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Recently Sold Oakland Homes

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  • /2

    $1,025,000 Sold Jul 21, 2025

    • 2,711 Sq Ft
    • $378/SF
    • 77 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2023

    936 Allendale Ln, Winter Garden, FL 34787

    Exquisite Craftsman-Coastal Home Featured in Stroll Oakland Park Magazine!Welcome to the Mabel, a show-stopping 4-bedroom, 3-bathroom masterpiece by David Weekley Homes, built in 2023. Boasting 2,640 sqft of meticulously designed living space, this Craftsman-Coastal beauty seamlessly blends modern elegance with timeless charm.Step inside to soaring 10’ ceilings and an inviting open

    Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

    936 Allendale Ln, Winter Garden, FL 34787
  • /2

    $795,000 Sold Jul 18, 2025

    • 2,505 Sq Ft
    • $317/SF
    • 25 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2014

    101 W Oakland Ave, Oakland, FL 34760

    Experience the charm of Oakland living in this beautifully updated custom built home located in the heart of town—just minutes to Downtown Winter Garden, Plant Street Market, the West Orange Trail, the Lake Apopka boat ramp/dock and so much more! This move-in ready home is situated on a .27-acre corner lot with no HOA. When entering this 4-bedroom, 3-bathroom home, you’re welcomed by a spacious

    Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

    101 W Oakland Ave, Oakland, FL 34760
  • /2

    $387,900 Sold Jul 17, 2025

    • 1,809 Sq Ft
    • $214/SF
    • 144 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2019

    1509 Sweet Apple St, Oakland, FL 34787

    Welcome to lovely 3 bed 3 bath townhome in the heart of Oakland. This end unit town home is modern with luxury vinyl plank floors and new carpet in the bedrooms. On the first level you will find your open concept living space with access to your private courtyard which is an extension of the entertainment space of this home. The kitchen is modern with 42" upper cabinets, granite countertops,

    Robert Jones OFFERPAD BROKERAGE FL, LLC

    1509 Sweet Apple St, Oakland, FL 34787
  • /2

    $430,000 Sold Jul 16, 2025

    • Land
    • 0.37 Acre
    • $1,162,162 per Acre
    • 0 Days On Market

    1113 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

    1113 Prado Ln, Oakland, FL 34787
  • /2

    $800,000 Sold Jul 10, 2025

    • Land
    • 0.95 Acre
    • $842,105 per Acre
    • 0 Days On Market

    517 N Pollard St, Winter Garden, FL 34787

    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

    517 N Pollard St, Winter Garden, FL 34787
  • /2

    $800,000 Sold Jul 10, 2025

    • Land
    • 1.03 Acres
    • $776,699 per Acre
    • 0 Days On Market

    525 N Pollard St, Winter Garden, FL 34787

    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

    525 N Pollard St, Winter Garden, FL 34787
  • /2

    $420,000 Sold Jul 09, 2025

    • 1,621 Sq Ft
    • $259/SF
    • 24 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2003

    709 Strihal Loop, Oakland, FL 34787

    Nestled in the desirable gated community of Johns Landing in Oakland, this charming 3-bedroom, 2-bathroom home offers the perfect blend of comfort and convenience. Situated on a generously sized lot of nearly a quarter acre, the property boasts a fenced backyard and mature shade trees, providing an ideal space for creating your dream outdoor oasis. Inside, the home offers two distinct living

    Jessica Stone CENTURY 21 CARIOTI

    709 Strihal Loop, Oakland, FL 34787
  • /2

    $980,000 Sold Jul 08, 2025

    • 2,765 Sq Ft
    • $354/SF
    • 6 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2022

    1206 Civitas, Oakland, FL 34787

    HONEY, STOP THE GOLF CART! Your opportunity to own in OAKLAND PARK! Highly desirable Seaside model built by David Weekly in 2022! From the moment you arrive, this home welcomes you with warmth and timeless elegance from the generous front porch with porch swing to enjoy your coffee from— Inside, you'll find a seamless blend of comfort and sophistication in every thoughtfully crafted space.

    Gabriella Philippone INDEPENDENCE REALTY GROUP LLC

    1206 Civitas, Oakland, FL 34787
  • /2

    $388,000 Sold Jul 03, 2025

    • 1,620 Sq Ft
    • $240/SF
    • 86 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2020

    1312 Painted Bunting Ave, Oakland, FL 34760

    NEW PRICE! Discover the most spacious 2-bedroom townhome in Winter Garden! Unlike most 2-bedroom homes in the area averaging around 1,250 square feet, this 1,620-square-foot residence features a versatile loft space that’s ideal for a home office, guest area, or bonus living zone. Built in 2020 and meticulously maintained by its original owner, every detail and upgrade was carefully selected in

    Gavin Hatch SERHANT

    1312 Painted Bunting Ave, Oakland, FL 34760
  • /2

    $1,400,000 Sold Jun 27, 2025

    • 3,497 Sq Ft
    • $400/SF
    • 72 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2002

    141 Millholland St, Oakland, FL 34760

    Live the "Lake Life" in a Tropical Paradise – Key West Vibes in Oakland, Florida!Welcome to your own slice of paradise in the heart of The Town of Oakland – one of Central Florida’s most desirable and fastest-growing communities. Situated on a sprawling 1.12-acre lot along the shores of Lake Apopka – Florida’s 4th largest lake – this gorgeous custom home spans nearly 4,000 square feet of

    Matthew Matin CLOCK TOWER REALTY

    141 Millholland St, Oakland, FL 34760
  • /2

    $1,475,000 Sold Jun 20, 2025

    • 3,468 Sq Ft
    • $425/SF
    • 49 Days On Market
    • 4 Beds
    • 4 Baths
    • Built 2022

    921 Bradenville Ln, Winter Garden, FL 34787

    An unparalleled opportunity awaits to step into refined luxury without the delay or uncertainty of building. This bespoke residence, masterfully crafted by J&J Builders, graces an oversized corner lot directly across from the resort-caliber clubhouse of Oakland Park. From the moment you arrive, the home makes a commanding impression with its grand front porch—a quintessential feature of Oakland

    Ronald Ziolkowski RE/MAX PRIME PROPERTIES

    921 Bradenville Ln, Winter Garden, FL 34787
  • /35

    $645,000 Sold Jun 18, 2025

    • 2,311 Sq Ft
    • $279/SF
    • 13 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2001

    632 Strihal Loop, Oakland, FL 34787

    Active under contract w/ 72 hour kick-out clause! 4/3, 3 car garage, heated POOL home is immaculate! NEW ROOF 2021, exterior paint 2022, HVAC 2023, W/H 2023, Pool solar 2024! Large family room includes a custom stone wall with electric fireplace & large sliding doors that open to an enclosed heated pool and covered patio. Custom kitchen features tons of upgrades including quartzite countertops,

    Millie Gwin Coldwell Banker Coast Realty

    632 Strihal Loop, Oakland, FL 34787
  • /2

    $545,000 Sold Jun 16, 2025

    • 2,000 Sq Ft
    • $272/SF
    • 12 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    1757 Standing Rock Cir, Oakland, FL 34787

    Stunning Former Model Home in Oakland Trails – Minutes from Downtown Winter Garden!Welcome to this beautifully upgraded 3-bedroom, 2.5-bathroom former model home located in the highly desirable Oakland Trails community. Situated in the heart of Oakland and just moments from the vibrant Winter Garden Downtown District, this 2,000 sq ft single-story home perfectly combines elegance, comfort, and

    Shannon Christian EXP REALTY LLC

    1757 Standing Rock Cir, Oakland, FL 34787
  • /2

    $410,000 Sold Jun 04, 2025

    • Land
    • 0.31 Acre
    • $1,322,581 per Acre
    • 9 Days On Market

    0 N Daniels St, Oakland, FL 34760

    Discover this RARE 0.31-acre residential lot located in the charming town of Oakland, one of the most desirable and rapidly appreciating areas in West Central Florida. Just a few blocks from Oakland’s historic downtown, this property is set on picturesque unpaved and stone roads, adding a unique character and peaceful atmosphere to the neighborhood.Oakland is known for its warm community feel,

    Roberta Melo SELECTA REALTY LLC

    0 N Daniels St, Oakland, FL 34760
  • /2

    $2,098,500 Sold Jun 04, 2025

    • 3,956 Sq Ft
    • $530/SF
    • 0 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 2025

    1112 Sarah Mathews Dr, Oakland, FL 34787

    Pre-Construction. To be built. Discover the perfect blend of old-world charm and modern luxury in this stunning custom French Farmhouse to be built by the renowned Pioneer Builders. Nestled in a picturesque setting, this home will feature classic European-inspired architecture, upscale design, and superior craftsmanship.Step through an arched entryway into an inviting open floor plan adorned with

    Alexis Anderson REGENCY REAL ESTATE LLC

    1112 Sarah Mathews Dr, Oakland, FL 34787
  • /2

    $648,000 Sold Jun 03, 2025

    • 2,278 Sq Ft
    • $284/SF
    • 4 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2020

    2214 Bay Line Rd, Oakland, FL 34787

    WELCOME HOME TO HULL ISLAND! This home offers a serene retreat for those looking for a blend of modern living mixed with nature. Step inside to an open floor plan featuring 4 Bedrooms, 2 Baths and a dedicated home office. The HIGH ceilings and windows create a light-filled and most inviting atmosphere. Gorgeous WOOD-LOOK tile flooring throughout this OPEN-CONCEPT floor plan. Chef's kitchen is a

    Kelly Zannini HOMEVEST REALTY

    2214 Bay Line Rd, Oakland, FL 34787
  • /2

    $443,500 Sold May 30, 2025

    • 1,898 Sq Ft
    • $234/SF
    • 20 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2004

    308 Largovista Dr, Oakland, FL 34787

    Welcome to your Florida dream home, where location is everything. This stunning 3-bedroom, 2-bathroom home with an additional office/flex space is filled with an abundance of natural light and boasts a bright, open layout that’s perfect for both relaxing and entertaining. The spacious family room features vaulted ceilings, adding a sense of openness to the heart of the home. The updated kitchen

    Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

    308 Largovista Dr, Oakland, FL 34787
  • /2

    $1,835,000 Sold May 27, 2025

    • 3,796 Sq Ft
    • $483/SF
    • 17 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2022

    625 Cheekwood Alley, Winter Garden, FL 34787

    Welcome to this stunning custom-built POOL & PARK-FRONT home with IN-LAW SUITE located in the highly sought-after community of Oakland Park. Designed for both luxury & functionality, this exceptional residence boasts impeccable craftsmanship, high-end finishes, & a thoughtfully designed layout perfect for modern living. The main home includes 5 bedrooms (one does not have a closet) & 3.5 baths

    Ashley Boyd BHHS FLORIDA REALTY

    625 Cheekwood Alley, Winter Garden, FL 34787
  • /2

    $530,000 Sold May 23, 2025

    • 1,515 Sq Ft
    • $350/SF
    • 1 Day On Market
    • 3 Beds
    • 1 Bath
    • Built 1958

    321 E Gulley Ave, Oakland, FL 34760

    DOUBLE LOT .55 - GREAT LOCATION!- NO HOA - GOLF CART FRIENDLY COMMUNITY - ACCESS TO WINTER GARDEN'S HISTORICAL DOWNTOWN - CLOSE TO WEST ORANGE TRAIL - Spacious 3 Bedroom 1 Bathroom home. Open Concept Living with High Ceilings - Wood Floors - Plenty of Natural Light - Oversized Lot Offering Ample Room to Expand or Build New. Large Storage Shed - Newer Roof and A/C - Take Advantage of this Rare

    Rebecca Hall KELLER WILLIAMS WINTER PARK

    321 E Gulley Ave, Oakland, FL 34760
  • /2

    $475,000 Sold May 22, 2025

    • 2,071 Sq Ft
    • $229/SF
    • 100 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1962

    16247 Lake Johns Cir, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. Located in a sought-after area of Winter Garden, this beautifully renovated home sits on a spacious .45-acre lot in a private cul-de-sac with no HOA! Completely updated from top to bottom, this home features brand new flooring, a new roof, new windows and doors, offering a fresh and modern feel. Step into the remodeled kitchen, where you'll find

    Erica Diaz HOMEVEST REALTY

    16247 Lake Johns Cir, Winter Garden, FL 34787
  • /2

    $555,000 Sold May 21, 2025

    • 2,152 Sq Ft
    • $258/SF
    • 51 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2017

    1763 White Feather Loop, Oakland, FL 34787

    OAKLAND TRAILS community just off the WEST ORANGE TRAIL and just steps away from amenities !!! Don't miss the opportunity to own this TURN-KEY beautifully constructed 3 Bedroom / 2.5 Bathroom ENERGY EFFICIENT home built by Meritage Homes. You are sure to love the spacious living areas, with seamless transitions between rooms, making it ideal for both entertaining and comfortable day-to-day

    Kim Byerly THE REAL ESTATE COLLECTION LLC

    1763 White Feather Loop, Oakland, FL 34787
  • /2

    $3,175,000 Sold May 20, 2025

    • 6,428 Sq Ft
    • $494/SF
    • 0 Days On Market
    • 6 Beds
    • 5.5 Baths
    • Built 2026

    410 Briley Ave, Oakland, FL 34787

    Pre-Construction. To be built. Custom Home to be built by Element Home Builders. Welcome to your dream retreat in the Central Florida's most coveted new 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

    Alexis Anderson REGENCY REAL ESTATE LLC

    410 Briley Ave, Oakland, FL 34787
  • /2

    $770,000 Sold May 16, 2025

    • 1,982 Sq Ft
    • $388/SF
    • 32 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2022

    1118 Eagles Pass Way, Winter Garden, FL 34787

    Nestled on a premium corner lot in the sought-after Oakland Park community, this stunning 3-bedroom, 2.5-bathroom home plus an office offers the perfect blend of charm and modern luxury. A welcoming covered front porch invites you to relax and connect with neighbors while enjoying the beautiful Florida weather. Step inside to a bright foyer with luxury vinyl plank flooring that flows throughout

    Alex Vastardis COLDWELL BANKER REALTY

    1118 Eagles Pass Way, Winter Garden, FL 34787
  • /2

    $1,080,000 Sold May 14, 2025

    • 3,800 Sq Ft
    • $284/SF
    • 168 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2002

    627 Largovista Dr, Oakland, FL 34787

    Back on market! Huge price improvement... Schedule your personal tour of this captivating and stunning custom home. This is truly a luxury move-in ready, turn-key home, situated in the highly desirable Johns Landing gated community on Johns Lake. Recently remodeled throughout and fully furnished with all high-end desirable furniture that can be purchased with the home. Whether entertaining

    Heidi Pfeffer-Morgan DALTON WADE INC

    627 Largovista Dr, Oakland, FL 34787
  • /2

    $582,000 Sold May 13, 2025

    • 1,853 Sq Ft
    • $314/SF
    • 5 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2020

    2683 Bobcat Chase Blvd, Oakland, FL 34787

    Imagine coming home to your very own slice of paradise nestled in the heart of Winter Garden. 3-bedrooms, 2.5-bathrooms offering 1,853 sq ft of thoughtfully designed living space, perfectly blending comfort and style.This backyard will make all of your friends jealous. The custom-designed pool features a pebble tec finish, in-water bar stools, dual waterfalls, a sun shelf for lounging, and an

    Matthew Sutton BERGER REALTY & INVESTMENTS

    2683 Bobcat Chase Blvd, Oakland, FL 34787
  • /2

    $879,000 Sold May 13, 2025

    • 2,246 Sq Ft
    • $391/SF
    • 28 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    1073 Sadler Oaks Way, Winter Garden, FL 34787

    Welcome to 1073 Sadler Oaks, a stunning home in the sought-after Oakland Park community. This exceptional 3-bedroom, 3-bathroom home was completed in 2023. This award-winning floorplan offers upgraded features like: crown molding on the first level, a downstairs dedicated flex room, a 3-car garage, upgraded luxury vinyl plank flooring throughout and an impeccable design. Step inside from the

    Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

    1073 Sadler Oaks Way, Winter Garden, FL 34787
  • /2

    $690,000 Sold May 13, 2025

    • 2,274 Sq Ft
    • $303/SF
    • 69 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2020

    2157 Bay Line Rd, Oakland, FL 34787

    Welcome to your dream home in the heart of Hull Island at Oakland. This stunning home features a serene saltwater pool and is on a peaceful lot with conservation views. The open floor plan, high ceilings, and windows create an energizing flow of natural light throughout. Rich colors and lighting enhance its beauty. At the center of the home is the gourmet kitchen with an oversized island and

    Jamie Stolinas Crame CENTURY 21 CARIOTI

    2157 Bay Line Rd, Oakland, FL 34787
  • /2

    $620,000 Sold May 12, 2025

    • 2,811 Sq Ft
    • $221/SF
    • 124 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2003

    1215 Johns Cove Ln, Oakland, FL 34787

    Motivated SELLER! Price adjustment. Don't miss out on this AMAZING opportunity to own this adorable 4-bedroom, 2-bathroom custom pool home in the highly desirable Johns Cove community. If you love to fish, boating, skiing or jet-skiing this is the home for you. This small, sought-after gated community on Johns Lake with its own community boat ramp is ideally located just off the Florida Turnpike,

    Heidi Pfeffer-Morgan DALTON WADE INC

    1215 Johns Cove Ln, Oakland, FL 34787
  • /2

    $545,000 Sold May 08, 2025

    • 2,082 Sq Ft
    • $262/SF
    • 33 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2020

    1763 Standing Rock Cir, Oakland, FL 34787

    Stunning Model Home with Premium Upgrades & Prime Location!This gorgeous 3-bedroom, 2.5-bath home is packed with upgrades and designer touches, offering both style and convenience. Equipped with Surround Sound as well. This Gem of a Home is located in a prime area with easy access to shopping, dining, theme parks, and just about an hour to the beaches, this home is perfect for modern living.The

    Paulette Korr DALTON WADE INC

    1763 Standing Rock Cir, Oakland, FL 34787
  • /2

    $571,000 Sold Apr 29, 2025

    • 1,790 Sq Ft
    • $319/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1984

    201 W Briley Ave, Oakland, FL 34760

    Located in the heart of Downtown Oakland, this well-built and meticulously maintained CBS construction ranch house offers a perfect blend of comfort, style, and convenience. Located on a spacious corner lot, under heritage oak trees, the home features an open and airy split floor plan with high ceilings and sky lights, creating a bright and inviting atmosphere. With numerous updates and

    Kari Fleck THE REAL ESTATE COLLECTION LLC

    201 W Briley Ave, Oakland, FL 34760
  • /2

    $1,272,000 Sold Apr 29, 2025

    • 3,562 Sq Ft
    • $357/SF
    • 49 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2021

    1112 Hull Island Dr, Oakland, FL 34787

    Welcome to your stunning lake front home, enjoy breathtaking views the moment you walk through the front door. Discover this exquisite, one of a kind home featuring premium upgrades throughout. Kitchen is a chefs dream with gas cooktop, double ovens, tons of counter space, large island, separate dinette, and custom walk-in pantry featuring wall to wall shelving for maximum storage and

    Kelly Zannini HOMEVEST REALTY

    1112 Hull Island Dr, Oakland, FL 34787
  • /2

    $455,000 Sold Apr 25, 2025

    • 2,042 Sq Ft
    • $223/SF
    • 2 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2022

    13885 Title Way, Winter Garden, FL 34787

    Like New beautifully designed 4-bedroom, 3-bath home in the highly sought-after Storey Grove community in Winter Garden. Built in 2022, this two-story residence offers an open and functional floor plan filled with natural light, stylish finishes, and modern features. The kitchen is equipped with stainless steel appliances, sleek cabinetry, and a spacious island perfect for entertaining. First

    Iris Lee SPRUCE QUALITY RENTALS

    13885 Title Way, Winter Garden, FL 34787
  • /2

    $600,000 Sold Apr 25, 2025

    • 2,579 Sq Ft
    • $233/SF
    • 96 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2001

    1011 Johns Cove Ln, Oakland, FL 34787

    Price improvement! Welcome to this amazing opportunity to own what was the show home for Johns Cove. This remarkably well-kept home is situated in the highly desirable Johns Cove community. This small, sought-after gated community on Johns Lake is ideally located off the Florida Turnpike, close to Old Winter Garden, the airport, and all the Attractions. The community has its own private boat

    Heidi Pfeffer-Morgan DALTON WADE INC

    1011 Johns Cove Ln, Oakland, FL 34787
  • /2

    $980,000 Sold Apr 14, 2025

    • 3,070 Sq Ft
    • $319/SF
    • 47 Days On Market
    • 5 Beds
    • 4 Baths
    • Built 2023

    210 Hammock Preserve Loop, Oakland, FL 34787

    Luxury meets elegance in this extraordinary 5-Bedroom Home that can be described as a masterpiece of modern living. Located in the coveted Oakland Park community, This 5-bedroom, 4-FULL bathroom home redefines beauty with over $100,000 in custom upgrades, meticulously designed to exceed every expectation.The heart of the home is the astonishing kitchen, with high-end appliances,

    Matthew Sutton BERGER REALTY & INVESTMENTS

    210 Hammock Preserve Loop, Oakland, FL 34787
  • /2

    $855,000 Sold Apr 10, 2025

    • 2,255 Sq Ft
    • $379/SF
    • 6 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    234 Hammock Preserve Loop, Oakland, FL 34787

    Welcome to your dream home in the highly sought-after community of Oakland Park in Winter Garden, FL! This brand-new construction masterpiece boasts 3 bedrooms, 2.5 baths, first floor office space that could easily serve as a 4th bedroom and a bonus loft upstairs that could be a 5th bedroom. As you step through the front door, you'll be greeted by the charm and sophistication that defines this

    Lianna D'Angelo SOTERA LIVING

    234 Hammock Preserve Loop, Oakland, FL 34787
  • /2

    $615,000 Sold Apr 09, 2025

    • 2,490 Sq Ft
    • $247/SF
    • 25 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2001

    644 Strihal Loop, Oakland, FL 34787

    Welcome to your dream home in the charming town of Oakland, Florida! This stunning residence is nestled in the highly desirable gated community of John's Landing and sits along the shoreline of Johns Lake, offering an unparalleled blend of luxury, comfort, and convenience. Just minutes from the West Orange Trail, downtown Winter Garden, and major roadways like the Florida Turnpike, SR 429, and SR

    Julie Arnold REAL BROKER, LLC

    644 Strihal Loop, Oakland, FL 34787
  • /2

    $1,010,000 Sold Mar 31, 2025

    • 2,751 Sq Ft
    • $367/SF
    • 8 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2023

    1175 Celadon St, Oakland, FL 34787

    Welcome to this stunning 4-bedroom, 3.5-bathroom home nestled in the highly sought-after community of Oakland Park. From the moment you approach, a sense of warmth and elegance draws you in, starting at the welcoming front gate, up the steps of the inviting front porch, and into the stunning David Weekley Seaside model.Step inside to discover thoughtfully designed spaces where comfort and

    Hilary Hall COMPASS FLORIDA LLC

    1175 Celadon St, Oakland, FL 34787
  • /2

    $670,000 Sold Mar 28, 2025

    • 3,728 Sq Ft
    • $180/SF
    • 10 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 2005

    619 Largovista Dr, Oakland, FL 34787

    Discover the perfect blend of luxury and comfort in this 5-bedroom, 4-bathroom estate, nestled in the highly sought-after gated community of Johns Landing. With 3,718 sq. ft. of beautifully designed living space, this two-story home offers views of Johns Lake and an array of upgrades throughout.Step inside to find a thoughtfully designed layout with a main-floor primary suite, offering a

    Nia Medina SERHANT

    619 Largovista Dr, Oakland, FL 34787
  • /2

    $1,440,000 Sold Mar 28, 2025

    • 3,450 Sq Ft
    • $417/SF
    • 37 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2020

    816 Johns Point Dr, Oakland, FL 34787

    Lake front beauty. Nearly new custom home on expansive .57-acre lot on Johns Lake in beautiful Johns Cove. This gated community combines privacy and convenient access to Disney World, Universal, Sea World, downtown Orlando, Orlando International Airport, high- end and discount shopping, excellent restaurants and golf courses, and of course, the spectacular 2400 acre Johns Lake, excellent for

    Marc Harris FLORIDA REALTY INVESTMENTS

    816 Johns Point Dr, Oakland, FL 34787
  • /2

    $1,057,482 Sold Mar 27, 2025

    • 3,046 Sq Ft
    • $347/SF
    • 5 Beds
    • 3.5 Baths
    • Built 2025

    1216 Oak Fort Ln, Oakland, FL 34787

    Crabtree Model at Oakland Park in Winter Garden Florida is by homebuilder David Weekly Homes

    Stellar Non-Member Agent Stellar Non-Member Office

    1216 Oak Fort Ln, Oakland, FL 34787

Showing Results 1 - 40, Page 1 of 3

Frequently Asked Questions Why Live in Oakland

What is the average time to sell a house in Oakland, FL?
The houses for sale in Oakland, FL spend an average of 57 days on the market.
What is the number of active homes for sale in Oakland, FL?
There are 40 active homes for sale in Oakland, FL.

Home Trends in Oakland, FL

Housing Trends

Median Sale Price
$645,000
Median Single Family Sale Price
$660,000
Median Townhouse Sale Price
$387,900
Average Price Per Sq Ft
$320
Number of Homes for Sale
40
Last 12 months Home Sales
105
Months of Supply
4.60
Median List Price
$650,000
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
14%
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