34760 Zip Code FL Real Estate, Homes with Rain Gutters for Sale

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

$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

$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

$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

$1,250,000

6 Beds ⋅ 8 Baths ⋅ Oakland SubDv. ⋅ 34760 Zip Code

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!

620 N Tubb Street, Oakland

$360,000

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

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintained, this home features 3 spacious bedrooms and 2 full bathrooms. The open and inviting floor plan offers a bright living room filled with natural light, a cozy family room ideal for relaxing, and a large dining area that’s perfect for hosting gatherings. The welcoming foyer greets you with a flexible space that can be used as a home office, reading nook, or a stylish sitting area. The kitchen boasts ample cabinet space, modern appliances, and a breakfast bar for casual dining. Additional highlights include: Central air conditioning and heating throughout the home Ceiling fans with lighting in each bedroom Freshly painted interiors with neutral tones Brand new Laminate wood-style flooring for easy maintenance Indoor laundry area for added convenience Fully fenced yard offering privacy and security Gated driveway with plenty of parking space Spacious backyard perfect for pets, play, or outdoor entertaining Whether you’re looking for your first home, a family retreat, or a peaceful escape close to everything, 507 W Oakland Avenue is the perfect choice. Don’t miss out on this rare gem — call today to schedule your private tour and experience the charm of Oakland living!

507 W Oakland Avenue, Oakland

$480,000

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

Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs + half kitchen upstairs — possibilities of in-law suite, rental potential, or multi-generational living - 14' x 12' elevated deck / covered patio — outdoor entertaining or private oasis - Optional furnished sale for a move-in ready experience - 10' gate to access backyard— boat, RV, or trailer storage - 18' x 22' carport as well as 12' x 30' gravel lot offers ample parking - Roof estimates available—opportunity for buyers to personalize or negotiate Outdoor Appeal: A spacious backyard offers room to expand patios, garden, or build additional outdoor amenities. The elevated deck and gated access make it both functional and private—perfect for Florida living. Location: Enjoy small-town charm with easy access to major highways, schools, parks, and the community of Oakland. Zoned for top-rated schools and close to everything Central Florida has to. Don't miss your chance to own this energy-efficient, flexible-use property in a sought-after location.

312 W Hull Avenue, 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

$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

$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

$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

$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

$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

$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

$305,000

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

Welcome to your dream home in the charming community of Oakland, FL! This 2-bedroom, 2-bathroom cottage is a haven of modern comfort, with a newer roof, HVAC, and water heater all installed in 2020. Nestled on a generous, fenced lot, this property offers the perfect backdrop for outdoor gatherings or serene solitude. Step inside to discover a cozy, open floor plan and tastefully updated bathrooms and kitchen that make everyday living a breeze. Conveniently located, you're just minutes away from Oakland's quaint parks, local shopping, and delightful dining options. This home is more than just a place to live—it's a lifestyle.

210 S Pollard Street, 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

$410,000

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

Beautiful oversized corner lot in charming Oakland. Nice open floor plan. Workshop is in the Garage and offers tons of storage. There is no HOA, so bring your boats and RV's to this property that has plenty of room to park/store them. This house has been under renovation, so requires work including a new roof. However, the property offers many possibilities to suit your vision of a dream home.

202 W Oakland Avenue, Oakland

34760 Zip Code Real Estate & Homes with Rain Gutters

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