Displaying: For Sale
Location: Oakland
Property Type(s): Single Family
Price: $500,000 to $599,000
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Oakland - 4 properties found
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,490
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2024
Middle School: Lakeview Middle
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)
1270 STATIONSIDE DRIVE DR, OAKLAND, FL 34787
$509,000111 Days on yellowkey MLS ID: O6376429
REDUCED by $10,000 (1.9%) on 06/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2046 Built: 2002Monthly Fee: $29 Tax: $6,010 (2024)Community: Trailside Station Replat 44/23Single Family
Taxes:$6,010
Elementary School: None
High School: None
Middle School: None
Remarks: Nested right along the scenic West Orange Trail, this spacious 4 bedroom, 2 bath home offers the perfect balance of recreation and relaxation. The open interior flows seamlessly to private pool, creating an ideal oasis for Florida living. Located for ultimate convenience, just 15 mins from Downtown Winter Garden with The Turnpike nearby for an easy commute. Enjoy being 30 mins of Orlando's world class attractions, including Disney, Universal Studios, and Downtown Orlando. Benefit from the highly rated Orange County School system.
Listing is courtesy of: HOME INVEST REALTY INC (407-895-8891)
Listing Agent: Ky Lam (407-895-8891)
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
Tax Year: 2025
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)
2259 WHITE FEATHER LOOP, OAKLAND, FL 34787
$525,000117 Days on yellowkey MLS ID: O6381627
1 Days Off yellowkey (back on 5/5/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2204 Built: 2017Monthly Fee: $110 Tax: $5,025 (2024)Community: Oakland Trls Ph 1Single Family
Taxes:$5,025
Remarks: Under contract-accepting backup offers. 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)
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