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$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
$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
$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
$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
$604,000
5 Beds ⋅ 3 Baths ⋅ Oakland Heights SubDv. ⋅ 34760 Zip Code
Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character meets small town charm in the heart of Oakland, FL. This beautifully maintained 4-bedroom, 2-bath, plus the Multi-generational suite home offers almost 2,500 square feet of living space, blending vintage appeal with the comfort and flexibility today's buyers are seeking. Nestled on a quiet street just minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the living room along with the built-in shelving, to the exposed beams in the dining room, this home is inviting and full of character. The home’s thoughtful layout includes the spacious in-law suite that includes a private entrance and an ADA accessible bathroom, prime for multigenerational living, hosting guests, or creating a private work-from-home retreat. Step inside and discover generously sized bedrooms and a living space that flows effortlessly through the dining space overlooking your outdoor oasis. Step out onto the vaulted ceiling, screened-in lanai that overlooks a spacious backyard—perfect for relaxing evenings, lively gatherings, or enjoying Oakland’s peaceful atmosphere. Whether you’re looking for a forever home with vintage charm or an opportunity to personalize a home with great bones, this is your canvas. Don't miss your chance to own a piece of Oakland's history! Schedule your private showing today and experience firsthand the character, comfort and community this home has to offer.

410 E Gulley Avenue, Oakland
$865,000
5 Beds ⋅ 3 Baths ⋅ Southern Oaks At Oakland Shores SubDv. ⋅ 34760 Zip Code
First Buyer Failed to Close. This is YOUR opportunity. BACK-UP Offers are ENCOURAGED! *** 2.25% ASSUMABLE rate is available for a Buyer! *** NEW ROOF will be installed prior to closing with negotiated offer. Experience LUXURY living in this stunning, CUSTOM-built POOL home, perfectly redesigned to capture elegance and modern comfort. Nestled in the charming town of Oakland in the GOLF CART DISTRICT with partial WATER views, this exceptional residence sits on over a quarter of an ACRE (.3) and features an open-concept layout with high-end finishes. The gourmet kitchen boasts premium appliances, while the expansive living area seamlessly connects to the outdoor oasis, offering a sparkling pool and a spacious covered patio, perfect for entertaining. This home has maximized its space by offering a family 5 bedrooms and 3 baths. The newly RENOVATED kitchen features Australian Dolomite counters, CAFE appliances, including an induction cooktop with vented hood, built-in oven with air fryer, built-in microwave/convection oven, and beverage fridge, under cabinet lighting, solid WOOD shaker cabinetry with soft close doors and drawers, tile backsplash, ample seating at the island, instant hot water and filtered water dispenser, and coastal style lighting to complete the design. Folding GLASS doors were added to enhance the indoor-outdoor living space. Step into your oasis for an evening by the SALTWATER-HEATED pool and enjoy a cold beverage by the fire-pit. The first floor is enhanced with wood plank TILE flooring, shiplap accent ceilings and walls, a STONE wood burning fireplace, updated vanities and mirrors in the baths, and a custom built laundry area. The downstairs PRIMARY suite connects to the pool deck through FRENCH doors and includes a dual vanity, TUB, shower, and walk-in closet. An additional room is located downstairs, which could be utilized as an OFFICE or guest suite. Upstairs you’ll find three additional rooms and one full bath. One bedroom features a 3X10 area that can easily accommodate a desk. The middle room is unique in its design and could be used as a bedroom, play room, or office. The shower and vanity area in the upstairs bath is separated by a pocket door, providing privacy and freedom for use by multiple family members. Key UPDATES: extensive redesigned kitchen, interior PAINT (walls, trim, doors, & ceiling), first floor wood plank TILE, vinyl FENCE (2024), POOL heat pump and filter (2022), pool salt cell (2024), 4-ton AC (2021), 80 gallon Hybrid Water Heater (2024), water heater (~2/3 years old), lighting fixtures, flat LED recessed lighting, garage door opener, spring, & wheels (2021-2023), custom floor to ceiling garage shelving, and a new roof coming soon! 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 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!

70 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
$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
$1,696,482
5 Beds ⋅ 5 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code
Custom Home Sold Off Market.

21 Daniels Street, 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