Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
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, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. 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.
Courtesy: Jaime L Boone LLC
786-600-4465
Foreclosure Auction Ends February 17, 2026 at 11:00 AM EST. Discover this inviting 3-bedroom, 2.5-bathroom townhome, offering a wonderful opportunity to live in the desirable Longleaf at Oakland community. The list price is the opening bid for the online auction. Sold As-is.
Courtesy: LIBERTY HOME SALES INC
321-256-0500
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 2019 and the A/C in 2024. 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. New A/C 12/21/2020. New Roof 11/2019.
Courtesy: PINK MIAMI
305-504-0807
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.
Courtesy: LPT REALTY, LLC
877-366-2213
Welcome home to Hull Island, where refined design meets serene Florida living. This impeccably maintained 4-bedroom, 3-bath home offers the rare combination of conservation privacy, thoughtful upgrades, and resort-style community amenities—truly better than new. Backing to a protected nature preserve with no rear neighbors, the home provides a peaceful retreat while still being moments from everything. Inside, you’ll find wood-look tile flooring throughout (no carpet), plantation shutters, high ceilings, and abundant natural light that enhances the open, airy feel. Electric shades on the sliding glass doors add both convenience and a polished, modern touch. Smart-home features include a NEST thermostat and Ring doorbell, offering comfort, efficiency, and peace of mind. The heart of the home is the spacious open-concept kitchen, living, and dining area—ideal for both everyday living and entertaining. The kitchen features stainless steel appliances, a modern backsplash, generous counter space, and a large center island with seating. This home also offers gas service and is fully equipped with a whole-house generator, providing comfort and reliability year-round.An EV charger in the garage adds a valuable, future-ready convenience. A standout feature rarely found: custom built-in shelving in the pantry and all bedroom closets, offering exceptional storage and organization. The primary suite is a true sanctuary, easily accommodating large furniture and featuring a spa-inspired en-suite bath. One of the secondary bedrooms includes its own private en-suite bathroom, making it ideal for guests, visitors, or multi-generational living. Two additional bedrooms and a full bath provide flexibility for family, home office space, or hobbies. Enjoy Florida living at its best with both an inviting front porch and a screened, extended lanai with brick-paver patio, overlooking tranquil conservation views—perfect for morning coffee, evening gatherings, or simply unwinding in nature. Located in a lakefront community on Lake Apopka, residents enjoy exceptional amenities including a community pool, fishing pier, dock, dog park, and park spaces, creating a lifestyle that feels like a year-round vacation. Situated in the charming Town of Oakland, you’re just minutes from Downtown Winter Garden, the West Orange Trail, weekly farmers markets, Winter Garden Village, and the lakefront dining of Clermont—plus easy access to Orlando, major roadways, and Central Florida attractions. This is a move-in-ready, low-maintenance home offering privacy, quality, and an unbeatable location. A rare opportunity-don't miss it.
Courtesy: ORLANDO PROP MGMNT RLTY LLC
407-283-5065
Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere. The large open kitchen offers a large island with seating for four, granite countertops, 42-inch cabinetry, and stainless-steel appliances. Oversized windows fill the space with natural light, while the adjacent laundry room includes storage shelving and a walk-in pantry for added convenience. Step out of the kitchen to a private brick-paver courtyard perfect for relaxing or entertaining. Upstairs, the primary suite boasts a walk-in closet and an en-suite bath with dual granite vanities and a spacious walk-in shower. Two additional bedrooms and a full bathroom provide ample space for family or guests. The home is also pre-wired for a security system with the option to add cameras. Residents of Longleaf at Oakland enjoy community amenities including a pool, playground, and sidewalks throughout the neighborhood. Conveniently located near shopping, dining, and major roadways. Enjoy a hike at the Oakland Nature preserve with a boardwalk to Lake Apopka, and conveniently located next to the West Orange Trail.
Courtesy: MARKET CONNECT REALTY LLC
407-250-4708
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.
Courtesy: NEW HOMES REAL ESTATE, INC.
407-947-2475
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!
Courtesy: NUMBER 1 BROKER, LLC
407-566-3400
This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters, and center island with breakfast bar. The family room and the rear lanai feat peaceful views of the rear lawn and conservation area. The first floor master suite feat a large walk in closet and the master bath complete with dual sinks, walk in shower, and garden tub. Upstairs you will find 4 additional bedrooms all with large closets, and served by 2 additional full baths. The flexibility of this home is endless as the upstairs features an additional LOFT SPACE as well as a 2nd Floor DEN. You get a large house without large energy bills as Meritage Homes is relentless with energy efficiency in their products. The Oakland Trails community centers around a generous park area and includes community pool, playground, and dog park! The community is located near the West Orange Trail, historic downtown Plant Street, and a short drive from Winter Garden Village. The location of this home can't be beat for ease of access to the Turnpike, shopping, and dining. Call today to see this home!
Courtesy: KELLER WILLIAMS ADVANTAGE III
407-207-0825
THIS ONE IS A MUST SEE!! UPGRADES ON UPGRADES ON UPGRADES . Welcome to Oakland Trails, a beautiful and well-established community located in the charming, small-town City of Oakland. This spacious 5-bedroom, 3.5-bath home features a thoughtfully designed layout offering flexibility, comfort, and room to grow—perfect for today’s lifestyle.From the moment you enter, you are welcomed by a cozy Great Room and formal Dining Room, highlighted by a modern staircase with sleek railing, setting the tone for the home’s contemporary design. The layout flows seamlessly into the open-concept Living Room and upgraded Kitchen, ideal for entertaining and everyday living. The kitchen features stylish upgrades, ample cabinetry, generous counter space, and a beautiful designer backsplash, creating a functional yet eye-catching centerpiece.The first-floor primary suite offers a private retreat with a spacious master bedroom accommodating a king-size bed and additional furnishings. The luxurious master bathroom includes dual vanities, a large walk-in shower, and a separate soaking tub, complemented by a dreamy, oversized walk-in closet with abundant storage.Also located on the first floor are an interior laundry room and a 2-car garage for added convenience. Upstairs, you’ll find a generous loft area perfect for a secondary living space, media room, or play area. The additional bedrooms are well-proportioned and thoughtfully spaced, along with a versatile bonus room that can serve as a home office, den, or optional 6th bedroom. This home is ideally situated on a quiet cul-de-sac lot with no front neighbors and a peaceful conservation view in the rear, offering exceptional privacy. Step outside to enjoy a resort-style backyard, thoughtfully upgraded with low-maintenance artificial grass and beautifully extended pavers. The artificial grass not only enhances the aesthetic appeal but also saves time and effort on lawn care, offering convenience and year-round enjoyment without the need for mowing, watering, or constant maintenance—perfect for a busy lifestyle or family fun. Prime location highlights include access to top-rated area schools, quick access to the Florida Turnpike, and proximity to surrounding cities such as Winter Garden, Clermont, and Orlando. Enjoy nearby shopping malls, dining, entertainment, movie theaters, and world-class attractions, all within a short drive. This exceptional home seamlessly combines space, modern upgrades, privacy, and an unbeatable location—offering the ultimate Central Florida lifestyle.
Courtesy: KELLER WILLIAMS WINTER PARK
407-545-6430
ASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home located in the charming town of Oakland, FL. Offering 3 bedrooms, 2.5 bathrooms, and 2,078 square feet of thoughtfully designed living space, this home features an open floor plan that’s perfect for both everyday living and entertaining. The spacious layout is complemented by an upstairs loft, ideal for a home office, media room, or additional living area, while abundant natural light enhances the modern, airy feel throughout. This home is loaded with high-end upgrades and smart-home features. Venetian blinds are installed throughout, including app-controlled motorized blinds on the dramatic high windows above the stairs. Smart lighting adds convenience and efficiency, while every room is pre-wired for Cat5 and cable, making it perfect for remote work or streaming. A large aerial OTA antenna in the attic provides excellent over-the-air TV reception, and the whole-home water conditioner and softener ensure comfort and quality water throughout. Energy efficiency and reliability truly set this property apart. Tesla solar panels paired with two Powerwalls provide exceptional energy savings and peace of mind—meaning you’ll never lose power. The two-car garage includes convenient overhead storage for added organization. With its cutting-edge technology, functional design, and desirable Oakland location, this home offers a rare blend of comfort, efficiency, and modern living. ROOF: 2020 AC: 2020 ELECTRICAL: 2020 PLUMBING: 2020 HWH: 2020
Courtesy: THE REAL ESTATE COLLECTION LLC
407-656-7814
Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and inviting atmosphere. To the left, a spacious living and dining room combination provides an ideal setting for entertaining and offers convenient access to the kitchen. The kitchen is well-appointed with solid wood cabinetry, granite countertops, stylish backsplash, a breakfast bar, and stainless steel appliances. The kitchen opens to a generous living area featuring sliding glass doors that lead to a large paver patio with fruit trees—perfect for indoor-outdoor living and relaxing gatherings. The primary suite is thoughtfully tucked down the hallway and showcases engineered hardwood flooring, a walk-in closet, and a beautifully renovated en-suite bath. The primary bath features a standalone shower, garden tub, and dual vanities. Three additional bedrooms, a guest bathroom, and a laundry room complete the interior layout. Residents of Johns Landing enjoy resort-style amenities including basketball, tennis, and pickleball courts, a playground, an open dock with private boat ramp, and a gazebo. Upgrades include: Water Heater (2024), Roof (2018), Double Pane Windows and New Slider (2024). Conveniently located near downtown Winter Garden, downtown Clermont, downtown Oakland, and major highways, this home offers both tranquility and accessibility. Don’t miss the opportunity to enjoy lake-access living in this desirable community!
Courtesy: URBAN-O REAL ESTATE SOLUTIONS
407-822-1063
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.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive Euro-style 9'+ bifold slider, and a stunning gas fireplace anchoring the main living space. The chef’s kitchen boasts Wolf and Sub-Zero appliances, exquisite Quartzite counters in both the main and back kitchens, and a fully equipped back kitchen designed for effortless entertaining. A custom primary closet with lighted rods adds a boutique touch to everyday living. Outdoor living is equally exceptional. Enjoy a lap pool and hot tub, gas fire pit, and luxurious marble coping and pool decking, all beautifully framed by a $70,000 professionally designed landscaping package and a fully fenced yard for privacy. Additional upgrades include Sonos speakers, security system with cameras, clay tumbled pavers on the porches, and a Generac generator for added comfort and peace of mind. With a 4-car garage, impeccable craftsmanship, and a leaseback opportunity, this home offers the best of luxury and convenience. Furniture is negotiable, allowing you to tailor the space to your vision. Discover refined living in one of Oakland’s most desirable communities—this model home truly sets the standard.
Courtesy: OAKSTRAND REALTY
888-912-5258
This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!
Courtesy: CORCORAN PREMIER REALTY
407-965-1155
Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully curated for comfort, sophistication, and style. From the moment you arrive, the home commands attention with its architectural presence and grand entryway. Inside, soaring ceilings, designer finishes, and expansive living spaces create a refined yet inviting atmosphere. The heart of the home is the gourmet chef’s kitchen, seamlessly connected to the main living areas and perfect for both intimate gatherings and large-scale entertaining. A private office provides the ideal work-from-home environment, while multiple ensuite bedrooms ensure comfort and privacy for family and guests. The 4-car garage offers ample space for vehicles, storage, or a future car collection. Resort-style outdoor living takes center stage with a beautifully appointed summer kitchen, covered lanai, and a sparkling custom pool with spa, all overlooking the lush, manicured grounds of the corner lot. Whether hosting celebrations or enjoying quiet evenings at home, this outdoor oasis elevates everyday living. Nestled within one of Oakland’s most coveted luxury communities- Briley Farm, this home offers exclusivity, elegance, and convenience—just minutes from vibrant Winter Garden, top-rated schools, charming parks, and premier dining. A true masterpiece in Briley Farm, this residence delivers the ultimate blend of luxury and lifestyle.
Courtesy: PREMIER SOTHEBYS INT'L REALTY
407-581-7888
Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or relaxing with friends. Go outside to your extended patio and unwind with morning coffee or evening wine, all while enjoying privacy of no rear neighbors. Upgrades abound, including a gourmet kitchen with granite countertops, stainless steel appliances and elegant luxury vinyl flooring, designed with comfort and efficiency in mind, this home includes a state-of-the-art fresh air system, spray foam insulation, and high-speed fiber optic internet for exceptional performance and connectivity. The fully fenced backyard and paver driveway offer style and convenience. Community amenities include a resort-style pool, dog parks, and playground, providing fun and relaxation for everyone. The neighborhood is just two minutes away to the West Orange Trail Head, offering easy access to outdoor recreation. It is also conveniently between Winter Garden and Clermont, you'll be just minutes from top-rated schools, shopping, dining and easy access to major highways. Fall in love. Make it yours.
Courtesy: WEMERT GROUP REALTY LLC
407-743-8356
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!
Courtesy: RE/MAX EXCLUSIVE COLLECTION
407-447-2829
Find out about the unique chance to be the owner of a 2,700 sqft home which sits on 2.55 private acres which we think is the ideal setting for space, privacy, and great growth. This 1983 built home has been very well preserved in it’s original condition which makes it the perfect choice for buyers who are after land, character and the freedom to update the home to suit their own style. In the home you’ll find a large open floor plan which has high vaulted ceilings and large picture windows that allow in lots of natural light. We have a fantastic floor to ceiling stone fire place which is a great spot for get together or a quiet night in. The kitchen is the heart of the home large with TONS of cabinetry, a large center island, built in appliances and it has plenty of space for friends and family to gather. It is a hard space to find today. A large enclosed summer room sunroom which extends your living area even more. In this space you may set up a game room, fitness area, home office, or use it for year round relaxation which includes the beauty of the back yard. The home has 4 large bedrooms and 2 full bathrooms which still present in the beautiful 1983 character they did back when, which we think is a great chance for a buyer that wants to update, modernize or keep the vintage look. Outside we have many options. With 2.55 acres which is plenty for gardens, animals, outdoor workshops, RV storage, or creating your own private retreat. Also included in the deal is a detached casita that is perfect for guests, extended family, an office, or has the chance to be used for a future rental income. The home has a private well and septic which means you have full independence and lower utility costs, ideal is who prefer rural living without giving up convenience.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Courtesy: REGENCY REAL ESTATE LLC
407-469-5021
Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floorplan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Sunburst also features a 3-car garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Upstairs, enjoy a stunning covered terrace, ideal for morning coffee, evening gatherings, or simply taking in the views of your surroundings. With its blend of functionality and sophistication, every space in the Sunburst is designed to make daily living both easy and elegant. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Sunburst model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Courtesy: HOMEVEST REALTY
407-897-5400
One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue Charter School and minutes from Historic Downtown Winter Garden, where you can explore boutique shops, award-winning restaurants, and the scenic West Orange Trail. Inside, the thoughtfully designed layout features primary suites on both the first and second floors, offering flexible living arrangements perfect for multigenerational families or guests. The open floor plan and spacious living areas create a comfortable flow throughout, ideal for everyday living and entertaining alike. Step outside to your own backyard oasis, complete with a sparkling pool and spa surrounded by lush landscaping—perfect for relaxing weekends or hosting gatherings. Additional highlights include a brand-new roof installed in September 2025, offering long-term peace of mind and value. With its ideal location, privacy, and resort-style outdoor living, this home perfectly captures the essence of Florida living!
Courtesy: BHHS FLORIDA REALTY
407-876-2090
*** Back on market after being temporarily off while the Seller moved (~45 days). *** Stunning former MODEL HOME on a premium CORNER lot – 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, 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!
Courtesy: REAL BROKER, LLC
855-450-0442
Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary bedroom provides a peaceful retreat with ample space and natural light throughout. New Roof 2022 & New AC 2025! Step outside to discover your personal oasis featuring a screened-in solar-heated pool area with a generous patio – ideal for year-round Florida living and entertaining. The premier lot offers breathtaking pond views, creating a serene backdrop for morning coffee or evening gatherings. This exclusive gated community provides residents with exceptional amenities including private lake access, a fishing pier for those peaceful weekend mornings, tennis courts for staying active, and a playground for family fun. The community perfectly balances privacy with recreation opportunities. Location couldn't be better – you're just minutes from charming downtown Winter Garden with its vibrant dining and shopping scene. All major parkways are easily accessible, making commuting a breeze. Theme Parks enthusiasts will appreciate being only 25 minutes from world-famous attractions like Disney and Universal Studios. Nearby conveniences include grocery shopping at the local market less than a mile away, and nature lovers will enjoy Oakland Nature Preserve just around the corner for hiking and wildlife viewing. This property combines luxury living with practical convenience in one of Florida's most desirable communities.
Courtesy: BHHS FLORIDA REALTY
407-876-2090
Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney. Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious open floor plan, soaring 14-foot ceilings, and oversized 8-foot doors throughout, the home is both grand in scale and thoughtfully functional. Fully handicap accessible and designed with mobility in mind, it offers seamless, barrier-free living that accommodates all stages of life. At the heart of the home lies a gourmet kitchen, professionally designed by a chef and custom builder. This culinary centerpiece features top-of-the-line appliances, generous prep space, and luxury finishes—perfect for everything from everyday meals to large-scale entertaining. The open-concept design continues into expansive living and dining areas that flow effortlessly into the outdoors, creating an ideal environment for both intimate gatherings and lively celebrations. Step outside to your own private oasis: a beautifully screened-in pool, complemented by a fully equipped summer kitchen and ample patio space for lounging or dining under the stars. Whether you’re enjoying a quiet morning coffee poolside or hosting a weekend cookout, the outdoor living area is designed to elevate your lifestyle year-round. Located just steps from the Oakland Farmers Market, Charter School, Heritage Center, and Post Office, this home is at the center of a walkable, welcoming community where neighbors know one another and nature thrives. With direct golf cart access to vibrant Downtown Winter Garden, you’re only minutes from award-winning restaurants, unique shops, live entertainment, and a bustling weekly farmers market. Outdoor enthusiasts will love the nearby West Orange Trail and Lake Apopka’s scenic shoreline, perfect for biking, walking, birdwatching, or kayaking. And when adventure calls, you’re a short drive from some of the world’s most celebrated destinations, including Walt Disney World, Universal Studios, and Downtown Orlando. Combining small-town charm with big-city convenience, this location is truly second to none. More than just a residence, 101 N Starr Street is a destination for those seeking refined, accessible living in one of Central Florida’s most desirable communities. With its custom design, premium features, and unbeatable location, this home offers a lifestyle of beauty, comfort, and lasting value.
The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) Program of the Space Coast Association of REALTORS®, Inc. Real estate listings held by brokerage firms other than the owner of this site are marked with the Space Coast Association of REALTORS®, Inc. logo and detailed information about them includes the name of the listing brokers. Copyright 2026 Space Coast Association of REALTORS®, Inc. All rights reserved.
Oakland is located in Florida. Oakland, Florida has a population of 3,444. Oakland is more family-centric than the surrounding county with 42.26% of the households containing married families with children. The county average for households married with children is 31.51%.
The median household income in Oakland, Florida is $124,856. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Oakland is 37.1 years.
The average high temperature in July is 92.2 degrees, with an average low temperature in January of 46.8 degrees. The average rainfall is approximately 52.1 inches per year, with 0 inches of snow per year.
