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NO HOA! VERY LARGE LOT! Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home. Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020, All new duct work in 2026, Septic pumped 2026, All weather porch windows 2026, new windows in 2023, and a brand-new water heater in 2024. The kitchen showcases wood cabinets paired with elegant quartz countertops installed in 2025, complemented by stainless steel appliances. The home's standout feature is the screened porch that runs the full length of the house, perfect for relaxing while overlooking the spacious backyard. This outdoor space offers plenty of room for entertaining, gardening, or simply enjoying Florida's beautiful weather. Location is key with this property. Situated in the heart of Oakland, you'll be close to local favorites including a coffee shop, florist, and cafe. The popular West Orange Trail is just a short distance away, ideal for biking, walking, or jogging. Downtown Winter Garden is nearby, offering additional dining and entertainment options. Daily conveniences are easily accessible with shopping centers and restaurants located throughout the area. This location provides the perfect blend of small-town charm and modern amenities. Whether you're looking for your first home or your next home, this Oakland property offers comfortable living in a great neighborhood The combination of recent improvements, outdoor living space, and prime location makes this house a great opportunity for your next chapter.

3 Beds ⋅ 2 Baths ⋅ Ryan Court SubDv. ⋅ 34760 Zip Code

NO HOA! VERY LARGE LOT! Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home. Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020, All new duct work in 2026, Septic pumped 2026, All weather porch windows 2026, new windows in 2023, and a brand-new water heater in 2024. The kitchen showcases wood cabinets paired with elegant quartz countertops installed in 2025, complemented by stainless steel appliances. The home's standout feature is the screened porch that runs the full length of the house, perfect for relaxing while overlooking the spacious backyard. This outdoor space offers plenty of room for entertaining, gardening, or simply enjoying Florida's beautiful weather. Location is key with this property. Situated in the heart of Oakland, you'll be close to local favorites including a coffee shop, florist, and cafe. The popular West Orange Trail is just a short distance away, ideal for biking, walking, or jogging. Downtown Winter Garden is nearby, offering additional dining and entertainment options. Daily conveniences are easily accessible with shopping centers and restaurants located throughout the area. This location provides the perfect blend of small-town charm and modern amenities. Whether you're looking for your first home or your next home, this Oakland property offers comfortable living in a great neighborhood The combination of recent improvements, outdoor living space, and prime location makes this house a great opportunity for your next chapter.

131 Ryan Court, Oakland

$1,627,000

Pre-Construction. To be built. Experience custom living at its finest in this beautifully crafted J&J Building home, ideally located in the heart of charming Oakland. Offering 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this home combines thoughtful design with modern appeal. The primary suite is conveniently located on the main floor, providing a private retreat. Enjoy Florida’s year-round sunshine and entertain with ease in the outdoor summer kitchen, perfect for gathering with family and friends. Situated directly across from Speer Park which features pickle ball, a tennis court and a basketball court. Located just moments from Lake Apopka, the West Orand Trail, three miles to downtown Winter Garden, and steps from the charm of downtown Oakland, this home offers a unique blend of outdoor recreation, small-town character, and custom craftsmanship. Don’t miss the opportunity to make this exceptional property your own!

4 Beds ⋅ 4 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Experience custom living at its finest in this beautifully crafted J&J Building home, ideally located in the heart of charming Oakland. Offering 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this home combines thoughtful design with modern appeal. The primary suite is conveniently located on the main floor, providing a private retreat. Enjoy Florida’s year-round sunshine and entertain with ease in the outdoor summer kitchen, perfect for gathering with family and friends. Situated directly across from Speer Park which features pickle ball, a tennis court and a basketball court. Located just moments from Lake Apopka, the West Orand Trail, three miles to downtown Winter Garden, and steps from the charm of downtown Oakland, this home offers a unique blend of outdoor recreation, small-town character, and custom craftsmanship. Don’t miss the opportunity to make this exceptional property your own!

20 W Vick Avenue Unit 2, Oakland

$1,645,000

Under Construction. Discover the perfect blend of custom craftsmanship, modern style, and small-town charm in this beautifully designed J&J Building home. Featuring 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this distinctive residence offers a thoughtfully designed layout with the primary suite conveniently located on the second floor. Sleek vinyl windows add a contemporary touch, while the summer kitchen creates the perfect setting for outdoor entertaining and enjoying Florida living year-round. Ideally situated across from Speer Park where you can enjoy an active lifestyle featuring pickleball, tennis, and basketball courts. Just up the street from Lake Apopka, the West Orange Trail, three miles from downtown Winter Garden, and right next to charming downtown Oakland, this home offers a wonderful opportunity to enjoy the beauty of nature and the appeal of a welcoming community, all close to home. Experience the best of custom living in a location that truly stands out!

4 Beds ⋅ 4 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

Under Construction. Discover the perfect blend of custom craftsmanship, modern style, and small-town charm in this beautifully designed J&J Building home. Featuring 4 bedrooms, 3.5 bathrooms, and a 2-car garage, this distinctive residence offers a thoughtfully designed layout with the primary suite conveniently located on the second floor. Sleek vinyl windows add a contemporary touch, while the summer kitchen creates the perfect setting for outdoor entertaining and enjoying Florida living year-round. Ideally situated across from Speer Park where you can enjoy an active lifestyle featuring pickleball, tennis, and basketball courts. Just up the street from Lake Apopka, the West Orange Trail, three miles from downtown Winter Garden, and right next to charming downtown Oakland, this home offers a wonderful opportunity to enjoy the beauty of nature and the appeal of a welcoming community, all close to home. Experience the best of custom living in a location that truly stands out!

20 W Vick Avenue Unit 1, Oakland

$600,000

A vaulted central living space carries the eye from the front dining room through an island kitchen to glass doors opening onto a garden-framed patio, giving this single-story Oakland home a natural indoor-outdoor rhythm. The kitchen serves as the everyday hub, with an expansive island, breakfast-bar seating, abundant cabinetry and clear sightlines that keep meal preparation connected to the main gathering area. Just beyond the living room, the open-air patio is arranged beneath pergola-style shade and surrounded by planted beds, creating an inviting place for morning coffee, outdoor meals or a quiet evening beneath the trees. The split-bedroom plan adds practical separation, positioning the primary suite apart from two secondary bedrooms and a full hall bath. Multiple windows and a tray ceiling shape the primary bedroom, while its en suite bath includes dual sinks, a separate tub and shower and a walk-in closet. Ceramic tile extends through the main living areas, kitchen and bathrooms, with carpet in the bedrooms and an interior laundry area supporting an easy daily routine. Set on a 0.28-acre corner lot with no HOA, the property combines open lawn, mature landscaping and room to enjoy the outdoors, while an attached two-car garage and broad driveway add useful parking and storage. Located in a golf cart-friendly community, you’ll enjoy easy access to downtown Winter Garden’s shops, restaurants and local events, along with the nearby West Orange Trail for walking and biking. This Oakland location offers a relaxed residential setting with convenient access to everything that makes the Winter Garden area so enjoyable.

3 Beds ⋅ 2 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code

A vaulted central living space carries the eye from the front dining room through an island kitchen to glass doors opening onto a garden-framed patio, giving this single-story Oakland home a natural indoor-outdoor rhythm. The kitchen serves as the everyday hub, with an expansive island, breakfast-bar seating, abundant cabinetry and clear sightlines that keep meal preparation connected to the main gathering area. Just beyond the living room, the open-air patio is arranged beneath pergola-style shade and surrounded by planted beds, creating an inviting place for morning coffee, outdoor meals or a quiet evening beneath the trees. The split-bedroom plan adds practical separation, positioning the primary suite apart from two secondary bedrooms and a full hall bath. Multiple windows and a tray ceiling shape the primary bedroom, while its en suite bath includes dual sinks, a separate tub and shower and a walk-in closet. Ceramic tile extends through the main living areas, kitchen and bathrooms, with carpet in the bedrooms and an interior laundry area supporting an easy daily routine. Set on a 0.28-acre corner lot with no HOA, the property combines open lawn, mature landscaping and room to enjoy the outdoors, while an attached two-car garage and broad driveway add useful parking and storage. Located in a golf cart-friendly community, you’ll enjoy easy access to downtown Winter Garden’s shops, restaurants and local events, along with the nearby West Orange Trail for walking and biking. This Oakland location offers a relaxed residential setting with convenient access to everything that makes the Winter Garden area so enjoyable.

100 Mather Smith Drive, Oakland

$1,445,000

FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking in the peaceful surroundings and views of the West Orange Trail just beyond your front door. Step inside to soaring spaces, abundant natural light, and architectural details that immediately make an impression. A grand staircase leads to a striking bridge-style balcony overlooking the family room, while a beautiful brick gas-burning fireplace anchors the living space and creates a warm, inviting centerpiece for gathering and entertaining. Designed with both everyday living and flexibility in mind, the spacious floor plan features a formal dining room, dedicated office, bonus room, and enclosed sunroom offering even more space to relax and enjoy the Florida lifestyle year-round. A generously sized walk-in closet provides exceptional storage, while thoughtful features such as a central vacuum system add everyday convenience. Roof Replacement in 2025 and HVAC replacement in 2022 add peace of mind for years to come. Located within Oakland's golf cart district, this home offers extra garage space for your golf cart, bikes, and moreWhether you're enjoying coffee on the porch swing, relaxing beside the fireplace, or simply taking in the peaceful small-town atmosphere, this home offers a wonderful combination of space, character, and location in sought-after Oakland. Come experience the charm and lifestyle that make this community such a special place to call home!

4 Beds ⋅ 4 Baths ⋅ Town/Oakland SubDv. ⋅ 34760 Zip Code

FRONT PORCH CHARM, WEST ORANGE TRAIL VIEWS, AND A HOME FULL OF CHARACTER IN THE HEART OF OAKLAND! Start your mornings from the covered front porch and porch swing, taking in the peaceful surroundings and views of the West Orange Trail just beyond your front door. Step inside to soaring spaces, abundant natural light, and architectural details that immediately make an impression. A grand staircase leads to a striking bridge-style balcony overlooking the family room, while a beautiful brick gas-burning fireplace anchors the living space and creates a warm, inviting centerpiece for gathering and entertaining. Designed with both everyday living and flexibility in mind, the spacious floor plan features a formal dining room, dedicated office, bonus room, and enclosed sunroom offering even more space to relax and enjoy the Florida lifestyle year-round. A generously sized walk-in closet provides exceptional storage, while thoughtful features such as a central vacuum system add everyday convenience. Roof Replacement in 2025 and HVAC replacement in 2022 add peace of mind for years to come. Located within Oakland's golf cart district, this home offers extra garage space for your golf cart, bikes, and moreWhether you're enjoying coffee on the porch swing, relaxing beside the fireplace, or simply taking in the peaceful small-town atmosphere, this home offers a wonderful combination of space, character, and location in sought-after Oakland. Come experience the charm and lifestyle that make this community such a special place to call home!

137 Petris Avenue, Oakland

$786,999

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code

Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.

16 Oakland Pointe Circle, Oakland

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