Location: Longwood
Do Not Show Listings
101 CHERRY HILL CIR, LONGWOOD, FL 32779
$699,00022 Days on yellowkey MLS ID: O6410123
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2359 Built: 1977Monthly Fee: $29 Tax: $6,170 (2025)Community: Brantley Hall EstatesSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,170
Elementary School: Forest City Elementary
High School: Lake Brantley High
Tax Year: 2025
Middle School: Teague Middle
Remarks: This 4 bedrooms/3 bathrooms home is ideal for families and those who enjoy entertaining. Recently renovated with a contemporary modern luxurious feel, this home offers both character and timeless appeal. Situated in the heart of Longwood, on a spacious half-acre lot with deeded boat ramp access to Lake Brantley, this home provides ample room for outdoor activities with a large pool deck, gardening, or simply relaxing in a private, tranquil setting. Inside, you'll be greeted by a fresh, modern ambiance, featuring Newly installed 2025 Roof, windows and doors, new plumbing and electrical fixtures, and newer appliances. The luxurious quartz countertops add a touch of elegance to the space with lots of cabinets. The generously sized bedrooms ensure comfort and privacy with a split plan, while the standout lagoon-style pool transforms your backyard into a resort-like retreat. A screened-in patio lit the rear of the house overlooks the pool, making it the perfect for large gatherings. The property is convenience to grocery stores, shops, and hospitals. Its proximity to major highways also facilitates easy commuting. This home presents a rare opportunity to enjoy a blend of comfort, style, and modern luxury with its classic charm, with its newly updated interior, and an inviting outdoor area, it's ready for you to create lasting memories. Schedule your showing today.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Susan Dering (407-497-5231)
230 HUNTERS TRL, LONGWOOD, FL 32779
$749,00017 Days on yellowkey MLS ID: O6411144
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3180 Built: 1980Monthly Fee: $44 Tax: $3,493 (2025)Community: Markham PlaceSpa: YesSingle Family
Taxes:$3,493
Elementary School: Woodlands Elementary
High School: Lake Mary High
Middle School: Markham Woods Middle
Remarks: Opportunity in Markham Place! Situated on a premier corner lot just off Longwood’s highly sought-after Markham Woods corridor, this timeless two-story brick residence offers the perfect blend of warmth, elegance, and functionality. Designed for both entertaining and everyday living, the expansive 4-bedroom, 3-bath floorplan welcomes you with a grand foyer and sweeping staircase. Rich architectural details including crown molding, wainscoting, and chair rail accents create a classic, refined ambiance throughout. The kitchen features maple cabinetry, updated stainless-steel appliances, brick flooring, and a spacious breakfast nook with French doors opening to a newly enclosed, air-conditioned lanai overlooking the sparkling pool and spa. Formal living and dining rooms showcase oversized bay windows and abundant natural light, while the family room offers a cozy wood-burning fireplace and seamless access to the outdoor living areas. Upstairs, generously sized bedrooms feature beautiful wood flooring, while the luxurious primary suite includes its own fireplace, remodeled bath, and French doors leading to a private screened sun deck. Completing the home is an oversized 20’ x 40’ resurfaced pool and spa, creating the ultimate private retreat. All this with a reasonable HOA fee, and incredible proximity to world-class attractions, restaurants, shopping, and great schools. 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)
335 GOLFSIDE CV, LONGWOOD, FL 32779
$310,00058 Days on yellowkey MLS ID: O6399625
REDUCED by $10,000 (3.1%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1648 Built: 1984Monthly Fee: $23 Tax: $2,417 (2024)Community: Wekiva Villas On The Green 2Condo
Taxes:$2,417
Elementary School: Wekiva Elementary
Tax Year: 2024
Remarks: Welcome home to this beautiful 3 bed / 2 bath single story condo, across the street and steps away from a relaxing, community pool. Vaulted 16' ceilings with plenty of natural light, greet you with an open floor plan, providing a feeling of comfort and space. Private brick courtyard in the front. Updated kitchen counters in quartz and plenty of storage. Newer appliances including an induction cook top and a built-in air fryer in the oven! Wonderful wooden blinds decorate the back windows. Washer and Dryer included, located in the garage. An enclosed Sunroom extends living area; perfect for relaxing, reading or just enjoying the nature views. The Primary Bedroom has an Ensuite Bathroom and walk-in closet. The community features a pool, walking trails throughout Wekiva, 18-hole golf course nearby, clubhouse, playground, and tennis courts are available. Wekiva Elementary School is less than a 5-minute drive. Seller providing an Assurant Enhanced Plan Home Warranty with the property. Schedule a showing today, as this property and community look forward to welcoming you home!
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Douglas Yannucci, Pa (407-454-3494)
1405 CRICKET CT, LONGWOOD, FL 32750
$315,00062 Days on yellowkey MLS ID: O6397641
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1372 Built: 1984Monthly Fee: $68 Tax: $3,994 (2024)Community: Westlake Manor Unit 2BTownhouse
Taxes:$3,994
Elementary School: None
High School: None
Middle School: None
Remarks: BACK ON MARKET BUT TO YOUR BENEFIT. Ask about CREDIT FOR DECK REPLACEMENT for buyer. Wake up to tranquil lake views in this beautifully updated Coventry home, where comfort meets effortless elegance. This 3-bedroom, 2-bath residence offers a spacious design and a 2-car garage, complemented by thoughtful upgrades throughout. At the heart of the home, newer luxury vinyl plank flooring in living, dining and kitchen in addition to a fully remodeled kitchen that shines with quartz countertops, custom cabinetry, new appliances, and refined finishes—perfect for both quiet mornings and stylish entertaining. Recent improvements, including a new A/C and water heater (2023), add lasting peace of mind. Set within a well-kept community featuring a pool, tennis, and basketball courts, this home delivers a rare blend of scenery, sophistication, and value. Buyer and buyer agent to verify all data/measurements.
Listing is courtesy of: CFRP REALTY LLC (407-682-8686)
Listing Agent: Tonya Giddens (321-277-3291)
129 HIDDEN OAK DR, LONGWOOD, FL 32779
$489,90044 Days on yellowkey MLS ID: O6403496
4 Days Off yellowkey (back on 5/30/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2194 Built: 1973Monthly Fee: $175 Tax: $4,887 (2024)Community: The Spgs Glenwood Village Sec 2Townhouse
Taxes:$4,887
Elementary School: Sabal Point Elementary
High School: Lyman High
Middle School: Rock Lake Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. The Springs Beautifully renovated single-story 4-bedroom, 2-bath corner townhome located behind the 24-hour guarded gates of The Springs community in Longwood. This turnkey property has been freshly painted inside and out and combines quality updates with timeless style, featuring high ceilings, oversized rooms, abundant closet space, brand-new flooring, a new roof, stunning renovated kitchen, and updated bathrooms. The sunken living area with built-in seating and a double-sided fireplace creates a striking focal point, while the spacious primary suite offers a huge master bath, walk-in closet, and private access to the backyard with serene open green views and no rear neighbors. Additional highlights include a two-car garage and premium corner location. Conveniently located near I-4, shopping, and dining, residents enjoy resort-style amenities including a natural spring, waterfront complex, community pool, clubhouse, horse stables, RV/boat storage, and more.
Listing is courtesy of: FLORIDA REALTY OF MIAMI CORP (305-598-5488)
Listing Agent: Janet Garay (786-355-7514)
123 TOMOKA TRL #123, LONGWOOD, FL 32779
$249,900451 Days on yellowkey MLS ID: V4941609
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1243 Built: 1974 Tax: $2,219 (2024)Community: Wekiva Villas CondoSpa: YesCondo
Taxes:$2,219
Remarks: True Florida Paradise ! Possible owner financing is just an added bonus True gated and guarded Community. Enjoy your ground level 2 bedroom, 2 bath home with many community features. new CARPETS, STOVE, flooring and lighting. Home has nice fireplace in Living room that overlooks the private courtyard. Master has New carpet new lighting and over look private courtyard! Community features of the beautiful Wekiva to include large community building, playgrounds, walking paths, tennis courts and horse barn, The Springs' is a guarded gated community that offers guarded security but also a ton of amenities for the residents to enjoy. From the beach and clubhouse to tennis courts, basketball courts, and even a horse barn, there's something for everyone. Also, the proximity to over 100 acres of preserved land and access to natural wonders like the Palm and Sanlando Springs and the Little Wekiva River makes it an ideal location for nature lovers seeking tranquility and outdoor adventures. And with its convenient access to I-4, commuting to downtown Orlando, international airports, beaches, and amusement parks is a breeze. Right off S.R. 434 and I-4 in Longwood you’re close to diverse restaurants, groceries, Sunrail, and more. The Springs features a natural wonderland as the entire area is dedicated as a wildlife sanctuary.
Listing is courtesy of: DELTONA LAKES REALTY INC (386-574-1401)
Listing Agent: Sheila Campbell (407-687-7900)
105 FAIRWAY DR, LONGWOOD, FL 32779
$170,000323 Days on yellowkey MLS ID: O6330225
REDUCED by $4,999 (2.9%) on 05/18/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1140 Built: 1973Monthly Fee: $566 Tax: $1,370 (2024)Community: Fairway VillasCondo
Taxes:$1,370
Remarks: THE SPRINGS LIFESTYLE AT AN UNBEATABLE VALUE Imagine waking up in the heart of one of Longwood’s most coveted gated enclaves. This ground-floor, end-unit retreat in Fairway Villas offers more than just a home; it offers a total lifestyle transformation. Whether you are seeking a peaceful "lock-and-leave" residence or upgrade, this condo delivers a rare combination of character, comfort, and privacy. CHARECTER & COMFORT The open-concept layout is anchored by soaring wood-beamed ceilings, creating an atmosphere that is both rustic and modern. Features sliding glass doors that lead to your massive private deck, perfect for morning coffee or hosting friends under a canopy of mature trees. PREMIUM UPDATES Enjoy the peace of mind that comes with updated counters, solid surface finishes, and the convenience of a primary suite located entirely on the main floor. As an end unit, you benefit from additional natural light and enhanced privacy that other units simply don't offer. WORLD-CLASS AMENITIES You aren't just buying a condo; you’re gaining 24-hour gated security and access to The Springs' legendary amenities: a private clubhouse, fitness center, tennis courts, community stables, and a natural spring for swimming. ACT FAST Properties at this price point within The Springs are a rare find. Maintenance fees are all-inclusive, covering water, exterior upkeep, 24/7 security, and all recreational facilities. Schedule your private showing today. Welcome home!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Carl Vano (407-495-2040)
119 MEADOWFIELD LN, LONGWOOD, FL 32779
$365,00025 Days on yellowkey MLS ID: G5112577
0 Days Off yellowkey (back on 5/29/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1200 Built: 1974 Tax: $3,811 (2025)Community: Meredith Manor Golf View Estates SecSingle Family
Taxes:$3,811
Remarks: Under contract-accepting backup offers. Welcome to an amazing opportunity in Longwood! Situated on an oversized lot with no HOA, this pool home offers the space, major updates, and flexibility buyers are looking for while still leaving room for a new owner to add their own personal touches and style over time. The fully fenced backyard is designed for enjoying Florida living year-round, featuring a saltwater pool resurfaced just three years ago, fruit trees that add to the outdoor charm, and plenty of space to relax or entertain. Inside, you’ll find no carpet throughout, with vinyl flooring running through most of the home along with tile in select areas, updated bathrooms, and a fully enclosed Florida room under AC that creates valuable flex space ideal for a second living area, home office, gym, or playroom, along with an additional screened porch for even more functional living space. Major improvements include ROOF 2020, HVAC 2018, WATER HEATER 2021, updated windows, new gutters, updated duct work and insulation, and more, helping provide peace of mind for the next owner. Conveniently located just off 434 with easy access to shopping, dining, and everyday conveniences, this home combines comfort, functionality, and outdoor living in the heart of Longwood. Easy to show! *Aerial photo property lines are an estimate and to be verified by buyer.
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Brandie Mathison-Klein (407-488-3446)
1562 DOWNY BIRCH LN, LONGWOOD, FL 32750
$314,90059 Days on yellowkey MLS ID: O6396660
REDUCED by $5,100 (1.6%) on 05/12/2026
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
Elementary School: Longwood Elementary
Middle School: Greenwood Lakes Middle
Remarks: 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)
3301 SUNSET RIDGE CT, LONGWOOD, FL 32779
$1,990,00047 Days on yellowkey MLS ID: O6402005
2 Days Off yellowkey (back on 5/29/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5962 Built: 2009Monthly Fee: $50 Tax: $13,177 (2025)Community: Sandy Lane Reserve Phase 2Spa: YesSingle Family
Taxes:$13,177
Remarks: Under contract-accepting backup offers. Situated on a privately fenced .50-acre corner homesite within Sandy Lane Reserve, an enclave of 24 custom-built homes near Lk Brantley & Markham Woods corridor, this one-owner, METICULOUSLY DETAILED estate offers just under 6,000sf of refined LUXURY LIVING. SOARING CEILINGS are enhanced by LAYERED ARCHITECTURAL DETAILS including COFFERED & tray designs, while rich, warm cabinetry, WOOD FLOORING & travertine carried throughout the main living areas establish a cohesive & elevated interior. Multiple sets of RETRACTABLE SLIDERS & French doors extend the primary living spaces to a lanai spanning the entire rear elevation, creating a SEAMLESS INDOOR/OUTDOOR experience. DESIGNER LIGHTING from Buster & Punch of England & Hubbardton Forge introduce a refined presence. Upon entry through ARCHITECTURALLY CRAFTED wood doors, a masterpiece unfolds beginning w/ the formal living room, anchored by a gas fireplace w/ custom tile surround & built-in cabinetry, while adjoining gathering spaces transition effortlessly into the stately dining room & grand kitchen. A dual-sided butler’s pantry welcomes you w/ glass-accented cabinetry & Sub-Zero wine refrigeration. A well-appointed kitchen is centered around an expansive island, supported by a hidden walk-in pantry & extensively refined cabinetry. A high-end appliance package including WOLF convection & steam ovens & steamer, THERMADOR refrigerator, DACOR 6-burner gas cooktop, pot filler, BOSCH dishwasher, warming drawer, dual sinks & eat-in bar, artfully complimented w/ striking stone countertops. Steps beyond a Tuscan WINE CELLAR, you'll find a stunning OFFICE w/ rich cabinetry & dual workstations. The primary is a retreat w/ picturesque wall of windows, captivating chandelier, ample sitting area & direct access to pool & lanai. Beyond the stately his/hers custom closets, the primary bath features travertine flooring, custom cabinetry, dual vanities, jetted tub & walk-in travertine shower. A MAIN-LEVEL MOTHER-IN-LAW SUITE offers multi-family convenience w/ en-suite bath, complimented w/ a walk-in shower, oversized closet, SAUNA & direct access to the limitless lanai. Beyond a striking winding staircase are 2 generously sized upstairs bedrooms featuring full baths & walk-in custom closets, a SPACIOUS LOFT & 2 ample storage/tech custom closets. The main-level THEATRE ROOM experience is unmatched, offering automated seating & movie-quality surround sound. CRESTRON AUTOMATION provides ONE-TOUCH lighting, audio, alarm & security control while pool & MOTORIZED window treatments are also smart-controlled. The outdoor living component is showstopping w/ a FULL-WIDTH LANAI featuring TRAVERTINE flooring, double-sided GAS FIREPLACE, 6 RETRACTABLE SCREENS, hand-painted mural & multiple seating. The SUMMER KITCHEN includes commercial-grade grill, sink, beverage refrigeration, custom cabinetry & media. A travertine pool deck surrounds a resort-style pool w/ sun shelf, spillover fountains, fire bowls, spa & fire pit all set within newly landscaped grounds. Addt'l features: WHOLE-HOUSE GENERATOR, SALTLESS WATER FILTRATION, hurricane windows, 2 tankless water heaters, 4 HVAC units, oversized 3-car garage w/ epoxy flooring, extensive cabinetry & attic storage. Ideally located w/ convenient access to top-rated public & private schools, dining, shopping & all thoroughfares. With its level of finishes and IMPECCABLE execution, this MASTERPIECE reflects a standard of living rarely found!
Listing Agent: Penney Lawrence (407-353-7019)
1652 RUTLEDGE RD, LONGWOOD, FL 32779
$709,00049 Days on yellowkey MLS ID: V4948735
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)
737 E CHURCH AVE, LONGWOOD, FL 32750
$405,000176 Days on yellowkey MLS ID: O6365251
REDUCED by $14,000 (3.3%) on 05/28/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 2542 Built: 1973 Tax: $5,240 (2024)Community: Wildmere Resurvey Of Blk 4Spa: NoApartment
Taxes:$5,240
Remarks: Income-Producing Duplex in the Heart of Longwood. Income-producing duplex ideally located in the heart of Longwood, near US Hwy 17-92 and SR-434, offering convenient access to shopping, restaurants, banks, supermarkets, SunRail, I-4, and major corridors. Built in 1973 and well-maintained, the property features two units, each offering 2 bedrooms and 2 full bathrooms. No HOA! Both units are tenant-occupied with under-market rents, providing an attractive opportunity for future rent growth. Unit 737 E Church Ave (2Bed/1.5Bath) is currently rented for $1,350/month with a lease in place through July 31, 2026, and includes a new dishwasher installed in September 2025 and an A/C replaced in February 2023. Unit 739 E Church Ave (2Bed/1.5Bath) is currently rented for $1,300/month on a month-to-month basis, and includes a new A/C installed in April 2024 and a new stove installed in July 2025. Tenants in both units are responsible for their electricity, water, cable, internet, and lawn maintenance. Excellent central location near everyday essentials, including Publix (2.5 miles, 6 minutes), CVS (1.1 miles, 5 minutes), and Starbucks (0.2 miles, 1 minute), and a variety of dining spots, local cafés, and takeout options. Distances and drive times are approximate. Don’t miss this outstanding opportunity; the location offers the perfect blend of convenience and comfort. Schedule a showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Ayesha Verma (407-639-0345)
808 SWEETWATER CLUB BLVD, LONGWOOD, FL 32779
$3,799,000260 Days on yellowkey MLS ID: O6339805
Bed: 7 Bath: 8.0 Gar: 5 Liv Area Sq Ft: 14801 Built: 1977Monthly Fee: $370 Tax: $29,413 (2024)Community: Sweetwater Club Unit 1-ASpa: NoSingle Family
Taxes:$29,413
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)
1950 ELKHORN CT, LONGWOOD, FL 32750
$824,85098 Days on yellowkey MLS ID: TB8482417
REDUCED by $25,050 (2.9%) on 05/27/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3422 Built: 2001Monthly Fee: $120 Tax: $5,359 (2024)Community: Hidden CoveSpa: YesSingle Family
Taxes:$5,359
Remarks: A rare opportunity to own in Hidden Cove, an intimate gated community of just 37 homes where privacy and exclusivity meet refined living. This beautifully maintained 5-bedroom (or 4-bedroom and study) plus upstairs bonus room, 4 full bathrooms and a 3-car garage home offers an impressive blend of comfort, thoughtful upgrades, and resort-style outdoor living. Set on a fully fenced lot, the home welcomes you with elegant interior finishes including a custom-built entertainment center in the family room with TV, plantation shutters, crown moulding, French doors, custom drapes, blinds, built-in speakers, and California Closets in every bedroom, creating a seamless balance of sophistication and functionality throughout. The spacious primary suite serves as a private retreat featuring an ensuite bath with a relaxing whirpool tub. Designed for both everyday comfort and entertaining, the home features a whole-house water filtration and softener system, generator hookup, and convenient attic ladder access. Professional outdoor lighting in both the front and back yard enhance the look of the home in the evenings. Step outside to your private backyard oasis. The beautifully designed saltwater pool and spa are enhanced by solar pool panels, a pool cover, and a safety alarm, offering both efficiency and peace of mind. A poolside kitchen setup makes outdoor entertaining effortless, while mature fruit trees bring a touch of tropical Florida living to your backyard. Recent updates add even more value, including a newer Lennox Elite series AC system (2022) and a separate Mitsubishi mini-split unit for the bonus room (2023). Ideally located, the home is zoned for highly rated Seminole County schools and offers convenient access to grocery shopping, restaurants and close proximity to world-famous amusement parks. This home is a short commute to Lake Mary, Orlando International Airport and Downtown Orlando, making both travel and entertainment easily accessible. Do not miss the opportunity to own this home, make an appointment today. All information and measurements deemed reliable, buyer to verify.
Listing is courtesy of: FUTURE HOME REALTY INC (813-855-4982)
Listing Agent: Marie Tomlinson (727-771-3609)
135 SPRINGWOOD CIR #E, LONGWOOD, FL 32750
$99,00753 Days on yellowkey MLS ID: O6400969
REDUCED by $10,116 (9.3%) on 05/27/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 666 Built: 1973 Tax: $1,135 (2024)Community: Springwood VillageCondo
Taxes:$1,135
Elementary School: Altamonte Elementary
Remarks: Welcome to Springwood Village, a well-located community just off Interstate 4 at the Longwood exit. Tucked just behind a convenient shopping plaza, this condo offers both accessibility and a comfortable place to call home. This spacious 1-bedroom, 1-bathroom unit features a single-floor layout, making it easy to live in and maintain. The open feel and functional design provide plenty of room to relax and unwind. Residents of Springwood Village enjoy a variety of amenities, including: Two swimming pools, Tennis court, Basketball court, Clubhouse with fitness center, Three on-site laundry facilities. Whether you’re a first-time buyer, downsizing, or looking for an investment property, this condo offers great value in a prime location. Don’t miss your chance to own in a convenient and amenity-rich community!
Listing is courtesy of: LIVE FLORIDA NOW LLC (407-448-7977)
Listing Agent: Dean Erlandson (407-719-5426)
1000 CROOKED OAK COURT, LONGWOOD, FL 32779
$599,900122 Days on yellowkey MLS ID: O6378220
REDUCED by $20,000 (3.2%) on 04/30/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2808 Built: 1974Monthly Fee: $54 Tax: $6,597 (2024)Community: Sweetwater OaksSpa: NoSingle Family
Taxes:$6,597
Remarks: One or more photo(s) has been virtually staged. Updated Sweetwater Oaks! 4-bedroom, 3-bath retreat, 2,808 sq ft **open tropical pool**, **screened lanai**comfortable living on an expansive Thoughtfully modernized this. Set on a Cul-de-sac street, the property enjoys a unique presence with 2 front entrances, enhancing both convenience and curb appeal. Open-concept single story with a lot natural light. Superb family room with a cozy fireplace, Large, Bright, & Beautiful Kitchen with Stainless steel appliances and an eat-in nook. **oversized living room** and a **spacious dining room** ideal for hosting. Recent upgrades elevate the home’s **to "new flooring in 3 bedrooms, and new porcelain tile flooring in Florida room". (2026)**, a **new roof (Dec 2025)**, **new AC compressor (2024)**, **new pool pump (2024)**, and a **pool resurfacing (2019)**. Throughout the home, **laminate and tile flooring** offers durability and style., **fenced yard**, and **sun-splashed patio** serene backdrop for relaxation, play, and outdoor entertaining. Sought-after community amenities, enjoy access to a **playground, tennis courts, basketball court, volleyball court, covered picnic area**, and exclusive **lake access to Lake Brantley**, complete with a sandy beach area. **Wekiva River access** Move in ready! Hurry! Won't last!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Caroline Moffitt Lawton (407-670-9797)
300 NEW WATERFORD PL #202, LONGWOOD, FL 32779
$269,90036 Days on yellowkey MLS ID: O6404367
0 Days Off yellowkey (back on 5/27/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1176 Built: 1986 Tax: $1,203 (2025)Community: Lakeview Gardens At Wekiva Cove 1 A CondoCondo
Taxes:$1,203
Remarks: Perfect for First-Time Buyers or Those Ready to Downsize! Don’t miss this rare opportunity to own a beautifully updated condo in the highly sought-after Wekiva Cove community. Wake up every day to stunning lake views and enjoy a move-in-ready home featuring a remodeled kitchen and bathrooms, plus luxury vinyl flooring throughout. This inviting layout offers 2 spacious bedrooms and 2 full baths, designed for comfort and easy living. Enjoy added convenience with a storage unit and separate one-car garage. Step outside and take advantage of resort-style amenities, including a community pool, fishing dock, baseball field, tennis courts, and pickleball courts—something for everyone to enjoy. Even better, the HOA covers all exterior maintenance and the roof, giving you peace of mind and low-maintenance living. Opportunities like this don’t come often—schedule your showing today!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Donna Krumwiede (321-363-6974)
3540 LEGACY HILLS CT, LONGWOOD, FL 32779
$4,499,00018 Days on yellowkey MLS ID: O6408704
Bed: 7 Bath: 8.5 Gar: 4 Liv Area Sq Ft: 12006 Built: 2005Monthly Fee: $885 Tax: $30,230 (2025)Community: Alaqua Lakes Ph 5BSpa: YesSingle Family
Taxes:$30,230
Remarks: A rare opportunity to own one of the most extraordinary estate residences in Alaqua Lakes. Privately positioned behind the exclusive gates of The Enclave at Alaqua Lakes on a 1.2 acre double lot, this exceptional 12,000-square-foot custom Dave Brewer estate offers unparalleled privacy, luxury, and time-honored craftsmanship throughout. A rare achievement for any builder is when their name becomes synonymous with exceptional quality, timeless design, and uncompromising integrity. In Central Florida, the Dave Brewer name on a custom residence represents exactly that distinction, and this estate is a flagship property of his vast portfolio. An astonishing 7 bedrooms(6 on the main level), and 7 full baths with 3 half baths, this residence is designed for both grand-scale entertaining and everyday living, and showcases an extensive list of high-end upgrades. Discover elegant travertine flooring, a professionally designed chef’s kitchen with double ovens, dual Sub-Zero built-in refrigerators, two dishwashers, a six-burner Dacor gas cooktop, an oversized center island with freezer drawers, and an expansive walk-in pantry/prep kitchen complete with additional refrigeration and prep space. The thoughtfully designed floor plan features a dedicated children’s wing with a private play area, an upstairs nanny or guest suite, and a luxurious owner’s retreat with a beverage center, spa-inspired bath, and extraordinary custom walk-in closets. A richly appointed executive office with dual custom workstations and adjoining storage rooms enhances the home’s functionality. Exceptional custom details continue throughout the residence, including extensive built-in cabinetry and a spectacular 1,000-gallon saltwater double-sided aquarium serving as a dramatic focal point within the family room and game room. The outdoor living experience is equally impressive, featuring a gated motor court leadng to an oversized 5 car garage, while the rear boasts a resort-style saltwater pool and spa, expansive pavered lanai and entertaining areas, custom summer kitchen, and lush professionally designed landscaping creating a truly private resort atmosphere. This is a one-of-a-kind luxury offering in one of Central Florida’s most sought-after golf and country club communities. Located just steps from the community’s exceptional amenities, residents of Alaqua Lakes enjoy access to a pavilion, 7-acre park, junior Olympic pool, Har-Tru tennis courts, beach volleyball, basketball courts, multipurpose fields, playground, and social events all within a natural gas community known for its exclusivity and lifestyle. All this and more with incredible proximity to major highways, world-class shopping, dining, attractions, and great schools. This property may be under audio/visual surveillance.
127 SPRINGWOOD CIR #A, LONGWOOD, FL 32750
$100,000514 Days on yellowkey MLS ID: O6271210
REDUCED by $11,900 (10.6%) on 05/26/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 665 Built: 1973 Tax: $979 (2023)Community: Springwood VillageCondo
Taxes:$979
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Discover the perfect downstairs one bedroom, one bath condo conveniently located in Longwood, Florida. Just a short stroll from your favorite dining spots like Starbucks, Bonefish Grill, Pickles Authentic, Chianti's Pizza and near Longwood Farmers Market and quick access to Altamonte Mall, Uptown Altamonte, hospital, beaches, attractions and I-4. This charming condo with new AC 5/25 & a new electric panel 10/25, new water heater 11/25 & offers a spacious living room, dining area, kitchen with refrigerator, dishwasher, range, a back splash & pantry. The large master bedroom has a large walk-in closet. The building sits on the east side of the complex, has a newer roof and there’s lots of parking for guest. Association dues pay for water, sewer, garbage, security, along with exterior maintenance of the building and grounds all for only $370 per month. The condominium has night-time security on premises, you can have peace of mind while enjoying the amenities, including two sparkling pools, tennis and basketball courts, a fitness room, a clubhouse, on-site laundry, and a car wash station with vacuum. Springwood Village offers sturdy all block and stucco construction. Property may be under video/audio surveillance.
Listing Agent: John Herndon (407-252-5736)
811 GREENSHIRE CT, LONGWOOD, FL 32779
$1,349,00057 Days on yellowkey MLS ID: O6399384
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4293 Built: 1989Monthly Fee: $367 Tax: $7,316 (2025)Community: Sweetwater Club Unit 7Spa: YesSingle Family
Taxes:$7,316
Remarks: Welcome to 811 Greenshire Ct, a rare opportunity to own a fully renovated private estate in the heart of Longwood, FL, where luxury, space, and multigenerational living come together on nearly 2 acres. Ideally located just minutes from Wekiva Island, Publix at Shoppes of Sweetwater, and top-rated Seminole County schools, this exceptional 5-bedroom, 4-bath residence offers 4,293 square feet of thoughtfully designed living space with no carpet throughout and a true move-in-ready feel. Designed for today’s lifestyle, this home delivers exactly what buyers are searching for—privacy, flexibility, and high-end upgrades—making it ideal for multigenerational living, extended stays, or long-term value. The standout feature is the approximately 800-square-foot attached multigenerational suite built in 2022, offering complete independence with its own full kitchen, living area, spacious bedroom, additional enclosed flex space with Murphy bed, ADA-compliant bathroom, wheelchair-accessible doors, separate septic system, private propane generator, and a dedicated washer and dryer—perfect for in-laws, guests, or private living quarters. Inside the main home, refinished travertine floors and new wood flooring in every bedroom create a seamless blend of elegance and warmth, complemented by an updated kitchen with refinished cabinetry and newer appliances, a luxurious primary suite with a spa-inspired bath and Roman tub, and a beautifully remodeled guest bath featuring a custom stained-glass window, new tile shower, and updated cabinetry. Hunter Douglas Roman shades are installed throughout, and all windows and doors were replaced between 2021 and 2022, adding both efficiency and peace of mind. The outdoor living experience is equally impressive, featuring a saltwater pool with a variable speed pump and computer-controlled lighting, an enclosed courtyard for added privacy, and an expansive fenced backyard with an additional cleared half-acre—ideal for entertaining, future expansion, or simply enjoying the space. A whole-home audio system extends to the pool, deck, and porch, creating a seamless indoor-outdoor lifestyle. Additional highlights include a heated and air-conditioned garage with epoxy flooring, smart sprinkler system, newer roof, dual-zone HVAC, and a full alarm system. Homes offering this level of land, upgrades, and true multigenerational flexibility in Longwood are rare, making this a standout opportunity for buyers seeking space, luxury, and long-term value. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS WINTER PARK (407-545-6430)
Listing Agent: Gina Hutchinson (386-793-4262)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.