20 listings found
812 JOHNS POINT DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 6 Bath · 4,373 SqFt · $629/SqFt
Days on Market: 21
County: Orange
Legal Subdivision Name: JOHNS COVE 43/104
Year built: 2001
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
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 ... Read more....»
1173 PRADO LANE
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 4,204 SqFt · $532/SqFt
Days on Market: 97
County: Orange
Legal Subdivision Name: GROVE AT THE HARVEST DISTRICT
Year built: 2026
Garage: Yes 3 vehicles
Private Pool: Yes
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 ... Read more....»
1146 PRADO LANE
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 3,992 SqFt · $534/SqFt
Days on Market: 97
County: Orange
Legal Subdivision Name: GROVE AT THE HARVEST DISTRICT
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
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 ... Read more....»
1258 RIDGE LAKE WAY
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 4 Bath · 4,557 SqFt · $460/SqFt
Days on Market: 91
Cumulative Days on Market: 452
County: Orange
Legal Subdivision Name: OAKLAND PARK
Year built: 2026
Garage: Yes 3 vehicles
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 ... Read more....»
1106 SARAH MATHEWS DRIVE
OAKLAND FL 34760
Residential / Single Family Residence
5 Bed · 5 Bath · 1 Half Bath · 3,596 SqFt · $549/SqFt
Days on Market: 10
County: Orange
Legal Subdivision Name: GROVE AT THE HARVEST DISTRICT
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
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 ... Read more....»
511 BRILEY AVENUE
OAKLAND FL 34760
Residential / Single Family Residence
5 Bed · 4 Bath · 1 Half Bath · 3,862 SqFt · $505/SqFt
Days on Market: 27
County: Orange
Legal Subdivision Name: BRILEY FARM PH 1A
Year built: 2026
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space. Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy layout. The main living areas seamlessly blend together, creating the perfect setting for entertaining, with a spacious great room flowing into a designer kitchen complete with a large island, walk-in pantry, and premium finishes. The primary suite, conveniently located on the main level, ... Read more....»
620 N TUBB STREET
OAKLAND FL 34760
Residential / Single Family Residence
6 Bed · 7 Bath · 1 Half Bath · 5,614 SqFt · $267/SqFt
Days on Market: 109
County: Orange
Legal Subdivision Name: OAKLAND
Year built: 1903
Garage: No
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 ... Read more....»
1412 JOHNS COVE LANE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 3,613 SqFt · $415/SqFt
Days on Market: 26
County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: JOHNS COVE
Year built: 2002
Garage: Yes 3 vehicles
Private Pool: Yes
Waterfront: Yes
Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! Pristine views of John's Chain, and full access from your incredible Boat House with dual power lifts. This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely reinvented since the current owners purchased it. Renovations include, a kitchen with all new appliances (2023), new granite countertops, additional lighting and a custom nook seating; enlargement of the 3-car garage door which now ... Read more....»
250 N WALKER STREET
OAKLAND FL 34760
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 2,469 SqFt · $525/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: OAKLAND TOWN
Year built: 2000
Garage: Yes 3 vehicles
Private Pool: Yes
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 ... Read more....»
1156 CIVITAS WAY
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 2,710 SqFt · $470/SqFt
Days on Market: 28
County: Orange
Legal Subdivision Name: OAKLAND PARKB-1
Year built: 2022
Garage: Yes 3 vehicles
Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes from historic downtown Winter Garden's acclaimed restaurants, boutique shops, and cultural venues, this home offers the perfect balance of serene outdoor living and convenient community access. The neighborhood is known for its resort-style amenities, including community pools and ... Read more....»
624 HULL ISLAND DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 2,708 SqFt · $330/SqFt
Days on Market: 156
County: Orange
Legal Subdivision Name: HULL ISLAND AT OAKLAND
Year built: 1983
Garage: Yes 2 vehicles
Lot Size (in acres): 2.55
Discover a rare opportunity to own a private estate property in one of West Orange County’s most desirable corridors. Situated in Oakland, this 2.55-acre parcel offers space, privacy, and future potential just minutes from the conveniences of West Colonial Drive, Florida Turnpike (Exit 275), Clermont, and the vibrant districts of Oakland and Downtown Winter Garden. Properties like this are increasingly difficult to find. The home sits in an unincorporated area, giving flexibility and freedom while still being close to everything that makes this area so special. Walk or bike to the West Orange Trail, enjoy easy access to local parks, ... Read more....»
8 WINTERS LANDING DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 2,850 SqFt · $311/SqFt
Days on Market: 4
County: Orange
Legal Subdivision Name: WINTERS LNDG PH 01 A D F & G
Year built: 2005
Garage: Yes 3 vehicles
One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), located in the heart of Oakland is just minutes from downtown Winter Garden. From the moment you step inside, you’ll appreciate the thoughtful design and elevated finishes throughout. This spacious home features a dedicated office, formal dining room, and formal living room—perfect for entertaining or creating flexible living spaces to fit your lifestyle. The open-concept layout seamlessly ... Read more....»
1231 FOLTZ LOOP
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 4 Bath · 1 Half Bath · 3,134 SqFt · $279/SqFt
Days on Market: 5
County: Orange
Legal Subdivision Name: HULL ISLAND/OAKLAND PH 2
Year built: 2022
Garage: Yes 2 vehicles
Community Pool: Yes
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. ... Read more....»
1970 STANDING ROCK CIRCLE
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 3 Bath · 3,528 SqFt · $226/SqFt
Days on Market: 132
County: Orange
Legal Subdivision Name: OAKLAND TRLS PH 2
Year built: 2019
Garage: Yes 3 vehicles
Community Pool: Yes
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 ... Read more....»
38 S POLLARD STREET
OAKLAND FL 34760
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 1,872 SqFt · $373/SqFt
Days on Market: 13
County: Orange
Legal Subdivision Name: OAKLAND TOWN
Year built: 2026
Garage: Yes 2 vehicles
Welcome to this beautifully crafted custom-built two-story home in the highly desirable Town of Oakland—offering the perfect blend of quality construction, modern design, and small-town charm with NO HOA. The thoughtfully designed floor plan features all main living areas on the first floor, including a spacious living room, dining area, and a well-appointed kitchen with high-quality appliances. French doors open to the back porch, and both front and back porches are finished with pavers. Additional highlights include a 2-car garage and generous storage under the stairs. Upstairs offers a versatile family room/bonus space, three secondary bedrooms with walk-in closets, and a full ... Read more....»
729 STRIHAL LOOP
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,583 SqFt · $190/SqFt
Days on Market: 35
Cumulative Days on Market: 180
County: Orange
Legal Subdivision Name: JOHNS LANDING PH 01 44/47
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
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 ... Read more....»
2065 WHITE FEATHER LOOP
OAKLAND FL 34787
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,089 SqFt · $263/SqFt
Days on Market: 48
Cumulative Days on Market: 82
County: Orange
Legal Subdivision Name: OAKLAND TRLS PH 2
Year built: 2019
Garage: Yes 2 vehicles
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, ... Read more....»
2259 WHITE FEATHER LOOP
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 2,204 SqFt · $238/SqFt
Days on Market: 41
County: Orange
Legal Subdivision Name: OAKLAND TRLS PH 1
Year built: 2017
Garage: Yes 2 vehicles
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, ... Read more....»
1270 STATIONSIDE DRIVE DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 2,046 SqFt · $254/SqFt
Days on Market: 49
County: Orange
Legal Subdivision Name: TRAILSIDE STATION REPLAT 44/23
Year built: 2002
Garage: Yes 2 vehicles
Private Pool: Yes
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.
1051 STATIONSIDE DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 2,120 SqFt · $231/SqFt
Days on Market: 2
County: Orange
Subdiv/Community Name: Not Applicable
Legal Subdivision Name: TRAILSIDE STATION
Year built: 2001
Garage: Yes 2 vehicles
Welcome to this beautifully maintained 4-bedroom, 3-bath home in the heart of Oakland, where everyday living feels connected, convenient, and just a little more elevated. This home enjoys amazing views of the Oakland Nature Preserve. Ideally located within walking distance to the West Orange Trail and just minutes from the charm of downtown Oakland and Winter Garden’s vibrant shops, dining, and weekly farmers market. Inside, the home opens to a flexible front room that works beautifully as a formal dining space, home office, or additional living area. From there, the layout flows into a spacious open-concept living area with volume ... Read more....»
The information relating to real estate for sale on this website comes in part from the My Florida Regional MLS DBA Stellar MLS. This information is provided exclusively for consumers' personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS.
