34760 Zip Code FL Real Estate, Homes with Pool for Sale

5 Beds ⋅ 8 Baths ⋅ Grove/Oakland SubDv. ⋅ 34760 Zip Code

Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.

1134 Prado Lane, 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

$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

$1,125,000

4 Beds ⋅ 3 Baths ⋅ Oakland Town SubDv. ⋅ 34760 Zip Code

SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.

250 N Walker Street, 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

$683,000

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

Beautifully renovated pool home in the desirable Town of Oakland, within the golf cart district, and no HOA. Located in an area seeing significant growth with nearby luxury new construction and vacant lots selling for a premium, this property offers both charm and long-term value in one of West Orange County’s most sought-after locations. This updated single-story ranch home features a bright, open layout with the kitchen flowing seamlessly into the living room. The renovated kitchen includes quartz countertops, updated cabinetry, and a large island with eat-in seating, creating a great space for everyday living and entertaining. The living room is warm and inviting with a wood-burning fireplace and plenty of natural light. Recent improvements include a new kitchen, updated bathrooms, new flooring, new windows, interior and exterior paint, gutters, and a resurfaced pool and paver pool deck. A spacious enclosed Florida room with large windows and a slider that overlooks the backyard and pool, providing additional living space filled with natural light. The home also features a very large indoor utility room that could easily function as a home office, flex space, or additional storage. Outside, you’ll find a large in-ground pool and a fully fenced backyard, perfect for relaxing or entertaining. Located just minutes from downtown Oakland, the West Orange Trail, and Plant Street in downtown Winter Garden, offering easy access to restaurants, shops, and community events. Updated pool homes with no hoa in this area are very rare.

310 E Gulley Avenue, Oakland

$1,975,000

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, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.

1106 Sarah Mathews Drive, 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

$2,675,000

4 Beds ⋅ 5 Baths ⋅ Grove At The Harvest District SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Custom Home by Element Home Builders

1179 Prado Lane, Oakland

$450,000

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

Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space. Inside, enjoy a warm and functional layout with 1,419 sq ft of living space and central heating and cooling. The living room is perfect for relaxing evenings by the fire, while the outdoor area is built for Florida living—splash in the pool or unwind under the shade of the trees. Located just minutes from downtown Winter Garden and the West Orange Trail, you’ll love the peaceful setting with quick access to local shops, restaurants, and parks.

310 E Gulley Avenue, 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

$3,175,000

6 Beds ⋅ 6 Baths ⋅ Briley Farm Ph 1a SubDv. ⋅ 34760 Zip Code

Pre-Construction. To be built. Custom Home to be built by Element Home Builders. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends! Conveniently located in Oakland, just minutes from shopping, dining, and entertainment options, this home offers the perfect combination of tranquility and convenience. Don't miss your chance to own this exceptional property and experience luxury living at its finest. Schedule your private tour today and make your dream home a reality!

410 Briley 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

$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

$575,000

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

Welcome home to the charming historic district of downtown Oakland. This beautiful .4304 Acre single family home sits directly across from Speer Park, .3 miles (2.5 blocks) away from the quaint and charming downtown Oakland, the West Orange Trail connection, and the Healthy West Orange Arts and Heritage Center at the town of Oakland. The Oakland Farmers Market is held every 2nd Thursday. Speer park offers, tennis courts, basketball, pickleball, playgrounds, a pavilion with picnic tables, and charming gazebo anchoring at the center. The public Tubb Street Fishing peer overlooking Lake Apopka is just .3 miles away. The property is approved to subdivide into 3 lots, per the town of Oakland. The area is now also open to the golf cart district to the historic downtown Winter Garden. This home features, 1320 SF, 1 story, block construction, above ground pool, fruit trees, a shed and RV hookups.

20 W Vick 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

$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

$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

$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

34760 Zip Code Real Estate & Homes with Pool

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