Location: Oakland
Do Not Show Listings
2017 BOSS HEWETT ST, OAKLAND, FL 34787
$699,90088 Days on yellowkey MLS ID: O6402045
REDUCED by $25,000 (3.4%) on 07/10/2026
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,043
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
710 REGINA CIR, OAKLAND, FL 34787
$659,90039 Days on yellowkey MLS ID: O6415350
REDUCED by $10,000 (1.5%) on 07/20/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3285 Built: 2002Monthly Fee: $96 Tax: $4,432 (2025)Community: Johns LandingSingle Family
Taxes:$4,432
Elementary School: Tildenville Elem
High School: West Orange High
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. *Sold As-is . Bring your design ideas! Seller offers a $10,000-$20,000 credit for updates and buyer's closing costs."
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Brenda Anglada (407-493-3464)
2259 WHITE FEATHER LOOP, OAKLAND, FL 34787
$515,000159 Days on yellowkey MLS ID: O6381627
REDUCED by $10,000 (1.9%) on 07/20/2026
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
Tax Year: 2024
Remarks: 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)
250 N WALKER ST, OAKLAND, FL 34760
$1,125,00098 Days on yellowkey MLS ID: G5110973
REDUCED by $20,000 (1.7%) on 07/17/2026
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)
1134 PRADO LN, OAKLAND, FL 34760
$2,595,00015 Days on yellowkey MLS ID: O6413035
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 4433 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove/OaklandSpa: YesSingle Family
Taxes:$399
Remarks: Nestled beneath century-old heritage oaks in one of Oakland's most coveted addresses, this stunning 4,433 square foot Citrus floorplan by Element Home Builders delivers an extraordinary standard of luxury estate living. Every detail speaks to a level of craftsmanship and thoughtfulness that simply cannot be replicated. Five generously sized bedrooms, each with its own private ensuite bath, provides unmatched comfort and privacy for family and guests alike. Two additional powder baths serve the main living areas, while a dedicated pool bath keeps the outdoor experience seamless. At the heart of the home, a dramatic double island kitchen commands attention — equal parts showpiece and hardworking hub — crowned by soaring coffered ceilings that lend architectural depth and timeless elegance throughout. Step outside to your own private resort, where a sparkling pool and spa, summer kitchen, and covered lanai with roll-down screens create the ultimate Florida lifestyle — open-air breezes or a fully enclosed retreat, all at the touch of a button. Beyond your front door, The Grove places you steps from The Harvest District's boutique shops and restaurants, with exclusive access to the resort amenities at nearby Briley Farm — all reachable by foot or golf cart.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Alexis Anderson (561-670-5901)
402 N POLLARD ST, OAKLAND, FL 34760
$3,495,00047 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 is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Carolina Dumit (407-325-8963)
812 JOHNS POINT DR, OAKLAND, FL 34787
$2,699,000116 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)
1603 JOHNS COVE LN, OAKLAND, FL 34787
$850,00026 Days on yellowkey MLS ID: O6419418
Bed: 6 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4001 Built: 2004Monthly Fee: $175 Tax: $7,975 (2025)Community: Johns CoveSpa: YesSingle Family
Taxes:$7,975
Remarks: Exceptional 6-bedroom, 4-bathroom home on a private cul-de-sac in the highly desirable gated community of Johns Cove. This spacious residence features formal living and dining rooms, a large family room, soaring vaulted ceilings, and a double staircase. The kitchen offers stainless steel appliances, granite countertops, a large island, abundant cabinetry, and a breakfast area with tranquil pond views. The first-floor primary suite overlooks the pool and includes an en-suite bath with dual vanities, garden tub, separate shower, and walk-in closet. Upstairs offers generously sized bedrooms and a dedicated movie room. Enjoy a screened heated saltwater pool and spa, updated full pool bath, covered lanai, private balcony, and no rear neighbors. Residents enjoy a private boat ramp on Johns Lake, ideal for bass fishing, boating, paddle boarding, and kayaking. Near West Orange Trail, Downtown Winter Garden, Winter Garden Village, dining, shopping, and top-rated schools.
Listing is courtesy of: RE/MAX TOWN & COUNTRY REALTY (407-695-2066)
Listing Agent: Dominick Florio (321-377-4045)
1412 JOHNS COVE LN, OAKLAND, FL 34787
$1,509,900123 Days on yellowkey MLS ID: O6391735
REDUCED by $38,100 (2.5%) on 07/15/2026
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. Discover your dream lakefront retreat on Johns Lake! Enjoy 176 feet of waterfront—perfect for skiing, boating, fishing, or relaxing. The oversized boathouse has water, power and accommodates two jet skis plus a boat with a touch-less remote-controlled cover. The home features a desirable floor plan with stunning lake views. The Family Room Over Garage (FROG) serves as a versatile bonus space—ideal as a game room or guest retreat. The chef-inspired kitchen offers ample counter space, storage, and a charming built-in nook bench with views of the pool and Johns Lake. Outside, the expansive private backyard includes a heated pool, spa, private gas fire pit, and nightly views of Disney's fireworks. Meticulously maintained and with many new upgrades. Situated in one of Central Florida’s most sought-after locations. You are just four minutes from a major highway, enjoy easy access to premier dining and shopping in nearby Winter Garden. Come by and experience the luxury lake living. We can’t wait to show you around!
Listing is courtesy of: NEXT RESIDENCE REALTY LLC (407-463-9209)
Listing Agent: Betsey West (407-463-9209)
223 LARGOVISTA DR., OAKLAND, FL 34787
$540,0005 Days on yellowkey MLS ID: O6425925
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2486 Built: 2004Monthly Fee: $96 Tax: $7,026 (2025)Community: Johns Landing Ph 2Single Family
Taxes:$7,026
Remarks: Virtually Staged. Welcome to this spacious two-story home located in the highly desirable gated community of John's Landing in beautiful Oakland. Offering 4 bedrooms, 2.5 bathrooms, and over 2486 square feet of living space, this home combines generous room sizes, a functional layout, and an exceptional location to create the perfect place to call home. Step inside to discover multiple living and gathering spaces designed for everyday living as well as entertaining family and friends. The well-designed floor plan offers an inviting flow between the main living areas, while all four bedrooms are thoughtfully situated upstairs, creating a comfortable separation between living and private spaces. The expansive primary suite provides the perfect retreat at the end of the day, with plenty of room to relax and unwind. Outside, you'll appreciate the oversized backyard offering plenty of room for outdoor entertaining, play, gardening, or simply enjoying Florida's beautiful weather. With nearly a third of an acre, there is space that's increasingly difficult to find in today's market. Residents of John's Landing enjoy the security of a gated entrance along with outstanding community amenities including a lakefront dock, tennis courts, and playground. Ideally located just minutes from historic downtown Winter Garden, the West Orange Trail, the Florida Turnpike, shopping, dining, and everyday conveniences, this home offers the perfect combination of privacy, recreation, and accessibility. If you've been searching for a spacious home on a large homesite in one of West Orange County's most desirable communities, this is an opportunity you won't want to miss. Schedule your private showing today and experience everything this exceptional property has to offer!
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)
Listing Agent: Corey Smallman (407-744-2765)
1937 STANDING ROCK CIR, OAKLAND, FL 34787
$499,00097 Days on yellowkey MLS ID: O6398113
2 Days Off yellowkey (back on 7/14/2026)
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: Under contract-accepting backup offers. 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)
2247 WHITE FEATHER LOOP, OAKLAND, FL 34787
$457,90053 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)
14001 RUGBY ST, OAKLAND, FL 34787
$825,00055 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
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)
2117 GOPHER TORTOISE TER, OAKLAND, FL 34787
$350,000116 Days on yellowkey MLS ID: O6385739
REDUCED by $10,000 (2.8%) on 07/11/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1497 Built: 2020Monthly Fee: $426 Tax: $5,594 (2024)Community: Longleaf/Oakland RepTownhouse
Taxes:$5,594
Remarks: PRICE Improvement and ready to sell! Be sure to ask about a lender provided reduced rate offering a rate buy down to help reduce your monthly payment and/or closing costs. Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining. The kitchen, where matching marble countertops and cabinetry create a clean and cohesive look. A charming office nook on the first floor provides the perfect spot for working from home or managing daily tasks while staying connected to the living areas. Upstairs, each bedroom is thoughtfully designed as its own private suite, complete with a full bathroom and walk in closet, offering comfort and privacy for all occupants. The layout provides flexibility for a variety of living arrangements while maintaining a sense of personal space throughout. Enjoy quiet evenings on the private patio featuring outdoor lighting and a smart home dimmer system that sets the perfect ambiance. A covered walkway leads to the detached garage, offering convenience and protection from the elements. The garage also includes space for a personal workout setup, creating an easy option for staying active at home. Located in a convenient Central Florida area with easy access to major roadways, shopping, dining, and everyday essentials. Enjoy peace of mind with a newer construction and an added UV light system in the HVC to inmporve indoor air quality. It is truly ready for its new owner to come in and live.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Mary Herrod De Boer (219-771-1332)
1106 SARAH MATHEWS DR, OAKLAND, FL 34760
$1,975,000161 Days on yellowkey MLS ID: O6375487
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3596 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove At The Harvest DistrictSpa: YesSingle Family
Remarks: Pre-Construction. To be built. Nestled within the exclusive Grove community, the Clementine Plan by Element Home Builders is a bespoke pre-construction offering that showcases timeless architecture, refined luxury, and exceptional craftsmanship. This thoughtfully designed residence features 5 bedrooms, 5 full bathrooms, a powder room, loft across 3,596 square feet of elegantly curated living space—where classic design meets modern sophistication. Buyers may personalize the home with a curated selection of upgrade options, including additional squarefootage, a custom pool and spa, summer kitchen, cabana, golf cart garage and storage, three-car garage, or a private garage apartment suite. Home plans, elevations, and design renderings are subject to change, with exterior finishes and roof materials influencing final elevation pricing. Ideally positioned within Oakland and Winter Garden's golf cart district, just minutes from Downtown Winter Garden and a short two-minute walk to the West Orange Trail, this residence offers an unmatched lifestyle—seamlessly blending luxury living with access to recreation, dining, and boutique shopping.
Listing Agent: Heather Spirazza (407-757-6022)
219 LARGOVISTA DR, OAKLAND, FL 34787
$1,025,00089 Days on yellowkey MLS ID: O6401756
REDUCED by $34,000 (3.2%) on 07/07/2026
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)
510 BRILEY AVE, OAKLAND, FL 34760
$3,575,00015 Days on yellowkey MLS ID: O6422258
0 Days Off yellowkey (back on 7/6/2026)
Bed: 5 Bath: 6.0 Gar: 4 Liv Area Sq Ft: 5478 Built: 2025Monthly Fee: $150 Tax: $4,241 (2024)Community: Briley FarmSpa: YesSingle Family
Taxes:$4,241
Remarks: Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive Euro-style 9'+ bifold slider, and a stunning gas fireplace anchoring the main living space. The chef’s kitchen boasts Wolf and Sub-Zero appliances, exquisite Quartzite counters in both the main and back kitchens, and a fully equipped back kitchen designed for effortless entertaining. A custom primary closet with lighted rods adds a boutique touch to everyday living. Outdoor living is equally exceptional. Enjoy a lap pool and hot tub, gas fire pit, and luxurious marble coping and pool decking, all beautifully framed by a $70,000 professionally designed landscaping package and a fully fenced yard for privacy. Additional upgrades include Sonos speakers, security system with cameras, clay tumbled pavers on the porches, and a Generac generator for added comfort and peace of mind. With a 4-car garage, impeccable craftsmanship, and a leaseback opportunity, this home offers the best of luxury and convenience. Furniture is negotiable, allowing you to tailor the space to your vision. Discover refined living in one of Oakland’s most desirable communities—this model home truly sets the standard.
1143 HULL ISLAND DR, OAKLAND, FL 34787
$749,00049 Days on yellowkey MLS ID: O6413213
0 Days Off yellowkey (back on 7/2/2026)
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: Under contract-accepting backup offers. 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 Agent: Rema Perras (802-233-5292)
1128 PRADO LN, OAKLAND, FL 34787
$2,800,00021 Days on yellowkey MLS ID: O6413047
0 Days Off yellowkey (back on 7/1/2026)
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4658 Built: 2026Monthly Fee: $150 Tax: $399 (2025)Community: Grove/OaklandSingle Family
Remarks: Under Construction. Introducing one of Central Florida's most distinguished new addresses — the Oakshade floor plan by award-winning Davila Homes, nestled within the exclusive, boutique enclave of The Grove at the Harvest District in the charming Town of Oakland, Florida. Spanning an impressive 4,658 square feet, this stunning residence offers six generously sized bedrooms, each with its own private ensuite bath, delivering the ultimate in comfort and privacy for family and guests alike. A dedicated home office provides the perfect retreat for focused work, while the airy upper-level loft adds flexible living space ideal for a media room, playroom, or secondary lounge. Step outside and experience true Florida luxury a custom pool serves as the centerpiece of the outdoor living area, perfectly positioned to capture serene pond views that make every morning and evening feel like a private escape. Seamless indoor-outdoor integration defines this home's design philosophy, with expansive windows flooding the interior with natural light and blurring the line between inside and out. Inside, Davila Homes' signature craftsmanship is evident at every turn: timeless architecture, high-end finishes, an open-concept layout designed for effortless entertaining, and a gourmet kitchen appointed with state-of-the-art appliances. Every detail was thoughtfully curated and personalized through Davila's exclusive Design Center experience. The Grove is one of Oakland's most intimate and sought-after communities, featuring just 44 homesites surrounded by lush common areas, water features, walking trails, and bike paths. Minutes from the vibrant shops and dining of Downtown Winter Garden, top-rated West Orange County schools, and the beloved West Orange Trail, yet tucked away in the quiet charm of one of Central Florida's most historic small towns.
2065 WHITE FEATHER LOOP, OAKLAND, FL 34787
$539,900166 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, where this 2019 Meritage Home combines modern style, energy efficiency, and a thoughtfully designed layout for everyday comfort. Ideally situated approximately 30 minutes from Walt Disney World, Universal Orlando, and Downtown Orlando, the home provides convenient access to Central Florida's most popular destinations while preserving the peaceful atmosphere of an established neighborhood. Designed with functionality and flexibility in mind, this residence offers 3 bedrooms, 2.5 bathrooms, a two-car garage, and over 3,200 square feet of total living space. The open floor plan connects the living area, dining space, and gourmet kitchen, creating an inviting setting for daily living and entertaining. A spacious first-floor flex room offers endless possibilities as a home office, media room, formal living room, playroom, fitness space, guest room, or potential fourth bedroom. The gourmet kitchen features KitchenAid stainless steel appliances, quartz countertops, a custom tiled island, abundant cabinetry, and generous workspace while overlooking the main living and dining areas. High ceilings and oversized interior doors enhance the bright, open feel throughout the home. Upstairs, the primary suite includes a custom walk-in closet system and an ensuite bathroom. Additional bedrooms are generously sized, with ample storage throughout. Built with Meritage Homes' renowned energy-efficient construction, the home includes spray foam insulation, an advanced HVAC system with fresh-air intake and enhanced air purification, a combination metal and shingle roof, and a full gutter system. Enjoy the private courtyard, perfect for relaxing or entertaining. Oakland Trails offers scenic walking and biking trails, a community pool, clubhouse, dog park, beautifully maintained common areas, and top-rated schools. Historic Downtown Winter Garden, with its restaurants, breweries, boutiques, farmers market, and year-round events, is just minutes away. The property is well suited for long-term rental investment. For buyers with pet-related allergies or sensitivities, it may be helpful to know that no pets have lived in the home during the current ownership. A detailed list of builder upgrades and owner improvements will be provided to prospective buyers. Quality construction, flexible living, and an exceptional location make this move-in-ready home an outstanding opportunity in one of Winter Garden's most sought-after communities.
Listing is courtesy of: PINK MIAMI (305-504-0807)
Listing Agent: Denis Bochkov (754-248-4417)
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