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$3,295,000
6 Beds ⋅ 7 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
Under Construction. This exceptional luxury residence by Element Home Builders is located in the prestigious Briley Farm community and offers 5,144 square feet of thoughtfully designed living space on a private 0.5-acre homesite. Featuring 6 bedrooms, 6 full bathrooms, and 1 half bath, this home showcases one of Element's most sought-after floor plans, blending timeless architecture with modern luxury. Designed for both everyday living and elegant entertaining, the open-concept layout features a gourmet chef's kitchen, expansive great room, private office, loft, and spacious covered lanai. Enjoy true Florida living with an extended outdoor entertaining area complete with a resort-style pool, spa, and fully equipped summer kitchen for seamless indoor-outdoor living. Every detail reflects the exceptional craftsmanship, premium finishes, and attention to detail that define Element Home Builders. With construction just beginning, buyers have the rare opportunity to personalize select finishes and own a brand-new custom luxury home in one of Oakland's most desirable communities. Briley Farm is an exclusive enclave just minutes from historic Downtown Winter Garden, the West Orange Trail, top-rated schools, boutique shopping, dining, and major highways, offering convenient access to Downtown Orlando, Walt Disney World, and Orlando International Airport. Experience the perfect blend of luxury, privacy, and convenience in one of Central Florida's premier custom home communities.ning, and major roadways, while maintaining the privacy and charm of luxury estate living. Renderings are for illustration purposes only. Features, specifications, and finishes are subject to change without notice.

312 Briley Avenue, Oakland
$3,375,000
5 Beds ⋅ 7 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
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.

510 Briley Avenue, Oakland
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
Luxury new construction model home by Element Home Builders located in the exclusive custom home community of Briley Farm in Oakland. This thoughtfully designed residence offers approximately 4,900 square feet of elevated living space with 5 bedrooms, 5.5 bathrooms, and a spacious 3-car garage. Designed for both everyday living and entertaining, the home features soaring ceilings, expansive open-concept living areas, designer finishes, and seamless indoor-outdoor flow. The chef’s kitchen is the centerpiece of the home with premium appliances, custom cabinetry, oversized island, generous prep and storage space, and a fully equipped back kitchen designed for seamless entertaining and everyday functionality. The luxurious primary suite offers a spa-inspired bath and oversized walk-in closet, while additional guest suites, flex spaces, and entertaining areas provide comfort and functionality throughout. Outdoor living is equally impressive with a resort-style pool, covered lanai, and beautifully designed entertaining spaces perfect for enjoying Florida living year-round. Professionally furnished by Arhaus, the home showcases elevated designer selections and a warm modern aesthetic throughout. Located just minutes from downtown Winter Garden, top-rated schools, restaurants, shopping, the West Orange Trail, and major highways, Briley Farm offers a rare combination of privacy, luxury, and convenience. This professionally designed model home is available with a lease-back opportunity from the builder, offering a unique investment opportunity with immediate income potential. A rare opportunity to own one of Central Florida’s premier luxury model homes in one of the area’s most desirable custom home communities.

402 N Pollard Street, Oakland
$2,353,078
4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Welcome to La Cascina — a stunning semi-custom home by Pioneer Builders nestled among century-old oaks in The Grove at The Harvest District. This 4-bedroom, 4-bath, 2-half-bath home with a dedicated office impresses from the moment you step inside, with soaring vaulted ceilings, a dramatic floating staircase, and a natural gas fireplace that anchors the main living space with warmth and elegance. The thoughtfully designed layout flows from a formal dining room into an eat-in kitchen with a breakfast nook — perfect for everything from quiet mornings to lively gatherings. Two dedicated laundry rooms add a level of everyday convenience rarely found at any price point. Outside your door, golf-cart your way to Downtown Winter Garden's shops and restaurants— this is Florida living at its finest.

1204 Water Maple Drive, Oakland
$799,999
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
$2,186,921
3 Beds ⋅ 6 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres in the beautiful Town of Oakland. The property is a seamless blend of charming Old Florida and modern-day Luxury Living at its finest. The community is thoughtfully designed to provide the ultimate retreat for our residents. Lot 15 will be custom pool home meticulously designed to complement its natural surroundings, with a spacious floor plan. Briley Farm offers a seamless combination of residential luxury and convenience, with custom homes designed for enjoying the best of indoor and outdoor living. At Briley Farm you'll discover comfortable countryside living amongst the welcoming trees, set to embody the lifestyle for which you've been searching, all nestled away from life's demands.

100 W Railway Avenue, Oakland
$3,800,000
5 Beds ⋅ 5 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Pre-Construction. To be built. Experience elevated living in this brand-new custom home by Element Home Builders, located within the highly sought-after Briley Farm community in Oakland. Set across 111 acres of beautifully preserved landscape, Briley Farm blends timeless Old Florida charm with modern luxury to create a peaceful and refined lifestyle. Surrounded by serene natural scenery and mature tree-lined views, this exceptional community offers the perfect balance of countryside tranquility and everyday convenience , with easy access to shopping, dining, and major highways. Designed as a private retreat for family and friends, Briley Farm embodies comfortable luxury living in one of Central Florida’s most desirable new communities.

533 N Pollard Street, Oakland
$2,395,000
5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1137 Prado Lane, Oakland
$2,045,357
5 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Pre-Construction. To be built. Nestled within the exclusive Grove community in the heart of Oakland and Winter Garden's coveted golf cart district, this bespoke pre-construction residence is a rare opportunity to own something truly one-of-a-kind. Five bedrooms, five full bathrooms, a powder room, and a gracious loft unfold across 3,725 square feet of living space where timeless architecture and modern sophistication coexist effortlessly — every detail considered, every finish deliberate. Element Home Builders has built its reputation on craftsmanship that doesn't cut corners and design that doesn't follow trends — because the Clementine wasn't designed to be fashionable. It was designed to be unforgettable. Step outside and you're two minutes from the West Orange Trail and just a short golf cart ride from the vibrant energy of Downtown Winter Garden — boutique shopping, acclaimed dining, weekend farmers markets, and the kind of small-town charm that's increasingly impossible to find this close to the city. This isn't just a home. It's a lifestyle you'll never want to leave.

1225 Water Maple Drive, Oakland
$1,949,000
5 Beds ⋅ 5 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code
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.

511 Briley Avenue, Oakland
$2,300,000
4 Beds ⋅ 6 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code
Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept floor plan features expansive living and dining areas highlighted by vaulted ceilings in the living room, a fireplace, and seamless indoor-outdoor flow. The gourmet kitchen showcases premium finishes and connects effortlessly to the main living spaces, making it ideal for both everyday living and entertaining. A private office provides a dedicated space for work or study. The primary suite offers a serene retreat with a spa-inspired bath, while each secondary bedroom includes an ensuite bathroom for added privacy. A standout feature of the home is the interior sauna, offering a true wellness experience within the comfort of your own residence. Outdoor living is elevated with a custom pool and spa, summer kitchen, and covered entertaining areas designed for year-round enjoyment. Additional highlights include a 3-car garage and high-end finishes throughout. Located just a 10-minute golf cart ride from downtown Winter Garden and a 2-minute walk to the West Orange Trail, this home combines luxury living with unmatched access to recreation, dining, and shopping.

1118 Sarah Mathews Drive, Oakland
$4,383,239
5 Beds ⋅ 8 Baths ⋅ Briley Farm SubDv. ⋅ 34760 Zip Code
Under Construction. Under Construction Custom Home by Element Home Builders. Welcome to your dream home in Briley Farm. Briley Farm is one of Central Florida's most desirable custom home communities. The property is a seamless blend of charming Old Florida and modern-day luxury. Briley Farm consists of 111 acres of lush landscape in Oakland, Florida. The personal residence is a custom blend of luxury finishes and stunning design. All measurements etc are estimates.

548 Walker Street, Oakland
$950,000
4 Beds ⋅ 3 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
Custom Entertainer’s Dream Courtyard Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living. From the moment you arrive, you’ll be captivated by the circular driveway with dual entrances, mature shade trees, and the impressive side-entry garage. Step inside to discover an open, light-filled floor plan with abundant windows and large sliding doors that seamlessly connect indoor and outdoor living spaces. Modern upgrades continue throughout the home, including three HVAC units—including new systems in 2024 and 2025, a 2022 water heater, energy-efficient construction with ICF (Insulated Concrete Forms), double-pane windows and sliders, and spray foam insulation in the attic. Other updates include a new roof (2024), fresh interior paint and pool deck paint (2025), and remodeled kitchens and bathrooms. The foyer leads to spacious formal living and dining areas, each with views of the expansive screened patio—ideal for entertaining. The chef’s kitchen boasts stone countertops, modern cabinetry with illuminated uppers, built-in ovens, a cooktop, undermount lighting, an outdoor vent system, a corner pantry, and a picturesque window over the sink. It overlooks the sunny dinette, soaring two-story family room with a cozy fireplace, and a striking wood staircase with wrought iron railings. Designed with a split-bedroom layout, each of the four bedrooms offers ensuite bath access. The 1st floor primary suite is a private retreat, featuring high ceilings, wood floors, patio/pool access, and a two-sided gas fireplace that enhances the bedroom and private bath. The ensuite includes a soaking tub, separate glass-enclosed shower, dual vanities, linen closet, water closet, and a spacious walk-in closet. The 2-story family room is delightful, featuring a fireplace, high ceilings, and multiple windows that provide ample natural light. Adjacent to the family room is the spacious dinette. Two double-pane sliding doors lead to the covered patio, where you can enjoy the fenced backyard, which includes a fire pit. Down the hall is another bedroom suite with a remodeled bath, a full-size laundry room, and garage access. Upstairs, you’ll find two additional bedrooms—one with a private balcony overlooking the corner park—and a bonus room with its own balcony view of the pool. Each room shares another jack-and-jill full bath with separate vanities. The backyard is a true Florida oasis—fully fenced with pavers for a clean look, a large screened-in pool area, and ample space for pets and play. With direct access to the popular West Orange Trail, outdoor adventures are just steps away. This exceptional home combines location, design, and functionality—perfect for visiting relatives and entertaining. Don’t miss your chance to own this one-of-a-kind property in one of Central Florida’s most desirable communities.

100 Demens Street, Oakland
$795,000
4 Beds ⋅ 3 Baths ⋅ Town Of Oakland SubDv. ⋅ 34760 Zip Code
Experience the charm of Oakland living in this beautifully updated custom built home located in the heart of town—just minutes to Downtown Winter Garden, Plant Street Market, the West Orange Trail, the Lake Apopka boat ramp/dock and so much more! This move-in ready home is situated on a .27-acre corner lot with no HOA. When entering this 4-bedroom, 3-bathroom home, you’re welcomed by a spacious front patio, beautiful foyer and open floor plan, perfect for entertaining. The flex space to the left of the front entryway offers a great space for an office, secondary dining area or den. The living room overlooks the breathtaking kitchen and exterior screened in patio with beautiful views of the private backyard. The downstairs bedroom and full bath offer flexibility, while the spacious upstairs includes a stunning primary suite with dual closets, and an en suite bath. There are two additional bedrooms upstairs with a shared Jack and Jill bathroom, as well as, a large laundry room with a stackable washer & dryer, sink and plenty of cabinet and countertop space. This home boasts countless updates throughout, including, but not limited to, New Taj Mahal quartzite countertops + backsplash (2024), brand new kitchen sink, hardware and faucet (2024), High end appliances and a brand new gas stove (2025) perfect for the chef at heart! The office features new custom built-in shelving (2024), and the entire interior has been freshly painted (2024). Stylish new fixtures, mirrors, and an updated fireplace façade add to the elegant aesthetic (2024). Move in stress free with upgrades such as a Newer Metal Roof (2022), Shingle Roof (2014), consistent servicing of the HVAC system, Double-Pane Windows throughout and new Plumbing & Electric (2014). Enjoy Florida living in your gorgeous backyard oasis—complete with new sod (2024), lush landscaping, a paver patio, hot tub, and a spacious screen-enclosed brick paver patio with an outdoor kitchen area. This home is truly turn-key and perfectly positioned for nature lovers, golf cart enthusiasts and downtown living alike. Don’t miss this rare opportunity to own this wonderful home in the sought-after Oakland neighborhood—schedule your private showing today!

101 W Oakland Avenue, Oakland
$1,400,000
4 Beds ⋅ 4 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
Live the "Lake Life" in a Tropical Paradise – Key West Vibes in Oakland, Florida! Welcome to your own slice of paradise in the heart of The Town of Oakland – one of Central Florida’s most desirable and fastest-growing communities. Situated on a sprawling 1.12-acre lot along the shores of Lake Apopka – Florida’s 4th largest lake – this gorgeous custom home spans nearly 4,000 square feet of beautifully designed space that embraces the outdoors at every turn. With 8-mile panoramic lake views that stretch across the water, you’ll wake up to breathtaking sunrises and unwind to the sounds of nature and incredible sunsets every evening. Just a short walk, bike or golf cart ride from the vibrant charm of Downtown Winter Garden, this Key West-style lakefront retreat blends luxury, nature, and laid-back living like no other. Step outside and into your own resort-style backyard, complete with a heated tropical pool oasis, cascading waterfall, spa, and hidden grotto, all surrounded by lush, vibrant landscaping that makes every day feel like a tropical getaway. Entertain guests, relax in the sun, or enjoy evenings by the lake under the stars – this backyard is pure magic! Inside, every inch of this home is built for comfort and peace of mind – including a whole-home Generac generator so you're always prepared. Whether you’re looking for a private retreat, love hosting unforgettable gatherings, or simply craving the serenity of a lakefront lifestyle, this home delivers. Best of all? You’re located within the golf cart district, just minutes from Plant Street Market, Crooked Can Brewery, charming restaurants, boutique shops, and everything downtown Winter Garden has to offer. You’re also just steps from the West Orange Trail – a 22-mile scenic mixed-use path that connects Oakland to Winter Garden and all the way to Apopka - perfect for biking, walking, skating, or just soaking up the Florida sun. This isn’t just a home – it’s a lifestyle. Come see it for yourself – paradise is waiting. Don’t miss the chance to make it yours!

141 Millholland Street, Oakland
$571,000
3 Beds ⋅ 2 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code
Located in the heart of Downtown Oakland, this well-built and meticulously maintained CBS construction ranch house offers a perfect blend of comfort, style, and convenience. Located on a spacious corner lot, under heritage oak trees, the home features an open and airy split floor plan with high ceilings and sky lights, creating a bright and inviting atmosphere. With numerous updates and renovations, to its roof, double pane, windows, wood flooring, fully renovated kitchen and primary bathroom with steam shower, PVC shutters, fresh interior, and exterior paint, HVAC system and more, ensure a move-in-ready experience. Living in Oakland is like stepping back in time to a more relaxed Florida lifestyle, where canopy tree-lined streets, historic charm, and a strong sense of community create a peaceful setting to call home. Just a short walk to the Lake Apopka pier and one block from the West Orange Trail, along with the Oakland Nature Preserve, .8 miles away, it offers endless outdoor activities. Plus, it’s only minutes from Historic Downtown Winter Garden, Oakland’s sister city, known as the area’s hub for entertainment, dining, shopping, the famed farmers market, a local brewery, and a thriving business district. This prime location catty-corner from Oakland's Speer Park, with tennis, pickle ball and BB courts and playground, this home is a rare find, offering both small-town charm and modern conveniences nearby!

201 Briley Avenue, Oakland
$1,100,000
4 Beds ⋅ 3 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
** Ask your lender about RATE BUY DOWN options. Did you know some lenders have minimal closing costs? Inquire for more information. ** Discover the beauty of lakefront living on the shores of Lake Apopka with this 4-bedroom, 3-bath, 3 CAR garage home with an air-conditioned BONUS space (~ 400 sqft) over the garage. Lake Apopka is the headwaters of the Ocklawaha Chain of Lakes, which connects to Lake Beauclair, Lake Dora, Lake Harris, Lake Griffin and the St Johns River. This waterway system allows boaters to travel from Lake Apopka all the way to the Atlantic Ocean via the St. Johns River, making it one of Florida’s most interconnected lake chains. Boasting expansive water views and stunning sunsets, this property offers a rare opportunity to create your dream waterfront oasis. Inside, you’ll find a spacious layout with an abundance of natural light, spacious living areas, and a primary suite with serene lake views. While the home needs some updating, the solid structure and unbeatable location provide the perfect canvas for customization. As you enter the home you’ll be captivated by the views. On the east side you’ll find the generously sized PRIMARY SUITE, which includes a garden tub, dual sinks, shower, walk-in closet, and FRENCH doors that lead to the screened-in patio. Adjacent to the primary suite is another bedroom and full bath. The 2nd bath also connects to the patio. On the west side of the home are two additional bedrooms, one full bath, and a spacious laundry room with utility sink. The kitchen, which includes stainless steel appliances, opens to the family room, eat-in kitchen area, and the breathtaking and elevated lake views. A separate formal dining space is carved out in the home which makes entertaining a breeze. The property has plenty of room for a pool should you desire to build a backyard oasis. Relax and unwind on the screened-in patio or stroll to the DOCK for an evening sunset cruise. Located in the GOLF CART district which connects to historic downtown Winter Garden where you can enjoy the brewery, shopping, outdoor dining, a play, the FARMERS MARKET, and so much more. Enjoy proximity to the Oakland Town Center, the 22 mile long West Orange Trail, Speer Park's playgrounds, tennis, pickleball & basketball courts, & picnic areas. Conveniently located near the Turnpike, East-West Expressway, 429, grocery shopping, theme parks, & golf courses, this home offers a lifestyle of unparalleled beauty & convenience. Embrace the enchanting Oakland-Winter Garden lifestyle & make this exquisite residence your next place to live!

111 Millholland Street, Oakland
$650,000
5 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
PRICE IMPROVEMENT!! Nestled in between Clermont and Winter Garden, this custom-built, 5-bedroom, 3-bathroom home has over 3,000 square feet! There’s also a 3-car garage, backyard lanai and screened in outdoor grill area that even has a storage area/workshop complete with electricity and lights. Outside you’ll immediately notice the meticulously cared for yard with lush landscaping, mature trees and an irrigation system. The roof and A/C were replaced in 2017, the entire interior has been freshly painted and the carpets have been steam cleaned. Once inside, there’s a large formal dining room with chandelier as well as a formal living room. This unique split floor plan features an oversized master bedroom with a walk-in closet, ensuite bathroom with dual sinks, a garden tub and separate handicapped accessible shower. The other side of the house has 3 more bedrooms that share a hallway bathroom. Upstairs there’s an enormous private loft bedroom with an ensuite bathroom and walk-in closet. There are extra cabinets scattered throughout the house for even more storage space. The kitchen features an island, an eat-in area with plenty of room for a big table, large pantry and plenty of cabinet and counter space for easy entertaining. The kitchen opens to the great room with vaulted ceilings, creating one massive space for living. There’s a laundry room right off the kitchen with plenty of under the staircase storage. Oakland still has that small town feel where residents can enjoy Speer Park and the Jack Voss Park fishing pier. The park has basketball, tennis and pickleball courts, a sizeable playground, lots of majestic shade trees and a gazebo. You can ride your bike to the West Orange Trail near the Arts and Heritage Center or take a short ride to the Killarney Station Trailhead. The Oakland Nature Preserve is also nearby and offers visitors a close-up look at nature and special events throughout the year. Right around the corner is historic downtown Winter Garden with its one-of-a-kind shops, restaurants and farmer’s market. And a short drive will bring you to Clermont with their state-of-the-art medical facilities, an abundance of shopping, grocery stores, restaurants, golf courses and more! The Florida Turnpike interchange is in Oakland, making for a short drive to the airport, attractions and all that Orlando has to offer. Make your appointment now to see this amazing house before it is gone!

8 Oakland Pointe Cir, Oakland
$570,000
5 Beds ⋅ 5 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Looking for a bit of Oakland History - NOW available 525 N Tubb! Property includes the main house, an apartment and a workshop. The house is a 3500 square foot home with three bedrooms, three baths, powder bathroom, large kitchen, large living room, dining room and much more. There are ten-foot ceilings throughout, and all appliances remain. Attached to the main house is a screened breeze way, a two-car garage, a 1300 square foot workshop and storage room. An amazing feature of this house is a 629 square foot apartment with a two-car carport and deck. This attached area can be a rental or an in-law suite. This circa 100-year-old home sits on 3/4 acre filled with various fruit and flowering trees and shrubs and giant oaks. The wiring, plumbing has been updated and the roof replaced in March of 2020.

525 N Tubb Street, Oakland
$700,000
4 Beds ⋅ 3 Baths ⋅ Town Of Oakland SubDv. ⋅ 34760 Zip Code
NO HOA | Golf cart district | 624 sqft ADU | 1-block from WEST ORANGE TRAIL | walking distance Speer Park | Blocks away from Lake Apopka. Welcome to this charming 4 bed 3 bath WITH GUEST SUITE WITH FULL KITCHEN, BATHROOM, WASHER AND DRYER (additional 624 sqft of living space) ranch-style home in the heart of historic Oakland, ideally located on a spacious corner lot in the highly desired Golf Cart District. Under the majestic canopy oak trees, this 2,282 sqft home offers the perfect Florida lifestyle with a great sense of community with NO HOA. Just a few blocks away from the West Orange Trail, Lake Apopka's dock, pickleball courts, and Spear Park, outdoor activities are right at your doorstep. Inside, the open and spacious layout, this well-designed floor plan features a cozy living room, a dedicated office space, and a kitchen perfect for large gatherings. One of the home's UNIQUE FEATURES is the above the garage GUEST SUITE. Complete with its own private bathroom, kitchenette, washer and dryer, and a separate entrance. Perfect for guests, in-laws, private workspace or man cave! Oakland’s downtown area retains its historical charm with preserved buildings and a community-centric layout. The town has a rich history from the late 19th century and maintains its small-town feel. Nearby, the Oakland Nature Preserve offers walking trails, educational programs, and lovely views of Lake Apopka. Hop on your golf cart and you’re minutes away from Historic Downtown Winter Garden, full of restaurants, shops, an award-winning farmers market, and tons of family activities. This home is also conveniently located just minutes away from the Turnpike and SR 429 for easy access to Downtown Orlando and Disney World. Don’t miss out on this awesome opportunity to own a piece of paradise in a prime location. Schedule your private showing today and see for yourself!

305 Briley Ave, Oakland
$730,000
5 Beds ⋅ 4 Baths ⋅ Starr Gardens Oakland SubDv. ⋅ 34760 Zip Code
Escape to your own private oasis in this stunning pool home nestled in sought after GOLF CART COMMUNITY in Oakland FL between Clermont and Winter Garden! This property boasts, not only a beautiful main house, but also a detached guest house, AND a detached office/mancave.NO HOA is a BIG PLUS. Immediately you'll be charmed by the mature landscaping and inviting front porch. Inside, the fully renovated kitchen in 2022 cabinets, upgraded appliances, subway tile backsplash, and oversized walk-in pantry is a chef's dream. The open-concept layout allows natural light to flow throughout the spacious living areas, creating a perfect atmosphere for entertaining. The split floor plan offers ultimate privacy for the master suite, complete with a massive walk-in closet and a luxurious bathroom.The elegant French doors in the master bedroom add a touch of sophistication and allows you to step outside to your sparkling screened-in pool with a block wall surround, perfect for enjoying the Florida sunshine. A convenient poolside bathroom means guests won't need to enter the main house. The detached guest house is a dream come true for visitor or In-Laws. It features a full kitchen with granite countertops, a great room, a dining area, and a flexible room that can be used as a bedroom or office. Upstairs, a spacious bedroom with a full bathroom and laundry hookups provides a peaceful retreat. This meticulously maintained property boasts an extensive list of recent upgrades, ensuring you can move right in and start living your Florida dream. There is also a THIRD STRUCTURE! This one room building could be your dream office, She-shed or man cave! Upgrades include new AC units, new flooring throughout, fresh interior and exterior paint, a French drain, pool resurfacing, new stoves in both the main house and guest house, upgraded insulation, new landscaping, a privacy fence, a new waterfall pump for the pool, new fans and light fixtures, and even a treehouse for all ages! BUT WAIT, there's more! This incredible property also features a solar system with a transferable lease, so you can enjoy significant energy savings on top of your veteran tax savings the owner has for the year. BONUS: RIDING MOWER INCLUDED IN THE SALE! Don't miss this incredible opportunity – schedule your private tour today!

410 E Henschen Avenue, Oakland
$619,000
3 Beds ⋅ 2 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
***New Price - Plus a Seller concession available to Buyer at closing***. This well-maintained, custom built split floorplan, home boasts pride of ownership. As you enter the property, you will be greeted by the lush lawn and mature landscaping. As you enter the home, the foyer leads you directly into the open great room with French doors accessing the expansive Florida room. Beyond the Florida room, the fully fenced backyard with mature trees offers a tranquil and private green space. The kitchen features custom oak cabinets, breakfast bar, dining area along with an adjacent dining room creating an ideal space for entertaining or large family gatherings. The 9’ ceilings, crown moldings, 5” baseboards, custom blinds and oak wood floors throughout the home are just a few of the custom touches you’ll notice. The spacious primary bedroom with ensuite features a garden tub and dual walk-in closets. The oversized garage has epoxy flooring and includes a workshop area, room for golf cart parking and a rear entrance garage door that leads to the covered outdoor patio perfect for grilling or an outdoor kitchen. There is also an air-conditioned flex space with a built-in desk and shelving perfect for an office or crafting room. New roof in 2023, new cypress fence in 2023, newer air conditioner. This home is in the Oakland Pointe community, nestled among majestic live oaks and dirt roads, in the heart of historic old town Oakland, located on the south shore of Lake Apopka. This home is within walking distance to the quaint Town Center, the West Orange Trail, the community park with a playground, tennis, pickle ball and basketball courts, along with the neighboring Jack Voss Park with a brand- new pier, making this location perfect for your family. The golf cart friendly area allows for a quick ride to all the fun Downtown Winter Garden Entertainment District has to offer, like great restaurants, shops, farmers market, festivals, events and just minutes to the Oakland Nature Preserve and more! The town of Oakland is conveniently located to all the major interchanges, only 25 min from Downtown Orlando, quick access to all the major attractions as well as multiple world-famous Florida beaches.

15 Oakland Pointe Circle, Oakland
$652,000
4 Beds ⋅ 2 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code
****MULTIPLE OFFERS....HIGHEST & BEST BY 5/6/2024 BY 2PM**** Welcome to this beautifully renovated 4-bedroom, 2-full bath home located at 200 Mather Smith Dr in the charming town of Oakland, Florida with NO HOA!! This stunning property has been completely transformed and boasts exquisite upgrades throughout. As you step inside, you'll be greeted by the spacious and open floor plan that seamlessly connects the living, dining, and kitchen areas. The tastefully designed kitchen features modern stainless-steel appliances, custom cabinetry, sleek countertops, and ample storage space, making it a chef's dream. The four bedrooms are generously sized and offer plenty of natural light, creating a serene and inviting atmosphere. The bathrooms have been meticulously upgraded with stylish fixtures and finishes, providing a spa-like experience. The huge backyard includes a large patio that is perfect for entertaining friends & family and a shed with shelving for plenty of storage. The 2-car garage has new paint, epoxy floor, and wooden storage shelves. This home is the perfect location for outdoor enthusiasts and those seeking the vibrant downtown Oakland experience & events. Situated just steps away from the West Orange Trail, you'll have easy access to miles of scenic biking, walking, and jogging paths in addition you will be walkable to Oakland Avenue Charter School Golf cart path to Downtown Winter Garden where you can explore the vibrant shops, boutiques, and restaurants, or take part in the various community events and festivals held throughout the year. Schedule a showing today and envision yourself living in this renovated gem!

200 Mather Smith Drive, Oakland
$1,600,000
5 Beds ⋅ 5 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
Introducing 100 Millholland St, an immaculate modern contemporary Custom-Built Home in the heart of Oakland! Situated in the coveted community of Southern Oaks, this home sits on just under a Half-Acre Elevated Lot boasting unparalleled Sunset Lakefront Views. Entering the home, you’re captivated by the Custom Saltwater Aquarium and Expansive Open Floor Plan featuring 20ft Ceilings in the Great Room with Floor to Ceiling Glass. The Luxury Kitchen features a beautiful island with seamless access to the pool deck, perfect for entertaining guests. Off the Great Room you’ll find a stunning, Formal Dining room encompassed by panoramic glass windows overlooking the lake. The awe-inspiring first-floor Primary Suite offers sanctuary with its 12ft Ceilings, a Floating Fireplace, and a Vast Picture Window framing Picturesque Lake Views. French Doors lead to the pool, while two expansive walk-in closets and a lavish Primary Bath await within, boasting a Large Steam Shower, Modern Soaking Tub, and a stylish Double Vanity illuminated by pendant lighting. Completing the first floor is a versatile Private Office/Bedroom and a spacious Bonus/Game/Pool Cabana Room with a luxurious Pool Bath and Private Entry, perfect for a Mother-in-law’s Suite! Ascend to the second floor to find a Second Primary Suite featuring Vaulted Ceilings, French Doors opening to an Oversized Balcony overlooking the lake, and an Ensuite Bath with Glass Shower, Garden Tub, and Dual Vanities. Another ensuite bedroom is located on this level as well. Travertine pavers lead you through the rock garden to the Incredible backyard Oasis where you’ll find the Multi-Level Pool and Fire Pit Deck that’s surrounded by stunning rock landscaping and artificial turf! The Heated Pool features a Large Spa, Sun Shelf with Bubblers and Digitally Controlled LED Lighting. There are also Two Large Covered Lania’s paired with the 20ft x 10Ft Fire Pit Deck features a 6ft Travertine Fire Pit offering the ideal outdoor setup for entertaining and family fun! The Home also Features Ensuite Bathrooms and Built-In Closets in all Bedrooms, Two Laundry Rooms, a Custom Stamped Concrete Driveway, Security System, Extensive Subsurface Drainage/Repurpose Watering System, 400 AMP Power Service and more. Originally built in 2015 with a recent Addition and Renovation in 2023, this home exudes meticulous attention to detail and maintenance. The home sits on a Corner Lot with no neighbors to the north and east offering privacy and unobstructed lakefront views. The home is also located directly beside Oakland Park, walking distance to the West Orange Trail and in the Golf Cart Friendly Zone of Winter Garden allowing a short ride to Downtown Winter Garden and its famous Shops, Restaurants, Bars and Breweries! This home is truly one-of-a-kind and a rare find in the Oakland/Winter Garden area! Call today to schedule a tour! Must See Marketing Video - https://player.vimeo.com/video/933670698?autoplay=1

100 Millholland Street, Oakland
$725,000
4 Beds ⋅ 4 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code
Discover the charm of this 4-bedroom, 3.5-bathroom single-family home in Oakland, Florida, boasting 2836 sq ft and a 2-car attached garage with NO HOA. Recently painted inside and out, this beautiful home features a new roof and numerous elegant updates throughout. Inside, an open floor plan includes a formal dining room (or office space) and breakfast nook, with the master suite conveniently located on the 1st floor, featuring a bath with double vanities and a walk-in shower. Two additional bedrooms, a full bathroom, and a half bathroom for guests are also on the 1st floor, while the 2nd floor offers a versatile bonus room suitable for various needs, along with the fourth bedroom and third full bathroom. Enjoy outdoor relaxation on the screened back porch. Located in the Golf Cart District just minutes from Historic Downtown Winter Garden, hop in your golf cart and enjoy local restaurants, shops, and a weekly farmers market with ease. Enjoy a morning or evening walk or run on the West Orange Trail located just a block away, or stroll down to Historic Downtown Oakland, where you can enjoy a large community park and playground, have a scoop of ice cream and other treats from Oakland General, see the seasonal community art at the Healthy West Orange Arts and Heritage Center, take in stunning Lake Apopka views at the nearby pier, or partake in the numerous community events put on by this charming small town, including holiday events, block parties, and local farmers’ markets. Don't forget to enjoy Florida's natural beauty at the Oakland Nature Preserve. Take advantage of the proximity to desirable schools, including Oakland Charter School and the international magnet program at Tildenville Elementary. This home is nestled among the historic oak trees of Oakland but conveniently located just minutes away from the Turnpike and SR 429 for easy access to Downtown Orlando and Disney World. Don't miss out on the opportunity to make this home your own—schedule a showing today!

206 Mather Smith Drive, Oakland
$842,500
3 Beds ⋅ 3 Baths ⋅ Oakland Shores SubDv. ⋅ 34760 Zip Code
Oh, what an amazing area Oakland is!! Even more amazing is this three-bedroom home with two and half baths featuring a massive 25x15 loft over garage. New Fresh Look the owners gave it, now we are up to new build standards and beyond. Impressive dental crown in the living areas. With the Recently completed Kitchen Renovation, walls were removed to open the floor plan to give you a spacious feel. Kitchen features a Wolf induction stove with a commercial grade hood with lights and a multitude of fan speeds. Z-Line dishwasher cabinet front. KitchenAid refrigerator, Huge farm sink sits in the middle of the quartz island that has additional deep cabinets below so you won’t need a ladder to get whatever it is you have stored. Over the Top quiet close cabinets deep for all your pots and pans with the coolest hardware for handles. All adorned with quartz backsplash. Two huge pantries that have pull out drawers and fully equipped with electricity for those appliances you want out of sight. French doors lead out back to a tropical paradise. With its lush landscaping you wouldn’t know you had neighbors. Just installed motorized awnings to prolong your days out back enjoying the pool area. Enjoy yearlong soaking in the upgraded led lights and heated pool. Your days will be perfect for recreation and relaxation. After your morning walk or run on the West Orange trail. You won’t be able to contain yourself thinking of the COMPLETE PRIVACY your Lot offers. When you get back to take a dip in your private oasis pool. Let's don’t forget to mention your magical side entrance. Stroll through the courtyard with pavers, fenced in along with beautiful hedges surrounding its perimeter giving the privacy desired. A second outdoor getaway location to be enjoyed! The Oversized garage is Nestled amongst the majestic oaks of Downtown Oakland and Winter Garden. Beautifully appointed in one of Oakland’s most sought-after neighborhoods. This residence is strategically positioned in the highly desired Golf Cart District. Just jump on your golf cart and in minutes you are in Historic Downtown Winter Garden. Also enjoy preferred enrollment & walking distance to renowned Oakland Charter School. Nestled just a stone's throw away from the West Orange Trail, this property provides easy golf cart access to the vibrant Downtown Winter Garden, brimming with an array of restaurants, shops, a weekend farmers market, and an abundance of family activities. Enjoy 22.26 miles of paved Trail from the Orange/Lake County line, the town of Killarney and Oakland, the city of Winter Garden, across U.S. 441, through downtown Apopka to Welch Road. Stop and enjoy the butterfly garden at the Tildenville outpost!

207 Mather Smith Drive, Oakland
$730,000
4 Beds ⋅ 2 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
This custom built home is on the market for the first time and is nestled in the heart of Oakland! Sitting on just under a half acre of land, this delightful property offers a perfect blend of comfort, style, and convenience, making it an ideal place to call home. As you enter this meticulously maintained residence you will be greeted by a spacious living area, perfect for relaxing or entertaining guests. The well-appointed kitchen features modern appliances, sleek stone countertops, and ample storage space, making meal preparation a breeze. This home boasts 4 bedrooms and 2 bathrooms split plan, providing plenty of space for the whole family. The master suite offers a peaceful retreat with a luxurious en-suite bathroom and a walk-in closet, ensuring privacy and comfort. Outside, you'll find a beautifully landscaped yard, ideal for enjoying the Florida sunshine and hosting outdoor gatherings with friends and family. The property also includes a 3-car garage with plenty of storage space and large driveway for your convenience. Located in the desirable Oakland area, this home offers easy access to Oakland Nature Preserve, The West Orange Trail, shopping and dining in nearby Downtown Winter Garden and is close to major roadways, making commuting a breeze. Schedule a showing to see your next home today.

112 W Sadler Avenue, Oakland
$535,000
3 Beds ⋅ 2 Baths ⋅ Hull Island At Oakland SubDv. ⋅ 34760 Zip Code
Welcome to this like-new home in the intimate community of Hull Island. This split floorplan 3 bedroom 2 bathroom home has been lovingly updated. As you step inside through the foyer, you are drawn to the two well-appointed secondary bedrooms, sharing a stylishly designed hall bath at the front of the house. Beautiful wood-look tile spreads throughout the home - no carpet here! The L-shaped kitchen is a culinary enthusiast's dream, featuring an abundance of 42” maple cabinets crowned with modern LED under-cabinet lighting that accentuates the backsplash, and luxurious quartz countertops. Not to mention a gas range! The island provides not only a quick spot for on-the-go meals but also a spacious prep area for the family chef. The generously sized walk-in pantry is your ideal companion for all of those bulk shopping trips. Adjacent to the kitchen, a tech-savvy desk area serves as a versatile hub for sorting mail, charging devices, or exploring your next Pinterest-worthy recipe. The primary suite, tucked away for privacy at the rear of the home, is bathed in natural light through its expansive windows and features an elegant tray ceiling. The deluxe ensuite bath is a sanctuary of comfort, showcasing a dual-sink quartz-topped vanity, an oversized shower adorned with upgraded subway tile and a river rock floor, a semi-frameless enclosure, an enclosed water closet, and a spacious walk-in closet. Step out onto the covered lanai and enjoy the privacy of a fenced-in backyard. Other upgrades include an interior laundry room with a utility sink, blinds on all windows, a tankless gas hot water heater, and an additional pavered area in the backyard. All appliances convey, making this a truly move-in ready home! Hull Island offers a community pool with a cabana area, a bark park, picnic trails, and a viewing dock off of Lake Apopka. Minutes away from downtown Winter Garden, the Florida Turnpike, and walking distance to the West Orange Trail. Schedule your showing today!

1808 Western Trailway Drive, Oakland
$957,000
4 Beds ⋅ 3 Baths ⋅ Oakland Pointe SubDv. ⋅ 34760 Zip Code
One or more photo(s) has been virtually staged. Price improvement just made on this beautiful property! In the heart of historic Oakland, welcome to the ultimate lakefront living experience with an opportunity to own a beautiful, 4 bedroom, 3 full bath home, on .64 acres, in this quaint town with over 118 feet of waterfront living on Lake Apopka! As you enter the property, when greeted beyond the foyer and 11 foot ceiling line family room, you are immediately swept away with breathtaking views of the 30,000 acre lake, making it the perfect setting for relaxation and entertainment. Imagine yourself enjoying your morning coffee while watching the sunrise on the large 30' x 40' ft deck, with an herb garden and citrus trees close-by, or the oversized dock closer to the water. The lake views are absolutely stunning, with the option to entertain family and friends with a barbecue on the back lawn 16' x 16' covered cabana to also experience the beautiful Florida sunsets. A private boat dock with a Leeson brand lift, measuring 21' x 26', allows immediate lakefront access where you can indulge in your favorite water activities, from wakeboarding, skiing, wake surfing, fishing, body boarding and kayaking, which is ideal for any boater or fishing enthusiast. It's a hidden gem to know that Lake Apopka is part of the Harris Chain of Lakes, which flows through the Apopka-Beauclair Canal with direct access North to the Ocklawah River, which continues through canals and locks that will take you all the way to the Atlantic Ocean in Jacksonville! A new full home 24kw Generac Generator adapting to two 420LP tanks conveys with the property. The oversized garage includes a workshop area. Water Heater and Air Conditioner are within 5 years new. The landscaping on this property is immaculate with a thorough french drain system that handles the irrigation flowing from the lake, which keeps your water bill low. Walking distance to the West Orange Trail and community park with a playground, tennis court and pickle ball court, along with the neighboring Jack Voss Park with its' brand new pier, make this location perfect for your family. It's location is also just a bike or golf cart away to the town schools, and everything fun and beautiful Downtown Winter Garden has to offer, like great restaurants, shops, farmers market, festivals and events! The town is also very close to major interchanges so you’re only 25 min from Downtown Orlando, Disney and Universal! Very low HOA costs, as this is a very small and quaint neighborhood. Don’t miss this rare opportunity and schedule your private showing today! <div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=71roZuXue7S&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div> Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

32 Oakland Pointe Circle, Oakland
$769,000
4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Small town living in nature-filled Oakland. Bring your golf cart! No HOA!! This 2-story custom home proudly stands on a .27-acre corner lot, just 2 blocks to the 20+ mile West Orange Trail, half a mile to Lake Apopka access/dock, and 1 mile to Oakland Nature Preserve! On days you want a break from exploring Florida’s wild beauty, this magazine-worthy property can accommodate. The 4 bedroom, 3 bathroom floor plan keeps 1 bedroom/bathroom downstairs, while the upstairs holds the primary bedroom/bathroom with dual closets, and 2 secondary bedrooms with a shared bath. The open-concept gathering areas share a gas fireplace for cozy evenings, and the formal but versatile dining room can be transformed to meet any other living space needs. Outdoors, the fenced backyard offers a screen-enclosed porch with outdoor kitchen area, and beyond the screen is another patio area with firepit and 6-person spa, completely open to Florida’s night sky. Over $60K in upgrades have been completed within the past 2 years to ensure an elegant living experience inside and out. Bonus: The oversized garage has room for 2 cars and your golf cart, plus the attic has flooring for storage. This Oakland treasure is located less than a half mile to Speer Park for playground, picnics & tennis. Convenient roadways West Colonial Dr and FL Turnpike are nearby, both which can start your journey to wherever you may need to go. Two miles to downtown Winter Garden with shopping, restaurants, breweries and more! Schedule a showing today!

101 W Oakland Avenue, Oakland