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34787 - O6419615 - 529 JOHNS LANDING WAY, OAKLAND, FL 34787 2 Days on yellowkey
$639,000 | Single Family Home | 4 beds | 3.0 baths | 2 gar
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)
34787 - O6419013 - 2101 GOPHER TORTOISE TER, OAKLAND, FL 34787 3 Days on yellowkey
$2,700 | Townhouse | 3 beds | 3.0 baths | 2 gar
Beautiful Townhome for rent now available in the sought after community of Longleaf at Oakland. This lovely, like new 3-bedroom, 3 bathroom townhome features one bedroom on the first floor. Open floor plan, overlooking the courtyard. On the second floor you’ll find the spacious Owner’s suite and guest bedroom each equipped with private bathrooms. This end unit open floorplan with an outside patio with a two-car garage. This townhome is in Oakland, just minutes away from Downtown Winter Garden and adjacent to West Orange Trail and Oakland Preserve. The community features sidewalks with a playground, and community pool with Cabanas. One Pet is allowed with a $350.00 pet deposit and carpet cleaning fee of $350.00. Pictures were taken prior the current tenants moved in.
Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)Listing Agent: Claudia D'Aquino (407-715-8810)
34787 - G5113959 - 2501 SKY STONE CT, OAKLAND, FL 34787 9 Days on yellowkey
$3,900 | Single Family Home | 4 beds | 2.5 baths | 2 gar
Beautifully maintained home in the desirable Oakland Trails community, ideally located on a quiet dead-end street with peaceful preserve views and no rear neighbors. The open layout features natural light, a spacious living area, a modern kitchen, and large, comfortable bedrooms. Enjoy community amenities, including a pool, playground, and walking paths, with direct access to the West Orange Trail. Just minutes from Downtown Wintergarden, Clermont, and major highways, including the Turnpike, 408, 429, and I-4. Move-in ready and easy to show
Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)Listing Agent: Lisa Reed (407-509-7995)
34787 - O6415350 - 710 REGINA CIR, OAKLAND, FL 34787 14 Days on yellowkey
$669,900 | Single Family Home | 5 beds | 4.0 baths | 3 gar
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)
34760 - O6405707 - 402 N POLLARD ST, OAKLAND, FL 34760 22 Days on yellowkey
$3,495,000 | Single Family Home | 5 beds | 5.5 baths | 3 gar
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)
34787 - O6413213 - 1143 HULL ISLAND DR, OAKLAND, FL 34787 24 Days on yellowkey
$749,000 Reduced | Single Family Home | 4 beds | 4.0 baths | 2 gar
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)
34787 - S5150852 - 2247 WHITE FEATHER LOOP, OAKLAND, FL 34787 28 Days on yellowkey
$457,900 | Single Family Home | 3 beds | 2.5 baths | 2 gar
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)
34760 - O6407615 - 1204 WATER MAPLE DR, OAKLAND, FL 34760 29 Days on yellowkey
$2,353,078 | Single Family Home | 4 beds | 5.0 baths | 3 gar
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.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)Listing Agent: Alexis Anderson (561-670-5901)
34760 - TB8513260 - 16 OAKLAND POINTE CIR, OAKLAND, FL 34760 29 Days on yellowkey
$799,999 | Single Family Home | 5 beds | 3.0 baths | 2 gar
Move-in-ready, airy and spacious 3,413-sq-ft home just two blocks from downtown Oakland, West Orange trail and directly across from Lake Apopka. Step into a home where character meets comfort and sophistication. Adorned with vibrant Tabebuia trees and blooming gardens, this property is a true gem. Every detail here tells a story of charm and warmth. Built in 1998 and fully updated with new flooring, new exterior and interior paint, modern lighting, fully renovated bathrooms, all brand new windows, newer roof, AC unit, and drainfield (within the last five years). Spacious layout perfect for entertaining, or working from home. Close proximity to A-rated schools. Enjoy lake views, walkable access to parks and recreation, and a prime location in one of Central Florida’s most desirable small town. House comes with golf cart, perfect for golf cart township. Minutes to downtown Winter Garden. One or more of the pictures have been virtually staged.
Listing is courtesy of: JACK KELLER INC (727-586-1497)Listing Agent: John Keller, Iii (727-586-1497)
34787 - G5112905 - 14001 RUGBY ST, OAKLAND, FL 34787 30 Days on yellowkey
$825,000 Reduced | Single Family Home | 5 beds | 4.0 baths | 2 gar
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)
34760 - O6408609 - 100 W RAILWAY AVE, OAKLAND, FL 34760 40 Days on yellowkey
$2,186,921 | Single Family Home | 3 beds | 5.0 baths | 3 gar
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)
34787 - O6407380 - 1108 RIVERWAY DR, OAKLAND, FL 34787 43 Days on yellowkey
$1,025,000 | Single Family Home | 5 beds | 3.0 baths | 2 gar
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)
34787 - G5112107 - 1216 HULL ISLAND DR, OAKLAND, FL 34787 45 Days on yellowkey
$1,799,000 | Single Family Home | 5 beds | 4.5 baths | 3 gar
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)
34787 - O6404554 - 918 HULL ISLAND DR, OAKLAND, FL 34787 51 Days on yellowkey
$729,900 | Single Family Home | 4 beds | 3.0 baths | 2 gar
Under contract-accepting backup offers. Welcome to this beautifully designed POOL home in the highly desirable WATERFRONT community of Hull Island in Oakland, where residents enjoy a lifestyle rich in amenities, including a scenic walking dock, community park, playground, dog park, and resort-style pool. This thoughtfully designed four bedroom - 3 bath home offers a functional and private split floor plan ideal for both everyday living and hosting guests. At the front of the home, a guest bedroom features its own en-suite bath—perfect for visitors or multi-generational living. Toward the rear of the home, the primary suite serves as a peaceful retreat, ideally positioned to overlook the pool and capture stunning SUNSET views. The suite includes a spacious spa-like bath with two separate vanities, quartz counters, a shower, two walk-in closets, including an expansive walk-in closet that conveniently connects directly to the laundry room for added ease and efficiency. The remaining two bedrooms are well-sized and share a full bath, creating a comfortable and versatile layout. Throughout the home, you’ll find tasteful customizations including upgraded lighting and stylish accent walls that add warmth and character, all while maintaining a clean, modern aesthetic. The kitchen has been beautifully updated with quartz countertops, under cabinet lighting, tile backsplash, stainless appliances, including a GE CAFE refrigerator, cooktop, built-in microwave and oven, and generous prep and gathering space—perfect for entertaining or casual family meals. Step outside to your private backyard oasis with no rear neighbors, offering enhanced privacy and tranquility. The SALTWATER pool invites year-round enjoyment, while the covered lanai, travertine decking, and screened enclosure create the perfect setting for relaxing—Florida style. As a bonus, the lanai is plumbed for an outdoor kitchen and ready to be connected! The two car garage features durable epoxy flooring, offering a clean, polished look. Turnkey and meticulously maintained, this home is everything you’ve dreamed about. Combining thoughtful design, premium upgrades, and a prime location, this property truly embodies the best of Florida living. The community itself is a haven for nature lovers, with a sparkling POOL, charming gazebo, and a picturesque boardwalk leading to a fishing pier offering breathtaking views of Lake Apopka. Enjoy the park, playground, dog park, and a private entrance to the 120+ acre Oakland Nature Preserve, complete with winding trails. For those who appreciate outdoor adventure, the 22-mile West Orange Trail is nearby, as well as easy access to major highways (Turnpike, 408, 429), shopping, dining, three vibrant towns (Clermont, Oakland, and historic downtown Winter Garden), golf courses, tennis and pickleball courts, and Orlando’s world-class amenities, including the international airport, theme parks, and beaches. This is more than just a home—it's a lifestyle. Seize this rare opportunity to own your own slice of PARADISE.
34760 - O6402288 - 1137 PRADO LN, OAKLAND, FL 34760 53 Days on yellowkey
$2,395,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
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, and a spacious loft across 3,712 square feet of elegantly curated living space—where classic design meets modern sophistication in the main house. Enhancing both versatility and privacy, the property also includes a beautifully appointed 785 square foot garage casita with its own private entrance, complete with a living room, kitchenette, bedroom, and full bathroom—ideal for guests, multigenerational living, or a private home office retreat. 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.
34787 - O6400317 - 505 E GULLEY AVE, OAKLAND, FL 34787 63 Days on yellowkey
$865,000 Reduced | Single Family Home | 4 beds | 3.5 baths | 3 gar
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)
34787 - O6402045 - 2017 BOSS HEWETT ST, OAKLAND, FL 34787 63 Days on yellowkey
$724,900 Reduced | Single Family Home | 4 beds | 4.0 baths | 2 gar
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)
34787 - O6401756 - 219 LARGOVISTA DR, OAKLAND, FL 34787 64 Days on yellowkey
$1,059,000 Reduced | Single Family Home | 5 beds | 4.0 baths | 2 gar
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)
34787 - O6398113 - 1937 STANDING ROCK CIR, OAKLAND, FL 34787 72 Days on yellowkey
$499,000 Reduced | Single Family Home | 3 beds | 2.5 baths | 2 gar
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)
34760 - G5110973 - 250 N WALKER ST, OAKLAND, FL 34760 73 Days on yellowkey
$1,145,000 Reduced | Single Family Home | 4 beds | 2.5 baths | 3 gar
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)
34787 - O6397651 - 17802 JEFFERSON ST, OAKLAND, FL 34787 78 Days on yellowkey
$2,595 | Single Family Home | 4 beds | 2.0 baths | 2 gar
Spacious 4 Bedroom, 2 Bath Split Plan Lake View House with Oversized Corner Lot. Owner has recently updated Home. New Paint on Interior. Tile throughout Home. Fireplace has Granite Hearth and Travertine Facing. Newer Custom Kitchen with granite tops, tumbled marble back splash with decorative tiles. Newer Stainless Steel Appliances. Master bath has Frameless Shower Door. No Sewer Bill. No Water Bill. Tenant maintained Water Softener Unit. Fenced in Back Yard! House is a short walking distance from John's Lake. Easy access to Florida Turnpike and I 4. Easy proximity to Boat Launch. This Boater's Paradise won't last long! Lawn Care Optional at $125/mo.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)Listing Agent: Barry Stephens (407-547-6500)
34787 - O6395167 - 15992 W COLONIAL DR, OAKLAND, FL 34787 87 Days on yellowkey
$3,200,000 | Apartment | 41 beds
15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily Opportunity Exceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland. Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style residences, mobile home/RV units, and additional rental pads, creating multiple income streams and long-term upside. Currently generating $34,860 per month in gross rental income the property delivers immediate cash flow while offering significant future value-add and redevelopment potential. Located just minutes from the Florida Turnpike interchange, Downtown Winter Garden, Clermont, and the greater Orlando employment hubs, this site sits directly in the path of West Orange’s continued expansion. The C-1 zoning and strategic frontage on SR-50 make this an especially compelling opportunity for investors seeking stable income today with the flexibility for future repositioning. Whetherd workforce housing and RV income asset, repositioned into a boutique rental community, or held for future redevelopment, opportunities with this combination of location, scale, frontage, and in-place revenue are increasingly rare. (Seller is selling 112 units in total varying in diffrent locations this is 32 of those 112)
Listing is courtesy of: REMAX SUNSTATE REALTY (416-450-7436)Listing Agent: Kyler Moreland (407-496-4196)
34760 - O6394442 - 38 S POLLARD ST, OAKLAND, FL 34760 88 Days on yellowkey
$629,999 Reduced | Single Family Home | 4 beds | 2.5 baths | 2 gar
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)
34787 - O6393970 - 1231 FOLTZ LOOP, OAKLAND, FL 34787 90 Days on yellowkey
$874,900 | Single Family Home | 4 beds | 4.5 baths | 2 gar
Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living area. The upgraded gourmet kitchen is a standout, featuring stainless steel GE Profile appliances, a gas range, quartz countertops, ceiling-height cabinetry, and a stunning oversized waterfall island with seating that overlooks the breakfast nook and family room. Perfect for entertaining, the main living space is filled with natural light from three large sliding doors that open to a covered lanai and private backyard, complete with a full outdoor bathroom. The first-floor primary suite serves as a relaxing retreat, offering a spa-like bathroom with dual vanities, a spacious shower, garden tub, and a generous walk-in closet. Upstairs, you will find three additional bedrooms and two bathrooms, including a secondary bedroom with a private en-suite, ideal for guests or multi-generational living. The expansive bonus/game room provides a versatile space for a home theater, gym, playroom, or lounge. This home is thoughtfully enhanced with wood-look tile flooring throughout the first floor, upgraded designer lighting, modern ceiling fans, decorator finishes, and abundant storage. Enjoy an elevated audio experience with integrated surround sound in the living room, lanai, primary suite, and upstairs bonus room, featuring built-in in-ceiling speakers for immersive TV and music throughout. Smart home features include Ecobee thermostats, a Ring doorbell, and a garage EV charger. Additional upgrades include 8-foot raised panel doors, a tankless gas water heater, an interior laundry room with utility sink and gas washer and dryer hookup, outdoor kitchen and pool prewiring, and a whole-house water softener. Residents of Hull Island enjoy resort-style amenities, including a pool and clubhouse, playground, dog park, dock, and fishing pier. Ideally located near the West Orange Trail, historic downtown Winter Garden, and Clermont’s lakefront dining, this home offers convenient access to shopping, dining, weekly farmers markets, major roadways, and Central Florida attractions. This is more than a home, it is a private retreat offering comfort, style, and an exceptional location.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)Listing Agent: Elisabeth Rusnak (845-729-5042)
34787 - O6393574 - 812 JOHNS POINT DR, OAKLAND, FL 34787 91 Days on yellowkey
$2,699,000 Reduced | Single Family Home | 5 beds | 6.0 baths | 3 gar
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)
34787 - O6385739 - 2117 GOPHER TORTOISE TER, OAKLAND, FL 34787 91 Days on yellowkey
$360,000 Reduced | Townhouse | 2 beds | 2.5 baths | 2 gar
PRICE Improvement PLUS seller concessions of HOA dues paid for the first year for the new buyer. 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)
34787 - O6391735 - 1412 JOHNS COVE LN, OAKLAND, FL 34787 98 Days on yellowkey
$1,548,000 Reduced | Single Family Home | 4 beds | 4.5 baths | 3 gar
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)
34787 - O6389319 - 1318 PAINTED BUNTING AVE, OAKLAND, FL 34787 108 Days on yellowkey
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)
34787 - O6376429 - 1270 STATIONSIDE DRIVE DR, OAKLAND, FL 34787 128 Days on yellowkey
$509,000 Reduced | Single Family Home | 4 beds | 2.0 baths | 2 gar
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)
34787 - O6381627 - 2259 WHITE FEATHER LOOP, OAKLAND, FL 34787 134 Days on yellowkey
$525,000 | Single Family Home | 4 beds | 2.5 baths | 2 gar
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)
34760 - O6375487 - 1106 SARAH MATHEWS DR, OAKLAND, FL 34760 136 Days on yellowkey
$1,975,000 | Single Family Home | 5 beds | 5.5 baths | 2 gar
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 is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)Listing Agent: Heather Spirazza (407-757-6022)
34787 - O6381069 - 729 STRIHAL LOOP, OAKLAND, FL 34787 137 Days on yellowkey
$679,900 | Single Family Home | 4 beds | 3.5 baths | 2 gar
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)
34787 - O6379741 - 2065 WHITE FEATHER LOOP, OAKLAND, FL 34787 141 Days on yellowkey
$539,900 Reduced | Single Family Home | 3 beds | 2.5 baths | 2 gar
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)
34787 - O6374216 - 2100 GOPHER TORTOISE TER, OAKLAND, FL 34787 152 Days on yellowkey
$375,000 | Townhouse | 2 beds | 2.5 baths | 2 gar
Imagine coming home to a space that feels open, comfortable, and perfectly placed for everyday life. This corner-unit townhome in the desirable Longleaf at Oakland community offers added privacy, abundant natural light, and a thoughtfully designed layout that truly works for today’s lifestyle. Inside, the home features a clean, modern feel with plank vinyl flooring, granite countertops, and recessed lighting, creating a space that’s both stylish and easy to maintain. The open-concept main living area flows seamlessly, making it ideal for daily living and entertaining. Upstairs, a versatile loft provides the perfect bonus space for a home office, playroom, or second living area. Step outside to a private courtyard-style patio, ideal for grilling, relaxing, or enjoying your morning coffee—an inviting outdoor space that adds to the home’s functionality and charm. Life in Longleaf at Oakland extends beyond the home itself. Residents enjoy a community pool and playground, perfect for relaxing weekends and family fun. Outdoor enthusiasts will appreciate being close to nearby nature trails, offering scenic walks and bike rides just minutes from home. With quick access to major highways, commuting is simple while still enjoying a peaceful residential setting. You’re conveniently located near shopping, dining, downtown Winter Garden, and everyday essentials—making this an excellent place to call home. This move-in-ready corner unit offers comfort, convenience, and a lifestyle that’s hard to beat. Schedule your private showing and experience it for yourself.
Listing is courtesy of: MARKET CONNECT REALTY LLC (407-250-4708)Listing Agent: Stiliany Collado Llc (407-285-3968)
34787 - O6373776 - 1258 RIDGE LAKE WAY, OAKLAND, FL 34787 162 Days on yellowkey
$2,098,000 | Single Family Home | 4 beds | 4.0 baths | 3 gar
Pre-Construction. To be built. Pre-Construction. To be built. A Custom home in the Reserve of the sought-after Oakland Park community. This is a RCB Homes custom-built two story, four-bedroom, four-bath floor plan that you will customize with all the luxury finishes you will pick yourself! The floorplan is an open concept design, but you can still make changes to the floorplan if you want! The lot affords beautiful views of Lake Apopka on a secluded cul-de-sac. The community is conveniently located minutes away from downtown Winter Garden, with a plethora of restaurants, shopping, and more. If outdoor recreation is up your alley, enjoy the various walking trails in the community or explore the 22-mile paved West Orange Trail connecting Oakland/Winter Garden to Apopka! Seize your opportunity to become a part of the luxury lifestyle inside Oakland Park with its multiple community living spaces, pools, playgrounds, and more. Don't settle for a community or home that doesn't have your wants and needs; build this home one to your specifications. Call us to find out more!
Listing is courtesy of: NEW HOMES REAL ESTATE, INC. (407-947-2475)Listing Agent: Chris Herlihy (407-947-2475)
34760 - O6362142 - 620 N TUBB ST, OAKLAND, FL 34760 217 Days on yellowkey
$1,499,000 | Single Family Home | 6 beds | 7.5 baths | 4 car
PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living room/ lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. The Oakland Manor House is conveniently located within 30 minutes of downtown Orlando, Disney, and Universal Studios. The West Orange Trail runs through the neighborhood. Easy biking distance to Winter Garden, which offers restaurants, farmer’s market, brewery, and music venues. The Oakland Nature Preserve is another nearby treasure. This is a unique opportunity to own a part of Oakland's history. Bring your business ideas or reside in your own retreat. The sky is the limit!
Listing is courtesy of: OAKSTRAND REALTY (888-912-5258)Listing Agent: Jennifer Wilson (407-921-9977)
34787 - O6361226 - 1970 STANDING ROCK CIR, OAKLAND, FL 34787 219 Days on yellowkey
$796,000 | Single Family Home | 5 beds | 3.0 baths | 3 gar
Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new.” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, ideal for high-speed connectivity. The DREAM KITCHEN is a showstopper with stylish cabinetry, stone countertops, a breakfast bar, built-in oven, cooktop stove with POT FILLER, tile backsplash, walk-in pantry, and a GALLEY-STYLE COFFEE BAR AREA—perfect for morning routines or entertaining. A spacious Kitchen dinette area overlooks the backyard, adding a warm and functional touch to the heart of the home. In the Living room, enjoy a CUSTOM ACCENT WALL (2023) and views of the large backyard through dual sliding glass doors. A separate Dining room offers flexibility for family gatherings or can easily serve as a formal living room. The first floor also includes a VERSATILE OFFICE/PLAYROOM, convenient under-stair storage, and ONE OF THE FIVE BEDROOMS—complete with laminate wood flooring—located next to a full bathroom, providing a perfect space for guests or multigenerational living. Upstairs, a GENEROUS LOFT creates a perfect secondary living area. The UPDATED PRIMARY SUITE (2025) features a beautiful tray ceiling, a LUXURIOUS EN SUITE BATH with dual vanities, a step-in shower, and a huge walk-in closet. Three additional bedrooms and another full bath offer plenty of comfortable space for family and guests. A paver driveway leads to the generous 3-CAR GARAGE featuring epoxy flooring, additional kitchen-style cabinetry, and PREWIRING for an electric vehicle. Outside, enjoy a large covered patio and an EXPANSIVE BACKYARD, ideal for future customization, gatherings, or play. Oakland Trails is loved for its peaceful setting and small-town charm, offering access to the West Orange Trail, playgrounds, green spaces, and TOP-RATED SCHOOLS. Ideally positioned near DOWNTOWN WINTER GARDEN, residents enjoy quaint dining and gatherings spots, PLANT STREET MARKET, charming shops, and easy access to SR 429 for seamless commuting. Every detail has been thoughtfully crafted for ELEVATED LIVING—come experience the exceptional quality and SOPHISTICATION this home offers. Schedule your showing today!
Listing is courtesy of: WEMERT GROUP REALTY LLC (407-743-8356)Listing Agent: Jenny Wemert (407-809-1193)
34787 - O6359354 - 1146 PRADO LN, OAKLAND, FL 34787 223 Days on yellowkey
$2,130,760 | Single Family Home | 5 beds | 5.5 baths | 2 gar
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.
34787 - O6359359 - 1173 PRADO LN, OAKLAND, FL 34787 223 Days on yellowkey
$2,238,120 | Single Family Home | 5 beds | 5.5 baths | 3 gar
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.
34787 - O6316643 - 1207 RIDGE LAKE WAY, OAKLAND, FL 34787 382 Days on yellowkey
$1,700,000 | Single Family Home | 5 beds | 3.5 baths
Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours - YOUR WAY! The Oakland Park subdivision is a short walk on the West Orange Trail to downtown Winter Garden. Enjoy easy access to the community pool & clubhouse, dining, shopping & entertainment. This is luxury living at its best. Call us to discuss your options!