23 listings found
510 BRILEY AVENUE
OAKLAND FL 34760
Residential / Single Family Residence
5 Bed · 5 Bath · 2 Half Baths · 5,478 SqFt · $653/SqFt
Days on Market: 26
County: Orange
Legal Subdivision Name: BRILEY FARM PH 1A
Year built: 2025
Garage: Yes 4 vehicles
Private Pool: Yes
Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two laundry rooms, and a detached casita with a full ensuite—ideal for guests, in-laws, or extended stays. Inside, the home showcases elevated finishes at every turn, including Sierra Pacific windows—62 in total—filling the home with natural light, an impressive ... Read more....»
312 BRILEY AVENUE
OAKLAND FL 34760
Residential / Single Family Residence
6 Bed · 6 Bath · 1 Half Bath · 5,144 SqFt · $582/SqFt
Days on Market: 47
County: Orange
Legal Subdivision Name: BRILEY FARM
Year built: 2025
Garage: Yes 4 vehicles
Private Pool: Yes
Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully curated for comfort, sophistication, and style. From the moment you arrive, the home commands attention with its architectural presence and grand entryway. Inside, soaring ceilings, designer finishes, and expansive living spaces create a refined yet inviting atmosphere. The heart of the home is the gourmet chef’s kitchen, seamlessly ... Read more....»
1118 SARAH MATHEWS DRIVE
OAKLAND FL 34760
Residential / Single Family Residence
4 Bed · 4 Bath · 2 Half Baths · 3,902 SqFt · $589/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: GROVE AT THE HARVEST DISTRICT
Year built: 2025
Garage: Yes 3 vehicles
Private Pool: Yes
Situated within the exclusive Grove community, this custom-built La Cascina residence by Pioneer Builders delivers refined luxury and exceptional craftsmanship throughout. Offering 4 bedrooms, 6 bathrooms, and 3,902 square feet of thoughtfully designed living space, this new construction home blends timeless design with modern comfort. The open-concept floor plan features expansive living and dining areas highlighted by vaulted ceilings in the living room, a fireplace, and seamless indoor-outdoor flow. The gourmet kitchen showcases premium finishes and connects effortlessly to the main living spaces, making it ideal for both everyday living and entertaining. A private office provides a dedicated space for work ... 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: 1
County: Orange
Legal Subdivision Name: GROVE/OAKLAND
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: 1
County: Orange
Legal Subdivision Name: GROVE/OAKLAND
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....»
1207 RIDGE LAKE WAY
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,909 SqFt · $435/SqFt
Days on Market: 158
County: Orange
Complex/CommunityName: OAKLAND PARK RESERVE
Legal Subdivision Name: OAKLAND PARK
Year built: 2026
Garage: Yes 3 vehicles
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. ... Read more....»
620 N TUBB STREET
OAKLAND FL 34760
Residential / Single Family Residence
6 Bed · 7 Bath · 1 Half Bath · 5,614 SqFt · $294/SqFt
Days on Market: 48
County: Orange
Legal Subdivision Name: OAKLAND
Year built: 1903
Garage: No
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 ... Read more....»
101 N STARR STREET
OAKLAND FL 34760
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 2,502 SqFt · $580/SqFt
Days on Market: 73
County: Orange
Legal Subdivision Name: OAKLAND TOWN
Year built: 2020
Garage: Yes 3 vehicles
Private Pool: Yes
Seller is offering First Mortgage Owner Financing up to $750,000 at 4.3% interest rate with a 3-year Balloon structure, to be organized by a real estate attorney. Welcome to 101 N Starr Street, an exceptional single-story, custom-built residence nestled in the heart of historic Oakland, Florida—where timeless craftsmanship, luxurious finishes, and everyday convenience blend effortlessly. Set beneath a canopy of majestic, centuries-old oaks, this meticulously designed home offers a rare combination of elegance, comfort, and accessibility. With a spacious open floor plan, soaring 14-foot ceilings, and oversized 8-foot doors throughout, the home is both grand in scale and thoughtfully functional. Fully ... Read more....»
4361 NE 13TH TERRACE
OAKLAND PARK FL 33334
Residential / Single Family Residence
3 Bed · 3 Bath · 1 Half Bath · 2,455 SqFt · $407/SqFt
Days on Market: 78
County: Broward
Legal Subdivision Name: CORAL HEIGHTS SEC 2 45-8 B
Year built: 1959
Garage: Yes 2 vehicles
Private Pool: Yes
Welcome to this beautifully renovated 3BR/3BA home in Oakland Park, FL, Broward County, offering spacious living and thoughtful updates. Vaulted ceilings and a large living room create an open, inviting atmosphere, while the huge kitchen features granite countertops, stainless steel appliances, and abundant cabinetry—perfect for everyday living or entertaining. The generous primary suite includes a private bath, and the split floor plan ensures comfort for family or guests. Outdoors, enjoy your private retreat with a heated pool, jacuzzi, open patio, plant beds, and an unfinished cabana bath ready for customization. Relax on the covered front porch or take advantage of ... Read more....»
624 HULL ISLAND DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 2,708 SqFt · $369/SqFt
Days on Market: 45
County: Orange
Legal Subdivision Name: HULL ISLAND AT OAKLAND
Year built: 1983
Garage: Yes 2 vehicles
Lot Size (in acres): 2.55
Find out about the unique chance to be the owner of a 2,700 sqft home which sits on 2.55 private acres which we think is the ideal setting for space, privacy, and great growth. This 1983 built home has been very well preserved in it’s original condition which makes it the perfect choice for buyers who are after land, character and the freedom to update the home to suit their own style. In the home you’ll find a large open floor plan which has high vaulted ceilings and large picture windows that allow in lots of natural light. We have ... Read more....»
501 E OAKLAND AVENUE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 1 Half Bath · 3,448 SqFt · $254/SqFt
Days on Market: 60
County: Orange
Legal Subdivision Name: WINTERS LNDG PH 01 A D F & G
Year built: 2007
Garage: Yes 3 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue Charter School and minutes from Historic Downtown Winter Garden, where you can explore boutique shops, award-winning restaurants, and the scenic West Orange Trail. Inside, the thoughtfully designed layout features primary suites on both the first and second floors, ... Read more....»
1970 STANDING ROCK CIRCLE
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 3 Bath · 3,528 SqFt · $227/SqFt
Days on Market: 51
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....»
2451 SKY STONE COURT
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,007 SqFt · $244/SqFt
New Listing!!! Days on Market: 1
County: Orange
Legal Subdivision Name: OAKLAND TRLS PH 1
Year built: 2020
Garage: Yes 2 vehicles
Welcome to Oakland Trails, a beautiful and well-established community located in the charming, small-town City of Oakland. This spacious 5-bedroom, 3.5-bath home features a thoughtfully designed layout offering flexibility, comfort, and room to grow—perfect for today’s lifestyle.From the moment you enter, you are welcomed by a cozy Great Room and formal Dining Room, highlighted by a modern staircase with sleek railing, setting the tone for the home’s contemporary design. The layout flows seamlessly into the open-concept Living Room and upgraded Kitchen, ideal for entertaining and everyday living. The kitchen features stylish upgrades, ample cabinetry, generous counter space, and a beautiful ... Read more....»
2450 STANDING ROCK CIRCLE
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 4 Bath · 3,163 SqFt · $226/SqFt
Days on Market: 52
County: Orange
Legal Subdivision Name: OAKLAND TRAILS
Year built: 2019
Garage: Yes 2 vehicles
Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or relaxing with friends. Go outside to your extended patio and unwind with morning coffee or evening wine, all while enjoying privacy of no rear neighbors. Upgrades abound, including a gourmet kitchen with granite countertops, stainless steel appliances and elegant luxury vinyl flooring, designed with comfort and efficiency in ... Read more....»
729 STRIHAL LOOP
OAKLAND FL 34787
Residential / Single Family Residence
5 Bed · 3 Bath · 1 Half Bath · 3,381 SqFt · $207/SqFt
Days on Market: 24
Cumulative Days on Market: 114
County: Orange
Legal Subdivision Name: JOHNS LANDING PH 01
Year built: 2001
Garage: Yes 2 vehicles
Private Pool: Yes
One or more photo(s) has been virtually staged. Experience the height of Florida luxury in this stunningly renovated 5-bedroom pool home, nestled within an exclusive gated community featuring a private boat ramp and lake access. Boasting soaring ceilings, quartz countertops, and a striking panoramic landing, this residence blends architectural elegance with modern sophistication. Peace of mind is built-in with a brand-new roof, new A/C, and fresh designer paint inside and out. The main-level primary suite offers a serene escape, while the meticulously renovated garage has been transformed into a pristine, high-end showroom that must be seen to be believed. Outside, ... Read more....»
529 JOHNS LANDING WAY
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 2,650 SqFt · $247/SqFt
Days on Market: 107
County: Orange
Legal Subdivision Name: JOHNS LANDING PH 02 48 138
Year built: 2004
Garage: Yes 2 vehicles
Private Pool: Yes
Waterfront: Yes
Welcome to your dream home in a prestigious gated community! This stunning 4-bedroom, 3-bathroom house offers 2,650 square feet of comfortable living space designed for both relaxation and entertainment. The thoughtfully designed layout includes a versatile fourth bedroom that can easily serve as a mother-in-law suite, perfect for multi-generational living or hosting extended guests. The primary bedroom provides a peaceful retreat with ample space and natural light throughout. New Roof 2022 & New AC 2025! Step outside to discover your personal oasis featuring a screened-in solar-heated pool area with a generous patio – ideal for year-round Florida living and entertaining. The ... Read more....»
326 LARGOVISTA DRIVE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 3,182 SqFt · $204/SqFt
Days on Market: 125
County: Orange
Legal Subdivision Name: JOHNS LANDING PH 02 48 138
Year built: 2004
Garage: Yes 3 vehicles
Private Pool: Yes
Welcome to your dream home in the highly sought-after Johns Landing community! This immaculate 4-bedroom, 3-bathroom residence offers a perfect blend of elegance, comfort, and convenience—nestled in the heart of charming Oakland, FL. From the moment you step inside, you’ll be greeted by soaring ceilings, abundant natural light, and an open-concept layout ideal for both entertaining and everyday living. This home has been meticulously maintained-- with fresh exterior paint, 2 nest thermostats, engineered hardwood flooring, electric water heater 2024, upgrades to bathrooms, new roof in 2021 and more! The chef’s kitchen boasts granite countertops, stainless steel appliances, and a spacious ... Read more....»
847 CURA COURT
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 3 Bath · 3,000 SqFt · $215/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: JOHNS LANDING PH 01 44/47
Year built: 2002
Garage: Yes 3 vehicles
Welcome to this beautifully maintained home located in the gated waterfront community of John’s Landing, nestled along the scenic 2,600-acre John’s Lake chain. This property offers a blend of upgraded features, generous living spaces, and an exceptional community lifestyle. A brand-new roof will be delivered at closing, as the replacement process is already underway through the insurance company. Step inside to a bright foyer and sitting area, enhanced by custom in-wall built-ins, crown molding, and shutters or blinds in every room. Additional features include upgraded ceiling fans, a fire wood fireplace, an intercom system, pre-wiring for a security system, and a ... Read more....»
2065 WHITE FEATHER LOOP
OAKLAND FL 34787
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,089 SqFt · $268/SqFt
Days on Market: 3
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 exceptional 2019 Meritage Home offers a blend of luxury, convenience, and modern living. Situated just 30 minutes from Orlando’s top attractions like Disney, Universal, and Downtown, this home is perfectly located for both entertainment and tranquility. The Oakland Trails community is known for its top-rated schools, extensive walking and biking trails, a clubhouse, and easy access to the charming Old Town Winter Garden with its array of restaurants, breweries, and shops. The community offers a pool, dog park, and a welcoming atmosphere, all while providing a spacious environment with wide lots ... Read more....»
2755 BOBCAT CHASE BOULEVARD
OAKLAND FL 34787
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 1,822 SqFt · $272/SqFt
Days on Market: 190
County: Orange
Legal Subdivision Name: LONGLEAF/OAKLAND REP
Year built: 2020
Garage: Yes 2 vehicles
Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a large pantry, and a functional layout ideal for everyday living or entertaining. Upstairs, the bonus room provides flexible space for an office, media room, or play area. The primary suite includes a walk-in closet and private bath ... Read more....»
2135 STANDING ROCK CIRCLE
OAKLAND FL 34787
Residential / Single Family Residence
3 Bed · 2 Bath · 1 Half Bath · 2,078 SqFt · $238/SqFt
Days on Market: 1
County: Orange
Legal Subdivision Name: OAKLAND (291003127)
Year built: 2020
Garage: Yes 2 vehicles
ASSUMABLE 2.4% Interest Rate. Welcome to this beautifully appointed single-family home located in the charming town of Oakland, FL. Offering 3 bedrooms, 2.5 bathrooms, and 2,078 square feet of thoughtfully designed living space, this home features an open floor plan that’s perfect for both everyday living and entertaining. The spacious layout is complemented by an upstairs loft, ideal for a home office, media room, or additional living area, while abundant natural light enhances the modern, airy feel throughout. This home is loaded with high-end upgrades and smart-home features. Venetian blinds are installed throughout, including app-controlled motorized blinds on the dramatic high windows ... Read more....»
717 STRIHAL LOOP
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 2,065 SqFt · $232/SqFt
Days on Market: 23
County: Orange
Legal Subdivision Name: JOHNS LANDING PH 01 44/47
Year built: 2002
Garage: Yes 2 vehicles
Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and inviting atmosphere. To the left, a spacious living and dining room combination provides an ideal setting for entertaining and offers convenient access to the kitchen. The kitchen is well-appointed with solid wood cabinetry, granite countertops, stylish backsplash, a breakfast bar, ... Read more....»
2435 STANDING ROCK CIRCLE
OAKLAND FL 34787
Residential / Single Family Residence
4 Bed · 2 Bath · 1 Half Bath · 2,017 SqFt · $234/SqFt
Days on Market: 152
County: Orange
Legal Subdivision Name: OAKLAND TRLS PH 1
Year built: 2017
Garage: Yes 2 vehicles
Perfectly situated in the desirable Oakland Trails neighborhood this perfectly updated and maintained home is a turnkey away from being yours! 4 bed, 2.5 bath, the primary bed in the second level. The landscape perfectly accentuates your front porch. Step inside your fully upgraded home; complete with luxury upgrades ranging from lighting, designer finishes, and brand-name appliances. Up the stairs, you will find an upgraded railing and an accent wall leading you to four oversized bedrooms, two full bathrooms. The floor plan upstairs is split surrounding your flex/loft space allowing plenty of privacy and space for everyone. The primary suite ... 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.
