Oakland Single Family Homes For Sale - 21 homes

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)

Remarks: 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: Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! Pristine views of John's Chain, and full access from your incredible Boat House with dual power lifts. This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely reinvented 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: 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: 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: Welcome to this beautifully maintained 4-bedroom, 3-bath home in the heart of Oakland, where everyday living feels connected, convenient, and just a little more elevated. This home enjoys amazing views of the Oakland Nature Preserve. Ideally located within walking distance to the West Orange Trail and just minutes from the charm of downtown Oakland and Winter Garden’s vibrant shops, dining, and weekly farmers market. Inside, the home opens to a flexible front room that works beautifully as a formal dining space, home office, or additional living area. From there, the layout flows into a spacious open-concept living area with volume ceilings and an abundance of natural light, creating a bright and inviting atmosphere. The kitchen is both functional and stylish, featuring a large breakfast bar, updated cabinetry, stainless steel appliances, and a mosaic tile backsplash. The primary suite offers a private retreat with a spacious layout, dual sink vanity, soaking tub, and separate shower. Step outside to a screened-in patio that extends your living space year-round, overlooking a fully fenced backyard with no rear neighbors. It is an ideal setting for entertaining, relaxing, or enjoying quiet evenings around the fire pit. Additional features include a 2-car garage, well-sized secondary bedrooms, and a layout designed for both comfort and flexibility. This is a rare opportunity to enjoy space, privacy, and a connected lifestyle in one of Oakland’s most desirable locations.

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

Listing Agent: Steve Healy (407-230-1441)

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: Welcome to this beautifully crafted custom-built two-story home in the highly desirable Town of Oakland—offering the perfect blend of quality construction, modern design, and small-town charm with NO HOA. The thoughtfully designed floor plan features all main living areas on the first floor, including a spacious living room, dining area, and a well-appointed kitchen with high-quality appliances. French doors open to the back porch, and both front and back porches are finished with pavers. Additional highlights include a 2-car garage and generous storage under the stairs. Upstairs offers a versatile family room/bonus space, three secondary bedrooms with walk-in closets, and a full bath with built-in shelving and a tub. A convenient laundry closet adds functionality. The primary suite, located at the rear of the home, features a custom walk-in closet, dual sink vanity, and a large walk-in shower. The home showcases high-end finishes throughout, including luxury vinyl plank flooring and porcelain tile in the bathrooms. Ideally located in the heart of Oakland, just minutes from the West Orange Trail, Downtown Winter Garden, Plant Street Market, and the Lake Apopka boat ramp—offering easy access to shopping, dining, and outdoor recreation. A rare opportunity to own a meticulously built home in one of Central Florida’s most desirable areas!

Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)

Listing Agent: Cassia Barros (407-285-1163)

Remarks: Nested right along the scenic West Orange Trail, this spacious 4 bedroom, 2 bath home offers the perfect balance of recreation and relaxation. The open interior flows seamlessly to private pool, creating an ideal oasis for Florida living. Located for ultimate convenience, just 15 mins from Downtown Winter Garden with The Turnpike nearby for an easy commute. Enjoy being 30 mins of Orlando's world class attractions, including Disney, Universal Studios, and Downtown Orlando. Benefit from the highly rated Orange County School system.

Listing is courtesy of: HOME INVEST REALTY INC (407-895-8891)

Listing Agent: Ky Lam (407-895-8891)

Remarks: Under contract-accepting backup offers. Welcome to your peaceful retreat in the heart of Oakland! Nestled within the highly sought-after Longleaf at Oakland community, this impeccably maintained 3-bedroom, 2 1/2-bathroom residence offers the perfect blend of 2020 construction and timeless Florida charm. Step inside to discover 1,811 square feet of bright, open-concept living space designed for both effortless entertaining and cozy family nights. The chef-inspired kitchen serves as the centerpiece, boasting sleek quartz countertops and modern stainless appliances, flowing seamlessly into the dining and living areas. Touches of refinement extend throughout the home, including elegant marble sinks in every bathroom. What truly sets this property apart is its rare positioning, with no neighbors directly in front or behind, providing an incredible sense of privacy especially as you enjoy morning coffee or an evening glass of wine on the screened lanai that provides a forest like feel of trees that are continuing to grow and provide a peaceful and private retreat. The details matter here, from the stylish paver driveway to the two-car attached garage featuring a professionally finished floor coating and recently replaced garage door springs. Living in Longleaf at Oakland means more than just a beautiful home; it’s a lifestyle. Residents enjoy access to a community pool, playground and beautifully maintained landscaping. The location offers the ultimate Central Florida convenience, situated just minutes from the historic charm of Downtown Winter Garden, the West Orange Trail, and the Oakland Nature Preserve, with easy access to Highway 50, SR-429, and the Florida Turnpike. Don't miss your chance to own a piece of Oakland’s finest—schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)

Listing Agent: Tania Matthews (407-497-9660)

Remarks: Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living area. The upgraded gourmet kitchen is a standout, featuring stainless steel GE Profile appliances, a gas range, quartz countertops, ceiling-height cabinetry, and a stunning oversized waterfall island with seating that overlooks the breakfast nook and family room. Perfect for entertaining, the main living space is filled with natural light from three large sliding doors that open to a covered lanai and private backyard, complete with a full outdoor bathroom. The first-floor primary suite serves as a relaxing retreat, offering a spa-like bathroom with dual vanities, a spacious shower, garden tub, and a generous walk-in closet. Upstairs, you will find three additional bedrooms and two bathrooms, including a secondary bedroom with a private en-suite, ideal for guests or multi-generational living. The expansive bonus/game room provides a versatile space for a home theater, gym, playroom, or lounge. This home is thoughtfully enhanced with wood-look tile flooring throughout the first floor, upgraded designer lighting, modern ceiling fans, decorator finishes, and abundant storage. Enjoy an elevated audio experience with integrated surround sound in the living room, lanai, primary suite, and upstairs bonus room, featuring built-in in-ceiling speakers for immersive TV and music throughout. Smart home features include Ecobee thermostats, a Ring doorbell, and a garage EV charger. Additional upgrades include 8-foot raised panel doors, a tankless gas water heater, an interior laundry room with utility sink and gas washer and dryer hookup, outdoor kitchen and pool prewiring, and a whole-house water softener. Residents of Hull Island enjoy resort-style amenities, including a pool and clubhouse, playground, dog park, dock, and fishing pier. Ideally located near the West Orange Trail, historic downtown Winter Garden, and Clermont’s lakefront dining, this home offers convenient access to shopping, dining, weekly farmers markets, major roadways, and Central Florida attractions. This is more than a home, it is a private retreat offering comfort, style, and an exceptional location.

Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)

Listing Agent: Elisabeth Rusnak (845-729-5042)

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: One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), located in the heart of Oakland is just minutes from downtown Winter Garden. From the moment you step inside, you’ll appreciate the thoughtful design and elevated finishes throughout. This spacious home features a dedicated office, formal dining room, and formal living room—perfect for entertaining or creating flexible living spaces to fit your lifestyle. The open-concept layout seamlessly connects the kitchen and family room, complete with a cozy breakfast nook ideal for casual dining. The fully renovated interior showcases wood-look tile throughout the main living areas and plush carpet in all bedrooms. Shiplap accent walls and plantation shutters add warmth, character, and timeless charm. Each of the three bathrooms has been uniquely designed, offering its own distinct style and personality. Step outside to your private, fully fenced backyard that backs to a conservation area—ensuring no rear neighbors, ever. Enjoy peaceful views and added privacy in a serene natural setting. This home is less than a 2-minute walk to Oakland Avenue Charter School and sits within the highly desirable golf cart district of downtown Winter Garden—making it easy to enjoy local shops, dining, and community events. **Some of these photos have been virtually staged**

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

Listing Agent: Danielle Norvell (512-797-6124)

Remarks: Under contract-accepting backup offers. *** Back on the market after being temporarily off while the Seller moved (~45 days).*** NEW PRICE *** MOTIVATED *** Stunning former MODEL HOME on a premium CORNER lot (FENCING is allowed)– loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both comfort and style. Step inside to discover a bright, open floor plan featuring elegant luxury plank flooring and oversized tile. The ACCENT WALLS add depth and sophistication, while motorized shades and custom lighting fixtures bring both convenience and ambiance. Motorized shades offer effortless control of natural light and privacy at the touch of a button! The gourmet kitchen is a chef’s dream, complete with QUARTZ countertops, stainless steel appliances, under and over cabinet lighting, pull out cabinet organizers, elegant tile backsplash, a touchless faucet, and a large island perfect for entertaining. The home is also pre-wired with SURROUND SOUND, creating an immersive experience for movie nights or background music throughout the home. Downstairs is complete with a dining area, a bedroom/office (no closet), half bath, and a screened-in patio with collapsible sliding glass doors and motorized shades for added privacy. Upstairs you’ll find the PRIMARY SUITE with spa-like bath, a loft, two additional bedrooms, one full bath with a tub/shower combination, and a laundry room with a utility sink and folding table. The primary suite is generous in size and features a tray ceiling, crown molding, dual sinks, stone counters, an oversized shower, linen closet, and a walk-in closet with custom shelving. The loft is the perfect place to feature a second living area, or you can turn it into a play area for the little ones. This home is the perfect blend of luxury, functionality, and location. The 2-car garage has ample room for storage and includes a paver driveway, epoxy flooring, and is EV -ready for your electric car.  You’ll find a large open field to enjoy your morning walks with your furry friends across from the home. The community features a waterfront pool, parks, and playgrounds. If you’re feeling up for an adventure, the 22 mile long WEST ORANGE TRAIL is across the street from the entrance of the neighborhood and takes you into the highly sought after area of downtown Winter Garden where you can enjoy rooftop dining, charming boutiques, and a lively Farmers Market. You can also enjoy close proximity to the Oakland Town Center, Oakland Nature Preserve, Speer Park's playgrounds, tennis & pickleball courts, basketball courts, picnic areas, & the Healthy West Orange Arts & Heritage Center. Enjoy the tranquility of this peaceful neighborhood, with easy access to the Turnpike, East-West Expressway, 429, grocery shopping, theme parks, and golf courses, this home offers a lifestyle of unparalleled beauty and convenience. Embrace the enchanting OAKLAND-WINTER GARDEN lifestyle and make this exquisite residence your next place to live!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Ashley Boyd (321-209-5540)

Remarks: Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours - YOUR WAY! The Oakland Park subdivision is a short walk on the West Orange Trail to downtown Winter Garden. Enjoy easy access to the community pool & clubhouse, dining, shopping & entertainment. This is luxury living at its best. Call us to discuss your options!

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

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

Remarks: THIS ONE IS A MUST SEE! Upgrades on upgrades on upgrades! Welcome to Oakland Trails in the charming City of Oakland. This spacious 5-bedroom, 3.5-bath home offers a flexible layout perfect for today’s lifestyle. Enjoy a cozy Great Room, formal Dining Room, and a stunning modern staircase that leads into an open-concept Living Room and beautifully upgraded Kitchen featuring ample cabinetry, generous counter space, and a designer backsplash. The first-floor primary suite is a private retreat with a luxurious bath, dual vanities, soaking tub, walk-in shower, and an oversized walk-in closet. Upstairs offers a large loft, spacious secondary bedrooms, and a versatile bonus room ideal for an office or optional 6th bedroom. Situated on a quiet cul-de-sac with no front neighbors and peaceful conservation views, the resort-style backyard showcases extended pavers and low-maintenance artificial grass—saving time while offering year-round beauty and convenience. The home is equipped with top-quality solar panels featuring over 400 watts per panel—the latest generation for maximum efficiency and performance. Paired with a premium Enphase inverter system, known as one of the best in the industry, this setup is designed to optimize energy production and deliver significant long-term savings.Solar Panel open to negotiation. Prime location near top-rated schools, the Florida Turnpike, Winter Garden, Clermont, and Orlando, with shopping, dining, and entertainment just minutes away. Space, privacy, upgrades, and location—this home truly has it all!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes from historic downtown Winter Garden's acclaimed restaurants, boutique shops, and cultural venues, this home offers the perfect balance of serene outdoor living and convenient community access. The neighborhood is known for its resort-style amenities, including community pools and walking trails, plus easy access to the 429 and Florida Turnpike for seamless access to downtown Orlando, area theme parks, and Orlando International Airport. Architectural Excellence and Light-Filled Interior will blow you away. Upon entering, you are immediately enchanted by the flowing design throughout, with USA-made Mannington laminate flooring flows throughout the first floor. Six handcrafted Bevolo lanterns add architectural detail and warmth to the exterior. Additional highlights include a combined mudroom and natural light pouring from expansive two-story windows and stunning designer lighting that complements the floor-to-ceiling stone fireplace, this focal point enhances the open-concept layout, creating a bright, inviting atmosphere throughout the home. A grand dual staircase with iron railings anchors the two-story living room, emphasizing the home's soaring volume ceilings and open, airy design. The oversized, black-framed sliding doors create effortless indoor-outdoor living for those social events. The Chef's Kitchen is quite the entertaining Hub with its elevated oversized quartz waterfall-edged island offering generous seating and a stunning focal point for entertaining. GE Café appliances with brushed bronze hardware, upgraded quartz countertops, and a spacious walk-in pantry support serious culinary pursuits. The seamless flow from kitchen to dining area, transforming entertaining into an effortless, connected experience. The second-floor primary suite features a tray ceiling and an expansive walk-in closet suitable for dressing room use. The spa-inspired bath is a private retreat, with a freestanding soaking tub set within a custom wood-accent alcove and quartzite vanity—the perfect escape after a busy day. Additional highlights include a generous sized laundry space for convenient household management, and a 3-car garage with custom overhead storage providing ample space for vehicles and seasonal storage. The outdoor Living Potential offers a partially fenced backyard with ample space for a future pool, ideal for creating your own resort-style retreat. The premium corner lot positioning provides privacy, abundant natural light, and those coveted Lake Apopka views. This is more than a home—it's a lifestyle positioned in one of Central Florida's most sought-after communities with uncompromising finishes. Don't miss out on this opportunity, Schedule you're showing today!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Heidi Pfeffer-Morgan (407-408-6101)

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: 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: Under contract-accepting backup offers. Located within the exclusive gated waterfront community of John’s Landing, this residence offers the perfect balance of Florida lifestyle, privacy, and everyday convenience, just minutes from Downtown Winter Garden and the scenic John’s Lake Chain. Set on an oversized lot at the end of a quiet cul-de-sac, the home features multiple living spaces, a bonus room / optional 5th bedroom, and a Florida room converted into a bar and game room, ideal for entertaining and flexible family living. The layout adapts effortlessly to growing households, remote work, or hosting guests. This move-in ready home provides long-term peace of mind with a brand-new roof delivered at closing and a 5-ton Carrier A/C (2020). The fully fenced backyard offers future expansion potential for a pool. Residents enjoy private lake access, a private boat ramp, tennis courts, and playgrounds, all within a prime location offering easy access to SR-429, Florida Turnpike, Montverde Academy, shopping, dining, and the vibrant lifestyle of Downtown Winter Garden. Whether as a forever home or a smart addition to a real estate portfolio, this property delivers strong long-term value in a highly desirable waterfront community.

Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)

Listing Agent: Jose Rojo (786-502-6162)