Oakland Homes For Sale & Real Estate - 26 homes

Remarks: THIS ONE IS A MUST SEE! Upgrades on upgrades on upgrades! Welcome to Oakland Trails in the charming City of Oakland. This spacious 5-bedroom, 3.5-bath home offers a flexible layout perfect for today’s lifestyle. Enjoy a cozy Great Room, formal Dining Room, and a stunning modern staircase that leads into an open-concept Living Room and beautifully upgraded Kitchen featuring ample cabinetry, generous counter space, and a designer backsplash. The first-floor primary suite is a private retreat with a luxurious bath, dual vanities, soaking tub, walk-in shower, and an oversized walk-in closet. Upstairs offers a large loft, spacious secondary bedrooms, and a versatile bonus room ideal for an office or optional 6th bedroom. Situated on a quiet cul-de-sac with no front neighbors and peaceful conservation views, the resort-style backyard showcases extended pavers and low-maintenance artificial grass—saving time while offering year-round beauty and convenience. The home is equipped with top-quality solar panels featuring over 400 watts per panel—the latest generation for maximum efficiency and performance. Paired with a premium Enphase inverter system, known as one of the best in the industry, this setup is designed to optimize energy production and deliver significant long-term savings.Solar Panel open to negotiation. Prime location near top-rated schools, the Florida Turnpike, Winter Garden, Clermont, and Orlando, with shopping, dining, and entertainment just minutes away. Space, privacy, upgrades, and location—this home truly has it all!

Listing is courtesy of: KELLER WILLIAMS ADVANTAGE III (407-207-0825)

Listing Agent: Krichely Gonzalez Rodriguez (407-953-4377)

Remarks: Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes from historic downtown Winter Garden's acclaimed restaurants, boutique shops, and cultural venues, this home offers the perfect balance of serene outdoor living and convenient community access. The neighborhood is known for its resort-style amenities, including community pools and walking trails, plus easy access to the 429 and Florida Turnpike for seamless access to downtown Orlando, area theme parks, and Orlando International Airport. Architectural Excellence and Light-Filled Interior will blow you away. Upon entering, you are immediately enchanted by the flowing design throughout, with USA-made Mannington laminate flooring flows throughout the first floor. Six handcrafted Bevolo lanterns add architectural detail and warmth to the exterior. Additional highlights include a combined mudroom and natural light pouring from expansive two-story windows and stunning designer lighting that complements the floor-to-ceiling stone fireplace, this focal point enhances the open-concept layout, creating a bright, inviting atmosphere throughout the home. A grand dual staircase with iron railings anchors the two-story living room, emphasizing the home's soaring volume ceilings and open, airy design. The oversized, black-framed sliding doors create effortless indoor-outdoor living for those social events. The Chef's Kitchen is quite the entertaining Hub with its elevated oversized quartz waterfall-edged island offering generous seating and a stunning focal point for entertaining. GE Café appliances with brushed bronze hardware, upgraded quartz countertops, and a spacious walk-in pantry support serious culinary pursuits. The seamless flow from kitchen to dining area, transforming entertaining into an effortless, connected experience. The second-floor primary suite features a tray ceiling and an expansive walk-in closet suitable for dressing room use. The spa-inspired bath is a private retreat, with a freestanding soaking tub set within a custom wood-accent alcove and quartzite vanity—the perfect escape after a busy day. Additional highlights include a generous sized laundry space for convenient household management, and a 3-car garage with custom overhead storage providing ample space for vehicles and seasonal storage. The outdoor Living Potential offers a partially fenced backyard with ample space for a future pool, ideal for creating your own resort-style retreat. The premium corner lot positioning provides privacy, abundant natural light, and those coveted Lake Apopka views. This is more than a home—it's a lifestyle positioned in one of Central Florida's most sought-after communities with uncompromising finishes. Don't miss out on this opportunity, Schedule you're showing today!

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Heidi Pfeffer-Morgan (407-408-6101)

Remarks: Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential atmosphere. Oakland Trails is known for its top-rated schools, scenic walking and biking trails, and thoughtfully planned amenities, including a community pool, clubhouse, and dog park. The neighborhood features wide streets, attractive entryways, and a welcoming environment, with close proximity to Historic Downtown Winter Garden, offering popular restaurants, breweries, shops, and community events. Built with energy efficiency in mind, this Meritage Home includes spray foam insulation, helping maintain consistent indoor comfort while reducing utility costs. The home is equipped with an advanced HVAC system featuring enhanced air purification and fresh-air intake, ideal for comfortable and healthy living. The interior showcases a gourmet kitchen with KitchenAid appliances, quartz countertops, and a custom-tiled island, complemented by high ceilings and tall doorways that create an open, airy feel throughout. Additional features include a partially metal and shingle roof, a full gutter system, a custom wood staircase, and a spacious primary suite with a built-in closet system. Generous storage throughout the home makes it well suited for families of any size. The property is ideal for long-term rental use. While short-term rentals are restricted by the HOA, the home’s modern construction, low-maintenance design, and strong location support long-term value and rental stability. Notably, the home has been strictly pet-free under current ownership, making it an excellent option for buyers with sensitivities. A detailed list of builder upgrades and owner improvements will be provided with the listing, offering full transparency into the home’s added value. Additional features include installed security cameras and a custom Tesla charging outlet, included at no additional cost with a full-price offer. Furniture is not included; however, the seller is open to selling select items separately if desired. A well-maintained, energy-efficient home in one of the area’s most sought-after communities — offering quality construction, lifestyle amenities, and long-term appeal.

Listing is courtesy of: PINK MIAMI (305-504-0807)

Listing Agent: Denis Bochkov (754-248-4417)

Remarks: INCREDIBLE OPPORTUNITY to own this stunningly gorgeous 4 bedroom 2.5 bathroom corner lot home in the HIGHLY DESIRABLE community of Oakland Trails! Boasting over 2200 sq. feet of living space this 2017 built gem is amply equipped to meet the needs of families of all sizes and is gushing with stylistic appeal! Enter the home into a bright and positive feeling OPEN CONCEPT GREAT ROOM highlighted by newer(2024) luxury plank flooring, a large living/dining area, built-in OFFICE SPACE, and a half sized bathroom. The kitchen is a CHEF'S DREAM featuring granite counters, a large eat-in island, stainless steel appliances, built-in oven and microwave, designer pendant lighting, closet style pantry, and a dedicated coffee/work station. WOW! Head upstairs and pass through the BONUS LOFT area into an OVERSIZED MASTER SUITE with tray ceilings, a large split vanity master bath, and a MASSIVE WALK-IN CLOSET equipped with built-in shelving and organizers. The second floor also contains three secondary bedrooms, a full size hallway bathroom, and a large laundry room. Additional features of the home include: a FULL SOLAR PANEL SYSTEM(providing significant energy savings), an oversized two car garage, built-in security system, and paver driveway. The Oakland Trails community includes a community pool and clubhouse, dog park, playground, and walking trails. Located minutes away from the WEST ORANGE TRAIL this area is a hotbed for outdoor recreation and is ZONED FOR EXCELLENT SCHOOLS! In close proximity to major commuting highways, downtown Winter Garden, and ample shopping amenities, this is a PRIME LOCATION home and MOVE-IN ready for it's next owners. DON'T DELAY!! Book your private showing today.

Listing is courtesy of: YOUNG REAL ESTATE (407-904-0069)

Listing Agent: Chuck Burt (407-676-4268)

Remarks: Under contract-accepting backup offers. Located within the exclusive gated waterfront community of John’s Landing, this residence offers the perfect balance of Florida lifestyle, privacy, and everyday convenience, just minutes from Downtown Winter Garden and the scenic John’s Lake Chain. Set on an oversized lot at the end of a quiet cul-de-sac, the home features multiple living spaces, a bonus room / optional 5th bedroom, and a Florida room converted into a bar and game room, ideal for entertaining and flexible family living. The layout adapts effortlessly to growing households, remote work, or hosting guests. This move-in ready home provides long-term peace of mind with a brand-new roof delivered at closing and a 5-ton Carrier A/C (2020). The fully fenced backyard offers future expansion potential for a pool. Residents enjoy private lake access, a private boat ramp, tennis courts, and playgrounds, all within a prime location offering easy access to SR-429, Florida Turnpike, Montverde Academy, shopping, dining, and the vibrant lifestyle of Downtown Winter Garden. Whether as a forever home or a smart addition to a real estate portfolio, this property delivers strong long-term value in a highly desirable waterfront community.

Listing is courtesy of: URBAN-O REAL ESTATE SOLUTIONS (407-822-1063)

Listing Agent: Jose Rojo (786-502-6162)

Remarks: Under contract-accepting backup offers. 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.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Matt Kester (772-494-8550)