Location: Oakland
Do Not Show Listings
710 REGINA CIR, OAKLAND, FL 34787
$669,90015 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
$1,059,00065 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)
14001 RUGBY ST, OAKLAND, FL 34787
$825,00031 Days on yellowkey MLS ID: G5112905
REDUCED by $20,000 (2.4%) on 06/25/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4240 Built: 2015Monthly Fee: $121 Tax: $5,903 (2025)Community: Verde Park Ph 1Single Family
Taxes:$5,903
Elementary School: None
High School: None
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Price improved and ready for its next owner, this beautifully maintained pool home in the sought-after Verde Park community offers more than 4,240 square feet of thoughtfully designed living space on a beautiful 0.26-acre corner lot in one of Winter Garden’s most beloved communities. With 5 bedrooms and 4 bathrooms, the home delivers an exceptional combination of space, comfort, and Florida outdoor living with a flexible layout designed for everyday living and entertaining. Inside, elegant formal living and dining rooms, architectural archways, and generous gathering spaces create a warm and welcoming first impression. The expansive family room connects seamlessly to a gourmet kitchen complete with granite countertops, stainless steel appliances, a cooktop, built-in wall oven, and a sunny breakfast nook overlooking the outdoor living area - the kind of space where mornings feel easy and gatherings happen naturally. The versatile floor plan offers room for a variety of needs, including a downstairs Murphy bed office that is perfect for guests or working from home, plus an additional downstairs bonus room with exciting potential as a next-generation living space ideal for multigenerational families or extended stays. Upstairs, the primary suite wraps you in comfort with a large bedroom, spa-like bath, garden tub, dual vanity, separate walk-in shower, and a custom oversized walk-in closet with built-in storage. The second floor also features a large open loft with a convenient kitchenette and a dedicated media room, creating the perfect setup for movie nights or entertainment. Outdoors, enjoy a private screened pool and lanai, covered patio, and summer kitchen designed for year-round enjoyment. The home is also EV charging ready, adding modern convenience for today’s lifestyle. When you’re ready to explore, everything is right at your doorstep. Enjoy walkable access to the West Orange Trail, perfect for morning bike rides, jogging, or evening strolls. Major shopping, including Costco, popular retail, and everyday conveniences, is just minutes away, charming downtown Winter Garden, with its vibrant farmers market, local dining, and boutique shops, is a short drive from home. Add easy access to Montverde Academy and the Florida Turnpike, and this location truly checks every box. Some photos are virtually staged. Aerial property lines are approximate and should be verified by buyer. *Aerial photo property lines are an estimate and to be verified by buyer, some photos are virtually staged
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Ann Mertens (407-452-8776)
1143 HULL ISLAND DR, OAKLAND, FL 34787
$749,00025 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
$639,0003 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
$1,548,00099 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)
1270 STATIONSIDE DRIVE DR, OAKLAND, FL 34787
$509,000129 Days on yellowkey MLS ID: O6376429
2 Days Off yellowkey (back on 6/24/2026)
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
Tax Year: 2024
Remarks: Under contract-accepting backup offers. 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)
2247 WHITE FEATHER LOOP, OAKLAND, FL 34787
$457,90029 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
$2,186,92141 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)
812 JOHNS POINT DR, OAKLAND, FL 34787
$2,699,00092 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)
38 S POLLARD ST, OAKLAND, FL 34760
$629,99989 Days on yellowkey MLS ID: O6394442
REDUCED by $30,000 (4.5%) on 06/21/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1872 Built: 2026 Tax: $815 (2025)Community: Oakland TownSingle Family
Taxes:$815
Remarks: 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.
Listing is courtesy of: MS LAND & BUILDING LLC (407-512-1213)
Listing Agent: Cassia Barros (407-285-1163)
402 N POLLARD ST, OAKLAND, FL 34760
$3,495,00023 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
$679,900138 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)
1108 RIVERWAY DR, OAKLAND, FL 34787
$1,025,00044 Days on yellowkey MLS ID: O6407380
0 Days Off yellowkey (back on 6/16/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2999 Built: 2024Monthly Fee: $208 Tax: $8,430 (2025)Community: Oakland ParkSingle Family
Taxes:$8,430
Remarks: Under contract-accepting backup offers. OAKLAND PARK—-a Parade of Homes Winning Community! This beautifully designed home (built in 2024) offers the perfect blend of comfort, style, and functionality. Featuring 4 bedrooms, 3 full baths, a LOFT, and an additional flex room with elegant glass FRENCH DOORS — ideal for a home OFFICE or study — this property is thoughtfully laid out for both everyday living and entertaining. Situated on nearly a quarter-acre lot (.21), there is plenty of room to create your dream backyard oasis, including space for a future POOL. Enjoy the outdoor living area featuring a covered patio with retractable screens for added privacy. The gourmet kitchen is equipped with quartz countertops, a cooktop, built-in oven and microwave, and walk-in pantry, making it both stylish and functional for the chef at heart. The open-concept layout creates a seamless connection between the kitchen, dining, and living spaces, offering an ideal setting for social gatherings and family time. Expansive sightlines and abundant natural light draw your eye through the heart of the home and out to the backyard retreat, creating a beautiful indoor-outdoor flow. Large windows and rear patio access effortlessly blend the living spaces, allowing the backyard to serve as a natural extension of the home’s elegant design and entertaining experience. The generously sized DOWNSTAIRS primary suite faces the backyard and offers a spa-like bath complete with a large vanity with dual sinks, a walk-in closet, oversized shower, and private water closet. An additional bedroom, optional 5th bedroom/OFFICE, full bath, spacious laundry room, and storage closets are located on the first level. Upstairs, you’ll find two additional bedrooms, a full bath, and a loft perfect for relaxing, gaming, or entertaining guests. The long driveway provides ample parking, and the home is surrounded by stunning custom-built residences, adding to the appeal and prestige of the neighborhood. Just a short GOLF CART ride away, you’ll find the charm and vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails, including access to the 22 mile long WEST ORANGE TRAIL. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Ashley Boyd (321-209-5540)
2017 BOSS HEWETT ST, OAKLAND, FL 34787
$724,90064 Days on yellowkey MLS ID: O6402045
REDUCED by $25,000 (3.3%) on 05/30/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2852 Built: 2022Monthly Fee: $165 Tax: $9,043 (2025)Community: Hull Island/Oakland Ph 2Single Family
Taxes:$9,043
Remarks: Virtually Staged. Enjoy single-level living in lakefront Hull Island in this meticulously maintained 2,852 sq ft home built in 2022, with owned rooftop solar that keeps utility costs well below the Florida norm for a home this size. Four bedrooms, four full baths, and a two-car garage, all just minutes from historic Winter Garden's shops, restaurants, and Saturday farmers market. All four bedrooms, including the primary suite, plus the kitchen and all main living areas, are on the first floor. The only upstairs space is a private bonus suite with its own full bath, which functions equally well as a media room, flex room, or guest quarters well removed from the rest of the house. The foyer opens into a connected great room, dining area, and kitchen, with three sliding glass doors along the back wall looking out to a covered and screened lanai. Ceramic tile runs throughout the main living areas. The kitchen features the upgraded gas-range configuration with a Bosch refrigerator, GE stainless appliances, Silestone quartz counters, and an oversized island with seating. Finishes include 42-inch cabinets stacked to the 9'4" ceiling with crown molding. Inside: soft-close dovetail drawers, a three-tier pot and pan organizer, and a pull-out pantry. The owned rooftop solar system was installed in 2023 and carries a 25-year limited warranty through 2048. Combined with the tankless gas water heater, it helps keep monthly utility costs exceptionally low. The primary suite sits at the back of the first floor with a tray ceiling, dual raised-height vanities, a large walk-in shower with a built-in recessed shelf, and a walk-in closet with custom shelving that passes directly through to the laundry room. The upstairs bonus suite measures 18'8" x 25'6" and has its own full bath. It is pre-wired as a dedicated media space, with structured Cat6 throughout, a ceiling-mounted projector outlet, and TV and data chases ready for a wall-mounted display. Additional features include a two-car garage with a 220V/30A outlet suitable for Level 2 EV charging, a workshop, or additional appliances; a Ring doorbell, alarm system, and cameras that convey with the home; upgraded satin nickel interior door hardware with a coordinated front door handleset; upgraded light fixtures; and front gutters. Hull Island amenities include a community pool, clubhouse, playground, and community fishing pier, with the West Orange Trail at the community's doorstep.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Peter Biskup (407-267-5187)
1146 PRADO LN, OAKLAND, FL 34787
$2,130,760224 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
$2,238,120224 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
$1,145,00074 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
$539,900142 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
$499,00073 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)
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