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Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the vibrant shops and cafes of Oakland’s quaint downtown are just a short stroll away. Inside, the home welcomes you with a warm and inviting layout. The living room, filled with natural light, provides a cozy space for relaxing or entertaining. It connects seamlessly to a well-appointed kitchen, featuring stainless steel appliances, granite countertops, and plenty of cabinetry for storage—ideal for home-cooked meals. The primary bedroom offers a peaceful retreat with a standard closet and an en-suite bathroom boasting dual vanities and a luxurious soaking tub. Two additional bedrooms, each with standard closets, provide versatile space for family, guests, or a home office, with a second full bathroom conveniently nearby. The exterior is a true highlight, with mature landscaping creating a private, tranquil setting. Towering oak trees provide shade and beauty, complemented by colorful, well-kept gardens. The spacious backyard is perfect for barbecues, gardening, or simply soaking in the calm of your own oasis. A charming front porch invites you to enjoy morning coffee while greeting neighbors on the peaceful dirt road. Located in the heart of Oakland, this home blends small-town charm with modern convenience. Enjoy local events, dining, and community spirit just steps away, with easy access to highways for commuting. With no HOA, you have the freedom to make this property your own.

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

Virtually Staged. Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the vibrant shops and cafes of Oakland’s quaint downtown are just a short stroll away. Inside, the home welcomes you with a warm and inviting layout. The living room, filled with natural light, provides a cozy space for relaxing or entertaining. It connects seamlessly to a well-appointed kitchen, featuring stainless steel appliances, granite countertops, and plenty of cabinetry for storage—ideal for home-cooked meals. The primary bedroom offers a peaceful retreat with a standard closet and an en-suite bathroom boasting dual vanities and a luxurious soaking tub. Two additional bedrooms, each with standard closets, provide versatile space for family, guests, or a home office, with a second full bathroom conveniently nearby. The exterior is a true highlight, with mature landscaping creating a private, tranquil setting. Towering oak trees provide shade and beauty, complemented by colorful, well-kept gardens. The spacious backyard is perfect for barbecues, gardening, or simply soaking in the calm of your own oasis. A charming front porch invites you to enjoy morning coffee while greeting neighbors on the peaceful dirt road. Located in the heart of Oakland, this home blends small-town charm with modern convenience. Enjoy local events, dining, and community spirit just steps away, with easy access to highways for commuting. With no HOA, you have the freedom to make this property your own.

409 E Gulley Avenue, Oakland

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.

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

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

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

Brand new 2026 construction with Certificate of Occupancy in place and ready for immediate move-in. This 4-bedroom, 2.5-bath home offers 1,872 sqft of modern living space with custom finishes and a functional open layout. Thoughtfully designed with a clean, contemporary style, the home provides low-maintenance living and the flexibility of a non-HOA setting. Now positioned to reflect current market conditions, this property presents an excellent opportunity for buyers seeking newer construction without delays or renovation needs. A compelling option for buyers looking for value, condition, and immediate occupancy.

38 S Pollard Street, Oakland

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!

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