Homes for Sale Near West Orange High in Oakland - 22 homes

Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **$10,000 towards closing costs**Welcome to this truly exceptional home offering space,flexibility & an unbeatable location!This beautiful,expansive residence features 4 spacious bedrooms,3.5 bathrooms,plus a versatile upstairs BONUS ROOM that can easily serve as a 5th bedrm—complete with closet & half bath already pre-plumbed for a full bathroom conversion.Enjoy breathtaking sunset views right from this elevated retreat.This home features a rare & highly desirable MOTHER-IN-LAW SUITE,complete with KITCHENETTE & ADA-compliant BATHROOM—ideal for multi-generational living or guest privacy.The 2nd bedrm conveniently connects to the kitchenette,enhancing the suite’s functionality.A 3rd bedrm,currently used as a home office,located near an adjacent bathroom that also provides direct access to the pool area.SPACIOUS PRIMARY suite serves as a private retreat,featuring an ensuite bathroom with dual sinks,a relaxing soaking tub& large walk-in closet.At the front of the home,a formal living & dining area offers versatile space that can easily serve as a den,library, or flex rm to suit your needs.The kitchen has 42" SOLID WOOD cabinets,granite counter tops & is equipped with NEW APPLIANCES 2025,including induction cooktop heats water in 3 minutes,convection oven & the rare convenience of 2 dishwashers—one being a quiet Bosch,ideal for large families or entertaining.The great rm features a cozy WOOD BURNING FIREPLACE & opens to your own private Florida oasis.Step outside to a HEATED,screen-enclosed POOL & SPA(pool heater installed in 2025,screen enclosure 2020),creating the perfect setting for year-round enjoyment.The expansive pool deck extends your living space outdoors,ideal for relaxing or entertaining.Beyond the pool,the private,partially fenced backyard offers additional space to unwind,accented by tranquil bamboo that sways in the breeze creating a peaceful atmosphere.The home backs to a State of Florida wildlife ravine,providing serene views of native birds,lush greenery& natural surroundings—your own quiet retreat right at home!The home boasts 2 AC zones for superior energy conservation:Both AC units are new in the last 5 years & maintained twice a year.NEW,OVERSIZED DOUBLE PANE WINDOWS throughout lower level are only a few months old,allowing for gorgeous VIEWS.NEW ROOF 2022.NEW,LARGE HYBRID WATER HEATER installed 2024,water Softener included.Complete with a 3 CAR GARAGE.LOCATION,LOCATION truly sets this home apart. Situated in a GOLF CART- FRIENDLY community,you’ll have direct access to the vibrant charm of DOWNTOWN WINTER GARDEN,just 2 miles away. Enjoy the award-winning Winter Garden Farmers Market,along with popular dining,shopping & year-round events.Outdoor enthusiasts will love being just steps from the scenic 22-mile West Orange Trail,perfect for biking, jogging or leisurely strolls.Nearby,the quaint&historic charm of Downtown Oakland,the scenic waterfront dock on Tubb Street & nearby Oakland Nature Preserve,offer even more to explore.Publix,Aldi,Winter Garden Village Mall,MAJOR ROADWAYS & highways are all nearby.The Turnpike is minutes away.EASY ACCESS to Theme parks, 20 minutes to Downtown Orlando & Orlando Intl Airport 30 minutes away.With only 58 homes,this quiet street offers a true sense of community.Residents enjoy friendly neighbors,regular patrols from the nearby police department & proximity to the fire station & Oakland Charter School(priority enrollment for Oakland residents).This is more than a home—it’s a lifestyle!

Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)

Listing Agent: Sandy Jones (407-929-7999)

Remarks: Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout. Designed for effortless entertaining, the open-concept layout showcases a chef’s kitchen with a waterfall quartz island, custom cabinetry, premium stainless steel appliances, and a full-slab backsplash, all flowing into an expansive living area with designer lighting and seamless indoor-outdoor access. The primary suite offers a private retreat with abundant natural light, custom closets, and a spa-inspired bath featuring a freestanding soaking tub and luxury walk-in shower. Step outside to a screened pool, upgraded travertine deck, and private pier, creating an unparalleled waterfront lifestyle ideal for relaxation and entertaining. Additional highlights include a concrete tile roof (maintained), smart home features, updated HVAC, epoxy garage, modern laundry room, and high-end upgrades throughout. Ideally located minutes from Downtown Winter Garden, premier dining, shopping, and top-rated schools, this is a rare opportunity to own an unparalleled lakefront property.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Any Alves (407-455-0618)

Remarks: Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home features, 2 of the bedrooms is a suite, high-end finishes, and a seamless modern design throughout. Porcelain tile flooring, a stunning gourmet kitchen with island with quartz countertops, custom cabinetry and a premium stainless steel appliances. Every details has been thoughtfully upgraded; spa inspired master bathroom include designer walk-in shower,LED mirrors, and luxury fixtures. Step outside to a private screened-in pool and spa, creating the perfect setting for entertaining and relaxed living. Residents enjoy gated access and private boat/jet sky ramp to John's Lake, ideal for boating and jet skis. Also prime location access to Turnpike Hwy and just minutes from Winter Garden, Clermont, Downtown Orlando and all Disney Parks.

Listing is courtesy of: NOVARE REAL ESTATE LLC (754-245-3136)

Listing Agent: Durval Da Rocha (754-245-3136)

Remarks: Oakland Trails is located right on the scenic West Orange Trail and just a bike ride away from the vibrant downtown Historic Winter Garden! **This home qualifies for loan options with NO DOWN PAYMENT required, 100% financing available for qualified buyers.** Step into an immaculately maintained three-bedroom, two-and-a-half-bathroom bungalow with updated wood-look plank luxury vinyl flooring (2024), new carpet in all bedrooms (2025), quartz countertops, and an open-concept living area. Functional floor plan design includes a downstairs half bathroom, a drop zone by the garage, and an understairs storage closet. A shaded front porch is perfect for enjoying coffee in the morning and decorating for the holidays! Two car garage and an extended pavered driveway. Upstairs you have a huge loft, all three bedrooms, and laundry. The primary bedroom features two large walk-in closets, a double-door entrance, and granite countertops in the bathroom. The loft is prewired for surround sound. This home has been lovingly maintained; the exterior was painted in 2023. The interior walls and trim were painted in 2024. Modern updates that make this home move-in ready also include new light fixtures throughout, fans in all bedrooms, and new garage door lanterns. Oakland is perfectly situated between Clermont, Winter Garden, and Orlando. You have quick and convenient access to the Florida Turnpike, the 429, 408, Highway 50, and Highway 27. Oakland Trails has a community pool, community playground, walking trails, and a dog park. Lots of dedicated street parking means you can welcome family and friends easily. The Oakland Nature Preserve is less than five minutes away, West Orange Trail's Killarney Station is just outside the neighborhood. Towering Live Oak Trees, the shore of Lake Apopka, and the extensive trail system make this neighborhood perfect for anyone who loves spending time outdoors!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Ken Pozek (407-813-2773)

Remarks: Welcome to your lake-front living in the highly sought-after gated community of Johns Cove! Soak in panoramic lake views of John's Chain, and full access from your incredible Boat House with dual power lifts. This beautiful ranch style estate home, features a "triple-split" bedroom plan, FROG bonus space, and HUGE private backyard space with heated pool, spa, fire pit and nightly views of themepark fireworks! The property has been meticulously maintained with many updates since the current owners purchased it. Renovations include, a kitchen with all new appliances (2023), new granite countertops, additional lighting and a custom nook seating; enlargement of the 3-car garage door which now includes a custom workbench, storage closet, multi-level storage shelves, refrigerator and a Tesla Charger; new front door that opens into a newly tiled foyer with a view of the pool area; redesigned dining area to accommodate a larger table; FROG (Family Room Over Garage) now includes a Full Bathroom Addition with a storage closet, new vinyl flooring and big Samsung TV, great flex space…. or Man Cave; bedrooms have new windows and their adjacent bathrooms have new tile and countertops; and finally, the primary bathroom remodeled in 2023 includes new cabinets, countertops, lighting, faucets, tile floors, sinks, pull out laundry bin cabinets, ceiling fan, 2nd primary closet addition (now two closets) with custom storage system, heated bathroom floors, heated shower floor, heated shower bench, and an oversized steam shower (Kohler) with two separate shower head systems, truly a spa-like atmosphere. Outside renovations include: low maintenance Azek planks from home to private fire pit area, continuing on to the boathouse; 2023 new driveway pavers with a lit walkway to the front door; new paved front porch; new gutter system; plastic soffit replaced with wood; outdoor lighting; new outdoor storage area; 2023 home was painted; additional 200 amps (total 400 amps) and new garage door. The boathouse has water and power, can house two jet skis, a bass boat or ski boat or optional pontoon boat. The boat area has a Touchless Boat Cover with a remote control lift. Boathouse is approximately 23 1/2 ft by 33 ft. With a Southeast exposure, the pool area is the perfect Stay-cation place to relax and enjoy family time. The perfectly elevated pool area boasts a large patio that wraps around the entire back of the home allowing for a large dining or seating area for you and your guests. You’ll love choosing between watching the 9PM Disney fireworks from either your hot tub or the private fire pit. Location, location, location… All this is conveniently located near major highways and local restaurants and shops. Seize this opportunity to experience the finest in luxury lake living in Central Florida!

Listing is courtesy of: NEXT RESIDENCE REALTY LLC (407-463-9209)

Listing Agent: Betsey West (407-463-9209)

Remarks: SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

Listing is courtesy of: COAST TO COAST REAL ESTATE PRO (352-296-8930)

Listing Agent: Alaina Dimare (407-457-1834)

Remarks: Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2-bath single-story home located in the desirable Longleaf at Oakland community. From the welcoming wraparound porch to the open and functional layout, this home offers thoughtful upgrades throughout, including wood-look laminate flooring, 9’ ceilings, 8’ interior doors, custom moldings, and designer finishes. The kitchen features KitchenAid appliances, quartz countertops, a natural stone backsplash, oversized island, and a bonus flex space perfect for a coffee bar or wine area. The split-bedroom floor plan provides added privacy, while the spacious primary suite includes dual vanities, a walk-in shower with rain shower head, linen closet, and two walk-in closets. Enjoy Florida living year-round on the paved and screened lanai overlooking beautifully landscaped, low-maintenance gardens. HOA includes lawn care for added convenience. Located just STEPS from the popular WEST ORANGE TRAIL, this home is perfectly positioned for outdoor living and an active lifestyle. Situated within the highly sought-after GOLF CART DISTRICT, you can easily cruise to HISTORIC DOWNTOWN WINTER GARDEN for shopping, dining, entertainment, and the award-winning Farmers Market. Community amenities include a pool, playground, and neighborhood park. Private showings available.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Rema Perras (802-233-5292)

Remarks: Under contract-accepting backup offers. Experience the ultimate lakefront lifestyle in this stunning MI Homes Endeavor, perfectly positioned on 83 feet of shoreline along Lake Apopka - No Flood Zone - in the highly desirable community of Hull Island. Built just 5 years ago, this exceptional residence offers 4,224 square feet of thoughtfully designed living space featuring 5 bedrooms, 4.5 bathrooms, bonus room, two dedicated office spaces (one on each floor), and a 3-car garage. Every detail of this home has been carefully curated with extensive post-builder upgrades and thoughtful custom touches throughout. With no rear or front neighbors, this property delivers both privacy and breathtaking natural beauty. Enjoy unforgettable sunset views from the newly installed Trex boat dock, the resort-style screened pool and patio, or nearly every west-facing room in the home. Out front, peaceful preserve views create the perfect backdrop for sunrise mornings. From the moment you step inside, you’re welcomed by soaring ceilings, abundant natural light, and stunning water views. The dramatic family room showcases impressive vaulted ceilings, creating an open yet inviting atmosphere ideal for both entertaining and everyday living. The gourmet kitchen is truly a chef’s delight, featuring a massive center island, natural gas cooktop, built-in convection oven, stainless steel appliances, and extensive cabinetry and prep space. The adjoining dinette area offers casual dining convenience, while the formal dining room provides an elegant setting for gatherings and celebrations. The first floor also includes a wine room, private office, guest bedroom, and full pool bath with direct outdoor access. Designed for exceptional indoor-outdoor living, the backyard retreat is nothing short of spectacular. The recently designed luxury pool features elegant waterfall and fountain elements, an oversized jacuzzi, custom natural gas fire pit, turf play area, and expansive covered lanai complete with tongue-and-groove ceiling and travertine flooring — all enclosed within a panoramic screen offering unobstructed lake views. Enjoy direct access to Florida’s natural beauty right from your backyard. Spend your evenings fishing from the private dock, launching your boat with ease from the electric lift for a sunset cruise on Lake Apopka, or exploring the connected Tavares Chain of Lakes and charming downtown Mount Dora by water. Upstairs, a striking staircase with sleek glass railings enhances the home’s modern design. The luxurious owner’s suite offers incredible lake views and a recently renovated spa-inspired ensuite featuring a freestanding soaking tub, oversized walk-in shower, and designer finishes. The spacious game/media room and second office overlooking the preserve offer incredible flexibility for work, entertainment, or multigenerational living. Secondary bedrooms enjoy beautiful views, while the fourth bedroom functions perfectly as a private mini-suite. Ideally located in the charming Town of Oakland, Hull Island offers convenient access to Winter Garden, Clermont, the Florida Turnpike, shopping, dining, and recreation. Community amenities include a pool, playground, dog park, and private dock access on the nature preserve - all with a low HOA. This is a rare opportunity to own an extraordinary lakefront retreat where luxury, comfort, and the Florida lifestyle come together seamlessly. Schedule your private showing today and experience lakeside living at its finest.

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Elizabeth Fowler (863-441-5304)

Remarks: Under contract-accepting backup offers. Discover a rare opportunity to own a private estate property in one of West Orange County’s most desirable corridors. Situated in Oakland, this 2.55-acre parcel offers space, privacy, and future potential just minutes from the conveniences of West Colonial Drive, Florida Turnpike (Exit 275), Clermont, and the vibrant districts of Oakland and Downtown Winter Garden. Properties like this are increasingly difficult to find. The home sits in an unincorporated area, giving flexibility and freedom while still being close to everything that makes this area so special. Walk or bike to the West Orange Trail, enjoy easy access to local parks, and connect quickly to shopping, dining, and major commuter routes. The residence offers approximately 2,700 square feet of living space and has been thoughtfully maintained in its original 1983 character, making it ideal for buyers seeking land, privacy, and the opportunity to personalize or modernize over time. Inside, you’ll find an open floor plan with soaring vaulted ceilings and large picture windows that fill the home with natural light. A dramatic floor to ceiling stone fireplace anchors the main living area and creates a warm focal point for gatherings or quiet evenings at home. The kitchen is spacious and functional, featuring abundant cabinetry, a large center island, built in appliances, and generous room for entertaining and everyday living. A large enclosed sunroom extends the living space and offers endless possibilities for a game room, fitness studio, home office, or year round relaxation overlooking the backyard. The home includes four generously sized bedrooms and two full bathrooms, all preserving their original charm and offering a strong foundation for updates, renovation, or a curated vintage aesthetic. Step outside and the true value of this property becomes clear. The 2.55 acres provide room for gardens, animals, workshops, RV and boat storage, or the creation of a private retreat. A detached casita adds flexibility for guests, extended family, a home office, or potential future income use. The property operates on a private well and septic system, offering independence, lower utility costs, and a rural lifestyle feel without sacrificing proximity to major roads, downtown Winter Garden, and the growing Oakland corridor. A unique blend of land, location, and opportunity this is a property where you can create, expand, and invest in a lifestyle that is increasingly rare in Central Florida.

Listing is courtesy of: RE/MAX EXCLUSIVE COLLECTION (407-447-2829)

Listing Agent: Carmelo Nuccio (321-441-6951)

Remarks: Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to popular Johns Lake. Home is updated with the entire roof replaced in November 2019 and new A/C in 12/21/2020. Perfectly positioned minutes from Florida Turnpike and within 25 minutes from Disney, Universal Studios, Downtown Orlando, Downtown Clermont, Downtown Winter Garden, and the Bike Trail which connects Clermont, Oakland, Winter Garden, and Orlando. All measurements are approximate and should be verified.

Listing is courtesy of: LIBERTY HOME SALES INC (321-256-0500)

Listing Agent: Subhas Sawh (407-402-1350)

Remarks: Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres in the beautiful Town of Oakland. The property is a seamless blend of charming Old Florida and modern-day Luxury Living at its finest. The community is thoughtfully designed to provide the ultimate retreat for our residents. Lot 15 will be custom pool home meticulously designed to complement its natural surroundings, with a spacious floor plan. Briley Farm offers a seamless combination of residential luxury and convenience, with custom homes designed for enjoying the best of indoor and outdoor living. At Briley Farm you'll discover comfortable countryside living amongst the welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Blaine Dooley (321-277-0933)

Remarks: Under contract-accepting backup offers. Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, offers a private retreat with a spa-inspired bathroom and generous walk-in closet. Upstairs, you’ll find additional bedrooms along with a versatile loft space ideal for a media room, office, or play area. Designed for the Florida lifestyle, the outdoor living space is truly exceptional. Enjoy a resort-style pool and spa, expansive lanai, and dedicated firepit area—perfect for relaxing or hosting gatherings year-round. Additional highlights include a two-car garage with a separate golf cart bay, high ceilings, and thoughtful architectural details throughout. This is a rare opportunity to own a beautifully crafted home in one of the area’s most desirable communities.

Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)

Listing Agent: Carolina Dumit (407-325-8963)

Remarks: One or more photo(s) has been virtually staged. You’re going to love this beautifully maintained 2-bedroom, 2.5-bath Townhome in the highly desirable Longleaf At Oakland which is perfectly located just a 1/2 mile from the Florida Turnpike, offering easy access to everything Central Florida has to offer. The entire interior was freshly painted in March 2026, giving the home a bright, fresh feel from the moment you walk in. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, making it ideal for both everyday living and entertaining. The inside utility room is conveniently located on the first floor with additional storage under the stairway. Upstairs you’ll find two private master suites, each with its own full bathroom. The primary suite boasts a massive walk-in closet with a window and the en-suite offers dual vanities and an easily accessible walk-in shower. The second bedroom includes a tub/shower combo and its own walk-in closet. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. This home is equipped with Google smart lighting switches, and a Google thermostat can easily be installed and controlled through your app. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community offers everything the Florida Lifestyle has to offer!

Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)

Listing Agent: Randy Adams Pa (321-438-1027)

Remarks: Under contract-accepting backup offers. INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by newer(2024) luxury plank flooring, a large living/dining area, built-in OFFICE SPACE, and a half sized bathroom. The kitchen is a CHEF'S DREAM featuring granite counters, a large eat-in island, stainless steel appliances, built-in oven and microwave, designer pendant lighting, closet style pantry, and a dedicated coffee/work station. WOW! Head upstairs and pass through the BONUS LOFT area into an OVERSIZED MASTER SUITE with tray ceilings, a large split vanity master bath, and a MASSIVE WALK-IN CLOSET equipped with built-in shelving and organizers. The second floor also contains three secondary bedrooms, a full size hallway bathroom, and a large laundry room. Additional features of the home include: a FULL SOLAR PANEL SYSTEM(providing significant energy savings), an oversized two car garage, built-in security system, and paver driveway. The Oakland Trails community includes a community pool and clubhouse, dog park, playground, and walking trails. Located minutes away from the WEST ORANGE TRAIL this area is a hotbed for outdoor recreation and is ZONED FOR EXCELLENT SCHOOLS! In close proximity to major commuting highways, downtown Winter Garden, and ample shopping amenities, this is a PRIME LOCATION home and MOVE-IN ready for it's next owners. DON'T DELAY!! Book your private showing today.

Listing is courtesy of: YOUNG REAL ESTATE (407-904-0069)

Listing Agent: Chuck Burt (407-676-4268)

Remarks: Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, ideal for high-speed connectivity. The DREAM KITCHEN is a showstopper with stylish cabinetry, stone countertops, a breakfast bar, built-in oven, cooktop stove with POT FILLER, tile backsplash, walk-in pantry, and a GALLEY-STYLE COFFEE BAR AREA—perfect for morning routines or entertaining. A spacious Kitchen dinette area overlooks the backyard, adding a warm and functional touch to the heart of the home. In the Living room, enjoy a CUSTOM ACCENT WALL (2023) and views of the large backyard through dual sliding glass doors. A separate Dining room offers flexibility for family gatherings or can easily serve as a formal living room. The first floor also includes a VERSATILE OFFICE/PLAYROOM, convenient under-stair storage, and ONE OF THE FIVE BEDROOMS—complete with laminate wood flooring—located next to a full bathroom, providing a perfect space for guests or multigenerational living. Upstairs, a GENEROUS LOFT creates a perfect secondary living area. The UPDATED PRIMARY SUITE (2025) features a beautiful tray ceiling, a LUXURIOUS EN SUITE BATH with dual vanities, a step-in shower, and a huge walk-in closet. Three additional bedrooms and another full bath offer plenty of comfortable space for family and guests. A paver driveway leads to the generous 3-CAR GARAGE featuring epoxy flooring, additional kitchen-style cabinetry, and PREWIRING for an electric vehicle. Outside, enjoy a large covered patio and an EXPANSIVE BACKYARD, ideal for future customization, gatherings, or play. Oakland Trails is loved for its peaceful setting and small-town charm, offering access to the West Orange Trail, playgrounds, green spaces, and TOP-RATED SCHOOLS. Ideally positioned near DOWNTOWN WINTER GARDEN, residents enjoy quaint dining and gatherings spots, PLANT STREET MARKET, charming shops, and easy access to SR 429 for seamless commuting. Every detail has been thoughtfully crafted for ELEVATED LIVING—come experience the exceptional quality and SOPHISTICATION this home offers. Schedule your showing today!

Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)

Listing Agent: Jenny Wemert (407-809-1193)

Remarks: Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)

Listing Agent: Alexis Anderson (561-670-5901)

Remarks: Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential atmosphere. Oakland Trails is known for its top-rated schools, scenic walking and biking trails, and thoughtfully planned amenities, including a community pool, clubhouse, and dog park. The neighborhood features wide streets, attractive entryways, and a welcoming environment, with close proximity to Historic Downtown Winter Garden, offering popular restaurants, breweries, shops, and community events. Built with energy efficiency in mind, this Meritage Home includes spray foam insulation, helping maintain consistent indoor comfort while reducing utility costs. The home is equipped with an advanced HVAC system featuring enhanced air purification and fresh-air intake, ideal for comfortable and healthy living. The interior showcases a gourmet kitchen with KitchenAid appliances, quartz countertops, and a custom-tiled island, complemented by high ceilings and tall doorways that create an open, airy feel throughout. Additional features include a partially metal and shingle roof, a full gutter system, a custom wood staircase, and a spacious primary suite with a built-in closet system. Generous storage throughout the home makes it well suited for families of any size. The property is ideal for long-term rental use. While short-term rentals are restricted by the HOA, the home’s modern construction, low-maintenance design, and strong location support long-term value and rental stability. Notably, the home has been strictly pet-free under current ownership, making it an excellent option for buyers with sensitivities. A detailed list of builder upgrades and owner improvements will be provided with the listing, offering full transparency into the home’s added value. Additional features include installed security cameras and a custom Tesla charging outlet, included at no additional cost with a full-price offer. Furniture is not included; however, the seller is open to selling select items separately if desired. A well-maintained, energy-efficient home in one of the area’s most sought-after communities — offering quality construction, lifestyle amenities, and long-term appeal.

Listing is courtesy of: PINK MIAMI (305-504-0807)

Listing Agent: Denis Bochkov (754-248-4417)

Remarks: This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, fans new carpet and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling. Community amenities include a pool and playground, with nearby nature trails for walking and biking. Convenient access to major highways, shopping, dining, and downtown Winter Garden makes this location highly desirable.

Listing is courtesy of: ASANO REAL ESTATE LLC (352-552-7232)

Listing Agent: Leslie Campasano (352-552-7232)

Remarks: Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!

Listing is courtesy of: NEW HOMES REAL ESTATE, INC. (407-947-2475)

Listing Agent: Chris Herlihy (407-947-2475)