Location: Oakland
Keyword(s): Lakeview Middle
Keyword(s) Middle School: Lakeview Middle
Do Not Show Listings
710 REGINA CIR, OAKLAND, FL 34787
$669,90014 Days on yellowkey MLS ID: O6415350
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3285 Built: 2002Monthly Fee: $96 Tax: $4,432 (2025)Community: Johns LandingSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,432
Elementary School: Tildenville Elem
High School: West Orange High
Tax Year: 2025
Middle School: Lakeview Middle
Remarks: Welcome to this exceptional pool home located in the sought-after gated lakefront community of Johns Landing. Situated on an oversized 13,000+ square-foot corner lot with a mostly fenced backyard, this spacious home offers over 3,000 square feet of thoughtfully designed living space. Featuring 4 bedrooms, 4 full bathrooms, a dedicated office, media room, and spacious loft, this home provides the perfect balance of comfort and functionality for today’s lifestyle. The open-concept floor plan is highlighted by soaring ceilings, abundant natural light, and a gourmet kitchen that seamlessly connects to the main living and dining areas, making it ideal for both everyday living and entertaining. The first-floor primary suite serves as a private retreat, complete with dual vanities, separate his-and-her walk-in closets, and a spacious en-suite bath. Upstairs layout is Bedroom/Full bath, loft and Large media room that could be 5th bedroom. Downstairs features 3 bedrooms and 3 full bathrooms. Step outside to your screened lanai and sparkling private pool, where you can enjoy Florida’s beautiful weather year-round. The expansive backyard offers plenty of space for outdoor entertaining, while the three-car garage provides ample room for vehicles and storage. Residents of Johns Landing enjoy exclusive amenities including a private boat ramp and community dock, playground, tennis and pickleball courts, basketball court, and access to beautiful Johns Lake. Ideally located just minutes from historic downtown Winter Garden, the West Orange Trail, Costco, shopping, dining, and major highways, this home offers the perfect combination of luxury, convenience, and an active Florida lifestyle. Recent updates include a new roof (2019) and two HVAC systems (2019 and 2017), providing added peace of mind for years to come. Don’t miss this incredible opportunity to own a beautiful home neighborhood located on the John's chain of Lakes.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Brenda Anglada (407-493-3464)
219 LARGOVISTA DR, OAKLAND, FL 34787
$1,059,00064 Days on yellowkey MLS ID: O6401756
REDUCED by $40,000 (3.6%) on 05/26/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3951 Built: 2004Monthly Fee: $96 Tax: $5,294 (2025)Community: Johns LandingSpa: YesSingle Family
Taxes:$5,294
Remarks: Beautiful house, fully remodeled luxury residence in the exclusive gated community of John's Landing. Offering nearly 4,000 sq/ft, this impressive 5 bedrooms, 4 bath home features, 2 of the bedrooms is a suite, high-end finishes, and a seamless modern design throughout. Porcelain tile flooring, a stunning gourmet kitchen with island with quartz countertops, custom cabinetry and a premium stainless steel appliances. Every details has been thoughtfully upgraded; spa inspired master bathroom include designer walk-in shower,LED mirrors, and luxury fixtures. Step outside to a private screened-in pool and spa, creating the perfect setting for entertaining and relaxed living. Residents enjoy gated access and private boat/jet sky ramp to John's Lake, ideal for boating and jet skis. Also prime location access to Turnpike Hwy and just minutes from Winter Garden, Clermont, Downtown Orlando and all Disney Parks.
Listing is courtesy of: NOVARE REAL ESTATE LLC (754-245-3136)
Listing Agent: Durval Da Rocha (754-245-3136)
1318 PAINTED BUNTING AVE, OAKLAND, FL 34787
$360,000108 Days on yellowkey MLS ID: O6389319
0 Days Off yellowkey (back on 6/25/2026)
REDUCED by $10,000 (2.7%) on 05/05/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1472 Built: 2019Monthly Fee: $425 Tax: $4,710 (2025)Community: Longleaf/Oakland RepTownhouse
Taxes:$4,710
Remarks: Under contract-accepting backup offers. Virtually Staged. You’re going to love this beautifully maintained 2-bedroom, 2.5-bath Townhome in the highly desirable Longleaf At Oakland which is perfectly located just a 1/2 mile from the Florida Turnpike, offering easy access to everything Central Florida has to offer. The entire interior was freshly painted in March 2026, giving the home a bright, fresh feel from the moment you walk in. The inviting front porch is the perfect place to enjoy your morning coffee. Inside, abundant natural light flows through the numerous windows, enhancing the spacious open-concept layout. The large kitchen features an island, stainless steel appliances, granite countertops, and an oversized pantry, making it ideal for both everyday living and entertaining. The inside utility room is conveniently located on the first floor with additional storage under the stairway. Upstairs you’ll find two private master suites, each with its own full bathroom. The primary suite boasts a massive walk-in closet with a window and the en-suite offers dual vanities and an easily accessible walk-in shower. The second bedroom includes a tub/shower combo and its own walk-in closet. Step outside to the private courtyard, perfect for grilling and enjoying Florida’s beautiful weather with plenty of space for outdoor seating or even a hot tub. This home is equipped with Google smart lighting switches, and a Google thermostat can easily be installed and controlled through your app. The two-car garage offers private rear entry into the home with a spacious driveway that provides additional parking along with guest parking nearby. There is additional parking in the front of this home also. Enjoy being just steps away from the beautiful community pool overlooking the pond and the neighborhood playground. This home and community offers everything the Florida Lifestyle has to offer!
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Randy Adams Pa (321-438-1027)
1143 HULL ISLAND DR, OAKLAND, FL 34787
$749,00024 Days on yellowkey MLS ID: O6413213
REDUCED by $25,900 (3.3%) on 06/25/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2788 Built: 2021Monthly Fee: $165 Tax: $11,129 (2025)Community: Hull Island At OaklandSingle Family
Taxes:$11,129
Remarks: PRICE IMPROVMENT! Enjoy the best of Florida Living in the most popular M/I Homes Richmond floor plan with a spacious bonus room, located in the desirable Hull Island community in Oakland. Just steps from the WEST ORANGE TRAIL, you'll enjoy easy access to biking, walking, and outdoor recreation minutes from your doorstep. This exceptional 4-bedroom, 4-bathroom home offers a thoughtfully designed layout with all bedrooms and primary living spaces conveniently located on the first floor. Upstairs, the expansive bonus room w/balcony provides incredible flexibility and includes its own full bathroom, making it ideal as a media room, game room, home office, guest suite, or multi-generational living space. Quality upgrades are evident throughout the home, including tile flooring in the main living areas and new luxury vinyl plank flooring in all bedrooms, on the staircase, and in the bonus room. The gourmet kitchen features beautiful quartz countertops, GE stainless steel appliances, a gas range, designer lighting, and a walk-in pantry. The primary bathroom has also been tastefully upgraded. Recent improvements include an extended paver patio, French drain system, gutters, and a UV light added to the HVAC system for enhanced air quality and comfort. Relax on the welcoming front porch or rear balcony and enjoy partial views of the lake. Combining stylish upgrades, functional living space, and an unbeatable location, this move-in-ready home offers the best of Florida living in one of Oakland's most desirable communities, and a perfect place to call HOME! Please call to schedule your private showing.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Rema Perras (802-233-5292)
529 JOHNS LANDING WAY, OAKLAND, FL 34787
$639,0002 Days on yellowkey MLS ID: O6419615
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2650 Built: 2004Monthly Fee: $96 Tax: $3,911 (2025)Community: Johns Landing Ph 02 48 138Single Family
Taxes:$3,911
Remarks: Welcome home to this stunning 4-bedroom, 3-bathroom pool home tucked inside a sought-after gated community! Offering 2,650 square feet of thoughtfully designed living space, this home is perfect for both everyday comfort and entertaining. The versatile 4th bedroom is ideal as a mother-in-law suite, guest quarters, or home office — perfect for multi-generational living. The spacious primary suite offers a peaceful retreat with abundant natural light throughout. Major updates are already done for you, with a new roof (2022) and new AC (2025) providing lasting peace of mind. Step outside to your private, screened-in, solar-heated pool overlooking a premium pond-view lot — an ideal setting for morning coffee, evening relaxation, or year-round Florida entertaining. The generous patio space makes indoor-outdoor living effortless. This exclusive gated community offers exceptional amenities, including a private dock and boat ramp, a fishing pier for peaceful weekend mornings, tennis courts for staying active, and a playground for family fun — the perfect blend of recreation and privacy. The location is unbeatable: close to all major highways for an easy commute, just minutes from downtown Winter Garden's vibrant dining and shopping scene, and only 25 minutes from Disney and Universal Studios. A grocery store is less than a mile away, and nature lovers will love having Oakland Nature Preserve nearby for hiking and wildlife viewing. This home combines luxury, comfort, and convenience in one of the area's most desirable communities. Schedule your private showing today — this one won't last long!
Listing is courtesy of: REAL BROKER, LLC (407-922-8986)
Listing Agent: Denise Pellegrino (352-978-9720)
1412 JOHNS COVE LN, OAKLAND, FL 34787
$1,548,00098 Days on yellowkey MLS ID: O6391735
REDUCED by $40,000 (2.5%) on 04/15/2026
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3613 Built: 2002Monthly Fee: $173 Tax: $13,832 (2025)Community: Johns CoveSpa: YesSingle Family
Taxes:$13,832
Remarks: Virtually Staged. BACK ON MARKET! And Reimagined to IMPRESS! Gorgeous Lake Front Property on John's Chain with so many NEW UPGRADES! ALL NEW Flooring throughout! NEW Completely Repainted interior! Updated vanities and accents throughout bathrooms. Feels like a brand new home! "Triple-split" bedroom plan is a winner for those who desire 1-story living--all wrapped around those beautiful lake views! FROG bonus space offers endless opportunities as a game room or private guest retreat. Kitchen is a chef's dream with so much counter space and storage, and charming built in bench in nook, with perfect lake views! HUGE private backyard space with heated pool, spa, fire pit and nightly views of themepark fireworks! The property has been meticulously maintained with many updates since the current owners purchased it. Additional renovations include: updated kitchen appliances (2023), new granite countertops, additional lighting and a custom nook seating; enlargement of the 3-car garage door which now includes a custom workbench, storage closet, multi-level storage shelves, refrigerator and a Tesla Charger; updated entry doors, redesigned dining area to accommodate a larger table; FROG (Family Room Over Garage) Full Bathroom Addition with a storage closet (2023), primary bathroom overhaul (2023), 2nd primary closet addition, heated bathroom floors, heated shower floor, heated shower bench, and an oversized steam shower (Kohler) with two separate shower head systems, truly a spa-like atmosphere! Outside renovations include: low maintenance Azek planks from home to private fire pit area, continuing on to the boathouse; 2023 new driveway pavers with a lit walkway to the front door; new paved front porch; new gutter system; plastic soffit replaced with wood; outdoor lighting; new outdoor storage area; 2023 home was painted; additional 200 amps (total 400 amps) and new garage door. The boathouse has water and power, can house two jet skis, a bass boat or ski boat or optional pontoon boat. The boat area has a Touchless Boat Cover with a remote control lift. Boathouse is approximately 23 1/2 ft by 33 ft. All this is conveniently located near major highways and local restaurants and shops. Seize this opportunity to experience the finest in luxury lake living in Central Florida!
Listing is courtesy of: NEXT RESIDENCE REALTY LLC (407-463-9209)
Listing Agent: Betsey West (407-463-9209)
2247 WHITE FEATHER LOOP, OAKLAND, FL 34787
$457,90028 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
Taxes:$6,845
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)
100 W RAILWAY AVE, OAKLAND, FL 34760
$2,186,92140 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
Tax Year: 2024
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)
812 JOHNS POINT DR, OAKLAND, FL 34787
$2,699,00091 Days on yellowkey MLS ID: O6393574
REDUCED by $51,000 (1.9%) on 06/22/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4373 Built: 2001Monthly Fee: $173 Tax: $23,334 (2025)Community: Johns Cove 43/104Spa: NoSingle Family
Taxes:$23,334
Remarks: Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout. Designed for effortless entertaining, the open-concept layout showcases a chef’s kitchen with a waterfall quartz island, custom cabinetry, premium stainless steel appliances, and a full-slab backsplash, all flowing into an expansive living area with designer lighting and seamless indoor-outdoor access. The primary suite offers a private retreat with abundant natural light, custom closets, and a spa-inspired bath featuring a freestanding soaking tub and luxury walk-in shower. Step outside to a screened pool, upgraded travertine deck, and private pier, creating an unparalleled waterfront lifestyle ideal for relaxation and entertaining. Additional highlights include a concrete tile roof (maintained), smart home features, updated HVAC, epoxy garage, modern laundry room, and high-end upgrades throughout. Ideally located minutes from Downtown Winter Garden, premier dining, shopping, and top-rated schools, this is a rare opportunity to own an unparalleled lakefront property.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Any Alves (407-455-0618)
402 N POLLARD ST, OAKLAND, FL 34760
$3,495,00022 Days on yellowkey MLS ID: O6405707
0 Days Off yellowkey (back on 6/4/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5001 Built: 2026Monthly Fee: $175 Tax: $2,383 (2025)Community: Briley FarmSpa: YesSingle Family
Taxes:$2,383
Remarks: 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.
Listing Agent: Carolina Dumit (407-325-8963)
729 STRIHAL LOOP, OAKLAND, FL 34787
$679,900137 Days on yellowkey MLS ID: O6381069
3 Days Off yellowkey (back on 5/18/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3583 Built: 2001Monthly Fee: $92 Tax: $4,417 (2024)Community: Johns Landing Ph 01 44/47Single Family
Taxes:$4,417
Remarks: Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to popular Johns Lake. Home is updated with the entire roof replaced in November 2019 and new A/C in 12/21/2020. Perfectly positioned minutes from Florida Turnpike and within 25 minutes from Disney, Universal Studios, Downtown Orlando, Downtown Clermont, Downtown Winter Garden, and the Bike Trail which connects Clermont, Oakland, Winter Garden, and Orlando. All measurements are approximate and should be verified.
Listing is courtesy of: LIBERTY HOME SALES INC (321-256-0500)
Listing Agent: Subhas Sawh (407-402-1350)
1146 PRADO LN, OAKLAND, FL 34787
$2,130,760223 Days on yellowkey MLS ID: O6359354
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3992 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove At The Harvest DistrictSingle Family
Taxes:$399
Remarks: Pre-Construction. To be built. Introducing the Hearth Stone Model by Davila Homes. Discover the perfect blend of modern luxury and everyday comfort in the Hearth Stone, a beautifully designed 3,992-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floor plan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Heath Stone also features a 2-car detached garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Hearth Stone model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Listing Agent: Heather Spirazza (407-757-6022)
1173 PRADO LN, OAKLAND, FL 34787
$2,238,120223 Days on yellowkey MLS ID: O6359359
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4204 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove At The Harvest DistrictSingle Family
Remarks: Pre-Construction. To be built. Introducing the Sunburst Model by Davila Homes Discover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of today’s modern family. Step inside and experience a thoughtfully designed open-concept floorplan that seamlessly connects the gourmet kitchen, dining area, and great room—creating a warm, inviting space that’s perfect for both relaxed living and stylish entertaining. High-end finishes, designer details, and natural light throughout the home elevate every moment spent inside. The Sunburst also features a 3-car garage, providing ample room for vehicles, storage, or even a dedicated hobby space. Upstairs, enjoy a stunning covered terrace, ideal for morning coffee, evening gatherings, or simply taking in the views of your surroundings. With its blend of functionality and sophistication, every space in the Sunburst is designed to make daily living both easy and elegant. Located in The Grove community in the heart of Oakland, residents enjoy easy access to parks, scenic trails, top-rated schools, dining, and major highways—with a quick commute to Orlando and Disney. And coming soon, the Harvest District, a 30,000-square-foot retail complex, will add even more convenience and vibrancy to the area. The Sunburst model by Davila Homes truly defines inspired living—schedule your private tour today to experience its exceptional design and lifestyle firsthand.
Listing Agent: Alexis Anderson (561-670-5901)
250 N WALKER ST, OAKLAND, FL 34760
$1,145,00073 Days on yellowkey MLS ID: G5110973
REDUCED by $50,000 (4.2%) on 05/17/2026
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2469 Built: 2000 Tax: $10,745 (2025)Community: Oakland TownSpa: YesSingle Family
Taxes:$10,745
Remarks: SELLER OFFERING BUYER 20K!!!! TOWARDS CLOSING COSTS AND PREPAIDS. Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak trees with NO HOA and direct access to the Winter Garden Trail right from your backyard. Bring your boat, bring your toys—this one has room for it all! From the moment you arrive, the mature landscaping and inviting front porch set the tone for the peaceful retreat that awaits. Step inside to a fully renovated 2026 kitchen featuring upgraded quartz countertops, LVP flooring, subway tile backsplash, refaced cabinets with modern hardware, and a brand-new refrigerator—truly a chef’s dream. Just off the kitchen, new french doors lead to your private patio and show-stopping 2019 salt water pool complete with spa and slide, perfect for entertaining or unwinding after a long day. The first floor includes a large guest bedroom and a spacious primary suite with an oversized walk-in closet and a relaxing ensuite offering a soaking tub and separate shower. Upstairs, you’ll find two generously sized guest bedrooms and a beautifully appointed guest bath. This home is loaded with upgrades for peace of mind and comfort, including 2021 AC units, 2021 roof, 2026 LVP flooring, fresh interior paint and baseboards, newer windows, new fixtures, new landscaping, a new water heater, and a newly painted shed/workshop. Located in the heart of Oakland, you can golf cart to Downtown Winter Garden, Plant Street Market, the Lake Apopka boat ramp, shops, dining, and weekly events. Homes with this level of privacy, upgrades, and location rarely become available—and this one checks every box. Bring your golf cart and don’t miss your chance to own a truly unique custom home in the heart of Oakland. This property will not last! Let’s make it yours.
Listing is courtesy of: COAST TO COAST REAL ESTATE PRO (352-296-8930)
Listing Agent: Alaina Dimare (407-457-1834)
2065 WHITE FEATHER LOOP, OAKLAND, FL 34787
$539,900141 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
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
$499,00072 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)
505 E GULLEY AVE, OAKLAND, FL 34787
$865,00063 Days on yellowkey MLS ID: O6400317
0 Days Off yellowkey (back on 5/31/2026)
REDUCED by $20,000 (2.3%) on 05/28/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3399 Built: 2006Monthly Fee: $73 Tax: $6,649 (2025)Community: Winters LandingSpa: YesSingle Family
Taxes:$6,649
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **$10,000 towards closing costs**Welcome to this truly exceptional home offering space,flexibility & an unbeatable location!This beautiful,expansive residence features 4 spacious bedrooms,3.5 bathrooms,plus a versatile upstairs BONUS ROOM that can easily serve as a 5th bedrm—complete with closet & half bath already pre-plumbed for a full bathroom conversion.Enjoy breathtaking sunset views right from this elevated retreat.This home features a rare & highly desirable MOTHER-IN-LAW SUITE,complete with KITCHENETTE & ADA-compliant BATHROOM—ideal for multi-generational living or guest privacy.The 2nd bedrm conveniently connects to the kitchenette,enhancing the suite’s functionality.A 3rd bedrm,currently used as a home office,located near an adjacent bathroom that also provides direct access to the pool area.SPACIOUS PRIMARY suite serves as a private retreat,featuring an ensuite bathroom with dual sinks,a relaxing soaking tub& large walk-in closet.At the front of the home,a formal living & dining area offers versatile space that can easily serve as a den,library, or flex rm to suit your needs.The kitchen has 42" SOLID WOOD cabinets,granite counter tops & is equipped with NEW APPLIANCES 2025,including induction cooktop heats water in 3 minutes,convection oven & the rare convenience of 2 dishwashers—one being a quiet Bosch,ideal for large families or entertaining.The great rm features a cozy WOOD BURNING FIREPLACE & opens to your own private Florida oasis.Step outside to a HEATED,screen-enclosed POOL & SPA(pool heater installed in 2025,screen enclosure 2020),creating the perfect setting for year-round enjoyment.The expansive pool deck extends your living space outdoors,ideal for relaxing or entertaining.Beyond the pool,the private,partially fenced backyard offers additional space to unwind,accented by tranquil bamboo that sways in the breeze creating a peaceful atmosphere.The home backs to a State of Florida wildlife ravine,providing serene views of native birds,lush greenery& natural surroundings—your own quiet retreat right at home!The home boasts 2 AC zones for superior energy conservation:Both AC units are new in the last 5 years & maintained twice a year.NEW,OVERSIZED DOUBLE PANE WINDOWS throughout lower level are only a few months old,allowing for gorgeous VIEWS.NEW ROOF 2022.NEW,LARGE HYBRID WATER HEATER installed 2024,water Softener included.Complete with a 3 CAR GARAGE.LOCATION,LOCATION truly sets this home apart. Situated in a GOLF CART- FRIENDLY community,you’ll have direct access to the vibrant charm of DOWNTOWN WINTER GARDEN,just 2 miles away. Enjoy the award-winning Winter Garden Farmers Market,along with popular dining,shopping & year-round events.Outdoor enthusiasts will love being just steps from the scenic 22-mile West Orange Trail,perfect for biking, jogging or leisurely strolls.Nearby,the quaint&historic charm of Downtown Oakland,the scenic waterfront dock on Tubb Street & nearby Oakland Nature Preserve,offer even more to explore.Publix,Aldi,Winter Garden Village Mall,MAJOR ROADWAYS & highways are all nearby.The Turnpike is minutes away.EASY ACCESS to Theme parks, 20 minutes to Downtown Orlando & Orlando Intl Airport 30 minutes away.With only 58 homes,this quiet street offers a true sense of community.Residents enjoy friendly neighbors,regular patrols from the nearby police department & proximity to the fire station & Oakland Charter School(priority enrollment for Oakland residents).This is more than a home—it’s a lifestyle!
Listing is courtesy of: CLOCK TOWER REALTY (407-832-7332)
Listing Agent: Sandy Jones (407-929-7999)
1204 WATER MAPLE DR, OAKLAND, FL 34760
$2,353,07829 Days on yellowkey MLS ID: O6407615
0 Days Off yellowkey (back on 5/28/2026)
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 3902 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove At The Harvest DistrictSpa: NoSingle Family
Remarks: 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.
1216 HULL ISLAND DR, OAKLAND, FL 34787
$1,799,00045 Days on yellowkey MLS ID: G5112107
2 Days Off yellowkey (back on 5/22/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4224 Built: 2021Monthly Fee: $165 Tax: $20,050 (2025)Community: Hull Island/OaklandSpa: YesSingle Family
Taxes:$20,050
Remarks: Under contract-accepting backup offers. Experience the ultimate lakefront lifestyle in this stunning MI Homes Endeavor, perfectly positioned on 83 feet of shoreline along Lake Apopka - No Flood Zone - in the highly desirable community of Hull Island. Built just 5 years ago, this exceptional residence offers 4,224 square feet of thoughtfully designed living space featuring 5 bedrooms, 4.5 bathrooms, bonus room, two dedicated office spaces (one on each floor), and a 3-car garage. Every detail of this home has been carefully curated with extensive post-builder upgrades and thoughtful custom touches throughout. With no rear or front neighbors, this property delivers both privacy and breathtaking natural beauty. Enjoy unforgettable sunset views from the newly installed Trex boat dock, the resort-style screened pool and patio, or nearly every west-facing room in the home. Out front, peaceful preserve views create the perfect backdrop for sunrise mornings. From the moment you step inside, you’re welcomed by soaring ceilings, abundant natural light, and stunning water views. The dramatic family room showcases impressive vaulted ceilings, creating an open yet inviting atmosphere ideal for both entertaining and everyday living. The gourmet kitchen is truly a chef’s delight, featuring a massive center island, natural gas cooktop, built-in convection oven, stainless steel appliances, and extensive cabinetry and prep space. The adjoining dinette area offers casual dining convenience, while the formal dining room provides an elegant setting for gatherings and celebrations. The first floor also includes a wine room, private office, guest bedroom, and full pool bath with direct outdoor access. Designed for exceptional indoor-outdoor living, the backyard retreat is nothing short of spectacular. The recently designed luxury pool features elegant waterfall and fountain elements, an oversized jacuzzi, custom natural gas fire pit, turf play area, and expansive covered lanai complete with tongue-and-groove ceiling and travertine flooring — all enclosed within a panoramic screen offering unobstructed lake views. Enjoy direct access to Florida’s natural beauty right from your backyard. Spend your evenings fishing from the private dock, launching your boat with ease from the electric lift for a sunset cruise on Lake Apopka, or exploring the connected Tavares Chain of Lakes and charming downtown Mount Dora by water. Upstairs, a striking staircase with sleek glass railings enhances the home’s modern design. The luxurious owner’s suite offers incredible lake views and a recently renovated spa-inspired ensuite featuring a freestanding soaking tub, oversized walk-in shower, and designer finishes. The spacious game/media room and second office overlooking the preserve offer incredible flexibility for work, entertainment, or multigenerational living. Secondary bedrooms enjoy beautiful views, while the fourth bedroom functions perfectly as a private mini-suite. Ideally located in the charming Town of Oakland, Hull Island offers convenient access to Winter Garden, Clermont, the Florida Turnpike, shopping, dining, and recreation. Community amenities include a pool, playground, dog park, and private dock access on the nature preserve - all with a low HOA. This is a rare opportunity to own an extraordinary lakefront retreat where luxury, comfort, and the Florida lifestyle come together seamlessly. Schedule your private showing today and experience lakeside living at its finest.
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Elizabeth Fowler (863-441-5304)
2259 WHITE FEATHER LOOP, OAKLAND, FL 34787
$525,000134 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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