Homes For Sale in Oakland 34787 - 28 homes

Remarks: Under contract-accepting backup offers. Welcome to this beautifully designed POOL home in the highly desirable WATERFRONT community of Hull Island in Oakland, where residents enjoy a lifestyle rich in amenities, including a scenic walking dock, community park, playground, dog park, and resort-style pool. This thoughtfully designed four bedroom - 3 bath home offers a functional and private split floor plan ideal for both everyday living and hosting guests. At the front of the home, a guest bedroom features its own en-suite bath—perfect for visitors or multi-generational living. Toward the rear of the home, the primary suite serves as a peaceful retreat, ideally positioned to overlook the pool and capture stunning SUNSET views. The suite includes a spacious spa-like bath with two separate vanities, quartz counters, a shower, two walk-in closets, including an expansive walk-in closet that conveniently connects directly to the laundry room for added ease and efficiency. The remaining two bedrooms are well-sized and share a full bath, creating a comfortable and versatile layout. Throughout the home, you’ll find tasteful customizations including upgraded lighting and stylish accent walls that add warmth and character, all while maintaining a clean, modern aesthetic. The kitchen has been beautifully updated with quartz countertops, under cabinet lighting, tile backsplash, stainless appliances, including a GE CAFE refrigerator, cooktop, built-in microwave and oven, and generous prep and gathering space—perfect for entertaining or casual family meals. Step outside to your private backyard oasis with no rear neighbors, offering enhanced privacy and tranquility. The SALTWATER pool invites year-round enjoyment, while the covered lanai, travertine decking, and screened enclosure create the perfect setting for relaxing—Florida style. As a bonus, the lanai is plumbed for an outdoor kitchen and ready to be connected! The two car garage features durable epoxy flooring, offering a clean, polished look. Turnkey and meticulously maintained, this home is everything you’ve dreamed about. Combining thoughtful design, premium upgrades, and a prime location, this property truly embodies the best of Florida living. The community itself is a haven for nature lovers, with a sparkling POOL, charming gazebo, and a picturesque boardwalk leading to a fishing pier offering breathtaking views of Lake Apopka. Enjoy the park, playground, dog park, and a private entrance to the 120+ acre Oakland Nature Preserve, complete with winding trails. For those who appreciate outdoor adventure, the 22-mile West Orange Trail is nearby, as well as easy access to major highways (Turnpike, 408, 429), shopping, dining, three vibrant towns (Clermont, Oakland, and historic downtown Winter Garden), golf courses, tennis and pickleball courts, and Orlando’s world-class amenities, including the international airport, theme parks, and beaches. This is more than just a home—it's a lifestyle. Seize this rare opportunity to own your own slice of PARADISE.

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

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

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: Imagine coming home to a space that feels open, comfortable, and perfectly placed for everyday life. This corner-unit townhome in the desirable Longleaf at Oakland community offers added privacy, abundant natural light, and a thoughtfully designed layout that truly works for today’s lifestyle. Inside, the home features a clean, modern feel with plank vinyl flooring, granite countertops, and recessed lighting, creating a space that’s both stylish and easy to maintain. The open-concept main living area flows seamlessly, making it ideal for daily living and entertaining. Upstairs, a versatile loft provides the perfect bonus space for a home office, playroom, or second living area. Step outside to a private courtyard-style patio, ideal for grilling, relaxing, or enjoying your morning coffee—an inviting outdoor space that adds to the home’s functionality and charm. Life in Longleaf at Oakland extends beyond the home itself. Residents enjoy a community pool and playground, perfect for relaxing weekends and family fun. Outdoor enthusiasts will appreciate being close to nearby nature trails, offering scenic walks and bike rides just minutes from home. With quick access to major highways, commuting is simple while still enjoying a peaceful residential setting. You’re conveniently located near shopping, dining, downtown Winter Garden, and everyday essentials—making this an excellent place to call home. This move-in-ready corner unit offers comfort, convenience, and a lifestyle that’s hard to beat. Schedule your private showing and experience it for yourself.

Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)

Listing Agent: Stiliany Collado Llc (407-285-3968)

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: 15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily Opportunity Exceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland. Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style residences, mobile home/RV units, and additional rental pads, creating multiple income streams and long-term upside. Currently generating $34,860 per month in gross rental income the property delivers immediate cash flow while offering significant future value-add and redevelopment potential. Located just minutes from the Florida Turnpike interchange, Downtown Winter Garden, Clermont, and the greater Orlando employment hubs, this site sits directly in the path of West Orange’s continued expansion. The C-1 zoning and strategic frontage on SR-50 make this an especially compelling opportunity for investors seeking stable income today with the flexibility for future repositioning. Whetherd workforce housing and RV income asset, repositioned into a boutique rental community, or held for future redevelopment, opportunities with this combination of location, scale, frontage, and in-place revenue are increasingly rare. (Seller is selling 112 units in total varying in diffrent locations this is 32 of those 112)

Listing is courtesy of: REMAX SUNSTATE REALTY (416-450-7436)

Listing Agent: Kyler Moreland (407-496-4196)

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: 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)