88

Oakland, FL Homes for Sale

Section Image
  • /30

    $585,000

    • 4 Beds
    • 2 Baths
    • 2,490 Sq Ft

    610 Strihal Loop, Oakland, FL 34787

    Welcome to your beautifully updated home in the coveted gated community of John’s Landing in Oakland, Florida! Nestled near the shores of Johns Lake, this stylish residence combines modern upgrades with timeless appeal, all in one of Central Florida’s most desirable locations.Step inside to discover an open and airy floor plan, highlighted by a completely renovated kitchen featuring sleek

    Julie Arnold REAL BROKER, LLC

    610 Strihal Loop, Oakland, FL 34787
  • /63

    $495,000

    • 4 Beds
    • 2 Baths
    • 1,681 Sq Ft

    312 W Hull Ave, Oakland, FL 34760

    Welcome to this beautifully updated 4-bedroom, 2-bath home located in the heart of Oakland.Nestled in the golf cart district of the charming local town, this home has the blend of small-town charm and modern convenience.Within a short 10-minute walk, youll enjoy local shopping, the West Orange Biking Trail, and a quaint downtown area. Conveniently located 2 miles from the main highway

    Steven Koleno BEYCOME OF FLORIDA LLC

    312 W Hull Ave, Oakland, FL 34760
  • /9

    $780,000

    • Land
    • 0.39 Acre
    • $2,000,000 per Acre

    1281 Ridge Lake Way, Winter Garden, FL 34787

    LOT 258 final opportunity to build your dream custom home in Oakland Park!!!! Such a charming golf cart community along Lake Apopka and the West Orange Trail. This is the last lake lot on well known Lake Apopka of the final phase. Don't miss your chance to build your dream lake front home that is only 2 miles from adorable Downtown Winter Garden, and 20 minutes to world famous theme parks or 30

    Samantha Andrade KELLER WILLIAMS ELITE PARTNERS III REALTY

    1281 Ridge Lake Way, Winter Garden, FL 34787
  • /26

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,419 Sq Ft

    310 E Gulley Ave, Oakland, FL 34760

    Welcome to 310 E Gulley Ave—this inviting 3-bedroom, 2-bathroom home offers the perfect blend of comfort and character in the heart of Oakland, FL. Set on a spacious lot surrounded by mature trees, this property features a private pool, cozy wood-burning fireplace, and a deep garage ideal for extra storage or workshop space.Inside, enjoy a warm and functional layout with 1,419 sq ft of

    Liam Lugo LPT REALTY, LLC

    310 E Gulley Ave, Oakland, FL 34760
  • /35

    $648,900

    • 4 Beds
    • 3 Baths
    • 2,268 Sq Ft

    1382 Foltz Loop, Oakland, FL 34787

    ***ASSUMABLE VA MORTGAGE AT A 5.375 INTEREST RATE*** Absolute model condition—and that’s not said lightly. From the moment you arrive, the charm and care put into this home are undeniable. A cozy front porch with ample seating and attractive brick pavers sets the tone, leading to an upgraded 9-foot leaded glass front door that opens into a meticulously maintained interior.The upgraded

    Brooke Cangro RE/MAX 200 REALTY

    1382 Foltz Loop, Oakland, FL 34787
  • /24

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,336 Sq Ft

    500 W Oakland Ave, Oakland, FL 34760

    Discover the charm of this custom-built home, completed in 2010, with no HOA!Step inside this spacious two-story, 3-bedroom, 2-bathroom home and fall in love with the open floor plan and modern updates. The brand-new flooring and fresh interior paint create a bright, clean, and welcoming feel throughout.The heart of the home is the completely renovated chef’s kitchen, featuring

    Angela Worachek REAL BROKER, LLC

    500 W Oakland Ave, Oakland, FL 34760
  • /44

    $500,000

    • 3 Beds
    • 2 Baths
    • 1,630 Sq Ft

    409 E Gulley Ave, Oakland, FL 34760

    Tucked away in the heart of downtown Oakland, this adorable 3-bedroom, 2-bathroom home captures the essence of small-town living with its cozy charm and timeless appeal. Surrounded by mature landscaping and stately oak trees, this property offers a serene escape with no HOA to limit your creativity. Quiet dirt roads wind through the neighborhood, adding a touch of rural nostalgia, while the

    Erica Diaz HOMEVEST REALTY

    409 E Gulley Ave, Oakland, FL 34760
  • /11

    $1,395,000

    • Land
    • 1.26 Acres
    • $1,107,143 per Acre

    556 Walker St, Oakland, FL 34760

    Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your oasis—a timeless farmhouse, a classic Southern

    Chocky Burks CORCORAN PREMIER REALTY

    556 Walker St, Oakland, FL 34760
  • /11

    $895,000

    • Land
    • 1.03 Acres
    • $868,932 per Acre

    529 N Pollard St, Winter Garden, FL 34787

    Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your oasis—a timeless farmhouse, a classic Southern

    Matthew Burks CORCORAN PREMIER REALTY

    529 N Pollard St, Winter Garden, FL 34787
  • /14

    $450,000

    • Land
    • 0.45 Acre
    • $1,000,000 per Acre

    510 N Nixon St, Oakland, FL 34760

    As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

    Blaine Dooley REGENCY REAL ESTATE LLC

    510 N Nixon St, Oakland, FL 34760
  • /21

    $895,000

    • Land
    • 0.96 Acre
    • $932,292 per Acre

    513 N Pollard St, Winter Garden, FL 34787

    Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium LOT 36 offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your personal oasis—whether that’s a timeless farmhouse, a

    Heather Spirazza REGENCY REAL ESTATE LLC

    513 N Pollard St, Winter Garden, FL 34787
  • /24

    $1,250,000

    • Land
    • 0.82 Acre
    • $1,524,390 per Acre

    552 Walker St, Oakland, FL 34760

    Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your personal oasis—whether that’s a timeless farmhouse, a

    Alexis Anderson REGENCY REAL ESTATE LLC

    552 Walker St, Oakland, FL 34760
  • /92

    $949,900

    • 4 Beds
    • 3.5 Baths
    • 2,683 Sq Ft

    908 Tilden Oaks Trail, Winter Garden, FL 34787

    In the enchanting enclave of Oakland Park lies a home that seamlessly marries design with tranquility—welcome to 908 Tilden Oaks Trail. This Rockwell Homes masterpiece is more than just a residence; it is an experience of sophisticated living, smart-home innovation, and breathtaking natural beauty.As you approach, a serene landscape unfolds before you, with no neighbors to the front or rear.

    Matt McKee COMPASS FLORIDA LLC

    908 Tilden Oaks Trail, Winter Garden, FL 34787
  • /38

    $575,000

    • 4 Beds
    • 3 Baths
    • 2,820 Sq Ft

    235 Largovista Dr, Oakland, FL 34787

    Welcome to 235 Largovista Dr, tucked inside the gated Johns Landing community in Oakland, FL! This spacious 4-bedroom, 3-bath home includes a flex space already set up for a 5th bedroom perfect for guests, a home office, or extra room to grow.Outside, enjoy your private pool and outdoor living area, made for relaxing weekends and fun-filled gatherings. The new pool pump (2022) and fresh sod

    Liam Lugo LPT REALTY, LLC

    235 Largovista Dr, Oakland, FL 34787
  • /39

    $589,000

    • 4 Beds
    • 3 Baths
    • 2,418 Sq Ft

    1873 White Feather Loop, Oakland, FL 34787

    NEW PRICE ...Highly MOTIVATED owner !! Welcome to this stunning designed 4-bedrooms, 3-full bathrooms + office, nestled in one of Oakland / Winter Garden’s most desirable communities! With over 2400 sqft of thoughtfully designed living space, this home offers modern elegance and functional spaces.Spacious Open Layout: High ceilings, abundant natural light, and a seamless flow between living,

    Ana Bruder FLORIDA CONNEXION PROPERTIES

    1873 White Feather Loop, Oakland, FL 34787
  • /62

    $524,988

    • 3 Beds
    • 2.5 Baths
    • 2,345 Sq Ft

    17055 Wynford Ln, Oakland, FL 34787

    *****Buyer incentive!! up to $10,000 towards closing costs! ***** Why wait to build when you can MOVE RIGHT IN to this pristine home, shows like a model!!! Welcome to your beautiful 3 bedroom 2 1/2 bathrooms with spacious loft, window treatments and blinds! This beautiful home is where luxury meets comfort! Upon entering, you are greeted with stunning lighting fixtures and an open floor plan

    Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

    17055 Wynford Ln, Oakland, FL 34787
  • /3

    $374,900

    • Land
    • 0.24 Acre
    • $1,562,083 per Acre

    1215 Ridge Lake Way, Winter Garden, FL 34787

    LOT 247: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

    Tracey McFadden OAK AVENUE REAL ESTATE LLC

    1215 Ridge Lake Way, Winter Garden, FL 34787
  • /3

    $449,900

    • Land
    • 0.23 Acre
    • $1,956,087 per Acre

    1203 Ridge Lake Way, Winter Garden, FL 34787

    LOT 244: Don't miss your final opportunity to build your dream home in Oakland Park, a charming golf cart community along Lake Apopka and the West Orange Trail. These recently released lots are part the final phase of this coveted neighborhood and some of the best lots available. This is your chance to build an estate or lake front home that is only 2 miles for adorable Downtown Winter Garden,

    Tracey McFadden OAK AVENUE REAL ESTATE LLC

    1203 Ridge Lake Way, Winter Garden, FL 34787
  • /32

    $674,900

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft

    13557 Parkfield Way, Oakland, FL 34787

    Amazing highly desirable single story home in the popular Encore at Ovation in Winter Garden just minutes from Walt Disney World! This home sits on a beautiful lot ( only one side neighbor) with no one behind you. It has a gorgeous water and wooded view. The home has a wonderful front porch perfect for enjoying a cup of coffee along with a beautiful back patio overlooking the peaceful water.

    Paula Dale SOTERA LIVING

    13557 Parkfield Way, Oakland, FL 34787
  • /50

    $419,000

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft

    12043 Holystone St, Oakland, FL 34787

    “The property is currently active for sale but is rented with a lease valid until February 2026. The lease must be honored, so the property is best suited for investors looking for a rental income opportunity.”Welcome to Waterleigh community! This townhome has 3 bedroom 2.5 bathroom is conveniently located in Waterleigh Phase 4, near the Elementary and Middle School! It offers a welcoming

    Ruth Santos Blystone EMPIRE NETWORK REALTY

    12043 Holystone St, Oakland, FL 34787
  • /14

    $420,000

    • Land
    • 0.26 Acre
    • $1,615,385 per Acre

    1161 Prado Ln, Oakland, FL 34787

    Nestled in the heart of Oakland, Florida, this expansive homesite offers the perfect canvas to build your dream home with custom home builder, Pioneer Builders. Set in an illustrious community, called the Grove, this generously sized lot is ideal for crafting your unique custom home. The Grove is situated within Oakland’s most sought-after neighborhood known for its upscale charm and ideal

    Alexis Anderson REGENCY REAL ESTATE LLC

    1161 Prado Ln, Oakland, FL 34787
  • /42

    $999,999

    • 5 Beds
    • 4 Baths
    • 3,301 Sq Ft

    14429 Wabasso Loop, Oakland, FL 34787

    Excellent place close to 429 and turpike

    Alfredo Olivares CREDIT HOME CORP

    14429 Wabasso Loop, Oakland, FL 34787
  • /52

    $1,050,000

    • 5 Beds
    • 3.5 Baths
    • 3,910 Sq Ft

    9849 Lost Creek Dr, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience.From the moment you arrive, the immaculate

    Jennifer Ibarra REAL BROKER, LLC

    9849 Lost Creek Dr, Oakland, FL 34787
  • /4

    $821,829 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,101 Sq Ft

    16029 Honey Harvest St, Oakland, FL 34787

    Under Construction. New Construction - October Completion! Built by Taylor Morrison, America's Most Trusted Homebuilder. Welcome to the Cumberland at 16029 Honey Harvest Street in Harvest at Ovation. This spacious two-story Cumberland offers 5 bedrooms, 4.5 bathrooms, and flexible living for every stage of life. The open-concept great room, dining area, and gourmet kitchen flow effortlessly

    Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

    16029 Honey Harvest St, Oakland, FL 34787
  • /48

    $848,296 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    16146 Point Rock Dr, Oakland, FL 34787

    Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the casual

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    16146 Point Rock Dr, Oakland, FL 34787
  • /33

    $868,686 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,327 Sq Ft

    16158 Point Rock Dr, Oakland, FL 34787

    Under Construction. Waterleigh presents the Seacliff. This two-story all concrete block construction single-family home features 4 bedrooms and 3.5 bathrooms optimizing living space with an open concept feel. A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room. Go down the hallway and you’ll find a powder room and laundry room tucked

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    16158 Point Rock Dr, Oakland, FL 34787
  • /7

    $1,700,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,909 Sq Ft

    1207 Ridge Lake Way, Winter Garden, FL 34787

    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

    Chris Herlihy NEW HOMES REAL ESTATE, INC.

    1207 Ridge Lake Way, Winter Garden, FL 34787
  • /48

    $877,356 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    16164 Point Rock Dr, Oakland, FL 34787

    Under Construction. Waterleigh presents the Torrey. This two-story all concrete block construction single-family home features 5 bedrooms and 4.5 bathrooms optimizing living space with an open concept feel.A beautiful porch welcomes you to this home, as you enter the foyer, you are greeted with a formal dining room and butler’s pantry. The well-appointed gourmet kitchen overlooks the

    Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

    16164 Point Rock Dr, Oakland, FL 34787
  • /15

    $2,295,000 Open Sun 12AM - 4PM

    • 6 Beds
    • 5.5 Baths
    • 4,859 Sq Ft

    1244 Water Maple Dr, Oakland, FL 34787

    Pre-Construction. To be built. Introducing the Hamlin model by Element Home Builders—a stunning 4,859 square-foot residence designed for luxurious living and modern comfort. With 6 spacious bedrooms and 5.5 beautifully appointed bathrooms, this home offers ample space for families of all sizes and lifestyles.Step inside and experience an open-concept layout that combines elegance with

    Alexis Anderson REGENCY REAL ESTATE LLC

    1244 Water Maple Dr, Oakland, FL 34787
  • /15

    $2,175,000 New Construction

    • 5 Beds
    • 8 Baths
    • 4,433 Sq Ft

    1256 Water Maple Dr, Oakland, FL 34787

    Pre-Construction. To be built. Presenting the Citrus plan by Element Home Builders—a spacious home designed for modern living. With 5 bedrooms and 5 bathrooms, and 3 powder bathrooms, this expansive layout provides the perfect combination of comfort, style, and functionality. Every inch of this home is thoughtfully designed to create ample space for both private retreats and vibrant social

    Alexis Anderson REGENCY REAL ESTATE LLC

    1256 Water Maple Dr, Oakland, FL 34787
  • /15

    $2,150,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 4,388 Sq Ft

    1250 Water Maple Dr, Oakland, FL 34787

    Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas, perfect for

    Heather Spirazza REGENCY REAL ESTATE LLC

    1250 Water Maple Dr, Oakland, FL 34787
  • /3

    $655,990 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,843 Sq Ft

    Captiva, Oakland, FL 34787

    The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

    Dream Finders Homes

    Captiva, Oakland, FL 34787
  • /27

    $645,990 New Construction

    • 5 Beds
    • 3.5 Baths
    • 2,688 Sq Ft

    Anna Maria w/ Bonus, Oakland, FL 34787

    The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully

    Dream Finders Homes

    Anna Maria w/ Bonus, Oakland, FL 34787
  • /2

    $617,990 New Construction

    • 3 Beds
    • 2 Baths
    • 2,278 Sq Ft

    Lexington w/ Bonus, Oakland, FL 34787

    The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 2 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

    Dream Finders Homes

    Lexington w/ Bonus, Oakland, FL 34787
  • /3

    $577,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft

    Lexington, Oakland, FL 34787

    The Lexington floorplan is a spacious one-story design, featuring three comfortable bedrooms and two bathrooms, offering a total of 1,856 square feet. This home includes a versatile three-car garage with tandem space, perfect for extra storage or a workshop area. The open-concept layout connects the great room, café, and kitchen, creating a welcoming atmosphere for entertaining and everyday

    Dream Finders Homes

    Lexington, Oakland, FL 34787
  • /4

    $505,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,078 Sq Ft

    Cooper, Oakland, FL 34787

    Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the

    Dream Finders Homes

    Cooper, Oakland, FL 34787
  • /3

    $649,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,689 Sq Ft

    Biscayne, Oakland, FL 34787

    The Biscayne floorplan offers a spacious two-story design that perfectly balances functionality and flexibility, ideal for growing families. With four bedrooms and two and a half bathrooms, this layout provides ample space for everyday living and special moments alike. On the first floor, you'll find a flex room that can serve as a home office, gym, or an optional guest bedroom, depending on your

    Dream Finders Homes

    Biscayne, Oakland, FL 34787
  • /3

    $407,990 New Construction

    • 3 Beds
    • 2.5 Baths
    • 1,715 Sq Ft

    Porter, Oakland, FL 34787

    The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a

    Dream Finders Homes

    Porter, Oakland, FL 34787
  • /3

    $603,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,235 Sq Ft

    Anna Maria, Oakland, FL 34787

    The Anna Maria floorplan is a thoughtfully designed one-story home featuring four bedrooms and two and a half bathrooms, perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large

    Dream Finders Homes

    Anna Maria, Oakland, FL 34787
  • /99

    $1,675,000 New Construction

    • 4 Beds
    • 4 Baths
    • 3,186 Sq Ft

    166 Hammock Preserve Loop, Oakland, FL 34787

    Under Construction. UPDATE: Ahead of schedule with an estimated completion in Sept.–Oct. 2025, 166 Hammock Preserve Loop offers one of the finest new construction custom homes in Winter Garden, FL. Built by AR Homes—celebrating over 40 years of luxury homebuilding—this Carrabelle model sits in the highly sought-after Oakland Park community. Boasting 3,186 sq ft of impeccably crafted living space,

    AJ Lash CORCORAN PREMIER REALTY

    166 Hammock Preserve Loop, Oakland, FL 34787

Showing Results 41 - 80, Page 2 of 3

How to Buy a Home How to Finance a Home How to Sell a Home