Location: Longwood
Do Not Show Listings
101 CHERRY HILL CIR, LONGWOOD, FL 32779
$699,00054 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)
3301 SUNSET RIDGE CT, LONGWOOD, FL 32779
$1,990,00079 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
Elementary School: Wekiva Elementary
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 is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Penney Lawrence (407-353-7019)
737 E CHURCH AVE, LONGWOOD, FL 32750
$405,000208 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
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
3540 LEGACY HILLS CT, LONGWOOD, FL 32779
$4,499,00050 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.
Listing Agent: Frank Benevento (407-492-5153)
1130 BROWNSHIRE CT, LONGWOOD, FL 32779
$1,600,00061 Days on yellowkey MLS ID: O6408467
0 Days Off yellowkey (back on 5/24/2026)
Bed: 4 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 7451 Built: 1984Monthly Fee: $367 Tax: $18,909 (2025)Community: Sweetwater Club Unit 3Single Family
Taxes:$18,909
Middle School: Markham Woods Middle
Remarks: Under contract-accepting backup offers. Located within the exclusive Sweetwater Club Estates, this custom home sits at the head of a private cul-de-sac with sprawling grounds, circular driveway, and rear-entry garage. Step through the front doors to bright, open views of the private pool and outdoor entertaining area. The gourmet kitchen features a Viking six-burner range, multiple Sub-Zero refrigerators, center island, granite counters, and custom cabinetry. A butler’s pantry leads to the formal dining room, perfect for entertaining, along with a dedicated wine storage area. A second full kitchen with pass-through access to the outdoor patio overlooks the pool area. The split-bedroom floor plan offers privacy throughout the home. Upstairs, a spiral staircase leads to a loft ideal for a game room or library. The owner’s retreat includes a spacious primary bedroom, media room, spa-style bath with Jacuzzi tub, separate shower, bidet, and dual walk-in closet. Every detail of this one-of-a-kind property has been thoughtfully designed, creating a truly unforgettable home.
Listing is courtesy of: WATSON REALTY CORP (407-323-3200)
Listing Agent: Joshua Hofle (407-637-6951)
1446 VIVALDI PL, LONGWOOD, FL 32779
$825,000180 Days on yellowkey MLS ID: A4678437
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $24,900 (2.9%) on 04/28/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3310 Built: 2011Monthly Fee: $122 Tax: $7,442 (2025)Community: Bella VistaSpa: NoSingle Family
Taxes:$7,442
Remarks: *** MOTIVATED SELLER *** Gated Bella Vista elegant move in perfect 4bdr, 3ba, Pool Home + 3 car gar + Bonus Room. Gourmet Chef’s Kitchen and 3 Bathrooms completely remodeled in 2025 including soft close cabinets & drawers, quartz counter-tops throughout with large waterfall island with pendant lighting, and new tile backsplash. All new tile floor installed in 2025 as well. In addition, home features include extensive stone front elevation, tile roof, and brick pavers on driveway, both porches, and pool deck. Designed to impress & great for entertaining w/formal living, dining, and family rooms, extensive custom millwork including crown molding, chair rail, wainscoting, & custom wood trimmed windows, front door, and master entry. Open floor plan w/10’ ceilings and lots of natural light. Chef’s delight kitchen is open to the family room for large entertaining space. 120gallon propane tank, gas stove, and plumbed and wired for full house generator. Split bedroom layout features roomy master retreat w/ luxurious bath & custom closet; split side bedrooms are larger than normal w/oversized closets & features a custom workspace nook for hobbies or homework. Enormous bonus room / flex space game room / media room perfect for family entertaining. High-end Pool Table Included. Home is extremely energy efficient w/nest system thermostat and newer A/C system & hybrid hot water heater. Spray foam attic insulation & concrete block insulated voids & low E Thermal double pane hurricane glass windows. Sprinkler on metered grey water system for lower water bills. Great fenced completely private outdoor tropical oasis w/covered lanai, brick pavers, & inviting sparkling pool w/stone scape aggregate long life pool finish, new saltwater system, waterfall. Zoned for top rated Seminole County schools & nestled in desirable cul-de-sac / corner lot location adjacent to expansive community park w/abundant greenspaces… is like an extension of your yard! Convenient to all South Seminole County has to offer. This Home has it all.
Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)
Listing Agent: Moe Mossa (888-490-1268)
8201 OLYMPIA CT #8201, LONGWOOD, FL 32779
$195,000133 Days on yellowkey MLS ID: O6385064
REDUCED by $5,000 (2.5%) on 05/22/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1365 Built: 1984Monthly Fee: $488 Tax: $2,537 (2025)Community: Clubside At Sabal Point A CondoCondo
Taxes:$2,537
Elementary School: Sabal Point Elementary
High School: Lyman High
Middle School: Rock Lake Middle
Remarks: Incredible opportunity to own in Clubside at Sabal Point in the Longwood Wekiva area. This gorgeous corner unit condo is located on the second floor with calming views of natural Florida from every window. This move in ready home features a split bedroom floor plan providing privacy and peace and quiet for everyone. Your kitchen has ample room for an island or a bistro table perfect for coffee, breakfast and catching up on the latest news of the day with your family. Your new living and dining rooms are open and bright, perfect for entertaining over the holidays or just hosting movie night on the couch. This home is not only beautiful but also easy to clean- all tile and luxury vinyl flooring throughout. And of course, the location simply can't be beat. Clubside at Sabal Point is in the heart of Longwood and just around the corner from Wekiva Island, Publix, Starbucks and so much more! Hop on 1-4 or 434 and be anywhere you want to be quickly- including Daytona and New Smyrna beaches and Downtown Orlando for an Orlando Magic game or show at the Dr.Phillips Center for the performing Arts. Seminole county really is the ideal blend of natural Florida and convenience to all things commerce. You don't have to settle- schedule your private viewing of this stunning condo today!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Christina Rordam (407-928-8294)
3545 LEGACY HILLS CT, LONGWOOD, FL 32779
$4,800,00096 Days on yellowkey MLS ID: O6396829
REDUCED by $400,000 (7.7%) on 05/12/2026
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
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)
219 NOB HILL CIR, LONGWOOD, FL 32779
$589,750118 Days on yellowkey MLS ID: O6392082
REDUCED by $5,000 (0.8%) on 05/18/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2306 Built: 1963 Tax: $4,190 (2025)Community: Meredith Manor Nob Hill SecSingle Family
Taxes:$4,190
Remarks: READ BEFORE SHOWING—- Wake up to serene lake views in this beautifully updated home nestled in the highly sought-after Lake Brantley community—perfect for new homeowners looking for comfort, style, and lifestyle all in one. With access to a private boat ramp and an incredibly low optional HOA of just $13/month, you can enjoy lake life without the high costs. ***This fully remodeled 3-bedroom with 4th bedroom turned into a loft/study area***, 3-bath residence has been thoughtfully upgraded for peace of mind, including full repiping, new electrical, and a brand-new roof. Step inside and you’ll immediately notice the abundance of natural light pouring through large windows, creating a warm and inviting atmosphere throughout the home. The layout is both functional and flexible, featuring a spacious upstairs loft that’s perfect for a home office, playroom, or additional living space. The kitchen offers a charming eat-in area ideal for casual meals and morning coffee, while the open living areas make entertaining effortless. Upstairs, enjoy your own private balcony—an ideal spot to unwind and take in the tranquil surroundings. Outside, the spacious backyard offers endless possibilities for gatherings, gardening, or simply relaxing in your own outdoor retreat. Currently staged to highlight its full potential, this move-in ready home is a rare opportunity to own a stylish, updated property in a fantastic location. Whether you're starting your homeownership journey or looking for a peaceful place to settle in, this home truly has it all.
Listing is courtesy of: BEST HOMES, LLC. (305-879-3707)
Listing Agent: Evelyn Otero (407-259-1789)
1934 WINGFIELD DR, LONGWOOD, FL 32779
$924,50063 Days on yellowkey MLS ID: O6407478
2 Days Off yellowkey (back on 5/17/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3575 Built: 1990Monthly Fee: $104 Tax: $6,902 (2024)Community: Wingfield Reserve Ph 3Spa: NoSingle Family
Taxes:$6,902
Remarks: Under contract-accepting backup offers. Exceptional custom estate pool home offering luxurious indoor-outdoor living, expansive entertaining spaces, and resort-style privacy on a beautifully landscaped oversized homesite. This meticulously maintained residence combines elegant architectural design with high ceilings, abundant natural light, and an impressive single-story split floor plan designed for both comfort and sophistication. A circular drive and covered entry introduce a stunning interior highlighted by dramatic ceiling heights, oversized windows, custom architectural details, and spacious gathering areas throughout. The layout blends elegant formal living with relaxed everyday functionality while creating seamless transitions to the expansive outdoor living spaces. The spacious chef’s kitchen serves as the heart of the home and features extensive cabinetry, generous counter space, center island, breakfast bar seating, stainless steel appliances, double built-in ovens, and casual dining areas overlooking the lanai and pool. The adjoining family room showcases soaring ceilings, oversized windows, multiple French doors, and exceptional natural light that enhances the home’s open and inviting atmosphere. The oversized primary suite offers a luxurious private retreat with abundant natural light, spacious proportions, and direct access to the outdoor living areas. The spa-inspired primary bath includes dual vanities, soaking tub, oversized walk-in shower, and generous storage. Additional guest bedrooms are spacious and thoughtfully positioned with updated adjoining baths, while the dedicated executive office with soaring ceilings and oversized arched window creates the ideal work-from-home environment or flex space. The outdoor living experience is exceptional! An expansive covered lanai overlooks the screened resort-style pool and private backyard, an ideal environment for year-round Florida entertaining. Multiple covered seating and dining areas provide seamless indoor-outdoor flow, while the oversized screen enclosure and mature landscaping create privacy and architectural impact rarely found in similar homes. A dedicated pool bath adds convenience and functionality for guests and entertaining. The expansive backyard showcases mature oak trees, lush landscaping, and an impressive sense of space and privacy that further enhances the estate-like setting. Property Highlights Include: • Custom estate-style pool residence • Expansive single-story split floor plan • Circular driveway and impressive curb appeal • Soaring ceilings and oversized windows throughout • Chef’s kitchen with double built-in ovens • Extensive cabinetry, island, and breakfast bar seating • Spacious family room with multiple French doors • Luxurious oversized primary suite • Spa-inspired primary bathroom with soaking tub and oversized shower • Dedicated executive office/flex room • Updated guest baths and dedicated pool bath • Resort-style screened pool and oversized enclosure • Expansive covered lanai with multiple entertaining areas • Seamless indoor-outdoor living design • Mature oak trees and beautifully landscaped grounds • Exceptional backyard privacy and oversized homesite feel • Beautifully maintained interior and exterior • Convenient access to shopping, dining, golf, and major roadways This exceptional residence offers the rare combination of elegant design, spacious luxury living, and true resort-style outdoor entertaining in one of the area’s most desirable settings.
Listing is courtesy of: SMITH MCINTOSH PROPERTIES, INC (407-302-0446)
Listing Agent: Brian Smith (321-377-4355)
334 MAPLE DR, LONGWOOD, FL 32750
$469,900366 Days on yellowkey MLS ID: O6325785
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2311 Built: 1970 Tax: $2,482 (2024)Community: Sanlando SpgsSpa: NoSingle Family
Taxes:$2,482
Elementary School: Altamonte Elementary
Middle School: Milwee Middle
Remarks: One or more photo(s) has been virtually staged. PRICE IMPROVEMENT– HISTORIC LONGWOOD OPPORTUNITY! This charming indoor pool home presents a rare opportunity in the heart of Historic Longwood. Situated on a corner lot directly across from a peaceful protected green space with scenic trails, this property offers a unique blend of location, character, and potential in one of Seminole County’s most desirable and evolving areas. A distinctive courtyard-style layout welcomes you through the front entry into a private indoor pool area before entering the main living space—creating a true indoor-outdoor Florida lifestyle experience perfect for entertaining and year-round enjoyment. Inside, you’ll find vaulted wood ceilings, wood flooring, abundant natural light, and a functional layout featuring a formal dining area, cozy living room, and an open kitchen with granite countertops, skylight, and breakfast nook. A versatile enclosed flex space off the kitchen offers additional options for a home office, guest area, or bonus room to suit your lifestyle. The spacious primary suite features a private skylight and refreshed en suite bath with updated mirrors and lighting. Recently appraised and professionally measured at approximately 2,311 sq ft of living area, this home offers exceptional space and flexibility. With a roof replaced in 2024, screened two-car garage, interior laundry, and NO HOA, this property delivers strong value and endless potential. Conveniently located just minutes from I-4, Uptown Altamonte, Cranes Roost, Reiter Park, top-rated Seminole County schools, shopping, dining, and major hospitals. Seller is motivated — schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY ORLANDO LLC (407-288-8201)
Listing Agent: Ramona Biggs (321-947-6981)
441 WILD OAK CIR, LONGWOOD, FL 32779
$770,00068 Days on yellowkey MLS ID: O6405462
0 Days Off yellowkey (back on 5/15/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2812 Built: 1982Monthly Fee: $54 Tax: $3,972 (2024)Community: Sweetwater Oaks Sec 13Single Family
Taxes:$3,972
Remarks: Under contract-accepting backup offers. Tucked beneath a canopy of mature oaks on a quiet street, 441 Wild Oak Circle offers the space, privacy, and lifestyle that define Sweetwater Oaks living. Set on an expansive .64-acre homesite, this 4-bedroom, 3-bathroom residence spans over 2,800 square feet and has been thoughtfully maintained and updated throughout—offering both comfort and peace of mind. From the moment you arrive, the circular driveway and side-load 2-car garage create a welcoming presence, while the generous lot and natural surroundings set the tone for what’s inside. The home features an open, easy-flow layout designed for both everyday living and effortless entertaining, with spacious living areas and seamless connection to the outdoors. Natural light fills the interior, highlighting the home’s functional layout and inviting feel. Whether hosting guests or enjoying a quiet night in, the home lives comfortably with well-proportioned spaces and views that draw you outside. Step into your private backyard retreat, where a resurfaced pool is surrounded by an expansive paver patio, complete with a covered gazebo—creating the perfect setting for poolside entertaining, shaded lounging, and year-round gatherings. With over half an acre, the outdoor space offers a rare combination of privacy and flexibility, with plenty of room to expand, play, or simply unwind. Beyond its charm, this home has been meticulously cared for with major updates already completed, including new windows and doors, a whole-house generator, complete replumbing, and updated systems—providing true peace of mind for the next owner. Living in Sweetwater Oaks means embracing a lifestyle that’s hard to replicate. Residents enjoy access to a private, skiable Lake Brantley with a neighborhood boat ramp and beach, tennis and pickleball courts, playgrounds, and access to the Wekiva River for kayaking and outdoor adventures. All of this, zoned for top-rated Seminole County schools and conveniently located near shopping, dining, and major roadways. A rare combination of size, setting, and thoughtful upkeep—this is the kind of home that offers both immediate enjoyment and long-term value in one of Longwood’s most sought-after communities.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Tiffany Yates (321-684-2399)
2040 E TRIANGLE DR, LONGWOOD, FL 32779
$340,00064 Days on yellowkey MLS ID: O6406274
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1283 Built: 1985Monthly Fee: $28 Tax: $3,449 (2024)Community: Lake Brantley Isles 2Nd AddSingle Family
Taxes:$3,449
Remarks: Beautiful opportunity in the highly desirable Longwood area, perfectly located just minutes from Lake Brantley! This charming 3-bedroom, 2-bath home backs up to a peaceful conservation area, offering added privacy with no rear neighbors. Perfect for first-time homebuyers, investors, or anyone seeking affordable living in a prime location. Featuring a 4-year-old roof, granite countertops, stainless steel appliances, included washer and dryer, and a cozy wood-burning fireplace, this home blends modern updates with everyday comfort. The optional HOA provides access to an incredible lifestyle package with private access to Lake Brantley, including a boat ramp, fishing, playground, and pavilion—perfect for enjoying Florida living year-round. Located in an AE flood zone, flood insurance is required; however, the current owners pay just $2,790 annually for homeowners insurance including flood coverage, making ownership more affordable than expected. Conveniently located near shopping, dining, major roadways, and top-rated Seminole County schools, this property offers outstanding potential as a primary residence, rental property, or long-term investment. Don’t miss this chance to own a private, well-maintained home with exceptional amenities and value in one of Longwood’s most desirable communities. Schedule your showing today!
Listing Agent: Brenda Feliciani (407-405-0931)
262 OAKMONT RESERVE DR, LONGWOOD, FL 32750
$764,900149 Days on yellowkey MLS ID: O6382404
REDUCED by $5,000 (0.6%) on 05/11/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3430 Built: 2018Monthly Fee: $120 Tax: $7,565 (2025)Community: Oakmont ReserveSpa: YesSingle Family
Taxes:$7,565
Elementary School: Longwood Elementary
Middle School: Greenwood Lakes Middle
Remarks: SELLER'S MOTIVATED! Welcome to Oakmont Reserve, a gated community in the heart of Longwood. This spacious five-bedroom, 3.5-bath home offers a flexible, light-filled floor plan designed for everyday living and entertaining. The primary suite is conveniently on the first floor, while additional bedrooms provide ample space for family or guests. Kitchen boasts 42-inch cabinetry, oversized quartz island and stainless steel appliances and two walk-in pantries. Upstairs features four bedrooms plus dedicated office with double doors, and a dedicated theatre room with built-in surround sound speakers! Enjoy entertaining via the Florida lifestyle with a 40-foot covered lanai overlooking a screened-in Holland saltwater, heated pool and Jacuzzi with waterfall feature and LED light system. Enjoy a 2.5-car garage with extra storage space and custom overhead shelving. As a bonus, this home is upgraded with a solar panel system that makes the electric bill almost obsolete. Zoned for desirable Seminole County Schools, close to shopping, entertainment and world-renowned healthcare providers, and less than a one-hour drive to airports, beaches and Orlando's theme parks, this is your forever home!
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-333-1900)
Listing Agent: Kristen Wenderfer (973-868-9745)
2878 MARKHAM WOODS RD, LONGWOOD, FL 32779
$6,999,99975 Days on yellowkey MLS ID: O6403834
Bed: 10 Bath: 15.0 Gar: 17 Liv Area Sq Ft: 25706 Built: 2003 Tax: $70,734 (2025)Community: N/ASpa: YesSingle Family
Taxes:$70,734
Elementary School: Woodlands Elementary
Remarks: One or more photo(s) has been virtually staged. The Estate at Markham Woods. Set behind private electronic gates and a guarded entry, a rare sense of arrival unfolds across more than seven acres of secluded, high and dry landscape in the heart of Markham Woods. Here, architecture, land, and infrastructure converge to create something far beyond a residence, a fully realized, multi generational compound designed for those who value ultimate security, complete privacy, and a deeply personal expression of luxury living. This is not simply a home. It is a sanctuary. The main residence, spanning nearly 18,000 total square feet with over 11,000 square feet under air, is a study in European inspired elegance and enduring craftsmanship. Six bedrooms and ten baths are thoughtfully arranged to balance grand scale entertaining with intimate, everyday living. A sweeping staircase, private elevator, and curated architectural moments create a sense of quiet sophistication, while spaces like the library, gym, spa retreat, and hidden garden offer a more personal rhythm of life. Beyond the main residence, the estate reveals itself as a true compound. A fully independent guest house, a private cottage ideal for staff or extended family, and a climate controlled car barn with soaring ceilings create a layered environment where generations can gather, yet remain entirely self contained. Whether hosting, retreating, or simply living, every structure has been designed with purpose and discretion. Security here is not an afterthought, it is foundational. A guard house with full amenities, integrated systems, data infrastructure, multiple generators, this offers a sense of confidence and continuity. This is a property built not only for comfort, but for resilience. A private helipad further elevates both security and accessibility, offering a seamless connection to business, leisure, and global travel. Outdoors, the estate transforms into a private resort environment. Multiple pools, spa experiences, expansive lawns, and curated gathering spaces create an atmosphere equally suited for large scale entertaining or quiet family moments. Even the youngest members of the household are considered, with playful elements woven seamlessly into the landscape, reinforcing the estate’s identity as a true family legacy property. And yet, despite its complete seclusion, the estate remains remarkably connected. Within minutes, you are positioned at the center of everything that defines Central Florida living. Downtown Orlando, the region’s top private and public schools, and the area’s most important roadways including the I-4 express lanes are all easily accessible. Orlando International Airport, Orlando Executive Airport, and Sanford International Airport provide effortless travel options, while world class golf, the Dr. Phillips Performing Arts Center, Kia Center, Camping World Stadium, and Inter and Co Stadium place culture and entertainment within immediate reach. The beaches and theme parks are equally within your orbit, close enough for spontaneity, yet far enough to preserve the estate’s sense of calm. This is the rare balance. A property where one can live completely private, completely secure, and completely immersed in luxury, while remaining connected to everything that matters. For those seeking not just a home, but a generational legacy compound defined by discretion, scale, and intention, this is a singular opportunity in Central Florida.
Listing Agent: Matthew Mckee (407-948-0658)
116 SPRINGWOOD CIR #D, LONGWOOD, FL 32750
$169,99975 Days on yellowkey MLS ID: O6403702
2 Days Off yellowkey (back on 5/8/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1020 Built: 1973Monthly Fee: $370 Tax: $523 (2025)Community: Springwood VillageCondo
Taxes:$523
Remarks: Welcome to this beautifully updated 2-bedroom, 1-bath condo tucked away in a quiet, well-maintained community—perfect for both homeowners and investors. This move-in-ready unit features brand new vinyl flooring throughout, a fully renovated kitchen with modern cabinetry, sleek granite countertops, and a clean, contemporary design that truly stands out. The bathroom has been tastefully remodeled, offering a fresh and modern feel. What makes this unit truly unique is its private in-unit washer and dryer room—a rare feature in this community where most units rely on shared laundry. Enjoy peaceful mornings and relaxing evenings on your screened-in patio, the perfect space to unwind with coffee, tea, or a glass of wine in a quiet setting. The community offers an affordable HOA that includes water, garbage pickup, on-site management, maintenance, and security, providing both value and peace of mind. Residents also enjoy access to two swimming pools, a clubhouse with fitness center and party room, a lighted tennis court, basketball half court, multiple laundry facilities, and bike storage. With low property taxes and strong rental potential, this property is an excellent opportunity for both end-users and investors. Opportunities like this don’t last—schedule your showing today before it’s gone.
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)
Listing Agent: Ayoub Seffari (407-497-4015)
280 SPRINGSIDE RD S, LONGWOOD, FL 32779
$626,640186 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
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: STARLINK REALTY (239-693-7263)
Listing Agent: Dr April Joh Johnson (813-545-9218)
7302 OLYMPIA CT, LONGWOOD, FL 32779
$249,90071 Days on yellowkey MLS ID: O6405170
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1365 Built: 1984 Tax: $2,457 (2025)Community: Clubside At Sabal Point A CondoCondo
Taxes:$2,457
Remarks: Welcome home to this beautifully maintained and move-in ready condo in the desirable Clubside at Sabal Point community in Longwood. Offering nearly 1,400 square feet of thoughtfully designed living space, this light-filled upper-level unit combines comfort, style, and convenience in one inviting package. Step inside to discover a spacious open floor plan with tile and laminate flooring throughout - no carpet for easy maintenance. The welcoming foyer leads to a convenient half bath, an in-unit laundry room with full-sized appliances, and a large closet straight ahead. The living and dining areas flow seamlessly into a generously sized kitchen featuring ample counter space, a pantry, and eat-in area, making it perfect for both everyday living and entertaining. The split-bedroom layout provides ideal privacy, with two oversized primary suites located on opposite sides of the home. Each bedroom includes its own ensuite bathroom - one with a tub/shower combination and the other with a walk-in shower - as well as large walk-in closets and additional linen storage. Whether for guests, roommates, or multi-generational living, this layout offers flexibility and comfort for all. Step outside to your private screened-in balcony or lanai, where you can relax with morning coffee or unwind in the evening while enjoying peaceful community views. Residents enjoy a low-maintenance lifestyle with HOA fees covering exterior maintenance, water, trash, pest control, and landscaping. Community amenities include a resort-style pool, fitness center, clubhouse, tennis courts, and beautifully maintained grounds with mature trees and walking paths. Ideally located just minutes from shopping, dining, parks, and outdoor recreation, with quick access to I-4, this home offers the perfect balance of natural Florida beauty and everyday convenience. Whether you're a first-time buyer, downsizing, or seeking an investment, this condo is a wonderful opportunity in a prime location.
Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)
Listing Agent: Cheryl Roda-Wu (407-595-9580)
749 SEMINOLE AVE, LONGWOOD, FL 32750
$299,00086 Days on yellowkey MLS ID: O6400530
INCREASED by $10,000 (3.5%) on 05/04/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1108 Built: 1971 Tax: $2,752 (2024)Community: Lake Wayman Heights Lake AddSingle Family
Taxes:$2,752
Remarks: Roof only one year old, Freshly Painted,All Tiled Floors,Electrical Updated,New Microwave,Some windows updated,Huge Back Yard,Great Location,Great Value
Listing is courtesy of: SOUTHERN REALTY ENTERPRISES (407-869-0033)
Listing Agent: Frank Filippelli (407-448-1042)
1469 GRACE LAKE CIR, LONGWOOD, FL 32750
$560,000261 Days on yellowkey MLS ID: O6355680
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2174 Built: 1982Monthly Fee: $40 Tax: $5,031 (2025)Community: North CoveSingle Family
Taxes:$5,031
Remarks: An ideal blank canvas for those seeking top-rated schools and a fantastic neighborhood! This 4-bedroom, 2.5 bath home features a screened-in pool, a cozy family room with beamed ceilings, and tile flooring throughout. The expansive sunroom, complete with a kitchen service window, is perfect for relaxing or entertaining. The large primary suite includes a spacious closet and an en suite bathroom. With a 2-car garage,this home sits on a desirable corner lot with mature tree coverage, a lovely manicured lawn in the highly sought after North Cove community.
Listing is courtesy of: MOREHOUSE REALTY INC (407-331-4444)
Listing Agent: Alvin Moore (407-331-4444)
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