Location: Longwood
Do Not Show Listings
1742 FIFESHIRE CT, LONGWOOD, FL 32779
$1,275,000Listed 04/08/2026 12:34PM MLS ID: O6396719
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4053 Built: 1993Monthly Fee: $65 Tax: $10,135 (2024)Community: Markham MeadowsSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,135
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Welcome home to your own immaculate sparkling screened in pool home nestled in a cul-de-sac in desirable Markham Meadows. This spectacular over one acre, 5 bedroom, 6 bathroom home has many features. The Primary master suite is privately situated to itself and showcases a sitting area in front of the wood burning fireplace and overlooking the pool, a large walk-in closet, and an ensuite bath complete with an oversized hydro-massage bath and separate shower stall and a private water closet. A separate office with built-ins which offers the perfect environment for working from home or pursuing personal projects. There is a wet bar, 3 wood burning fireplaces located in the family room, living room and master bedroom. The home has all tile and hardwood flooring throughout, an oversized 3 car garage. Numerous updates were made including installation of solar panels for low monthly utility cost, remodeled master bathroom and 2 guest bathrooms, installed exterior pool bathroom, remodeled the outdoor kitchen, and replaced the patio, pool deck, and porch tiles. A MUST SEE - GUEST/MOTHER-IN-LAW SUITE WITH KITCHENETTE, BATHROOM, WITH PRIVATE INTERIOR & EXTERIOR ENTRANCES. A great home for entertaining. A must see to appreciate. Wekiva Island is nearby as is an entrance to I-4 which will take you North to Daytona Beach where it terminates into I-95 or South to Downtown Orlando, past the attractions area and to Tampa where it terminates into I-75. What's Around & Near Markham Meadows? Grocery-Restaurants: Lake Mary Collection Mall: Altamonte Mall Hospital: Orlando Health South Seminole Hospital Attractions: Planet Obstacle & Wekiva Island Get Out & Play: Cross Seminole Trail Local Hang Out: Casey's Sports Bar Closest Beach: New Smyrna Beach
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Melissa Dietz Levering (321-388-4268)
1000 CROOKED OAK COURT, LONGWOOD, FL 32779
$639,90056 Days on yellowkey MLS ID: O6378220
REDUCED by $19,100 (2.9%) on 04/02/2026
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. Sweetwater Oaks!! Outstanding 4BD 3 FULL Baths! Tropical Pool. Open concept, single-story home with plenty of natural light. Large, Bright, & Beautiful Kitchen with Stainless steel appliances and an eat-in nook. New Flooring in 3 bedrooms (2026), New Roof (Dec 2025), New Pool pump (2024), New AC Compressor (2024).Pool Resurfaced (2019). Laminate & Tile flooring throughout. Superb Family Room with Fireplace. Oversized Living & Spacious Dining Room! Corner lot on over 1/2 acre. On a quiet double cul-de-sac. Large fenced backyard, move-in ready. Enjoy the Sweetwater Oaks amenities, with included access to Lake Brantley. Great Seminole County schools!! Hurry! Won't last!
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Caroline Moffitt Lawton (407-670-9797)
506 FREEMAN ST, LONGWOOD, FL 32750
$590,00062 Days on yellowkey MLS ID: O6378867
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3459 Built: 1998Monthly Fee: $51 Tax: $4,627 (2025)Community: Longwood PlantationSpa: NoSingle Family
Taxes:$4,627
Elementary School: Longwood Elementary
High School: Lyman High
Tax Year: 2025
Middle School: Greenwood Lakes Middle
Remarks: This impressive and spacious 5–6 bedroom, 4-bath pool home offers over 3,500 square feet of beautifully designed living space on a premium private conservation lot in a quiet, tree-lined neighborhood. The flexible open floor plan features dramatic living and dining rooms, a stunning remodeled cook’s kitchen with rich wood cabinetry, granite counters, breakfast bar, and eat-in space, all open to a welcoming family room. Additional living spaces include an upstairs bonus room and an office or optional 6th bedroom, ideal for today’s lifestyle. The private split-plan primary suite is oversized with a sitting area, large walk-in closet, and a luxurious updated bath with double granite vanity, soaking tub, and generous shower. Secondary bedrooms are well sized with walk-in closets, and three offer direct bath access. Enjoy outdoor living on the screened covered porch overlooking the solar-heated pool with waterfall, DiamondBrite surface, and automatic sweep—perfect for relaxing or entertaining. This home is loaded with upgrades and extras including vaulted ceilings, brick fireplace, porcelain tile, stainless appliances, crown molding, recessed lighting, California closet system, solid-surface counters, security system, water softener, R-30 attic insulation, 2020 architectural shingle roof, double-pane windows, sprinkler system, new water heater, new pool pump, new upstairs and downstairs A/C units, re-piping of the home and much more. The spacious 2-car garage offers ample storage and workspace. Community playground included. Truly a must-see home—schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE 2 REALTY (407-393-5901)
Listing Agent: Rick Brown (407-393-5901)
302 NEEDLES TRL, LONGWOOD, FL 32779
$514,00035 Days on yellowkey MLS ID: O6386794
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2147 Built: 1981Monthly Fee: $23 Tax: $2,619 (2024)Community: Wekiva Club Estates Sec 08Spa: YesSingle Family
Taxes:$2,619
Elementary School: Wekiva Elementary
High School: Lake Brantley High
Middle School: Teague Middle
Remarks: ***ROOF WILL BE REPLACED WITH A FULL PRICED OFFER*** Welcome to your private pool retreat in Wekiva Club Estates, one of the most sought-after communities in Longwood. This 4-bedroom, 2-bath home offers over 2,100 square feet of well-designed living space, combining comfort, functionality, and the Florida lifestyle buyers are searching for. From the moment you walk in, you’re greeted with natural light, a spacious layout, and multiple living areas that create the perfect balance between everyday living and entertaining. The split-bedroom floor plan provides privacy, with the primary suite tucked away and featuring direct access to the pool, dual vanities, a walk-in shower, and a generous walk-in closet, while the additional bedrooms are positioned on the opposite side with convenient access to a full pool bath. Step outside and experience where this home truly stands out—a screened-in pool with paver decking and a fully fenced backyard that creates your own private outdoor oasis, ideal for relaxing evenings, weekend gatherings, or enjoying Florida living year-round. The kitchen is equipped with stainless steel appliances, a breakfast nook, and easy flow into the main living spaces, making it both functional and inviting. Beyond the home itself, the location delivers a lifestyle that’s hard to match, with close proximity to Wekiva Springs State Park, Wekiva Island, and Wekiva Golf Club, along with access to miles of walking and biking trails, parks, and community amenities. You’re also conveniently located just minutes from shopping, dining, and major roadways, with easy access to Downtown Orlando and the airport. Homes in Wekiva offering this combination of space, outdoor living, and location are always in demand, especially for buyers looking to enjoy both privacy and community in one of Central Florida’s most established neighborhoods. If you’ve been searching for a pool home in Longwood that delivers lifestyle, value, and long-term appeal, this is one you won’t want to miss
Listing is courtesy of: EXP REALTY LLC (407-641-2808)
Listing Agent: Todd Schroth, Pa (407-641-2808)
280 SPRINGSIDE RD S, LONGWOOD, FL 32779
$626,64088 Days on yellowkey MLS ID: O6372736
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2436 Built: 1987Monthly Fee: $180 Tax: $6,507 (2024)Community: The SpringsSingle Family
Taxes:$6,507
Elementary School: Sabal Point Elementary
Remarks: **** Price Reduction*** Floor Plan: Excellent layout with the master bedroom downstairs and a large upstairs loft that can serve as a second master suite. Amenities: Screened private swimming pool with convenient access from three rooms (living room, master bath, guest bath). Interior Highlights: Vaulted ceilings, abundant natural light via skylights and transom windows, ceramic tile throughout, grand living room with fireplace, and a large dining room. Updates & Maintenance: Features a brand new AC (2020) and a replumbed system. The home also includes an inside laundry room, a 2-car garage with a generator hookup panel, and workbench space. Community Amenities (The Springs): Enjoy exclusive access to Seminole County's "best kept secret," which includes: 100 acres on the Little Wekiva River Sandy beach and crystal clear swimming area Clubhouse and community pool Sports courts (basketball, tennis, pickleball) Playground, nature trails, and horse stables
Listing is courtesy of: FIDICITY REALTY INC (772-678-8158)
Listing Agent: Dr April Joh Johnson (813-545-9218)
305 PALM SPRINGS DR, LONGWOOD, FL 32750
$475,00017 Days on yellowkey MLS ID: O6392490
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2391 Built: 1956 Tax: $1,784 (2025)Community: Sanlando SpringsSingle Family
Taxes:$1,784
Elementary School: Altamonte Elementary
Middle School: Milwee Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained and thoughtfully updated 3-bedroom, 2-bath home, ideally situated on a desirable almost 1/2 acre corner lot with a circular driveway and former golf-front setting. Directly across the street, the former Rolling Hills Golf Course has been transformed into the newly reestablished Rolling Hills Community Park, offering playgrounds, open green space, and a relaxing outdoor setting for recreation and neighborhood enjoyment. Best of all—NO HOA! This home showcases a stunning renovation with carefully curated, high-end designer finishes and energy-efficient upgrades throughout. Step inside through elegant double front doors with leaded glass to an inviting open-concept floor plan. The bright, eat-in kitchen is the heart of the home, featuring quartz countertops, a glass subway tile backsplash, a spacious center island with seating, and custom soft-close KraftMaid cabinetry with seeded glass accents, pull-out shelves, and drawers. Enjoy upscale appliances, including a convection oven with built-in air fryer, all complemented by elegant 20” x 20” Italian ceramic tile flooring (minimal grout lines) flowing seamlessly through the kitchen, family room, and foyer—creating both beauty and easy maintenance. Plantation shutters add timeless elegance and privacy, while energy-efficient double-pane windows enhance comfort throughout. The formal living room—currently used as a music room—features crown molding, rich Brazilian hardwood flooring, and two skylights that fill the space with natural light. Built-in shelving and pocket French doors add both charm and versatility. The spacious family room with vaulted ceilings opens effortlessly to the kitchen, creating the perfect gathering space. A thoughtfully designed addition provides an interior laundry room and an impressive oversized walk-in closet with built-in cabinetry, adding approximately 411 sq ft of additional living space. Step outside and enjoy Florida living at its finest. A large paver patio is perfect for relaxing or entertaining, with French doors creating a seamless indoor-outdoor flow. The private backyard is fully enclosed with a PVC fence and two gates, and features lush, mature landscaping with your own fruit trees—including fig, lemon, bay leaf, tangerine, and mulberry. Additional highlights include a large storage shed and a RainBird 6-zone irrigation system. Conveniently located near SunRail, I-4, Altamonte Mall, Seminole Wekiva Trail, top-rated Seminole County schools, medical facilities, dining, and year-round Longwood community events. NOTE: Primary Bedroom/Bathroom is going to be renovated to merge sinks into the bathroom. 3rd Bedroom Closet is being restored. Schedule your private showing today—this one-of-a-kind home offers the perfect blend of style, comfort, and location!
Listing is courtesy of: WATSON REALTY CORP (407-332-6000)
Listing Agent: Deborah Perry, Pa (407-310-3015)
1741 ALVARADO CT, LONGWOOD, FL 32779
$1,100,000Listed 04/08/2026 8:23AM MLS ID: O6387709
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4265 Built: 1984Monthly Fee: $104 Tax: $11,657 (2025)Community: Wingfield Reserve Ph 1Single Family
Taxes:$11,657
Remarks: Nestled within the prestigious Wingfield Reserve community on a sprawling 1.5+ acre private lot, this custom-built home delivers the pinnacle of Florida luxury living with 4 bedrooms and 4 baths all on one story — within one of Seminole County's most coveted top-rated school districts. From the moment you arrive, the circular drive and lush landscaped grounds set the stage for something truly special. Step through the front entry and into soaring 14-foot volume ceilings, where custom crown moldings and a seamless blend of rich hardwood and stunning marble tile floors create a airy welcoming environment. The heart of the home is a living room/ kitchen combination anchored by a dramatic floor-to-ceiling brick wood-burning fireplace, the living room also features a custom built in entertainment center and wet bar. The large kitchen is equally as impressive, offering two islands and two sinks with a breakfast bar and a sun-drenched breakfast nook that frames beatufiul views of the private backyard and pool area. Down the hall there is a dedicated office with custom built-ins adding versatility, ideal as a home office, study or fifth bedroom as well as three guest bedrooms and 3 full baths (one of the guest baths allows direct access in/out to the pool area). Additional spaces include a large formal dining room, indoor laundry room as well as separate family room. On the other side of the home, retreat to the primary suite, where warm wood floors and a spa-inspired bath — complete with Jacuzzi tub, walk-in shower, and separate vanities as well as a large walk-in closet. Outside, the pool and spa gleam within a screened lanai, creating a resort-style sanctuary perfect for entertaining. A 3-car side-entry garage and circular drive round out a property that is as functional as it is breathtaking. This is Wingfield Reserve living at its finest — schedule a viewing today!
Listing is courtesy of: EXIT REAL ESTATE RESULTS (352-933-0018)
Listing Agent: Kyle Petteway (407-461-9141)
6 ROBINWOOD DR, LONGWOOD, FL 32779
$789,99910 Days on yellowkey MLS ID: V4948197
REDUCED by $55,001 (6.5%) on 04/08/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 2678 Built: 1979 Tax: $7,329 (2024)Community: RobinwoodsSingle Family
Taxes:$7,329
Elementary School: Woodlands Elementary
High School: Lake Mary High
Middle School: Markham Woods Middle
Remarks: Best value on prestigious Markham Wood Road — this stunning 5 bed | 4 bath | 3 car garage home has been completely renovated from top to bottom, including a brand new AC system, and is truly move-in ready. From the moment you arrive, a lovely enclosed front courtyard with iron fencing and double front doors sets the tone for what awaits inside: a spacious foyer opening to a grand formal living room with a dramatic rock wood-burning fireplace, a private office with French doors overlooking the courtyard, and a large family/dining room flowing seamlessly into a chef's kitchen featuring all-new cabinetry, countertops, stainless steel appliances, and an oversized bar seating 4+. The home offers incredible flexibility with a dedicated in-law suite (private bedroom, bath, and living area), a shared Florida room, an additional guest room with private entry and its own bath, a home office, a formal dining room, and an oversized inside utility room — all finished with porcelain tile floors throughout and fresh interior paint. The primary suite features a walk-in closet, while two additional bedrooms are privately situated on their own wing. Outside, enjoy a freshly power-washed exterior, mature landscaping, and over an acre of land with an oversized 3-car garage and ample parking — all within the sought-after Seminole County school district and an unbeatable location.
Listing Agent: Anne Hall (407-748-6789)
342 COBLE DR, LONGWOOD, FL 32779
$545,00064 Days on yellowkey MLS ID: O6379074
REDUCED by $3,000 (0.5%) on 04/08/2026
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
Remarks: One or more photo(s) has been virtually staged. Welcome to your own private poolside oasis in the heart of Wekiva Hills! This stunning 3BR/2BA home delivers immediate wow-factor with soaring ceilings, skylights that bathe the interior in natural light, and a dramatic stone fireplace that anchors the living space with warmth and character. The charming formal dining room overlooks the living room, creating the perfect backdrop for memorable dinners and effortless entertaining. The beautifully updated kitchen blends style and function with modern finishes, a spacious walk-in pantry, and a bright, cheerful breakfast nook. Upstairs, the airy primary suite feels like a retreat—complete with additional skylights, a versatile sitting area, generous closet space, and an updated ensuite bath. Step outside and the magic continues. A delightful screened patio opens to your sparkling private pool surrounded by lush landscaping. A private rear gate leads directly to a serene walking trail—ideal for morning strolls, evening unwinding, or simply enjoying nature right from your backyard. Roof 2016. AC 2020. Electrical 2024. Pool equipment 2023. New Flooring 2023. Kitchen fully remodeled 2016. Fence installed 2023. With thoughtful updates, open design, and peaceful setting, this Wekiva Hills gem offers the true Florida lifestyle. Don’t miss your chance—schedule your private tour today!
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Veronica Parker (407-718-6983)
2878 MARKHAM WOODS RD, LONGWOOD, FL 32779
$7,500,000236 Days on yellowkey MLS ID: O6335062
Bed: 10 Bath: 15.0 Gar: 17 Liv Area Sq Ft: 25706 Built: 2003 Tax: $75,173 (2024)Community: N/ASpa: YesSingle Family
Taxes:$75,173
Remarks: One or more photo(s) has been virtually staged. Behind electronic gates and a newly built guard house, a rare sense of arrival unfolds across 7.61 high and dry acres a private luxury compound that feels worlds away while remaining conveniently connected to Central Florida’s major business, aviation, and lifestyle corridors. With no HOA and no community restrictions, The Estate at Markham Woods offers a level of freedom, privacy, and scale that is increasingly difficult to replicate. Designed as a true estate compound, the property is anchored by a 12,000sf European inspired main residence and supported by a 2,300sf guest house, an 800sf private cottage, and a 5,040sf fully air conditioned car barn with soaring 20ft ceilings. Seventeen garage spaces, RV accommodations, a private fueling station, and helicopter access reflect an exceptional level of infrastructure and versatility rarely found in a single residential offering. The main residence blends architectural presence with everyday livability. Six bedrooms, eight full baths, and three half baths are arranged across two levels and connected by a dramatic curved staircase and private elevator. Five gas fireplaces, stone accents, custom millwork, and designer lighting create a warm yet refined atmosphere throughout. Flexible living spaces include a primary suite with adjacent nanny room, library, private office, hobby studio, game room, upstairs den, gym, two laundry rooms, pet wash station, and a distinctive treehouse-style lounge that offers a unique retreat within the home. At the heart of the residence, the chef’s kitchen overlooks the tropical oasis pool area and is designed for gathering and entertaining,. Featuring Thermador gas cooking, Dacor ovens, SubZero refrigeration, Bosch dishwashers, warming drawers, beverage coolers, custom cabinetry, and an expansive prep island ideal for both daily use and large-scale hosting. Guest accommodations are thoughtfully separate, offering comfort and privacy for multigenerational living or visiting guests. The guest house includes three ensuite bedrooms, a full kitchen, half bath, and two-car garage, while the private cottage provides a bedroom, bath, kitchenette, and laundry ideal for staff, wellness, music studio, or a secluded retreat. Outdoor living mirrors a private resort, with expansive manicured lawns made for entertaining or quiet relaxation, a heated saltwater pool, pavilion, gazebo and family friendly amenities including a zip line and swings for little ones. Two fully fenced dog parks provide safe play areas for furry family members. Wellness offerings extend indoors with a resistance pool, spa, and steam shower for year-round enjoyment. The air conditioned car barn is a standout feature, offering 20ft ceilings, office suite, kitchenette, half bath, and capacity for ten or more vehicles, complemented by a covered RV bay with water and electric hookups, flexible event space, and helicopter pad. Recent upgrades ensure the estate is turnkey and built for long-term ownership, including fiber-optic gigabit internet, five new generators, sixteen new HVAC systems, three new water heaters, new roofs on the guest house, cottage, and car barn, and a newly screened front porch. Ideally located near major highways and private airports, The Estate at Markham Woods represents a rare legacy level opportunity for buyers seeking a secure, private luxury compound with unmatched acreage, infrastructure, and accessibility in one of Florida’s most desirable regions.
Listing is courtesy of: RE/MAX CENTRAL REALTY (407-333-4400)
Listing Agent: Amanda J Miller (321-303-9424)
1040 ARDEN ST, LONGWOOD, FL 32750
$465,000188 Days on yellowkey MLS ID: O6349085
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2374 Built: 1967 Tax: $1,954 (2024)Community: Sanlando SpgsSingle Family
Taxes:$1,954
Remarks: One or more photo(s) has been virtually staged. If no HOA and outdoor space is what you are looking for, look no further! This spacious ranch-style home is located on a large lot with plenty of room for all of your toys. Inside, this home has 4 bedrooms (potential for 5) and 2 bathrooms. The main living room leads to a large dining area, an updated, bright and airy kitchen, and a large family room with a brick fireplace overlooking the expansive back yard. The interior laundry room leads to a two-car garage, a secluded 4th bedroom, and an additional flex room that would be perfect for a secluded home office or home gym. Outside, there is room for cars, boats, rv's, or whatever you need. The asphalt parking pad/sport court behind the double-gate privacy fence has a metal carport canopy for vehicles or a covered entertainment space. This home has a country feel right in the city, with no HOA. Come see it today!
Listing is courtesy of: CARLISLE REALTY, LLC (407-557-4024)
Listing Agent: James Rouadi (407-557-4024)
104 STONEBROOK CT, LONGWOOD, FL 32779
$895,00033 Days on yellowkey MLS ID: O6386029
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3575 Built: 1982Monthly Fee: $108 Tax: $9,000 (2025)Community: Sweetwater OaksSingle Family
Taxes:$9,000
Middle School: Rock Lake Middle
Remarks: Come see this beautiful 3500+ square foot split level 5 bedroom, 3 bathroom Contemporary home on a cul-de-sac in desirable Sweetwater Oaks community. The home features an open concept kitchen and family room combination with vaulted ceilings, beautiful granite countertops, island with sink, dishwasher, two level countertop, and eat-in kitchen breakfast nook. The family/great room features a custom stone fireplace with built-in shelving. It opens up to the screened pool area with three panel sliding glass pocket doors that slide into wall creating a larger opening. The living room and dining room open concept combination features vaulted ceilings, sliding glass door, multiple windows with a view overlooking the screened in pool. Three bedrooms with a loft and bathroom located on the second floor. The 5th bedroom can also be used as an office or den. The primary suite is located on the first level. Smart outdoor controlled lighting installed for security, special events, or holidays. Enjoy the outdoors in this beautiful tree lined neighborhood community with private access to Lake Brantley, boat dock, basketball court, playground, beach volleyball, and tennis courts.
Listing is courtesy of: JERRY MCGEE REALTY, LLC (407-765-9147)
Listing Agent: Jerry Mcgee, Jr (407-765-9147)
301 SWEETWATER CLUB CIR, LONGWOOD, FL 32779
$1,250,00014 Days on yellowkey MLS ID: O6393809
1 Days Off yellowkey (back on 4/4/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5230 Built: 1979Monthly Fee: $367 Tax: $6,392 (2024)Community: Sweetwater Club Unit 1Spa: NoSingle Family
Taxes:$6,392
Remarks: Under contract-accepting backup offers. Some homes are built. Others are crafted with intention, elevated by time, and destined to leave a lasting impression on every soul that crosses the threshold. 301 Sweetwater Club Circle is unequivocally the latter. Nestled behind the private gates of one of Longwood's most prestigious luxury gated communities, this extraordinary estate sits on more than one acre of lush, manicured grounds and delivers a living experience that is nothing short of spectacular. The corner lot positioning affords commanding presence, maximum privacy, and grounds that feel genuinely estate-like in every direction a rare and coveted combination that sets this property apart from the very first glance. From the moment you pass through the gates and pull into the estate's signature porte-cochère, the home announces itself with unmistakable confidence. Exquisitely crafted and utterly one-of-a-kind, this covered motor court entrance rivals the arrival experience of any modern luxury hotel. Coming home here is not routine. It is a celebration, a daily reminder that you have arrived somewhere truly extraordinary and there is simply nothing else like it in the market. Spanning over 5,230 square feet of thoughtfully designed living space, this residence exudes old-world elegance and timeless architectural character at every turn. Four bedrooms, four full bathrooms, a powder room, and an oversized three-car garage deliver both grandeur and real-world functionality for today's most discerning buyer. The primary suite is a sanctuary unlike any other soaring double-height ceilings open to a private loft that floats above the room, offering limitless possibilities as a reading retreat, home office, or personal escape. A rare dual master configuration within the main home creates a seamless mother-in-law suite opportunity, ideal for multigenerational living, extended guests, or simply the elevated sense of privacy that a home of this caliber deserves. Two interior bars position this residence as the ultimate gathering place for family and friends. Whether hosting an intimate dinner party or a landmark celebration, the layout flows with effortless grace and the old-world ambiance delivers a mood and atmosphere that simply cannot be manufactured. This is a home that people remember long after the evening ends and talk about long after they leave. Step outside and the estate truly reveals its full character. A sprawling private pool anchors the outdoor living space, flanked by a dedicated pool cabana complete with a full bathroom an amenity more commonly reserved for five-star resorts than private residences. A handcrafted brick gazebo, framed by lush mature tropical landscaping and sweeping manicured grounds, creates the perfect setting for al fresco dinners under a painted Florida sky or quiet mornings with coffee in a backyard that feels entirely like your own private resort. Sweetwater Club is one of Longwood's most coveted luxury gated communities, defined by its oversized estate lots, majestic mature tree canopy, and an atmosphere of quiet exclusivity that cannot be replicated. Residents enjoy access to tennis courts and pickleball courts within a beautifully maintained enclave ideally positioned near top-rated Seminole County schools, premier dining, and the very best of Central Florida living. Homes of this stature, in communities of this caliber, do not come along twice. Schedule your private showing today and experience the property.
Listing is courtesy of: THE NEWCOMER GROUP (904-599-5633)
Listing Agent: Ryan Raymond (904-315-4022)
1665 GRANGE CIR, LONGWOOD, FL 32750
$415,0003 Days on yellowkey MLS ID: O6396483
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2189 Built: 1986 Tax: $3,792 (2024)Community: Tiberon Hills Ph 3Spa: YesSingle Family
Taxes:$3,792
Remarks: Expect to be impressed with this beautiful 3-bedroom, 2-bathroom home featuring stunning upgrades throughout. As soon as you walk in, you’re greeted by a spacious living and dining room combination, perfect for both entertaining and everyday living. The home boasts a gorgeous kitchen that opens to a cozy family room, complete with a stylish bar area that is ideal for hosting guests or relaxing at the end of the day. Step outside and discover your own backyard oasis, featuring an above-ground spa, perfect for unwinding and enjoying Florida living year-round. Conveniently located near major highways, shopping, and highly sought after schools, this home offers both comfort and convenience. This one won’t last long, so schedule your showing today!
Listing is courtesy of: LEGENDS REALTY (407-333-1010)
Listing Agent: Maria Stinson (407-802-7595)
100 COUNTRYSIDE DR, LONGWOOD, FL 32779
$650,0001 Day on yellowkey MLS ID: O6392628
0 Days Off yellowkey (back on 4/7/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1848 Built: 1973Monthly Fee: $165 Tax: $5,456 (2025)Community: Sweetwater Oaks Sec 02Single Family
Taxes:$5,456
Remarks: Under contract-accepting backup offers. Welcome to the experience of high-end living at 100 Countryside Drive, a fully reimagined designer residence in the heart of Sweetwater Oaks. Recently completed by an interior designer, this four-bedroom, two-bath split-plan home delivers the best of modern luxury, with finishes and detail typically found in much higher-priced properties. Step inside to discover bright, open-concept living spaces filled with natural light from energy-efficient windows. Entertain or unwind around the modernized fireplace, formal dining area, or flexible family room—all centered on a D’Nook-designed gourmet kitchen featuring soft-close cabinetry, premium integrated appliances, a breakfast nook, custom lighting, and a signature architectural hood. The stone island serves as a stunning focal point, perfect for casual meals or elegant gatherings. Every surface reflects designer-level craftsmanship, from the custom countertops and high-grade luxury vinyl plank flooring to bespoke wood accents and cabinetry. The expansive owner’s suite brings spa-like serenity with dual sinks, a walk-in shower, freestanding tub, and a truly custom retreat atmosphere. Outside, enjoy nearly half an acre of outdoor living and a resurfaced sparkling pool with ample space for entertaining. Major updates ensure lasting peace of mind, including a newer roof (2023) and significant system upgrades completed in 2026. Style, charm, and substance converge here—this home is absolutely perfect. As a Sweetwater Oaks resident, you’ll enjoy private Lake Brantley access for boating, plus community tennis, pickleball, volleyball, and basketball courts, two playground parks, a private beach and clubhouse, and top-rated Seminole County schools. Ideally located just 20 minutes from Downtown Orlando and 40 minutes from Disney or the coast, this home defines refined Florida living at its best.
Listing is courtesy of: GALLERY PROPERTIES INTERNATIONAL (407-340-8487)
Listing Agent: Reynaldo Sanchez Bravo (814-852-8084)
1949 DEERVIEW PL, LONGWOOD, FL 32750
$798,0006 Days on yellowkey MLS ID: O6395646
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3498 Built: 2002Monthly Fee: $120 Tax: $4,966 (2024)Community: Hidden CoveSpa: YesSingle Family
Taxes:$4,966
Remarks: Don’t miss this stunning Mediterranean estate home in the highly sought-after gated community of Hidden Cove. This spacious residence features 4 bedrooms, including a dedicated office, 3.5 bathrooms, and an upstairs bonus room. The open floor plan showcases a beautifully finished open-concept kitchen, formal living and dining rooms, and a welcoming family room designed for both everyday living and entertaining. The owner’s suite offers a private retreat with a sitting area overlooking the pool and lanai, an expansive walk-in closet with custom shelving and separate dressing area, and a luxurious en-suite bath. Upstairs the oversized bonus room is perfect for movie nights and game days, complete with a wet bar, powder bath, and dedicated AC unit. Step outside to enjoy the screened-in swimming pool, large covered lanai with built-in grill, and generously sized backyard. Additional highlights include tile flooring in main living areas, soaring 15-foot tray ceilings, crown molding, plantation shutters, custom draperies, built-ins and decorative niches, a paver driveway, tile roof, and 3 car garage. Conveniently located to shopping, restaurants, and I-4.
Listing Agent: Katie Morrison (407-421-5025)
432 WILDERNESS DR, LONGWOOD, FL 32779
$735,00014 Days on yellowkey MLS ID: O6393288
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2832 Built: 1981Monthly Fee: $46 Tax: $6,626 (2024)Community: Cypress Landing At Sabal PointSpa: NoSingle Family
Taxes:$6,626
Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged for visual inspiration. Welcome to your dream home in the highly sought-after Sable Point community of Longwood, Florida—where charm, space, and thoughtful upgrades come together in all the right ways. This beautifully maintained five-bedroom, three-bath brick home sits proudly on a spacious corner lot, surrounded by mature trees and the kind of peaceful, established neighborhood setting buyers are always hoping to find. From the moment you arrive, you’ll feel that warm, inviting “this is the one” energy. Inside, you’re greeted with timeless finishes including granite countertops, plantation shutters, a farmhouse sink, rich wood flooring, and elegant wainscoting that flows throughout the main living areas and front bedrooms—adding just the right touch of character and sophistication. The kitchen is fully equipped with upgraded LG appliances, blending style and function for everyday living and effortless entertaining. The layout is thoughtfully designed for real life—whether you're hosting family gatherings, raising a busy household, or planning for multi-generational living. A standout feature is the private primary suite addition, offering his and hers walk-in closets, its own ensuite bath with a garden soaking tub, walk-in shower, direct access to the screened outdoor pool, and separation from the main living areas—perfect for next-gen living, guests, or simply a quiet retreat at the end of the day. Natural light pours in through skylights, brightening the spacious living areas, while the family den steals the show with its soaring cathedral ceilings, exposed beams, and a cozy wood-burning fireplace—creating a warm, inviting space that feels like the heart of the home. Upstairs, you’ll find a fun bonus room over the garage—ideal for a teen hangout, game room, or creative escape. Practical features haven’t been overlooked either, with a generously sized laundry room designed to keep things running smoothly behind the scenes. Step outside and you’ve got your own Florida oasis. The screened-in pool has been recently resurfaced, and the pool deck features a durable shark coating—ready for sunny afternoons and weekend get-togethers. The large yard gives you plenty of room to spread out, play, or entertain. And yes—there’s even a built-in doggy shower, because every member of the family deserves a little luxury. This home is not just charming—it’s smart, too. Enjoy energy savings with solar panels, a water softener system, a whole-home generator that will convey, and the peace of mind that comes with a brand-new roof completed within the past year. Located just minutes from **Wekiwa Springs State Park**, you’ll have easy access to kayaking, scenic trails, and some of Central Florida’s most beautiful natural surroundings—perfect for those who love an active, outdoor lifestyle. Along with top-rated schools, nearby parks, and tree-lined streets, this home offers that rare blend of comfort, convenience, and character. If you’ve been searching for space, flexibility, and a home that truly grows with you… this one is ready to welcome you home.
Listing is courtesy of: REALTY ONE GROUP MAGIC CITY (407-589-9080)
Listing Agent: Jory Williams (501-951-0799)
3138 WINDING PINE TRL, LONGWOOD, FL 32779
$1,349,0002 Days on yellowkey MLS ID: O6396505
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3739 Built: 2000Monthly Fee: $353 Tax: $9,522 (2024)Community: Alaqua LakesSpa: YesSingle Family
Taxes:$9,522
Remarks: Elegant custom-built Maroon home situated on a sought-after golf-front homesite in Seminole County's premier 24-hour guard-gated golf community of Alaqua Lakes. This IMPECCABLY-KEPT estate features numerous recent upgrades and enhancements, including a REPLACED TILE ROOF, newer A/C units and water heaters, updated pool equipment, new kitchen appliances, and a beautifully remodeled primary bath. This incredibly open and airy floorplan showcases soaring ceilings with detail abounding, inviting guests to a shimmering pool and massive covered lanai with tranquil golf vistas. Arrive at the oversized courtyard entry with brick paver drive, and guests are greeted with double glass front doors. Upon entry, soaring ceilings and an abundance of natural light showcase the inviting floor plan. The foyer, living room, and dining room set the stage with captivating views of the golf course, while the kitchen opens up to the family room and massive covered lanai overlooking the sparkling pool(resurfacing pending 4/2026). The primary bedroom is privately nestled unto itself and features a remodeled spa-quality bath and dual walk-in closets. The office has its own closet and can make for a 4th bedroom on the main level if needed, while the other 2 bedrooms are situated across the home and share an updated frameless glass shower and bath. Upstairs, a bonus room with private full bathroom and walk-in closet makes for the ultimate in living space flexibility. The oversized 3 car garage with high ceiling offer copious storage for all life's incidentals. As a resident of Alaqua Lakes, you'll have access to a unique 7-acre community park with an open-air pavilion, multipurpose field, tennis courts, and more—all just minutes from top-rated schools, upscale shopping, dining, business centers, 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)
741 LONGDALE AVE, LONGWOOD, FL 32750
$355,0005 Days on yellowkey MLS ID: O6395867
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1490 Built: 1962 Tax: $2,058 (2025)Community: LongdaleSingle Family
Taxes:$2,058
Elementary School: Highlands Elementary
High School: Winter Springs High
Remarks: Beautifully Maintained Pool Home – No HOA! This inviting pool home blends comfort, style, and updates throughout – plus the freedom of no homeowners association. Freshly painted interior with a bright, welcoming feel, New appliances in the kitchen with solid wood cabinetry and pull-out drawers Newly resurfaced pool (2017 - 2025) – sparkling and ready for year-round enjoyment,New ceiling fans.bathrooms were remodeled 2021. Expansive screened pool deck ideal for entertaining or relaxing outdoors,Updated master bath with modern finishes Air handler replaced i 2019 .Master suite with sliding glass doors opening to the pool and patio Large backyard shed for storage plus a side workshop for hobbies or projects for peace of mind Fantastic Location: Near major roads 17-92 and 434, just 10 minutes to I-4, close to hospitals, restaurants, shopping, and more. Don’t miss the opportunity to own this move-in ready pool home in one of the most convenient areas of Central Florida!
Listing is courtesy of: INVESTOR'S REAL ESTATE LLC (407-688-4355)
Listing Agent: Patty Perez Renteria (407-927-4731)
1386 S RIDGE LAKE CIR, LONGWOOD, FL 32750
$535,0006 Days on yellowkey MLS ID: O6383292
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2263 Built: 1986Monthly Fee: $45 Tax: $5,740 (2024)Community: NorthridgeSpa: NoSingle Family
Taxes:$5,740
Remarks: *** MULTIPLE OFFERS **** RARE FIND in the sought out Longwood community of Northridge. This show stopping POOL HOME is filled with character and thoughtful updates, offering architectural charm you don’t often see. From the moment you arrive, the curb appeal sets the tone . . . welcoming, established, and full of personality. Inside, skylights and high ceilings with exposed beams bring in natural light and warmth, while a cozy wood burning fireplace anchors the main living space. Large glass slider doors frame views of the pool and backyard, creating a seamless indoor-outdoor flow. The functional SPLIT FLOOR-PLAN offers the best of both worlds, with the primary suite privately positioned on one side and three generously sized bedrooms on the other . . . ideal for multi-generational living, guests, or flexible space needs. So many updates to appreciate. BRAND NEW KITCHEN (2026) with ceiling-height cabinetry, quartz countertops, soft-close drawers, updated lighting, and a built-in bar pantry. NEW FLOORING in the kitchen and laundry (2026), FRESH INTERIOR PAINT in the main areas, updated fixtures (2026), and a fully updated bathroom. Major systems are covered with a NEW AC (2024) and NEWER ROOF (2020). The primary suite offers direct access to the pool deck, dual vanities, pocket doors for added privacy, a large walk-in closet, and a custom walk-in shower. Step outside to your PRIVATE BACKYARD RETREAT with a LARGE SOLAR-HEATED POOL, perfect for year-round living. The secondary bathroom also offers direct pool access for added convenience. An EV-READY garage adds a modern touch. Located just minutes from Altamonte Mall and Cranes Roost Park, with easy access to Interstate 4, commuting to Downtown Orlando, Winter Park, and surrounding areas is simple and convenient. Zoned for Seminole County Public Schools. This is the kind of home that blends charm, function, and updates in a way that just feels right and is ready for its next owner to enjoy from day one.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Christine Smith (407-972-0404)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.