Location: Longwood
Do Not Show Listings
300 E SWEETWATER CREEK DR, LONGWOOD, FL 32779
$565,00046 Days on yellowkey MLS ID: O6389594
REDUCED by $10,000 (1.7%) on 04/21/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2074 Built: 1976Monthly Fee: $54 Tax: $2,650 (2024)Community: Sweetwater Oaks Sec 05Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,650
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: ***NO INCOME VERIFICATION*** with preferred lender. Located in one of Longwood’s most established and highly sought-after communities, Sweetwater Oaks, this beautifully updated home offers the perfect blend of modern upgrades, spacious living, and an incredible lifestyle. ***HUGE LOT 1.25 acres*** Thoughtfully renovated for comfort and peace of mind, the home features Major recent Improvements including a NEW ROOF/2026, brand-New Kitchen, designer bathrooms, NEW AC system, New Water Heater, and a New Electrical Panel, ensuring the home’s key mechanical systems are already taken care of. Inside, you’ll immediately notice the fresh, modern feel created by Soft-Close cabinetry, elegant Quartz countertops, and luxury vinyl plank flooring throughout the main living areas. The open, clean design provides both style and functionality, making the home ideal for everyday living and entertaining. The bathrooms have been tastefully redesigned with New vanities and beautifully tiled shower surrounds, delivering a contemporary look while maintaining comfort and practicality. Sweetwater Oaks is widely known for its beautiful tree-lined streets, oversized homesites, and welcoming community atmosphere. Residents enjoy exclusive neighborhood amenities including private access to Lake Brantley, a sandy beach area, parks, scenic walking paths, six tennis courts, eight pickleball courts, sand volleyball, playgrounds, and a clubhouse that hosts year-round community events. Outdoor enthusiasts will appreciate being just minutes from Wekiva Island, Wekiwa Springs State Park, and nearby championship golf courses, offering endless opportunities for recreation and relaxation. Convenience is another major advantage of this location. The home is close to shopping, dining, grocery stores, and local cafés along the Longwood and Wekiva Springs corridors, while major roadways including I-4, SR-434, and SR-436 provide easy access to downtown Orlando, Maitland’s business district, and Seminole County’s expanding tech and healthcare employment centers. With Top-rated schools, natural beauty, and continued growth throughout the Longwood area, Sweetwater Oaks remains one of Seminole County’s most desirable places to call home. If you’re looking for a home that offers modern updates, exceptional community amenities, and a prime location, this Sweetwater Oaks property delivers the lifestyle and long-term value buyers are searching for. SCHEDULE YOUR SHOWING TODAY!
Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)
Listing Agent: Jorge Trejo (407-319-1612)
342 COBLE DR, LONGWOOD, FL 32779
$545,00082 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
Elementary School: Wekiva Elementary
High School: Lake Brantley High
Middle School: Teague Middle
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 POOL home delivers immediate wow-factor with soaring ceilings, skylights flooding the interior in natural light, and a dramatic stone fireplace that anchors the living area with warmth and charm. The 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. Conveniently located near Wekiwa State Park’s natural springs, hiking trails and the popular Wekiva Island ideal for kayaking and paddelboarding. With thoughtful updates, open design, and peaceful setting, this Wekiva Hills gem offers serenity for years to come. Schedule a private tour and see for yourself.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Veronica Parker (407-718-6983)
3668 WATERCREST DR, LONGWOOD, FL 32779
$799,00065 Days on yellowkey MLS ID: O6384124
REDUCED by $16,000 (2.0%) on 04/17/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3186 Built: 1989Monthly Fee: $205 Tax: $8,942 (2025)Community: Sweetwater SpgsSpa: YesSingle Family
Taxes:$8,942
Elementary School: Sabal Point Elementary
Tax Year: 2025
Middle School: Rock Lake Middle
Remarks: Nestled in the heart of Sweetwater Springs, a beautiful, gated enclave bordering Wekiwa Springs State Park, this exceptional canal-front residence offers an opportunity to live immersed in Old Florida’s natural beauty. With deeded access to both the Wekiva River and spring-fed Lake Brantley, residents enjoy a lifestyle designed for skiers, paddlers, boaters, and nature enthusiasts alike. The neighborhood features multiple private parks, tennis and pickleball courts, playgrounds, a residents-only clubhouse, and a private kayak launch providing direct river access. From the Sweetwater Springs private riverfront park — exclusively for the 79 homes within the community — enjoy peaceful paddles into Wekiwa Springs State Park, where towering cypress trees, crystal-clear springs, and protected wildlife habitats define the landscape. Manatees, otters, deer, wild turkeys, and abundant native wildlife are frequent visitors, creating an environment that feels more like a private nature preserve than a neighborhood. Tucked on a quiet cul-de-sac, this 5-bedroom, 3.5-bath home with a bonus room (could be a 6th bedroom) offers a spacious two-story layout thoughtfully designed for both comfort and entertaining. Freshly updated with light, bright paint and finishes, the home maintains its traditional character while embracing a refreshed, move-in ready appeal. Custom built-in carpentry features throughout add warmth, craftsmanship, and architectural interest, enhancing the home’s timeless feel. The gourmet eat-in kitchen features granite counters, stainless appliances including a split oven and subtle elevated features such as a "pot-filler" water fixture above the stovetop. The kitchen flows seamlessly into the inviting family room anchored by a cozy wood-burning fireplace. A private guest suite and pool-access bath are conveniently located on the main level, along with a powder room for visitors. Upstairs, four additional bedrooms include the expansive primary suite, which overlooks the sparkling pool and tranquil canal waters beyond. A large upstairs balcony provides a peaceful vantage point to enjoy morning coffee while taking in serene water views. The versatile bonus room offers flexible space for a home office, media room, or playroom. Outdoor living shines with a beautifully resurfaced saltwater screened pool, a new pool heater, and freshly installed pavers enhancing both the pool deck and driveway. The expansive screened lanai creates an inviting setting for entertaining or unwinding after a day on the river and is pre-plumbed for a kitchen. Other significant improvements include a roof replacement in 2022 and a new water heater in 2024 providing peace of mind for future owners. Zoned for highly regarded Lake Brantley schools, this location perfectly balances privacy, natural beauty, and convenience to shopping, dining, and major roadways. For buyers seeking a nature-centered waterfront retreat in a gated, low-inventory community, this home is the one for you!
Listing is courtesy of: FANNIE HILLMAN & ASSOCIATES (407-644-1234)
Listing Agent: Kelly Hildebrand (407-310-5035)
3545 LEGACY HILLS CT, LONGWOOD, FL 32779
$5,200,00016 Days on yellowkey MLS ID: O6396829
Bed: 7 Bath: 8.0 Gar: 6 Liv Area Sq Ft: 10684 Built: 2002Monthly Fee: $885 Tax: $43,088 (2024)Community: Alaqua LakesSpa: YesSingle Family
Taxes:$43,088
Elementary School: Heathrow Elementary
High School: Lake Mary High
Middle School: Markham Woods Middle
Remarks: Behind three private gates, this extraordinary home offers a rare opportunity to own one of Central Florida’s most impressive luxury residences located in the gated Enclave within the guard-gated community of Alaqua Lakes! This compound is sited on 1.55 acres overlooking the 8th hole of the Legacy Club golf course and no neighbors on three sides is truly a buyer’s dream come true. The property includes a 3114 sq ft separate guest house complete with a kitchen and living space on the main level and a bedroom, bonus room/game room & massage room upstairs making it perfect for multigenerational families or hosting visitors. The main residence boasts elegant living featuring soaring ceilings, refined architectural details and thoughtfully designed living spaces. The first floor highlights an unrivaled owner’s retreat privately situated and complete with a marble-surround gas fireplace, sitting area, spa-like bathroom and expansive walk-in closets. A secondary en suite bedroom, formal living and dining spaces and an elevated office complete the main level of this home. The updated gourmet kitchen is a true showpiece featuring stainless steel appliances, custom cabinetry, a stunning marble island and a large walk-in pantry all opening seamlessly to the family room. Unique features such as a saltwater aquarium and a private side porch with remote-operated screens overlooking the koi pond and putting green add to the home’s distinctive charm. Upstairs you’ll find 4 bedrooms and two expansive entertaining areas. The game room and bar make entertaining effortless as this entire level feels like its own private lounge with a beautiful bar and custom cabinetry through out. The adjacent second entertaining area is a fully loaded home theater complete with a bar to take movie nights to a new level designed for an immersive experience right at home. The outdoor living experience is nothing short of spectacular! Designed as a private resort, the grounds feature an extensive covered lanai, a summer kitchen, an outdoor cabana bar, adjacent pool bath & outdoor shower and a tropical heated pool and spa with a grotto with built-in bench seating and fountains all overlooking the sweeping golf course views. Enjoy tranquil moments by the koi pond, practice on the private putting green or entertain effortlessly in this one-of-a-kind setting. A basketball/sport court and whole home generator adds to the estate’s exceptional lifestyle offerings. A 6-car garage, 4 in the main residence and 2 in the guest house plus an add'l golf cart bay, and fully fenced property completes this remarkable property. With its prime golf course setting, extensive upgrades and unparalleled amenities, this estate represents the pinnacle of luxury living in one of Central Florida’s most sought after communities. Alaqua Lakes is set within a premier golf course community where residents enjoy world-class amenities including clay tennis courts, a resort-style pool, playground and sports field, a 24-hour guard-gated entrance and enhanced community security. Located near A-rated schools, Central Florida’s best attractions, upscale shopping and dining, major highways and international airports.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Ellen Bessette (407-496-0076)
1856 ALAQUA DR, LONGWOOD, FL 32779
$1,450,00033 Days on yellowkey MLS ID: O6392922
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: Welcome to Alaqua Drive, Luxurious Upgraded Excutive 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 Gourment Chef Kitchen w/ Large Island & State of the Art Applliances**Walk-in Pantry **Three-Car Garage**Large sparkling Heated Pool w/ Screen Enclosure**Oversized Lanai Built In-Stainless Steel Summer Kitchen Grill**Abundant Storager & Large Closets to be Found Everywhere** 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)
354 W HORNBEAM DR, LONGWOOD, FL 32779
$589,00010 Days on yellowkey MLS ID: O6399672
1 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2162 Built: 1977Monthly Fee: $54 Tax: $5,966 (2025)Community: Sabal PointSpa: NoSingle Family
Taxes:$5,966
High School: Lyman High
Remarks: Under contract-accepting backup offers. Come and see this beautiful 4 bedroom, 2 bathroom + office home within close proximity to Sabal Point Elementary School. This ranch style home features luxury vinyl flooring throughout, solid surface kitchen counters, stainless steel appliances, vaulted ceilings, skylights in kitchen and family room, indoor laundry room, plantation shutters on front bay windows, and a wood burning fireplace. There is a large, side entry, two-car garage and wide driveway. The large backyard has a wood privacy fence, open pool and gazebo. Relax on your screen porch after a long days activities. The home is located within the Sabal Point commuinity, which contains about 550 homes spread over 80-acres.
Listing is courtesy of: GREEN AVENUE REAL ESTATE LLC (404-610-1971)
Listing Agent: Julie Hamilton (407-739-6559)
427 BRENTWOOD CLUB CV, LONGWOOD, FL 32750
$775,00097 Days on yellowkey MLS ID: O6373846
REDUCED by $24,999 (3.1%) on 04/16/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3510 Built: 2006Monthly Fee: $148 Tax: $6,401 (2025)Community: Brentwood ClubSpa: NoSingle Family
Taxes:$6,401
Elementary School: Longwood Elementary
Middle School: Greenwood Lakes Middle
Remarks: Under contract-accepting backup offers. Updated and fully renovated four-bedroom, three-bathroom home has a three-car garage, large paver driveway, and 3,510 square feet of living space. 427 Brentwood Club Cove is located in a small gated community off Lake Emma Road in Longwood, FL. This unique home features multiple flex spaces: a private office with French doors, a large private loft upstairs, a home gym, a living room, a formal dining room, AND a great room. The office and loft could easily be modified to create bedrooms five and six, and the gym room could double as a nursery, attached to the primary bedroom! All bedrooms are on the first floor. The thoughtfully designed split-bedroom floor plan places the primary suite in its own private wing, creating a true retreat with new wood flooring, double closets, a spa-style bathroom with soaking tub and separate shower, and a dedicated workout room featuring a Tonal wall fitness system. The heart of the home is the beautifully renovated kitchen with new cabinetry, countertops, ambient cabinet lighting, and new appliances. The kitchen has a large dining space and overlooks the great room—perfect for entertaining and everyday living. A hallway off the main living area leads to three additional bedrooms and two large bathrooms. Step outside to enjoy Florida living at its best with a newly built 15×32 custom pool, hot tub, and screened enclosure, plus a covered patio. There is plenty of parking, including a three-car garage and a large paver driveway that accommodates up to six vehicles. Recent improvements provide peace of mind, including a roof replacement in October 2021, both HVAC systems replaced less than five years ago, a new water heater, a fully renovated kitchen, new whole-house flooring, a new pool/pool deck/screen enclosure, a fenced backyard, and a beautiful paver patio in the backyard for cookouts and stargazing. This move-in-ready home combines space, modern updates, a convenient location, and top-rated Seminole County schools. Schedule your viewing today!
Listing is courtesy of: Q BOUTIQUE SPECIALTY REALTY INC (407-863-7965)
Listing Agent: Laura Diss (407-388-4103)
302 NEEDLES TRL, LONGWOOD, FL 32779
$499,00053 Days on yellowkey MLS ID: O6386794
0 Days Off yellowkey (back on 4/21/2026)
REDUCED by $15,000 (2.9%) on 04/09/2026
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
Remarks: Under contract-accepting backup offers. 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)
1510 PELICAN ST, LONGWOOD, FL 32750
$349,9996 Days on yellowkey MLS ID: O6400827
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1269 Built: 1977 Tax: $4,558 (2024)Community: Sky Lark Unit 2 RepSingle Family
Taxes:$4,558
Elementary School: Highlands Elementary
High School: Winter Springs High
Middle School: Milwee Middle
Remarks: Completely Remodeled Home in Prime Location -NO HOA. Welcome to this beautifully renovated 3-bedroom , 2 -bathroom home located in a quiet , established neighborhood near both Lake Mary and Casselberry. Perfectly positioned with easy access to major roads, shopping, dining , and entertainment,this home offers both comfort and convenience . Step inside to discover luxury vinyl flooring throughout, creating a modern and cohesive feel . The fully updated kitchen features sleek cabinetry, stylish finishes, and brand-new stainless steel appliances with quartz counter top , making it ideal for both everyday living and entertaining . Enjoy the added convenience of a one car-garage and fully fenced backyard, perfect for pets, gatherings, or simply relaxing in your private outdoor space. With No HOA restrictions, you have the freedom to truly make this home your own. Don't miss opportunity to make it yours !
Listing is courtesy of: WORLD PROPERTIES GROUP (407-574-5920)
Listing Agent: Krasimira Kakarova (240-506-5959)
1443 CROCUS CT, LONGWOOD, FL 32750
$779,00010 Days on yellowkey MLS ID: O6399421
0 Days Off yellowkey (back on 4/20/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3359 Built: 1995Monthly Fee: $64 Tax: $385 (2024)Community: Bolling FarmsSpa: YesSingle Family
Taxes:$385
Elementary School: Woodlands Elementary
Remarks: Your Longwood Dream Home Awaits! This beautifully maintained, custom built 5-bedroom, 3-bath pool home was freshly painted and is set on a one-third acre cul-de-sac lot offering peaceful conservation views and a seamless blend of elegance, modern upgrades, and resort-style living. From the moment you arrive, the striking curb appeal, mature landscaping, and quiet setting create a warm welcome that continues throughout the home. Inside, you are greeted by soaring ceilings and brand new luxury vinyl plank flooring throughout the living areas of this inviting open layout. You are bathed in natural light from the wall of windows in the spacious living room, flowing effortlessly into the dining area, making it ideal for gatherings and entertaining. The updated chef’s kitchen showcases custom cabinetry and sleek quartz countertops and opens directly to the family room featuring a cozy fireplace, creating a comfortable and connected space for everyday living. There is also a bedroom and full bathroom downstairs making the perfect in-law suite! Upstairs, the expansive primary suite provides a true retreat with tranquil views, generous space, and a beautifully updated en-suite bath with modern fixtures and oversized custom walk-in closet. All additional bedrooms are bright and generously sized, offering flexibility for family, guests, or work-from-home needs. Step outside to your private backyard oasis, where the screened-in pool area is pristine and ready for year-round enjoyment. Surrounded by lush greenery and serene conservation views, it’s the perfect place to relax or entertain. This home is served by top A-rated Seminole County schools. Major updates include a roof replacement (2015), downstairs A/C (2025), upstairs A/C (2022), exterior paint (2025) and luxury vinyl plank flooring (2026). Located in Bolling Farms, one of Longwood’s most desirable established neighborhoods, the community is known for its spacious custom homes, mature landscaping, and strong sense of community. Its convenient location offers easy access to boutique shopping, dining, hospitals, major highways, downtown Orlando, world-renowned attractions, and even the beaches. A rare opportunity to own a beautifully cared-for home in a highly sought-after Longwood setting. **Multiple offers have been received. Highest and best offer deadline is Sunday at 6 pm.**
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Ken Dalton (407-928-8587)
283 LAKAY PL, LONGWOOD, FL 32779
$849,00047 Days on yellowkey MLS ID: O6389639
REDUCED by $20,000 (2.3%) on 04/14/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3596 Built: 2004Monthly Fee: $169 Tax: $6,719 (2024)Community: Terra OaksSpa: NoSingle Family
Taxes:$6,719
Remarks: Priced to sell! Live the Florida lifestyle in the private, gated community of Terra Oaks in Longwood. Set on over a quarter-acre with a stunning heated pool, this beautifully maintained home impresses from the start with manicured landscaping, a tile roof, paver driveway, and a grand, welcoming entry. Inside, you’ll find soaring 21-foot ceilings and a bright, open layout with solid wood and tile flooring throughout the main level, custom drapery, and a motorized screen at the family room sliders. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, wood cabinetry, stainless steel appliances, tile backsplash, a pantry, bar seating, and even two sinks opening to a breakfast nook with views of the pool. The adjacent dining room is accented by chair railing and an elegant crystal chandelier. Step outside to your private backyard retreat. The newer custom heated pool showcases a sun shelf for lounging, LED lighting, a waterfall pergola, and additional water features creating a true resort-style escape. The covered lanai offers the perfect space for year-round gatherings and indoor-outdoor living. The spacious primary suite is conveniently located on the main level and includes two walk-in closets and a spa-like bath with dual vanities, a glass-enclosed shower, and a jetted tub. There is a dedicated office/living room and a separate guest bedroom with a full nearby bath on the main level. Upstairs, two generously sized en-suite bedrooms offer great closet space, along with a versatile loft ideal for a playroom, gym, or media room. Enjoy evenings on the upstairs veranda overlooking the fenced backyard. Recent updates include a fresh exterior paint job and new flooring on the stairs, main-level guest bedroom, and loft. Ideally located near top-rated schools including Lake Brantley High, plus excellent dining, shopping, and major roadways for easy access throughout Central Florida. Don’t miss this remarkable home and be sure to view the virtual tour.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
121 BEARSS CIR, LONGWOOD, FL 32750
$399,00038 Days on yellowkey MLS ID: O6391757
2 Days Off yellowkey (back on 4/15/2026)
REDUCED by $11,000 (2.7%) on 03/31/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1352 Built: 1976 Tax: $4,313 (2024)Community: Lake Searcy ShoresSpa: NoSingle Family
Taxes:$4,313
Remarks: Under contract-accepting backup offers. Beautifully renovated 3 bedroom, 2 bathroom pool home situated on a spacious corner lot in desirable Longwood with no HOA! This charming residence offers the perfect blend of modern updates and timeless character, making it truly feel like home from the moment you arrive. Step inside to find wood-look tile flooring throughout, providing both durability and a cohesive, stylish look. The home is enhanced with modern fixtures that elevate each space. The open-concept kitchen is ideal for both everyday living and entertaining, featuring stainless steel appliances, ample counter space and a convenient breakfast bar that flows seamlessly into the main living areas. You’ll love the cozy dining area and the inviting family room with a fireplace, perfect for relaxing evenings or gathering with friends and family. Natural light fills the home, highlighting its warmth, character and thoughtful design. The renovated bathrooms showcase updated finishes, adding comfort and a touch of luxury to your daily routine. Each bedroom offers a comfortable layout with plenty of space to unwind. Step outside to your private backyard oasis, complete with a large, fully fenced yard and a sparkling pool. Perfect for enjoying Florida living year round. Whether you’re hosting gatherings, spending time with loved ones or simply relaxing poolside, this outdoor space offers endless possibilities. Conveniently located just minutes from historic downtown Longwood, Seminole Hospital, nearby parks, shopping, dining and major roadways. This home truly combines comfort, convenience and charm in one exceptional property. Schedule your private tour today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Christina Dalton (407-587-6083)
107 PINEAPPLE CT, LONGWOOD, FL 32750
$432,90045 Days on yellowkey MLS ID: O6390238
REDUCED by $10,000 (2.3%) on 04/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1996 Built: 1975 Tax: $6,434 (2024)Community: Lake Searcy ShoresSingle Family
Taxes:$6,434
Remarks: One or more photo(s) has been virtually staged. This well-maintained property features three comfortable bedrooms and two full bathrooms, providing ample space for daily living. Recent major updates include a new HVAC system installed in 2024 and a complete roof replacement in 2023, ensuring reliable comfort and protection. Two expansive screen porches extend the living area, creating protected spaces for relaxation and entertainment throughout the seasons. These covered areas provide comfortable spots for dining or simply enjoying the surroundings. The backyard includes a swimming area fo recreation and exercise, while the outdoor firepit creates a natural gathering spot for evening conversations and warmth during cooler months. With no homeowners association restrictions, residents enjoy complete freedom in personalizing and maintaining the property according to their preferences. The established neighborhood setting creates a peaceful environment while maintaining easy access to local conveniences. Schedule your private showing today and experience all the comfort and convenience.
Listing is courtesy of: ELITE REAL ESTATE & FINANCE LLC (904-510-1608)
Listing Agent: Brice Gill (904-510-1608)
714 WEST CT, LONGWOOD, FL 32750
$339,80030 Days on yellowkey MLS ID: O6394329
REDUCED by $100 (0.0%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1413 Built: 1972 Tax: $3,448 (2024)Community: Longwood NorthSingle Family
Taxes:$3,448
Remarks: Charming and beautifully maintained 3-bedroom, 2-bath home offering both comfort and efficiency. Enjoy significant energy savings with a fully installed solar system, while major upgrades—including a complete home re-pipe and conversion from septic to city sewer—provide peace of mind for years to come. The property features a spacious corner lot with a partially fenced backyard, perfect for both privacy and outdoor enjoyment. A well-maintained irrigation system keeps the yard lush and green, and a large, high-quality shed offers excellent additional storage. Relax year-round on the inviting screened porch, ideal for entertaining or unwinding in comfort. This thoughtfully updated, move-in-ready home combines modern improvements with everyday convenience—an exceptional opportunity you won’t want to miss.
Listing is courtesy of: PARK PLACE REAL ESTATE (407-504-1110)
Listing Agent: Pat Glenn (407-504-1110)
140 RANGELINE WOODS CV, LONGWOOD, FL 32750
$575,00027 Days on yellowkey MLS ID: V4948172
REDUCED by $19,900 (3.3%) on 04/20/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2351 Built: 2002Monthly Fee: $50 Tax: $2,567 (2025)Community: Rangeline WoodsSingle Family
Taxes:$2,567
Remarks: One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT, don't miss out on this POOL HOME. Nestled in a cul-de-sac on 1/3-acre home site with fenced yard, this one story, 4 bedrooom, split plan has a screened pool and was recently updated. Easy care hard surface flooring throughout makes maintenance a breeze with our warm weather and Florida living. Convenient to I-4, shopping and restaurants and zoned for top schools in the area. Entertaining on the spacious covered lanai and large patio and pool will be ideal for BBQ’s and splashing into spring and summer! **Roof was replaced in 2022, Hot water heater- 2026, PVC fencing -2026, Dishwasher- 2026 and AC- 2015.** You’ll appreciate the architectural details on the exterior with high ceilings and archways highlighted by fresh paint inside and outside of the home. Entering the home the view of your backyard oasis with pool is visible and the spaciousness with the high ceilings gives a grand appearance to the formal living space. As you make your way back to the gathering areas the large windows and sliders continue with the view of the upgraded kitchen open to casual dining and great room. Warm, wood cabinets with granite counters and stainless appliances will make cooking and entertaining a breeze. The island is great for meal preps and serving with additional cabinets. Double door pantry ensures you’ll have plenty of room for your groceries. An archway connects to the formal dining area for easy serving. As you make your way back through the formal living area, the 4th bedroom/office is off foyer with new luxury vinyl plank and walk-in closet with organizer with shelving. The primary suite has a foyer entrance and plenty of wall space for furniture. Two walk-in closets with organizers give ample room for wardrobe and shoes. The spacious en-suite bathroom has a large vanity with make-up area and dual sinks. The garden soaking tub will relax you after a day at the office and a separate glass, enclosed shower and private lavatory. The split bedroom plan takes you to the other side of the home where the two guest bedrooms with double door closets and hall bath are off a separate hallway. The 2nd bathroom has new glass enclosure on shower and a door to the pool. Laundry room features a new sink and built-in folding table with storage cabinets. Huge privacy fenced backyard is perfect for pets, playsets and gardening. A separate paver patio provides a place for grills or firepit. Plenty of parking with long driveway and spacious two car garage. Such a convenient location just 1 mile to Publix, shopping and restaurants, 2 miles to I-4, 15 miles to downtown Orlando and 35 miles to Disney. Downtown Longwood features a farmer’s market, festivals and events for all ages. This home may be under audio-video surveillance.
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Donna Pastore (407-920-4667)
506 FREEMAN ST, LONGWOOD, FL 32750
$588,50080 Days on yellowkey MLS ID: O6378867
REDUCED by $1,500 (0.3%) on 04/19/2026
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
Remarks: Under contract-accepting backup offers. 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)
3322 CANYON GRAND PT, LONGWOOD, FL 32779
$725,00058 Days on yellowkey MLS ID: O6385555
REDUCED by $44,000 (5.7%) on 04/20/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2707 Built: 2021Monthly Fee: $197 Tax: $8,263 (2024)Community: Retreat At Lake BrantleySpa: NoSingle Family
Taxes:$8,263
Remarks: One or more photo(s) has been virtually staged. Picture this… You’re driving through the gates, and it just feels different. Neighbors wave as they pass. Kids are riding bikes, laughter carrying through the air. There’s a group playing a homerun derby game down the street, and it’s the kind of place where people actually know each other - where weekends turn into impromptu get-togethers and evenings slow down just enough to enjoy them. Welcome to the kind of neighborhood people hope to land in - and rarely leave. Now imagine pulling into your own driveway. This 4-bedroom, 4-bath retreat in the highly sought-after Retreat at Lake Brantley isn’t just a home - it’s your place within it all. You walk inside and immediately feel the space open up - natural light pouring in, high ceilings, and a layout that just works. Everything flows effortlessly, whether it’s a quiet morning coffee or hosting friends on a Friday night. The kitchen is where everyone ends up - designed to be both beautiful and functional, with plenty of room to gather, cook, and connect. The primary suite becomes your reset button - a calm, private space to unwind at the end of the day. And every bathroom? Finished with the kind of detail that makes daily life feel just a little more elevated. Out back, the possibilities open up even more. Picture summer dinners outside, kids playing until the sun goes down, or finally building that dream pool you’ve been thinking about. And beyond your front door - you’ve got private access to Lake Brantley, a gated sense of security, top-rated Seminole County schools, and everything you need just minutes away. This isn’t just about the home itself. It’s about the life that comes with it. The kind people wait for. The kind people talk about. And the kind that doesn’t come available often.
Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)
Listing Agent: Danielle Pensala (407-529-5752)
235 S SHADOWBAY BLVD, LONGWOOD, FL 32779
$425,000308 Days on yellowkey MLS ID: O6320596
1 Days Off yellowkey (back on 4/20/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1916 Built: 1981Monthly Fee: $156 Tax: $2,265 (2024)Community: Shadowbay Unit 1Single Family
Taxes:$2,265
Remarks: Under contract-accepting backup offers. This single-family home is amazing in every way and is truly a must see! Nestled in the highly coveted Shadowbay Community on Lake Brantley. Brand NEW HVAC with 10 year transferable parts warranty. Brand NEW 50 Gallon Water Heater! NEW ROOF 2023! A perfect location just minutes to everything. This residence boasts an array of desirable features. Three bedrooms and two full baths with oversized primary bedroom. As you enter through the striking front door and stunning foyer, you are mesmerized by the beauty and flow of home. Separate formal dining room and expansive living area creating a stylish, classic feel. Living room bright and open with sliding glass doors that take you out to the paved patio. Crown molding throughout and a beautiful wood burning fireplace. Skylights in kitchen, bathrooms, and laundry room. Split floorplan for privacy and convenience. Stunning, oversized primary bedroom overlooking the private back yard. Substantial closets offering more than ample storage. Additional two bedrooms with sliding glass doors leading out to private, open garden area. Enjoy your morning coffee in the breakfast nook with exquisite chair molding and picturesque Bay Window. Brand NEW stainless steel appliances. Kitchen centered between large breakfast area and spacious formal dining room. Timeless Wet Bar of living and dining room. Perfect home for entertaining. Gorgeous luxury vinyl flooring combining durability and elegance. No carpet. Throughout entire home NEW flooring, interior paint, and appealing textured ceilings. Owner with pride of ownership. Private backyard with mature landscaping and some fencing for your fury family. Oversized 2 car garage with an abundant of storage options both inside and out. This is the ideal home in so many ways. What more could you ask for!? Shadowbay Community with so much to enjoy with tennis court, basketball court, park and private boat launch. I-4 just minutes away for Disney or a day at the Beach. Close to Historical Downtown Longwood and Winter Park with desired Park Avenue and weekly Farmer’s Market. Then you have the convenient SunRail taking you around Central Florida. Supermarkets, restaurants, shopping and so much more. Excellent A-Rated Seminole County Schools. Location, Location, Location. Welcome Home!!!
Listing is courtesy of: KORR REALTY CORP (407-732-6987)
Listing Agent: Denise Korrey (407-221-2801)
2228 EARLEAF CT, LONGWOOD, FL 32779
$2,785,0009 Days on yellowkey MLS ID: O6399964
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 7696 Built: 1990Monthly Fee: $104 Tax: $11,667 (2024)Community: Wingfield Reserve Ph 3Spa: YesSingle Family
Taxes:$11,667
Remarks: At the end of a quiet cul-de-sac and backing to the protected beauty of Wekiwa Springs State Park, this extraordinary waterfront estate offers a rare blend of privacy, scale and natural serenity in the desired Markham Woods Corridor. Fully fenced and positioned to capture sweeping conservation and water views, the setting alone places this residence in a category few can match. Impressive private gates and a brick paver circular drive introduce a dramatic arrival, where a grand porte-cochere and expansive six-car motor court set the tone. Inside, the home has been completely reimagined through a comprehensive renovation, unveiling soaring ceilings, walls of glass and abundant natural light. A striking 5-by-8-foot pivot door opens to a refined foyer with porcelain tile and white oak flooring, immediately drawing the eye to the shimmering pool and tranquil pond beyond. Designed for grand entertaining and effortless living, the main areas unfold in a seamless open-concept layout. With 14-foot ceilings and expansive living, dining, family and kitchen spaces flowing together, the home offers impressive volume and connectivity. Anchoring the heart of the home, a dramatic double-sided wood-burning fireplace creates a warm focal point between kitchen and family room. The chef’s kitchen is a showpiece, featuring Wolf appliances, built-in refrigeration and an oversized island with seating for six, finished with elegant waterfall-edge countertops. Outdoor living is equally captivating. A vast travertine lanai transitions to an oversized resort-style pool, all set against a breathtaking backdrop of water and untouched conservation. Nearly every room is oriented to capture these remarkable views, creating a constant connection to the landscape. The primary suite is a sanctuary of grand scale, offering serene water and wooded vistas. Its bespoke bath features leather-finished stone countertops, dual vanities, a soaking tub, and picture windows framing the natural setting. A spa-inspired steam shower with multiple shower heads and a built-in bench completes the experience. Dual custom walk-in closets elevate functionality, one with a center island and scenic window, the other concealing a hidden safe room. Versatility defines the additional spaces. A dedicated office with walk-in closet and direct bath access can serve as an additional bedroom. A generously sized bonus room is ideal for a home theater, library or lounge, while a separate gym with luxury vinyl flooring can easily function as a second office. A thoughtfully positioned flex space between the main residence and guest quarters opens to the lanai and pool bath, ideal for a cabana lounge or wellness retreat. The guest quarters is a residence unto itself, featuring two bedrooms, two baths, a spacious great room, full kitchen with center island, separate motor court access, and its laundry, offering exceptional accommodations for guests or multigenerational living. Homes of this caliber rarely come to market. The extensive renovation, remarkable scale, and exceptional attention to detail are paired with Seminole County’s desirable locations. Zoned for top-rated schools and ideally positioned near Longwood and Lake Mary, with convenient access to major highways, regional hospitals, airports, beaches and Central Florida’s world-renowned attractions, this is a legacy property that defines elevated Florida living.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Mel Bernstein (407-810-4726)
375 BRENTWOOD CLUB CV, LONGWOOD, FL 32750
$705,00021 Days on yellowkey MLS ID: O6396065
REDUCED by $29,900 (4.1%) on 04/18/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2997 Built: 2006Monthly Fee: $148 Tax: $4,171 (2024)Community: Brentwood ClubSingle Family
Taxes:$4,171
Remarks: Welcome to 375 Brentwood Club Cove, a beautifully maintained residence tucked within the gated community of Brentwood Cove in desirable Longwood. This immaculate five-bedroom (one is an ideal office), three-bath home offers 3,000 square feet of thoughtfully designed living space, blending comfort, style, and true move in readiness. From the moment you arrive, the home makes a striking impression with its brick paver driveway and pristine presentation. Every detail has been meticulously cared for, with the exterior freshly pressure washed and the carpets professionally cleaned, the space is spotless and inviting. Inside, expansive living areas flow effortlessly, offering both functionality and elegance for everyday living and entertaining. Outside is your private outdoor retreat, where a sparkling blue pool is surrounded by a beautiful brick paver deck and enclosed within a screened lanai, delivering the ultimate Florida lifestyle. The large yard with perimeter vinyl fencing provides exceptional space for recreation, pets and outdoor enjoyment. Additional highlights include a spacious two car garage, a newer roof installed in 2019, kitchen exhaust to exterior behind microwave, fans and light fixtures in all rooms including garage, blinds for all windows and sliding doors, separate irrigation line and faucets in front and rear, plus a termite bond already paid for the year, offering valuable peace of mind. Ideally located, Brentwood Cove places you just moments from major highways, premier shopping, dining and leading regional hospitals. The property is also zoned for some of the most sought-after schools serving both Longwood and nearby Lake Mary, adding exceptional long-term value and appeal. This is a turnkey opportunity to enjoy refined Florida living in a home that is as impressive as it is welcoming.
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