Displaying: For Sale
Location: Oakland
Property Type(s): Single Family
Beds: 3 to 3
Do Not Show Listings
Oakland - 5 properties found
2247 WHITE FEATHER LOOP, OAKLAND, FL 34787
$457,90011 Days on yellowkey MLS ID: S5150852
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1838 Built: 2018Monthly Fee: $105 Tax: $6,845 (2025)Community: Oakland TrailsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,845
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Welcome to this exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 1,838 square feet of thoughtfully designed living space with an open and functional floor plan that truly stands out in the neighborhood. From the moment you arrive, you’ll notice the extended brick paver driveway, providing additional parking and excellent curb appeal. The inviting front porch is perfectly positioned with elevated views overlooking the peaceful walking trails — an ideal spot to enjoy your morning coffee or unwind in the evenings. Inside, the bright and airy layout flows seamlessly, creating an inviting atmosphere for both everyday living and entertaining. High ceilings and tall doorways enhance the spacious feel throughout the home. The open-concept living, dining, and kitchen areas are designed for comfort and functionality. The beautifully upgraded kitchen features polished granite countertops, an expansive breakfast bar island, rich espresso shaker cabinetry with crown molding, stainless steel appliances, recessed lighting, a spacious pantry, and a bright window above the sink — combining style and practicality for modern living. Upstairs, the spacious primary suite offers a private retreat, while two additional bedrooms, a versatile loft area, and a convenient second-floor laundry room provide flexibility for family, guests, or a home office. Built with energy efficiency in mind, this Meritage home includes spray foam insulation to help maintain indoor comfort while reducing utility costs. The home is also equipped with an advanced HVAC system featuring enhanced air purification and fresh-air intake for improved comfort and healthier living. Ideally located approximately 30 minutes from Disney, Universal Studios, and Downtown Orlando, this home offers convenient access to major attractions while maintaining a peaceful residential setting. Oakland Trails is known for its top-rated schools, scenic walking and biking trails, low HOA, and thoughtfully planned amenities, including a community pool, clubhouse, and dog park. Just minutes away, Downtown Winter Garden offers the popular Winter Garden Farmers Market, charming boutiques, restaurants, and cultural attractions in one of Central Florida’s most beloved small-town districts. For commuters, easy access to the Florida Turnpike allows convenient travel throughout Orlando and to the airport. Investors will also appreciate the home’s strong long-term rental potential, supported by modern construction, low-maintenance design, and consistent tenant demand. This home perfectly blends peaceful neighborhood living with outstanding convenience, style, and everyday functionality. Don’t miss your opportunity to own one of Oakland’s standout homes!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Carolina Cote Munoz (863-605-1987)
2065 WHITE FEATHER LOOP, OAKLAND, FL 34787
$539,900124 Days on yellowkey MLS ID: O6379741
REDUCED by $10,000 (1.8%) on 06/04/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2089 Built: 2019Monthly Fee: $105 Tax: $5,490 (2024)Community: Oakland Trls Ph 2Single Family
Taxes:$5,490
Tax Year: 2024
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)
1937 STANDING ROCK CIR, OAKLAND, FL 34787
$499,00055 Days on yellowkey MLS ID: O6398113
REDUCED by $16,000 (3.1%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2069 Built: 2018Monthly Fee: $105 Tax: $5,728 (2025)Community: Oakland Trails Ph 2Single Family
Taxes:$5,728
Remarks: Oakland Trails is located right on the scenic West Orange Trail and just a bike ride away from the vibrant downtown Historic Winter Garden! **This home qualifies for loan options with NO DOWN PAYMENT required, 100% financing available for qualified buyers.** Step into an immaculately maintained three-bedroom, two-and-a-half-bathroom bungalow with updated wood-look plank luxury vinyl flooring (2024), new carpet in all bedrooms (2025), quartz countertops, and an open-concept living area. Functional floor plan design includes a downstairs half bathroom, a drop zone by the garage, and an understairs storage closet. A shaded front porch is perfect for enjoying coffee in the morning and decorating for the holidays! Two car garage and an extended pavered driveway. Upstairs you have a huge loft, all three bedrooms, and laundry. The primary bedroom features two large walk-in closets, a double-door entrance, and granite countertops in the bathroom. The loft is prewired for surround sound. This home has been lovingly maintained; the exterior was painted in 2023. The interior walls and trim were painted in 2024. Modern updates that make this home move-in ready also include new light fixtures throughout, fans in all bedrooms, and new garage door lanterns. Oakland is perfectly situated between Clermont, Winter Garden, and Orlando. You have quick and convenient access to the Florida Turnpike, the 429, 408, Highway 50, and Highway 27. Oakland Trails has a community pool, community playground, walking trails, and a dog park. Lots of dedicated street parking means you can welcome family and friends easily. The Oakland Nature Preserve is less than five minutes away, West Orange Trail's Killarney Station is just outside the neighborhood. Towering Live Oak Trees, the shore of Lake Apopka, and the extensive trail system make this neighborhood perfect for anyone who loves spending time outdoors!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
1507 WILD SWEETGRASS WAY, OAKLAND, FL 34787
$565,00020 Days on yellowkey MLS ID: O6409105
0 Days Off yellowkey (back on 5/23/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1975 Built: 2019Monthly Fee: $286 Tax: $8,748 (2025)Community: Longleaf At OaklandSingle Family
Taxes:$8,748
Remarks: Under contract-accepting backup offers. Beautifully maintained 3-bedroom, 2-bath single-story home located in the desirable Longleaf at Oakland community. From the welcoming wraparound porch to the open and functional layout, this home offers thoughtful upgrades throughout, including wood-look laminate flooring, 9’ ceilings, 8’ interior doors, custom moldings, and designer finishes. The kitchen features KitchenAid appliances, quartz countertops, a natural stone backsplash, oversized island, and a bonus flex space perfect for a coffee bar or wine area. The split-bedroom floor plan provides added privacy, while the spacious primary suite includes dual vanities, a walk-in shower with rain shower head, linen closet, and two walk-in closets. Enjoy Florida living year-round on the paved and screened lanai overlooking beautifully landscaped, low-maintenance gardens. HOA includes lawn care for added convenience. Located just STEPS from the popular WEST ORANGE TRAIL, this home is perfectly positioned for outdoor living and an active lifestyle. Situated within the highly sought-after GOLF CART DISTRICT, you can easily cruise to HISTORIC DOWNTOWN WINTER GARDEN for shopping, dining, entertainment, and the award-winning Farmers Market. Community amenities include a pool, playground, and neighborhood park. Private showings available.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Rema Perras (802-233-5292)
100 W RAILWAY AVE, OAKLAND, FL 34760
$2,186,92123 Days on yellowkey MLS ID: O6408609
0 Days Off yellowkey (back on 5/17/2026)
Bed: 3 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3555 Built: 2026Monthly Fee: $150 Tax: $2,949 (2024)Community: Briley FarmSingle Family
Taxes:$2,949
Remarks: 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.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Blaine Dooley (321-277-0933)
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