Displaying: For Sale
Location: Longwood
Property Type(s): Single Family
Beds: 4 to 4
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Longwood - 97 properties found
216 TOLLGATE TRL, LONGWOOD, FL 32750
$399,0004 Days on yellowkey MLS ID: NS1088092
0 Days Off yellowkey (back on 5/2/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2011 Built: 1971 Tax: $2,002 (2025)Community: The WoodlandsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,002
Elementary School: Woodlands Elementary
High School: Lyman High
Tax Year: 2025
Middle School: Rock Lake Middle
Remarks: Welcome to a home full of opportunity in one of the area’s most charming and active neighborhoods! This 4-bedroom, 2-bath home offers over 2,000 sq. ft. of living space and sits on a spacious oversized lot in the tranquil Woodlands neighborhood. With quiet streets and friendly neighbors often seen out walking and enjoying the Florida lifestyle, this property offers the perfect blend of community, comfort, and potential. The major updates have already been taken care of, giving buyers peace of mind and a strong foundation for future improvements. The home features a new roof (2024), full-house generator (2019), updated windows, whole-house replumbing, and a Lennox Smart Hub A/C system (2021) for modern efficiency and reliability. An alarm system is also in place for added security. Inside, you’ll find a newly updated kitchen with a gas range and beautiful granite countertops, along with a spacious layout and a cozy wood-burning fireplace. The living areas offer great bones and are ready for your personal updates and design vision. Step outside to your private backyard retreat, complete with a pool, fully fenced yard, large shed, and plenty of space to create the outdoor oasis of your dreams. Located in a wonderful neighborhood with an optional HOA, and top-rated Seminole County schools, this home offers an incredible opportunity to add value with cosmetic updates, and giving the landscaping a little TLC. Don’t miss your chance to own a well-maintained home with major upgrades already complete—all it needs is your finishing touch to make it your own! Schedule your private showing today!
Listing is courtesy of: WHITE WHALE REAL ESTATE (388-689-5171)
Listing Agent: Rebecca Henry (407-341-3355)
1398 COR JESU CT, LONGWOOD, FL 32750
$465,000180 Days on yellowkey MLS ID: O6358213
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2222 Built: 1984 Tax: $4,124 (2024)Community: Cor JesuSingle Family
Taxes:$4,124
Elementary School: Longwood Elementary
Tax Year: 2024
Middle School: Greenwood Lakes Middle
Remarks: Welcome home to this beautifully maintained 4-bedroom, 2-bath residence with a 2-car garage, offering comfort, functionality, and style in every detail. Located in a wonderfully maintained neighborhood with no HOA, this home provides all the benefits of a well-kept community without the added fees or restrictions. Step inside to discover a home that has been thoughtfully refreshed throughout. The split floor plan design provides excellent privacy and flow, complemented by tile and laminate flooring and an abundance of natural light streaming through the large windows. The updated kitchen is a standout, showcasing granite countertops, a travertine tile backsplash, and stainless appliances. A convenient built-in bar area and cozy dinette sit just off the kitchen — perfect for casual meals or entertaining guests. The family room features vaulted ceilings, skylights, and a charming travertine-accented fireplace, creating an inviting atmosphere. Sliding doors open to a bonus room, which offers additional living space with tile flooring and French doors leading out to the backyard deck. The spacious master suite includes sliding doors that open to a private outdoor courtyard, ideal for a quiet retreat. The master bathroom has been tastefully remodeled, featuring dual sinks, recessed lighting, a large tiled walk-in shower, and a roomy walk-in closet. The guest bathroom, also beautifully remodeled, offers double sinks, a tub/shower combo, recessed lighting, and direct access to the bonus room. Additional highlights include an indoor laundry room conveniently located off the hallway to the garage. Step outside and enjoy the deck with wood-look tile flooring overlooking a large, fenced backyard with plenty of space to relax, play, and entertain under the shade of mature trees. NEW DRAIN FIELD! Don’t miss your chance to see this wonderful home — call today for your private showing!
Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)
Listing Agent: Tara Mruk (724-705-2122)
1401 WINDSOR AVE, LONGWOOD, FL 32750
$759,900101 Days on yellowkey MLS ID: O6376311
0 Days Off yellowkey (back on 3/23/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3576 Built: 1970Monthly Fee: $13 Tax: $4,109 (2024)Community: KnollwoodSpa: NoSingle Family
Taxes:$4,109
Elementary School: Altamonte Elementary
Middle School: Milwee Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Elegantly renovated single-family residence offering 4 bedrooms and 3.5 bathrooms in the sought-after Longwood area, conveniently located near I-4, premier shopping, and dining. This home has been thoughtfully updated throughout, featuring a new roof, updated AC and electrical systems, fresh interior and exterior paint, and enhanced landscaping with irrigation. The custom kitchen showcases solid wood cabinetry, stone countertops, and stainless steel appliances, complemented by beautifully renovated bathrooms with updated lighting and fixtures throughout the property. A spacious screened-in pool with a new enclosure creates a private outdoor retreat, while a large exterior shed provides additional storage. The impressive bonus great room features refinished wood flooring and a wet bar, creating an exceptional space for entertaining. A rare opportunity to own a move-in-ready home with extensive upgrades!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Blake Bolton (407-318-0361)
105 CEDAR OAK TRL, LONGWOOD, FL 32750
$625,0005 Days on yellowkey MLS ID: O6403317
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2212 Built: 1973 Tax: $2,305 (2024)Community: Woodlands Sec 4Spa: YesSingle Family
Taxes:$2,305
Elementary School: None
High School: None
Middle School: None
Remarks: Absolutely Everything You’ve Been Looking For — in the Sought-After Woodlands Community of Longwood! This lovingly maintained home has been cherished by the same owners for 39 years and is now ready to welcome new memories. With an ideal multigenerational floor plan, in-law suite, sparkling pool, and huge yard, this home truly has it all. Key Features Spacious Layout: Bright, open floor plan with flexible living spaces — perfect for entertaining or quiet family living. Gourmet Kitchen: A chef’s dream with an abundance of rich wood cabinetry featuring soft-close drawers, granite countertops, double oven, cooktop, microwave, and tons of counter space. A large window overlooks the pool, and the breakfast bar is ideal for casual meals. Comfortable Gathering Spaces: The kitchen opens to a large family room with French doors leading to a massive 30-foot screened lanai with gorgeous wood ceiling and huge paddle fans, perfect for summer barbecues and poolside relaxation. A separate dining area features elegant built-in cabinetry. Versatile Living Room: A huge formal living room (or flex space) features a gorgeous gas fireplace surrounded by beautiful stone and framed by custom shelving—ideal for a game room, home theater, or play area. Private Primary Suite: The spacious primary retreat includes French doors overlooking the pool, dual closets, and an ensuite bath with double sinks and walk-in shower. Large Bedrooms: Spacious secondary bedrooms with large closets and conveniently located near full bath with pool access. In-Law Suite: Thoughtfully designed addition with its own private entrance, full bath, dual sinks, walk-in shower, and a generous 23’ x 12’ living space—perfect for guests or multigenerational living. Outdoor Oasis: Enjoy the 8-foot-deep screened pool with gas heater for year-round swimming. The 30’ x 17’ lanai has a natural gas hookup for grilling and entertaining. Despite the large pool, there’s still ample green space on your .29-acre yard for gardening. separate Well for Irrigation System keeps your plants lush and green. Bonus size indoor laundry rom, exta storage closets throughout and large two car garage. Updates include: Brand-new plumbing, new electrical panels, 2020 roof, replaced windows, exterior paint and freshly painted living areas. Four-point inspection will be available. Location & Lifestyle In the heart of Seminole County, zoned for top-rated schools and just minutes from I-4, world-famous attractions, dining, and shopping. This home blends classic character with modern comfort in one of Longwood’s most desirable neighborhoods. Come see why this home truly has everything you’ve been searching for—and more!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Mindy Machock (407-461-1866)
212 TOLLGATE TRL, LONGWOOD, FL 32750
$490,0003 Days on yellowkey MLS ID: O6404009
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1834 Built: 1972Monthly Fee: $8 Tax: $1,770 (2024)Community: Woodlands TheSpa: NoSingle Family
Taxes:$1,770
Remarks: Welcome to The Woodlands! This beautifully maintained 4 bedroom, 2 bathroom, POOL home checks all the boxes, and is move-in ready! There's also a BRAND NEW ROOF! The living room, dining room, family room, and primary bedroom all feature beautiful hardwood floors, and the remaining bedrooms are carpeted. All bedrooms have ceiling fans with lights, and generous closet space. Both bathrooms are nicely updated with designer vanities and granite countertops. The kitchen features solid wood cabinets, granite countertops, a beautifully tasteful backsplash, and updated appliances. Off the kitchen you will find the large utility room with lots of storage. Peak around the corner in the garage to find a hidden bonus/storage room with a wall-unit AC - perfect for extra storage or even a private office! Head out back to enjoy the screened-in lanai and large saltwater swimming pool. This HUGE back yard is a dream - and fully fenced! Additional remarkable features of this property include a natural gas grill, a whole house generator on natural gas, and a natural gas tankless water heater. This home is zoned for AMAZING Seminole County Schools - Woodlands Elementary, Rock Lake Middle, and Lyman High! Do not miss this fantastic opportunity!
Listing Agent: Emily Halpern (407-625-9246)
105 SWEET BAY LN, LONGWOOD, FL 32779
$785,0003 Days on yellowkey MLS ID: O6401023
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2853 Built: 1978Monthly Fee: $229 Tax: $7,454 (2025)Community: Springs The Deerwood EstatesSpa: YesSingle Family
Taxes:$7,454
Elementary School: Sabal Point Elementary
Remarks: Set on a private, tree-canopied lot with a courtyard-style layout, pool, spa, waterfall, and preserve views, this custom home offers one of the most distinctive living experiences in the community. The Springs is a guard gated community located within Central Florida's original tourist attraction, the pristine Sanlando Springs. Residents enjoy access to a host of amenities including this private spring with crystal clear water, numerous rivers, hiking trails, tennis and pickleball courts, private community, large clubhouse and community venue, horse stables, and more, all located within 15 minutes of Downtown Orlando and 30 minutes to the theme parks! As you approach the home you’ll find a canopied driveway lined with towering trees that leads to a home dressed in warm cream siding with stone accents and a distinctive architectural roofline that speaks to the home’s custom architectural character. Step onto the brick-paved covered front patio with cedar ceiling, coach lighting, and a double front door with sidelights, and you already feel the warmth of this home before you've crossed the threshold. Inside, you’re greeted by one of the home's most captivating features, the private interior courtyard. This skylit stone-paved atrium is wrapped on all sides by the home itself, lush with tropical plantings and accessible from multiple rooms, it functions as an outdoor sanctuary that is completely your own. The formal living room is a beautiful place to gather with friends and family, enjoy quiet conversation, or settle in with a good book and cup of coffee beneath exposed timber beams and natural wood-look flooring. Adjacent, the light-filled dining room elevates holidays and celebrations with space for up to 12 guests, walls with panel molding, custom built-ins, crown molding, and a designer chandelier. The kitchen delivers in both form and function: white shaker cabinetry, granite countertops, an extra large center island, stainless steel appliances, two pantries, and subway tile backsplash with ribbon tile inlay, all sit beneath a continuation of the signature vaulted ceiling, soaring to incredible heights with panoramic sliders and large transom windows offering stunning views of the backyard patio, pool, and nature preserve. Deer and other stunning Florida wildlife can regularly be seen grazing or traversing outside the fence making this home a truly unique escape. The primary suite is resort-caliber: a spa bath featuring a freestanding soaking tub, oversized glass walk-in shower with designer tile banding, double vanity with marble tops, and direct access to a custom walk-in closet with full built-in shelving, shoe storage, and hardwood floors, all with direct access to a remarkably private outdoor balcony with covered seating and sprawling backyard views. Secondary bedrooms are generously sized with hardwood floors, natural light, and extraordinary closet space. A dedicated laundry room and multiple well-appointed bathrooms round out the interior. Out back, the property fully delivers on its promise of offering a relaxed Florida lifestyle with a resort-style freeform pool, an integrated spa, a dramatic natural stone waterfall feature, and multiple sun steps, all wrapped in a fully fenced, tree-canopied backyard that feels miles away from everything. This is Florida living at its finest.
Listing is courtesy of: DON HARKINS REALTY LLC (321-377-0341)
Listing Agent: Scott Major (407-697-9301)
478 SABAL TRAIL CIR, LONGWOOD, FL 32779
$645,0006 Days on yellowkey MLS ID: O6403175
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2529 Built: 1984Monthly Fee: $85 Tax: $6,601 (2025)Community: Sabal Point Sabal Trail AtSpa: NoSingle Family
Taxes:$6,601
Remarks: Welcome to the desirable Sabal Point community! Located at 478 Sabal Trail Circle in Longwood, this well-maintained home sits on a nearly one-third acre lot, offering a spacious front yard and one of the larger rear yards in the neighborhood. The home features a split-bedroom floor plan and an open layout with both a large living room and separate family room, providing flexibility for everyday living or entertaining. The living room can easily be utilized as a spacious home office. The expansive covered rear porch overlooks a screened-in pool and deck, along with a large open patio area—ideal for enjoying Florida outdoor living. Interior features include solid wood cabinetry in the kitchen and bathrooms, solid surface countertops, and quality laminate flooring throughout the main living areas and bedrooms. Major updates include a full re-plumb with PEX piping, an upgraded HVAC system, a new roof installed in 2024, and a new pool heat pump added in 2022. Electric vehicle charging hookup in garage. Conveniently located near major roadways, shopping, dining, and zoned for great schools, this property offers space, functionality, and key upgrades within an established Longwood community.
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Daniel Araque (321-276-0747)
284 ISLAND SOUND CT, LONGWOOD, FL 32779
$799,9996 Days on yellowkey MLS ID: O6401810
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2692 Built: 2021Monthly Fee: $159 Tax: $6,766 (2025)Community: Retreat At Lake BrantleySingle Family
Taxes:$6,766
Elementary School: Wekiva Elementary
High School: Lake Brantley High
Middle School: Teague Middle
Remarks: Step into refined elegance and effortless sophistication in this nearly new Dockside masterpiece located within the exclusive, gated community of The Retreat at Lake Brantley. Offering 4 bedrooms, 3 bathrooms, and 3,755 total square feet, this expansive single-story estate is thoughtfully designed for the discerning buyer who values both luxury and livability. From the moment you arrive, the home makes a striking first impression with its upgraded designer front door and spacious 3-car garage—perfect for luxury vehicles and additional storage. Inside, a seamless open-concept floor plan unfolds, anchored by oversized designer tile flooring that flows throughout the main living spaces. At the heart of the home, the gourmet kitchen is a true showpiece—featuring gleaming granite countertops, custom cabinetry, premium stainless steel appliances, and an oversized island that invites both intimate gatherings and grand entertaining. Every detail has been curated to elevate both form and function. The owner’s suite is a private retreat, offering a serene escape with a spacious custom walk-in closet, spa-inspired walk-in shower with full-height tile, and dual vanities designed for everyday luxury. Secondary bedrooms are generously sized, including a private en-suite ideal for guests or multigenerational living. Expansive pocket sliding glass doors create a seamless indoor-outdoor experience, opening to a sunlit entertaining space perfect for hosting or relaxing in style. This home is enhanced with modern smart home features, delivering convenience and control at your fingertips. Beyond the home, residents enjoy exclusive access to a private community boat ramp on Lake Brantley, offering a lifestyle centered around recreation, relaxation, and waterfront living. Ideally located near top-rated Seminole County schools, including Lake Brantley High School, and with easy access to major highways, this residence perfectly balances tranquility and accessibility. This is more than a home—it’s a statement of lifestyle, comfort, and elevated living. Experience the pinnacle of luxury in The Retreat at Lake Brantley—your private lakeside sanctuary awaits.
Listing is courtesy of: UNITED REAL ESTATE PREFERRED (407-243-8840)
Listing Agent: Verdelle Lambert Rice (407-242-3757)
219 NOB HILL CIR, LONGWOOD, FL 32779
$594,75046 Days on yellowkey MLS ID: O6392082
REDUCED by $5,000 (0.8%) on 04/23/2026
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
Elementary School: Forest City Elementary
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)
308 SMOKERISE BLVD, LONGWOOD, FL 32779
$649,00059 Days on yellowkey MLS ID: O6387465
REDUCED by $1,000 (0.2%) on 04/26/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2352 Built: 1979Monthly Fee: $108 Tax: $5,564 (2025)Community: Sweetwater Oaks Sec 12Spa: NoSingle Family
Taxes:$5,564
Remarks: Welcome to 308 Smokerise Blvd., tucked away on a quiet corner lot within a cul-de-sac in the highly sought-after Sweetwater Oaks community of Longwood. Situated on an expansive .40-acre homesite framed by majestic oak trees and mature landscaping, this 4-bedroom, 2-bath residence offers 2,352 heated square feet of inviting, thoughtfully designed living space. From the moment you step inside, the home feels warm and welcoming. Skylights fill the space with natural light, and the split floor plan provides both privacy and comfortable gathering areas. At the heart of the home is the den — a cozy yet spacious retreat featuring a wood-burning fireplace and adjoining entertaining bar area. This inviting space is what originally captured the current owners’ hearts. It’s easy to imagine evenings gathered around the fire, hosting friends at the bar, or simply unwinding at the end of the day. It’s a room designed for connection. The primary suite offers its own private escape. The ensuite bath feels like a boutique resort spa, highlighted by distinctive, whimsical wallpaper that adds personality and charm — an unexpected and delightful design statement. Step outside to your screened pool oasis surrounded by brick pavers and lush greenery. With plenty of yard space on this oversized corner lot, outdoor living comes naturally here. The Blackstone grill conveys, making the backyard perfectly set up for sunset dinners and weekend gatherings. Major updates provide valuable peace of mind: • Brand new roof • A/C replaced in 2022 • Variable-speed pool pump (2025) • Water treatment system (2021) • Three updated electrical panels (2021) Sweetwater Oaks residents enjoy private lake access and boat ramps to Lake Brantley, along with multiple parks, tennis courts, pickleball courts, a clubhouse, and scenic community spaces. Located near Wekiva Springs State Park, major highways and toll roads, Orlando attractions, beaches, shopping, and dining, the community offers both tranquility and convenience. It is also golf cart friendly :-) This is more than just a home — it’s a place where memories are made, gatherings feel effortless, and everyday living feels just a little bit special...
Listing is courtesy of: CENTURY 21 ALTON CLARK (407-636-4637)
Listing Agent: Ginny Peters (407-443-3965)
2 HUDSON CV, LONGWOOD, FL 32750
$544,00033 Days on yellowkey MLS ID: O6395131
REDUCED by $5,000 (0.9%) on 04/15/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1913 Built: 1974Monthly Fee: $25 Tax: $2,399 (2024)Community: Sleepy Hollow 1St AddSpa: NoSingle Family
Taxes:$2,399
Remarks: Tucked at the end of a quiet cul-de-sac in the established Sleepy Hollow community, this fully renovated 4-bedroom, 2-bath home sits on an oversized ~0.40 acre lot in the heart of Longwood. With mature surroundings and a little extra breathing room between homes, it offers a setting that’s getting harder to find—while still being just minutes from I-4 and SR 434 for an easy commute. Inside, the home has been completely refreshed with new LVP flooring throughout and a beautifully updated kitchen featuring quartz countertops, a tiled backsplash, brand-new appliances, and brass-toned hardware for a clean, modern finish. The layout offers both living and dining spaces, with French doors from the dining room opening out to a spacious screened porch. The primary suite is filled with natural light, has its own access to the porch, and features a fully remodeled ensuite with a large tiled shower. A separate family room with a wood-burning fireplace provides a second living area and also connects to the porch, creating an easy flow for everyday living or entertaining. The screened porch (approx. 36x10) overlooks a private open-air pool and backyard, with a convenient pool bath that also serves the additional bedrooms—all of which have been updated. Additional highlights include a new roof (in progress) and fresh exterior paint on the stucco, while the original brick has been preserved for added character.
Listing is courtesy of: LEGACY REALTY & BROKERS LLC (407-887-7779)
Listing Agent: Skip Juma (206-349-7547)
105 E COTTESMORE CIR, LONGWOOD, FL 32779
$550,0003 Days on yellowkey MLS ID: O6403980
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2244 Built: 1977Monthly Fee: $23 Tax: $3,894 (2024)Community: Wekiva Hunt Club 3 Fox Hunt Sec 3Single Family
Taxes:$3,894
Remarks: Sought after Wekiva home located off Hunt Club. This is a 4 bedroom, 2 bath home with an extra bonus room right off the prime bedroom. Spacious house that is well maintained, all stainless steel appliances, working fireplace, shutters in windows. Back yard has access to the wekiva trail for walking and running. Paved pool patio, pool. Two parks with in walking distance. This house comes with an electrical disconnect for a generator in case a power outage.
Listing is courtesy of: PRIMAC GROUP, INC (407-889-7075)
Listing Agent: Andre Diaz (407-252-8533)
106 LONESOME PINE DR, LONGWOOD, FL 32779
$655,0003 Days on yellowkey MLS ID: O6403779
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2379 Built: 1976Monthly Fee: $54 Tax: $2,761 (2025)Community: Sweetwater Oaks Sec 08Single Family
Taxes:$2,761
Remarks: One or more photo(s) has been virtually staged. Welcome to 106 Lonesome Pine Drive, where everyday living feels a little more like getting away! Nestled in Longwood’s treasured Sweetwater Oaks community and set on an extra deep .69 acre lot, this home offers something rare: room to breathe. Room to entertain. Room to live the way you’ve always pictured — with nature as your backdrop and comfort woven into every corner. *NEW: Electric pool heater 2025, exterior paint 2024, All light switches and receptacles 2024, pool saltwater system 2023, outdoor fireplace 2022, pool renovation, screen enclosure & Shellock pavers 2022, 200amp Leviton smart electrical panel, LED energy efficient lights throughout house & interior paint 2021!* From the moment you arrive you’re greeted with a sense of privacy that’s hard to find in a neighborhood setting. Once inside this home opens up with warm, welcoming spaces designed for real life showcasing thoughtful updates and well-kept finishes reflecting a true pride of ownership. You’ll find casual dining and living rooms with custom wood floors made of oak, walnut and mahogany plus a spacious family room enhanced by tile floor, vaulted ceiling with beautiful wood beams and dual skylights, a floor-to-ceiling stone fireplace and sliding glass door to the patio. Upgraded kitchen is loaded with personality boasting wood panel cabinets galore with bar area, granite counter with double bevel edge, working island with breakfast bar, decorative backsplash, complete stainless steel appliance package plus a large picture window offering pool and yard views. But it’s the outdoor living that truly sets this home apart! The backyard unfolds like a private resort, offering multiple places to unwind, dine, and enjoy the Florida lifestyle year round. This space offers several covered patio spaces, tongue and groove ceiling, cool slate floor, mounted TVs, hot tub right off primary, sparkling renovated pool has pebble tech bottom, shelf with two Adirondak chairs & pretty blue tile, modern pavers, outdoor wood burning fireplace & lots of market lights! Whether you’re hosting a lively poolside afternoon, relaxing fireside at dusk, or simply taking in the peaceful view of the deep lot stretching behind you, this space invites you to slow down and stay awhile. Step out back into huge fully fenced yard plus lot goes back behind fence, offering endless possibilities! As if that isn't enough, you'll have peace of mind year round with a whole house generator! If you’ve been waiting for a home that offers privacy without isolation, style without pretense, and outdoor living that feels like a true extension of the home, this home is the one that delivers! Incredible Longwood location with easy access to 434, 436, I4 plus close to multiple Publix, schools, lots of dining, Wekiva Island, Wekiwa Springs Park, Uptown Altamonte, Orlando Health, Advent Health and so MUCH MORE!! <>
Listing is courtesy of: FLORIDA HOME TEAM REALTY LLC (407-774-8100)
Listing Agent: Stacy Wayne (407-415-9484)
1508 CANARY ST, LONGWOOD, FL 32750
$345,0003 Days on yellowkey MLS ID: O6402841
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1595 Built: 1973 Tax: $1,210 (2025)Community: Sky Lark SubSingle Family
Taxes:$1,210
Elementary School: Highlands Elementary
High School: Winter Springs High
Remarks: One or more photo(s) has been virtually staged. Welcome to 1508 Canary Street in Longwood! This charming 4-bedroom, 2-bath home features a desirable split floorplan, offering both privacy and functionality for everyday living. With no HOA, you’ll enjoy the freedom to truly make this property your own. Step outside to a spacious, fully fenced backyard with mature trees, perfect for relaxing, entertaining, or letting pets roam freely. Whether you're hosting gatherings or simply enjoying a quiet evening at home, this outdoor space offers endless possibilities. Air conditioning, water heater, electric and plumbing have been updated. Conveniently located near shopping, dining, and major roadways, this home is a great opportunity to enjoy comfortable living in the heart of Longwood.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Dawn Grigsby (407-970-9051)
216 THISTLEWOOD CIR, LONGWOOD, FL 32779
$657,90038 Days on yellowkey MLS ID: O6394238
REDUCED by $2,000 (0.3%) on 05/01/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2272 Built: 1980Monthly Fee: $54 Tax: $6,425 (2024)Community: Sweetwater Oaks Sec 12Single Family
Taxes:$6,425
Remarks: Located in the highly desirable Sweetwater Oaks neighborhood of Longwood with Lake Access. This beautifully renovated 4-bedroom, 2.5-bath Pool home sits on an expansive .32-acre fenced lot and features a spacious 2-car garage. From the moment you arrive, the home’s exceptional curb appeal, lush manicured landscaping, and inviting presence set the tone for what awaits inside. Step through the front door to discover luxury vinyl flooring and a bright, open-concept layout designed for both comfort and elegant living. The beautifully updated kitchen showcases stainless steel appliances, quartz countertops, and overlooks the pool area, creating the perfect setting for entertaining or enjoying everyday moments at home. Each bedroom is thoughtfully designed with ceiling fans, large windows, and abundant natural light. The primary suite provides a private retreat, highlighted by a spacious spa-inspired bathroom featuring a large tile-lined shower with dual shower heads. Sliding glass doors from the living area open to a screened-in pool patio and expansive backyard, providing an ideal outdoor space for entertaining, relaxing poolside, or enjoying Florida’s stunning sunsets in your own private oasis. Residents of Sweetwater Oaks enjoy access to an exceptional array of community amenities that make the neighborhood truly special. The community features private access to Sweetwater Beach on Lake Brantley, where residents can enjoy a lakeside park, sandy beach area, and opportunities for boating, water skiing, sailing, kayaking, and fishing. The neighborhood also comes with multiple recreational facilities including tennis courts, pickleball courts, sand volleyball, playgrounds, and a community center that hosts events and gatherings throughout the year. Just nearby, Riverbend Park provides additional outdoor recreation with access to the Wekiva River, sports fields, kayaking and canoeing launches, fishing spots, and scenic nature trails. The home is also located within the boundaries of highly regarded schools, including Sabal Point Elementary, Rock Lake Middle School, and Lake Brantley High School.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
1889 RANCHLAND TRL, LONGWOOD, FL 32750
$998,9006 Days on yellowkey MLS ID: V4948599
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2333 Built: 1998 Tax: $6,016 (2024)Community: MeadowlandsSingle Family
Taxes:$6,016
Remarks: Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated on 2 acres of agricultural land in Longwood with Lake Mary city limits. Originally designed as an equestrian estate, this unique property offers the perfect blend of modern living and rural charm. The home was completely updated in 2022 and features a stylish kitchen with newer cabinetry, granite countertops, and ample space for entertaining. All bathrooms have been thoughtfully renovated with elegant ceramic tile, glass-enclosed showers, and LED mirrors, creating a sleek, contemporary feel. The spacious primary suite offers a comfortable retreat with a large walk-in closet, while the additional three bedrooms are generously sized and include built-in closets. Step outside to enjoy your private oasis—featuring a fully resurfaced pool and freshly painted pool deck, ideal for relaxing or hosting gatherings. The expansive property also includes approximately 8,000 square feet of installed pavers throughout the driveway and surrounding areas, adding both functionality and curb appeal. Equestrian enthusiasts will appreciate the well-equipped barn with 4 stalls, a feed room, and 4 shower poles—ready for your horses or farm animals. Additional upgrades include a new roof (2022), new well system and pump, tankless water heater, and an electric gated entrance for added privacy and security. This one-of-a-kind property offers space, upgrades, and versatility—don’t miss your opportunity to own a truly special estate. Schedule your private showing today!
Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)
Listing Agent: Yanet Garcia, Pllc (214-574-0785)
470 FREEMAN ST, LONGWOOD, FL 32750
$490,0004 Days on yellowkey MLS ID: O6403714
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2261 Built: 1998Monthly Fee: $51 Tax: $4,198 (2024)Community: Longwood PlantationSingle Family
Taxes:$4,198
Remarks: Set on an oversized lot with Water VIEWS in the desirable Longwood Plantation community, 470 Freeman Street offers a rare combination of privacy, functionality, and scenic backyard views with no rear neighbors, a peaceful conservation backdrop, and a pond just beyond your fence line. This single-story 4-bedroom, 2-bath home features an open, light-filled layout with high ceilings and seamless flow between the main living spaces, creating an ideal setup for both everyday living and entertaining. The kitchen is well-appointed with granite countertops, wood cabinetry, stainless steel appliances, and an island with additional seating, all overlooking the main living areas and backyard. The spacious primary suite includes dual vanities, a soaking tub, and a separate shower, while the additional bedrooms offer flexibility for guests, family, or a home office. Step outside to a large covered and screened lanai that extends your living space year-round, opening to a fully fenced backyard with plenty of room to add a pool, a storage shed for added convenience, and unobstructed views that are hard to find at this price point. With a 2017 roof, 2020 HVAC system, and an updated electrical panel already in place, this home delivers both comfort and long-term peace of mind, all within a well-maintained neighborhood with low HOA fees and access to top-rated Seminole County schools, shopping, dining, and major roadways.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Chase Tate, Pllc (217-899-2619)
1209 ROXBORO RD, LONGWOOD, FL 32750
$799,999112 Days on yellowkey MLS ID: O6373160
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3332 Built: 1969Monthly Fee: $13 Tax: $4,384 (2024)Community: Knollwood 1St AddSpa: NoSingle Family
Taxes:$4,384
Remarks: Stunning Remodeled Estate Home in Knollwood - Longwood! Welcome to this exceptionally remodeled estate home located in the highly desirable Knollwood community of Longwood. Set on a generous 0.70-acre lot, this 3,332-square-foot residence offers four bedrooms and two and a half bathrooms, blending luxury, flexibility, and everyday comfort—ideal for modern living and entertaining. From the moment you enter, you’ll appreciate the bright, open layout and desirable split floor plan designed to provide privacy for the primary suite. The inviting foyer opens to a formal dining room, where a newly added powder room is conveniently located for guests. Across the foyer, the spacious living area flows seamlessly into the heart of the home and is anchored by a cozy wood-burning fireplace, adding warmth and character. The gourmet kitchen is a true showpiece, featuring shaker-style cabinetry, luxurious quartzite countertops, and top-of-the-line appliances, including a 48-inch eight-burner double-oven gas range. Thoughtful details such as a farmhouse sink, pot filler, oversized island with seating for six, and a large pantry with open shelving make this space as functional as it is beautiful. Just off the kitchen is a dedicated laundry room with full size washer and dryer with a utility sink that is easily accessible to the garage, adding everyday convenience. Extensive renovations include a new home addition along with updated flooring, lighting, drywall, millwork, ductwork, HVAC, plumbing, and electrical systems, providing modern comfort and peace of mind throughout. Engineered hardwood flooring adds both elegance and durability. Double doors lead into the private primary bedroom suite, which features vaulted ceilings, large window, and a walk-in closet. The spa-inspired en-suite bathroom includes a dressing room and separate linen closet, granite countertops, a 1930s clawfoot soaking tub, a glass-enclosed shower with dual rain showerheads, and a private water closet. Two newly constructed bonus rooms adjacent to the primary suite provide flexibility that can be used as a home office, nursery, or additional storage. Three additional bedrooms are located on the opposite side of the home and share a beautifully renovated full bathroom, offering comfort and style for family and guests alike. Outdoor living is equally impressive, featuring a newly renovated lanai with a tongue-and-groove ceiling, a covered patio, and an expansive fully fenced backyard. The property also includes two storage sheds and a workshop with its own bathroom, providing excellent potential for a future guest suite, studio, or creative space. Additional features include double-pane windows, updated lighting, and an optional HOA with a voluntary fee of just $150 annually. Ideally located near top-rated schools, shopping, dining, healthcare, and popular destinations such as Uptown Altamonte, Wekiva Island, Altamonte Mall, and Cranes Roost, with easy access to major roadways for a smooth commute. This thoughtfully upgraded Knollwood estate offers space, style, and flexibility in an unbeatable Longwood location. Schedule your private showing today—homes like this are rarely available.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Alison Forbes (407-766-5243)
3508 VESTAVIA WAY, LONGWOOD, FL 32779
$509,0004 Days on yellowkey MLS ID: V4948800
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2347 Built: 1984Monthly Fee: $20 Tax: $2,343 (2024)Community: VestaviaSingle Family
Taxes:$2,343
Remarks: LOCATION, LAYOUT, AND FLEXIBILITY. THIS ONE STANDS OUT. Welcome to this well-designed split-level home located in one of Longwood’s most desirable areas, zoned for top-rated Seminole County schools and surrounded by a quiet, established neighborhood with mature trees and low HOA. As you enter, you’re welcomed into the center of the home with a true split-level layout that creates both flow and privacy. Head upstairs to find 3 bedrooms and 2 bathrooms, along with comfortable living space for everyday life. The main level features a private primary suite, giving separation from the rest of the home. Downstairs offers incredible flexibility with an additional living area, bedroom, and a full bathroom with shower, perfect for a mother-in-law setup, guests, or a private retreat. This level also features its own separate A/C system, providing added comfort, privacy, and energy efficiency. With multiple rooms downstairs, there is also potential for additional bedroom space, making this an excellent option for larger households or multi-generational living. Step outside and enjoy a spacious backyard and deck, perfect for relaxing or entertaining, all set within a peaceful residential setting with minimal through traffic. Location is a major advantage. You are just minutes to Wekiva Springs State Park, parks, trails, shopping, and dining. Easy access to I-4, 417, and 429 makes commuting simple, with quick drives to Lake Mary, Altamonte Springs, and Downtown Orlando. You are also within reach of Disney, Universal, and the East Coast beaches. Homes offering this kind of layout, flexibility, and location do not come up often. Schedule your private showing today.
Listing Agent: Seth L Rowlands, Llc (407-796-1932)
3301 SUNSET RIDGE CT, LONGWOOD, FL 32779
$1,990,0007 Days on yellowkey MLS ID: O6402005
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5962 Built: 2009Monthly Fee: $50 Tax: $13,177 (2025)Community: Sandy Lane Reserve Phase 2Spa: YesSingle Family
Taxes:$13,177
Remarks: Situated on a privately fenced .50-acre corner homesite within Sandy Lane Reserve, an enclave of 24 custom-built homes, this one-owner, METICULOUSLY DETAILED estate offers just under 6,000 sf of highly refined LUXURY LIVING, distinguished by its level of finishes, scale & completeness. VOLUME CEILINGS are enhanced by miles of LAYERED ARCHITECTURAL DETAILS including COFFERED & tray designs, while rich, warm cabinetry, WOOD FLOORING & select STONE FLOORING carried throughout the main living areas establish a cohesive & elevated interior. Multiple 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 introduces 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 & built-in Sub-Zero wine refrigeration. A well-appointed kitchen is centered around an expansive island, supported by a hidden walk-in pantry & extensively refined cabinetry. High-end appliance package including WOLF convection & steam ovens w/ built-in steamer, THERMADOR refrigerator, DACOR 6-burner gas cooktop, pot filler, BOSCH dishwasher, warming drawer, dual sinks & eat-in bar, complimented w/ striking stone countertops. The primary wing, outfitted w/ a generous sitting area overlooks the meticulously landscaped grounds & stunning pool. A spa bath features statement chandelier, travertine flooring, custom cabinetry, dual vanities, jetted tub & expansive walk-in travertine shower. His/hers CALIFORNIA CLOSET systems are of the highest standards. A secondary MAIN-LEVEL GUEST SUITE offers comparable scale, including walk-in travertine shower, oversized closet w/ sauna, gun safe & direct access to the limitless lanai. Beyond a wood & wrought iron staircase, upstairs are 2 generously sized bedrooms featuring full baths & walk-in California 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 areas. 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 include WHOLE-HOUSE GENERATOR, SALTLESS WATER FILTRATION, 2 tankless water heaters, 4 HVAC systems, oversized 3-car garage w/ epoxy flooring, extensive cabinetry & attic storage. Ideally located w/ convenient access to top-rated Seminole County schools, dining, shopping & major thoroughfares—offering a well-connected and effortless lifestyle. With the level of finishes and IMPECCABLE execution, this MASTERPIECE reflects a standard of living rarely found!
Listing Agent: Penney Lawrence (407-353-7019)
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