30

Oakland, FL Homes for Sale under $600,000

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  • /4

    $505,990

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

    Cooper Plan at Serenade at Ovation - Bungalows, 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 Builder
    14229 Lanyard Way Unit 36487507, Oakland, FL 34787
  • /58

    $375,000

    $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    2100 Gopher Tortoise Terrace, Oakland, FL 34787

    Imagine coming home to a space that feels open, comfortable, and perfectly placed for everyday life. This corner-unit townhome in the desirable Longleaf at Oakland community offers added privacy, abundant natural light, and a thoughtfully designed layout that truly works for today’s lifestyle. Inside, the home features a clean, modern feel with plank vinyl flooring, granite countertops, and

    Stiliany Collado LLC MARKET CONNECT REALTY LLC

    2100 Gopher Tortoise Terrace, Oakland, FL 34787
  • /40

    $539,900

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    2065 White Feather Loop, Oakland, FL 34787

    Welcome to the highly desirable Oakland Trails, where this 2019 Meritage Home combines modern style, energy efficiency, and a thoughtfully designed layout for everyday comfort. Ideally situated approximately 30 minutes from Walt Disney World, Universal Orlando, and Downtown Orlando, the home provides convenient access to Central Florida's most popular destinations while preserving the peaceful

    Denis Bochkov PINK MIAMI REAL ESTATE

    2065 White Feather Loop, Oakland, FL 34787
  • /34

    $599,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 1,860 Sq Ft

    1808 Western Trailway Dr, Oakland, FL 34787

    Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,800 square feet of thoughtfully designed living space in the highly sought-after Hull Island community of Oakland. Tasteful décor and stylish finishes create a warm, inviting atmosphere, while the open-concept floor plan features a spacious kitchen with stainless steel appliances, a large center island with counter

    Susan Koptieff FLORIDA IN MOTION REALTY INC

    1808 Western Trailway Dr, Oakland, FL 34787
  • /28

    $599,000

    • 5 Beds
    • 3.5 Baths
    • 3,020 Sq Ft

    706 Strihal Loop, Oakland, FL 34787

    Virtually Staged. BRAND NEW ROOF! This five-bedroom, three-and-a-half-bathroom residence sits in a gated community with a new roof and architectural shingles, offering security and peace of mind. The property combines thoughtful interior finishes with direct access to some of the area's most desirable outdoor recreation opportunities. Inside, the kitchen features stainless steel appliances and a

    Patrick D'Agostino GLORY INTL. REAL ESTATE CO

    706 Strihal Loop, Oakland, FL 34787
  • /8

    $432,490

    New Construction $5K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,580 Sq Ft

    3043 Repose Dr, Oakland, FL 34787

    Under Construction. This dazzling Frey II, two-bedroom home provides convenient single-story living. A secondary bedroom and a study are secluded near the front of the home, leading to an inviting open-concept floorplan that boasts convenient access to a covered patio for seamless indoor-outdoor living. The owner’s suite is nestled into a private rear corner, complete with a full bathroom and

    Ben Goldstein LENNAR REALTY

    3043 Repose Dr, Oakland, FL 34787
  • /41

    $457,900

    • 3 Beds
    • 2.5 Baths
    • 1,838 Sq Ft

    2247 White Feather Loop, Oakland, FL 34787

    Welcome to this exceptional home in the highly sought-after Oakland Trails community! This beautifully designed 3-bedroom, 2.5-bath residence offers approximately 1,838 square feet of thoughtfully designed living space with an open and functional floor plan that truly stands out in the neighborhood. From the moment you arrive, you’ll notice the extended brick paver driveway, providing additional

    Carolina Cote Munoz LPT REALTY, LLC

    2247 White Feather Loop, Oakland, FL 34787
  • /68

    $400,000

    $25K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,768 Sq Ft

    16461 Prairie School Dr, Oakland, FL 34787

    PRICED TO SELL Welcome to your future home in the highly desirable, sought-after Hawksmoor community of Horizon West / Winter Garden.This beautifully maintained, move-in ready 4-bedroom, 2.5-bathroom townhome offers the perfect blend of modern comfort, functional design, and a low-maintenance lifestyle. The main level features an inviting open-concept layout filled with abundant natural light,

    Jhoana Loyo Urrutia LA ROSA REALTY LLC

    16461 Prairie School Dr, Oakland, FL 34787
  • /59

    $515,000

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,204 Sq Ft

    2259 White Feather Loop, Oakland, FL 34787

    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

    Chuck Burt YOUNG REAL ESTATE

    2259 White Feather Loop, Oakland, FL 34787
  • /20

    $549,990

    New Construction $83K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,199 Sq Ft

    3108 Namaste Dr, Oakland, FL 34787

    Under Construction. The Aspen single-story home emphasizes convenience and modern comfort, with four bedrooms and 3 bathrooms. Off the foyer are three secondary bedrooms, each with easy access to a nearby bathroom. Down the hallway is an open-concept layout connecting a well-equipped kitchen, dining room and family room with access to a large lanai. Adjacent to this space is the lavish owner’s

    Ben Goldstein LENNAR REALTY

    3108 Namaste Dr, Oakland, FL 34787
  • /4

    $508,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,083 Sq Ft

    Newbury Plan at Serenade at Ovation - Bungalows, Oakland, FL 34787

    Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36490206, Oakland, FL 34787
  • /55

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,152 Sq Ft

    2241 White Feather Loop, Oakland, FL 34787

    Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining. Step outside and enjoy all the amenities

    Brynn Munro CORCORAN PREMIER REALTY

    2241 White Feather Loop, Oakland, FL 34787
  • /36

    $350,000

    $15K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,497 Sq Ft

    2117 Gopher Tortoise Terrace, Oakland, FL 34787

    PRICE Improvement and ready to sell! Be sure to ask about a lender provided reduced rate offering a rate buy down to help reduce your monthly payment and/or closing costs. Skip the projects, this 2020 built home is ready for you! This open-concept layout creates a bright and inviting space perfect for entertaining. The kitchen, where matching marble countertops and cabinetry create a clean and

    Mary Herrod De Boer SERHANT

    2117 Gopher Tortoise Terrace, Oakland, FL 34787
  • /3

    $409,990

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

    Porter Plan at Serenade at Ovation - Townhomes, 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 Builder
    14229 Lanyard Way Unit 36452383, Oakland, FL 34787
  • /55

    $540,000

    • 4 Beds
    • 2.5 Baths
    • 2,486 Sq Ft

    223 Largovista Dr, Oakland, FL 34787

    Virtually Staged. Welcome to this spacious two-story home located in the highly desirable gated community of John's Landing in beautiful Oakland. Offering 4 bedrooms, 2.5 bathrooms, and over 2486 square feet of living space, this home combines generous room sizes, a functional layout, and an exceptional location to create the perfect place to call home. Step inside to discover multiple living and

    Corey Smallman MARKET CONNECT REALTY LLC

    223 Largovista Dr, Oakland, FL 34787
  • /22

    $469,000

    • 3 Beds
    • 3 Baths
    • 1,808 Sq Ft

    14014 Scarlet Aster Aly, Oakland, FL 34787

    Rare Dual Owner's Suite Townhome — Priced to Move, Near Disney This 3-bedroom, 3-bath, 1,808 sq ft Newton model townhome in Harvest at Ovation is one of the best values in the community right now. Built in 2024 and less than 2 years old, it shows like a model and is ready for immediate move-in, while comparable new construction in the area runs 7+ months out. What sets this home apart is its dual

    Jarrett Brown LPT REALTY, LLC

    14014 Scarlet Aster Aly, Oakland, FL 34787
  • /4

    $498,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,836 Sq Ft

    Brantley Plan at Serenade at Ovation - Bungalows, Oakland, FL 34787

    Discover the charm of the Brantley Floor Plan, a bungalow perfect for families and entertaining. This plan features 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The gourmet kitchen boasts top-end designer finishes and flows seamlessly into the living areas, ideal for gatherings. An extra-large corner pantry provides ample storage for bulk purchases, enhancing functionality. Check out

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36498626, Oakland, FL 34787
  • /25

    $479,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,720 Sq Ft

    14099 Lochend Way, Oakland, FL 34787

    Welcome to luxury living at its finest! Nestled in the prestigious West Haven at Ovation community in Winter Garden, this almost brand new 3-bedroom, 2.5-bathroom townhome is the epitome of modern elegance. As you step inside, you're greeted by an inviting open floor plan boasting an abundance of natural light and high-end finishes throughout. The spacious living area is perfect for entertaining

    Anahi C Rosario INTERNATIONAL REAL ESTATE LLC

    14099 Lochend Way, Oakland, FL 34787
  • /39

    $429,000

    $27K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,574 Sq Ft

    15157 Aqua Sol Ln, Oakland, FL 34787

    Step into refined, low-maintenance living in this beautifully upgraded villa located in Del Webb Oasis, one of Horizon West’s premier 55+ communities. With builder villa inventory now sold out, this villa stands out as one of the best available for its location, upgraded finishes, and price. Designed for comfort and convenience, this villa offers true single-level living with a spacious two-car

    Beth Assif RE/MAX SELECT GROUP

    15157 Aqua Sol Ln, Oakland, FL 34787
  • /2

    $541,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,908 Sq Ft

    13031 Tollcross Way, Oakland, FL 34787

    Superior contemporary design. The Liston's welcoming covered porch and entry open immediately onto the expansive great room, with views to the lovely dining room and desirable large covered lanai beyond. The well-equipped gourmet kitchen is enhanced by a large center island with breakfast bar, plenty of counter and cabinet space, and generous walk-in pantry. The gorgeous primary bedroom suite is

    Toll Brothers, Inc. Builder
    13031 Tollcross Way, Oakland, FL 34787
  • /64

    $599,000

    $26K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,906 Sq Ft

    13067 Tollcross Way, Oakland, FL 34787

    Located in the heart of Horizon West in Winter Garden, just minutes from the gates of Walt Disney World, this beautiful bungalow is nestled within Westhaven At Ovation, a sought-after residential community by Toll Brothers. The location is truly exceptional, offering quick and easy access to State Road 429, the Flamingo Crossings shopping and dining district, and all the magic Disney has to

    Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

    13067 Tollcross Way, Oakland, FL 34787
  • /23

    $575,000

    $75K PRICE INCREASE
    • Land
    • 19,602 Sq Ft
    • $1,277,778 per Acre

    514 N Pollard St, Winter Garden, FL 34787

    Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

    Alexis Anderson REGENCY REAL ESTATE LLC

    514 N Pollard St, Winter Garden, FL 34787
  • /35

    $505,000

    $20K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,094 Sq Ft

    12308 Bracco St, Oakland, FL 34787

    Beautiful and nearly new home in the quiet and friendly Highland Ridge community. This home was built only two years ago and is in perfect condition, offering over 2,114 sq. ft. of air-conditioned space. The layout is open and bright, with a modern kitchen that overlooks the large living and dining areas, perfect for family time and hosting friends. A big plus for this property is the oversized

    Diller de Abreu Junior ELITE INTERNATIONAL REALTY INC

    12308 Bracco St, Oakland, FL 34787
  • /23

    $575,000

    $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,477 Sq Ft

    9360 Mclaren Aly, Oakland, FL 34787

    **SELLER MOTIVATED - NEW PRICE*** Welcome to this beautifully appointed, move-in-ready home located in the highly desirable, resort-style master-planned community of Waterleigh in Winter Garden. This home offers the perfect blend of modern sophistication and everyday functionality across a bright, open-concept design. From the moment you enter through the front door, the airy foyer welcomes you

    Leslie Heimer PREMIER SOTHEBYS INT'L REALTY

    9360 Mclaren Aly, Oakland, FL 34787
  • /3

    $411,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,729 Sq Ft

    Sage Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Sage floorplan offers a thoughtfully designed two-story layout, ideal for comfortable living and modern convenience. This 3-bedroom, 2.5-bathroom townhome features an open concept on the first floor, highlighted by a spacious great room, a cozy lanai, and a breezeway that connects to a 2-car garage. Upstairs, the second floor boasts all three bedrooms, along with a versatile loft space,

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36488308, Oakland, FL 34787
  • /31

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,082 Sq Ft

    14123 Frasier St, Oakland, FL 34787

    SPECIAL FINANCING AVAILABLE! The seller is offering a promotional 3.875 interest rate through a rate buy-down program, plus ALL closing costs paid when using the preferred lender—creating an incredible opportunity for qualified buyers to significantly reduce their monthly payment and cash needed at closing. Welcome to this stunning newer construction home located in the highly desirable Horizon

    Yornelly Sanchez Manrique LEVO REAL ESTATE LLC

    14123 Frasier St, Oakland, FL 34787
  • /57

    $535,000

    • 4 Beds
    • 3.5 Baths
    • 2,486 Sq Ft

    17167 Writing Aly, Oakland, FL 34787

    Located in the heart of Horizon West, 17167 Writing Aly offers the space, flexibility, and location buyers are looking for in Winter Garden. Just minutes from Hamlin Town Center, the 429, Disney, and Downtown Winter Garden, this home is positioned in one of Central Florida’s fastest-growing areas while still offering a true neighborhood feel with community green spaces, walking paths, and

    Ken Pozek REAL BROKER, LLC

    17167 Writing Aly, Oakland, FL 34787
  • /17

    $401,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,644 Sq Ft

    Harbor Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

    The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36477638, Oakland, FL 34787
  • /3

    $577,990

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

    Lexington Plan at Serenade at Ovation - 50' Collection, 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, cafe, and kitchen, creating a welcoming atmosphere for entertaining and everyday

    Dream Finders Homes Builder
    14229 Lanyard Way Unit 36464864, Oakland, FL 34787
  • /3

    $449,000

    $26K PRICE DROP
    • Land
    • 22,215 Sq Ft
    • $880,392 per Acre

    17858 Hither Hills Cir, Winter Garden, FL 34787

    Discover the perfect blend of luxury and natural beauty with these stunning lakefront lots in the Lake Apopka Sound subdivision. Set along the shores of scenic Lake Apopka, these spacious homesites offer breathtaking water views, serene sunsets, and access to one of Central Florida’s most picturesque settings. Lake Apopka Sound provides the ideal backdrop for your custom dream home. With close

    Chris Kaminski FLORIDAY PROPERTIES INC

    17858 Hither Hills Cir, Winter Garden, FL 34787

Home Price Trends

Median Sale Price
$680,000
Median Single Family Sale Price
$785,000
Median Townhouse Sale Price
$386,950
Median 2 Bedroom Sale Price
$384,900
Average Price Per Sq Ft
$310
Number of Homes for Sale
38
Last 12 months Home Sales
115
Months of Supply
4.00
Median List Price
$749,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
5%
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