade sails or a custom covered seating area. The large lot provides mature landscaping, beautiful shade trees, and ample space to park an RV, boat, or additional vehicles with no HOA restrictions. Additional features include a covered carport with separate laundry room and utility sink, an extra storage room at the rear of the home, and a detached storage shed with an attached covered storage area ideal for lawn equipment, tools, or outdoor gear. Roof replaced in 2015, water heater installed in 2022, New Washer & Dryer 2022, and connected to public sewer. Whether you're searching for your first home, a solid investment property, or a home with room to expand and make your own, this versatile property offers endless possibilities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Kerry Stafford (407-821-8600)
116 WINDMILL WAY, LONGWOOD, FL 32750
$596,00076 Days on yellowkey MLS ID: O6396045
1 Days Off yellowkey (back on 6/15/2026)
REDUCED by $17,000 (2.8%) on 05/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3077 Built: 1973Monthly Fee: $25 Tax: $5,427 (2025)Community: Sleepy Hollow 1St AddSpa: YesSingle Family
Taxes:$5,427
Elementary School: Altamonte Elementary
Remarks: Under contract-accepting backup offers. Reduced price! Best value in the area! Beautiful, charming and spacious pool home on a nearly half-acre corner lot in the desirable Sleepy Hollow community of Longwood. This 4-bedroom residence offers over 3,000 square feet of living space with a functional split floor plan and generous living areas throughout. The ROOf IS NEW, only 2 years old, AC is 6 months old, and brand new insulation as well! The home features a beatiful pool with spa, and expansive outdoor space, perfect for entertaining, along with a large Florida room that provides additional flexible living space. Inside, you’ll find ceramic tile throughout, a welcoming family room with a stone fireplace, and a layout designed for both comfort and privacy. The primary suite includes dual closets, double vanities, and a walk-in shower. Additional highlights include a 2-car garage with extra storage and a fully fenced backyard with room for a boat or RV. Conveniently located near I-4, shopping, dining, and top-rated Seminole County schools.
Listing is courtesy of: URBAN CITY REALTY LLC (321-948-3411)
Listing Agent: Sandra Montano (321-948-3411)
605 WATER OAK LN, LONGWOOD, FL 32779
$499,00036 Days on yellowkey MLS ID: S5149703
REDUCED by $10,000 (2.0%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1831 Built: 1977Monthly Fee: $42 Tax: $4,720 (2024)Community: Sabal Point AmdSingle Family
Taxes:$4,720
Remarks: Florida Dream Home on Over Half an Acre in One of Longwood’s Most Desirable Neighborhoods! Seller motivate Don’t miss this incredible opportunity to own a beautifully updated home in a quiet, established community, while still being just minutes from shopping, dining, top-rated schools, and major highways. Located only 3 miles from Wekiwa Springs, Rock Springs, and King’s Landing, you’ll enjoy easy access to some of Florida’s most breathtaking natural attractions, famous for kayaking, outdoor adventures, and crystal-clear 72-degree mineral springs year-round. This spacious property offers endless possibilities with plenty of room to build your dream pool, create an outdoor oasis, or expand in the future. The home has been recently remodeled with major updates already completed, including a newer roof, gutters, and French drains (approximately 2 years old), updated AC, water heater, plumbing, and fresh exterior paint. Enjoy the perfect combination of privacy, modern comfort, and an unbeatable location close to everything Central Florida. This rare Longwood gem truly combines lifestyle, location, and value — schedule your private showing today before it’s gone! (Some photos have been virtually staged for visualization purposes.) Also option Available to LEASEDBACK . BUY NOW MOVE LATER
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Diana Sanchez (321-947-0107)
105 E COTTESMORE CIR, LONGWOOD, FL 32779
$539,00048 Days on yellowkey MLS ID: O6403980
REDUCED by $11,000 (2.0%) on 05/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2244 Built: 1977Monthly Fee: $23 Tax: $3,894 (2024)Community: Wekiva Hunt Club 3 Fox Hunt Sec 3Single Family
Taxes:$3,894
Remarks: Sought after Wekiva home located off Hunt Club. This is a 4 bedroom, 2 bath home with an extra bonus room right off the prime bedroom. Spacious house that is well maintained, all stainless steel appliances, working fireplace, shutters in windows. Back yard has access to the wekiva trail for walking and running. Paved pool patio, pool. Two parks with in walking distance. This house comes with an electrical disconnect for a generator in case a power outage. Beautifully maintained home featuring ceramic tile throughout—no carpet anywhere. Elegant crown molding enhances the living room, dining room, and primary bedroom, while custom interior shutters add timeless style to every window. Enjoy the bright Florida room for additional living space and a large private bonus room directly off the primary suite, perfect for an office, nursery, fitness room, or retreat. Step outside to your own backyard oasis with a saltwater pool featuring a brand-new Hayward salt cell, a premium hardwired hot tub with newer cover and pressure switch, covered patio, and private cabana. The fully fenced yard is surrounded by mature landscaping and illuminated by hardwired outdoor lighting, creating the perfect setting for relaxing or entertaining. Direct access to scenic walking trails behind the home adds even more appeal. Additional upgrades include a new A/C condenser, complete irrigation system for easy lawn maintenance, and a generator inlet box for quick emergency power connection. This home offers the perfect combination of comfort, convenience, and resort-style outdoor living.
Listing is courtesy of: PRIMAC GROUP, INC (407-889-7075)
Listing Agent: Andre Diaz (407-252-8533)
575 TIBERON COVE RD, LONGWOOD, FL 32750
$420,00047 Days on yellowkey MLS ID: O6404289
REDUCED by $5,000 (1.2%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1657 Built: 1982Monthly Fee: $8 Tax: $2,063 (2024)Community: Tiberon CoveSingle Family
Taxes:$2,063
Remarks: Welcome to this beautifully upgraded 3-bedroom, 2-bathroom home offering 1,657 square feet under air in the desirable Tiberon Cove community of Longwood. This meticulously maintained residence combines modern upgrades, quality craftsmanship, and stylish finishes throughout. Step inside to discover a fully renovated interior featuring a front door with decorative iron between the glass and Selva ash wood-look porcelain flooring throughout the main living areas and bedrooms—durable, anti-slip, and antimicrobial. The home is enhanced with 5-inch baseboards and crown molding throughout, along with new interior 6-panel doors and updated hardware, creating a clean and cohesive design. Window treatments include plantation shutters throughout. The stunning kitchen has been completely upgraded with: White shaker cabinetry Quartz countertops with full-height backsplash Deep double stainless steel sink with racks Frigidaire Professional microwave/convection oven Frigidaire Gallery 5-burner glass-top electric stove with convection/self-cleaning oven with air fry capability. Frigidaire Gallery stainless dishwasher (natural gas) Frigidaire 27.5 cu ft refrigerator with ice & water in door New garbage disposal Both bathrooms have been tastefully updated with new cabinetry, medicine cabinets, Moen fixtures, and one-piece dual flush toilets, while the primary bath features a Bath Fitter shower system. Major system upgrades provide peace of mind, including: New Rheem 15 SEER electric heat pump (2021) New gas water heater (2022) 140 MPH wind-rated architectural roof (installed 1/2023) Full home repipe with PEX-A (2025) by Repipe Specialists with transferable warranty Impact windows (2021) by Window World with transferable warranty New Genie garage door opener (2025) with 3-day battery backup 140 MPH-rated metal garage door with windows Enjoy outdoor living in the spacious 10x30 screened aluminum patio with tile flooring, overlooking a fully fenced yard with white vinyl fencing and enhanced landscaping for added privacy. Additional exterior highlights include a mahogany fiberglass front door with decorative privacy glass, brick mailbox with locked mail slot, and a recently serviced fireplace chimney. The 2-car garage includes built-in wood cabinetry for extra storage, making this home as functional as it is beautiful. Conveniently located near shopping, dining, parks, and major roadways, this move-in-ready home offers easy access to everything Longwood and Central Florida have to offer. This is a rare opportunity to own a fully upgraded, turnkey home with high-end features and major system updates—schedule your private showing today!
Listing is courtesy of: TRUDEALS REALTY CORP (833-878-3325)
Listing Agent: Candace Garber (224-489-4435)
1856 ALAQUA DR, LONGWOOD, FL 32779
$1,399,00086 Days on yellowkey MLS ID: O6392922
REDUCED by $51,000 (3.5%) on 05/14/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4007 Built: 1988Monthly Fee: $347 Tax: $8,385 (2025)Community: Alaqua Ph 1Spa: YesSingle Family
Taxes:$8,385
Remarks: PRICE REDUCED! Welcome to Alaqua Drive, Luxurious Upgraded Executive Home Reflects Timeless Appeal **Sprawling Over an Acre of Tropical Green & Fresh Landscape**Enclaved in the Estate Gates of Alaqua- the Areas Most Respected Gold Gated Communities**Features Include: Sun-filled Home**Natural Stone &Hardwood Floors on a spectacular Open Space that Boasts **5 Bedrooms* & *a Family Lounge. Large cathedral ceilings** Expansive Gourmet Chef Kitchen w/ Large Island & State of the Art Appliances**Walk-in Pantry **Three-Car Garage**Large sparkling w/ Screen Enclosure**Oversized Lanai Built In-Stainless Steel Summer Kitchen Grill**Abundant Storage & Large Closets to be Found Everywhere**NEW Roof being installed** Make this well-maintained Spectacular Home Your Own. Located just North of Downtown Orlando**Very Desirable Lake Mary School District**This Residence is 50 minutes from Both Attractions and Beaches**Convenient to Fine Dining**Shopping & All of the Amenities Seminole County Has to Offer*- call for more information**TANKLESS water heater**Solar heated Pool**Both Air Conditiong Units 5 Years Old**Water Heater 5 Years Old**Generator 5 Years Old**All Bathrooms And Kitchen Fully renovated.**House has been updated with newer pipes and so on.
Listing is courtesy of: DOVER INTERNATIONAL CO., INC. (407-333-0711)
Listing Agent: Louis Joachim (407-333-0711)
272 W WARREN AVE, LONGWOOD, FL 32750
$385,000238 Days on yellowkey MLS ID: O6354921
REDUCED by $10,000 (2.5%) on 06/10/2026
Bed: 4 Bath: 1.0 Liv Area Sq Ft: 1386 Built: 1927 Tax: $3,245 (2024)Community: LongwoodSingle Family
Taxes:$3,245
Remarks: Welcome to a truly unique opportunity in the heart of Historic Downtown Longwood, where charm, flexibility, and location come together in one exceptional property. Whether you're seeking a distinctive residence, a live/work lifestyle, or an investment with future potential, this historically designated property offers endless possibilities. Situated on an oversized lot with ample private parking, the property features four spacious rooms that can function as bedrooms, offices, creative studios, or flex spaces, along with a convenient kitchenette, half bath, handicap-accessible ramp, and excellent visibility near a prominent corner location. Recent improvements include a newer roof, newer HVAC system, and a transferable termite protection plan for added peace of mind. Zoned for residential, commercial, or mixed-use applications—including offices, boutique retail, bed and breakfast, professional services, and more—this property offers rare versatility in one of Seminole County's most desirable downtown districts. Enjoy a vibrant, walkable lifestyle just steps from Reiter Park, SunRail, local restaurants, shops, community events, and municipal buildings. With no HOA, potential for expansion, and a location rich in history and community character, this is a rare opportunity to live, work, invest, or create something truly special in Historic Longwood. Schedule your private showing today and discover the possibilities.
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Sarita Cabrera (321-438-4479)
1508 CANARY ST, LONGWOOD, FL 32750
$329,00048 Days on yellowkey MLS ID: O6402841
REDUCED by $16,000 (4.6%) on 06/05/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1595 Built: 1973 Tax: $1,210 (2025)Community: Sky Lark SubSingle Family
Taxes:$1,210
Elementary School: Highlands Elementary
Remarks: Virtually Staged. Welcome to 1508 Canary Street in Longwood! This charming 4-bedroom, 2-bath home features a desirable split floorplan, offering both privacy and functionality for everyday living. With no HOA, you’ll enjoy the freedom to truly make this property your own. Step outside to a spacious, fully fenced backyard with mature trees, perfect for relaxing, entertaining, or letting pets roam freely. Whether you're hosting gatherings or simply enjoying a quiet evening at home, this outdoor space offers endless possibilities. Air conditioning, water heater, electric and plumbing have been updated. Conveniently located near shopping, dining, and major roadways, this home is a great opportunity to enjoy comfortable living in the heart of Longwood.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Dawn Grigsby (407-970-9051)
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