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Oakland, FL Homes for Sale

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  • /31

    $545,000

    • 3 Beds
    • 2 Baths
    • 1,513 Sq Ft

    131 Ryan Ct, Oakland, FL 34760

    Discover your next home at 131 Ryan Ct in charming Oakland, FL. This well-maintained 3-bedroom, 2-bathroom house features beautiful wood-look tile floors throughout the entire home. Recent updates make this property move-in ready. The roof was replaced in 2021, followed by a new AC system in 2020, new windows in 2023, and a brand-new water heater in 2024. The kitchen showcases wood cabinets

    Agent Photo

    Deanna Meredith

    LUXE PROPERTIES LLC

    (321) 495-8071

    131 Ryan Ct, Oakland, FL 34760
  • /39

    $499,999

    • 4 Beds
    • 3 Baths
    • 2,352 Sq Ft

    651 Regina Cir, Oakland, FL 34787

    ***SELLER SAYS SELL! BEST priced home in the community!*** Welcome to John’s Landing, a gated lakefront community in the charming town of Oakland, offering private lake access and a community dock on Johns Lake. Step inside this spacious 4-bedroom, 3-bathroom home with a 3-car garage and make it your own. The thoughtfully designed split floor plan includes a family room, formal living room,

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    Savina Delgado Rodriguez

    THE PROPERTY FIRM

    (321) 495-8335

    651 Regina Cir, Oakland, FL 34787
  • /32

    $1,000,000

    • 4 Beds
    • 2 Baths
    • 2,708 Sq Ft

    624 Hull Island Dr, Oakland, FL 34787

    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

    Agent Photo

    Carmelo Nuccio

    RE/MAX EXCLUSIVE COLLECTION

    (321) 449-7661

    624 Hull Island Dr, Oakland, FL 34787
  • /52

    $535,000

    • 3 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    9029 Sonoma Coast Dr, Oakland, FL 34787

    Experience modern Florida living in this stunning, move-in-ready home at 9029 Sonoma Coast Dr, Winter Garden. Built in 2020, this light-filled residence features 3 spacious bedrooms, 2.5 bathrooms, and an open-plan layout that blends comfort with contemporary style, offering over 2,000 square feet of thoughtfully designed living space.? Step inside to discover a beautifully updated interior with

    Agent Photo

    Abraham Mendez

    NONA LEGACY POWERED BY LA ROSA

    (321) 766-5509

    9029 Sonoma Coast Dr, Oakland, FL 34787
  • /47

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 2,089 Sq Ft

    2375 Standing Rock Cir, Oakland, FL 34787

    Welcome to your perfect blend of serenity and convenience! This stunning 3-bedroom, 2.5-bath home offers over 2,000 square feet of living space and more than 3,200 square feet total. Situated on a corner lot, built in 2018, with a recently re-painted exterior and paid off solar panels, this home has curb appeal. The beautifully maintained property sits just steps from the West Orange Trail and

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    Jarred Denison

    POP REALTY POWERED BY SELLSTATE

    (321) 415-7083

    2375 Standing Rock Cir, Oakland, FL 34787
  • /33

    $504,995

    • 3 Beds
    • 2.5 Baths
    • 1,822 Sq Ft

    2755 Bobcat Chase Blvd, Oakland, FL 34787

    Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland community, where you'll find a modern 3-bedroom home with a bonus room—built in 2020, filled with upgrades and situated on a quiet cul-du-sac street. Located in Oakland, one of Central Florida’s most quaint and desirable small towns, 2755 Bobcat Chase offers a rare blend of peaceful living with unbeatable

    Agent Photo

    Tania Matthews

    KELLER WILLIAMS ELITE PARTNERS III REALTY

    (321) 495-8074

    2755 Bobcat Chase Blvd, Oakland, FL 34787
  • /53

    $835,000

    • 4 Beds
    • 4 Baths
    • 2,831 Sq Ft

    931 Kylee Alley, Winter Garden, FL 34787

    JUST REDUCED! Welcome to this exceptional David Weekley “Stoneybrook” residence in the highly sought-after Oakland Park community—just two years young and thoughtfully designed for both comfort and style. This four-bedroom, four-bath home spans 2,831 square feet of beautifully appointed living space, perfectly situated on a charming corner lot with inviting curb appeal. Step inside to discover an

    Barbara Vance PA PREMIER SOTHEBYS INT'L REALTY

    931 Kylee Alley, Winter Garden, FL 34787
  • /3

    $603,990 New Construction

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

    Anna Maria Plan at Serenade at Ovation - Single Family Homes, 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 Builder
    14229 Lanyard Way Unit 36464429, Oakland, FL 34787
  • /3

    $649,990 New Construction

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

    Biscayne Plan at Serenade at Ovation - Single Family Homes, 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 Builder
    14229 Lanyard Way Unit 36496529, Oakland, FL 34787
  • /4

    $505,990 New Construction

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

    Cooper Plan at Serenade at Ovation, 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
  • /25

    $645,990 New Construction

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

    Anna Maria w/ Bonus Plan at Serenade at Ovation - Single Family Homes, 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 Builder
    14229 Lanyard Way Unit 36501514, Oakland, FL 34787
  • /69

    $785,000

    • 4 Beds
    • 3 Baths
    • 2,909 Sq Ft

    9062 Sonoma Coast Dr, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Special Financing Available — Ask for Details!Experience resort-style living in the highly desirable Waterleigh community of Winter Garden. This one-of-a-kind home sits on a rare, oversized lot with no rear neighbors, offering ultimate privacy and tranquility — perfect for families or anyone seeking a private retreat in one of Central Florida’s

    Asher Chen AAA GLOBAL VENTURES PA

    9062 Sonoma Coast Dr, Oakland, FL 34787
  • /51

    $869,000

    • 4 Beds
    • 4.5 Baths
    • 2,741 Sq Ft

    3375 Hanging Tide St, Oakland, FL 34787

    An Enchanting Suburban Gem Marries the appeal of small-town life with the allure of urban conveniences. 4 Bedroom, 4.5 Bathroom POOL Home situated within the Gated Community of the stylish Lakeview Preserve on beautiful Johns Lake. Sitting on a private cul-de-sac, this residence offers breathtaking sunset views over the pool and an inviting indoor-outdoor living experience. The heart of the home

    Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

    3375 Hanging Tide St, Oakland, FL 34787
  • /100

    $969,000

    • 4 Beds
    • 4.5 Baths
    • 3,408 Sq Ft

    9988 Beach Port Dr, Oakland, FL 34787

    Welcome to 9988 Beach Port Drive in the beautiful community Waterleigh in Winter Garden! This stunning property offers the perfect blend ofmodern luxury and serene coastal living. This home provides a peaceful retreat that embodies the essence of relaxation and comfort. With itsspacious layout, stylish design, and picturesque surroundings, 9988 Beach Port Driver is truly a gem waiting to

    Yukey Hoo U KEY REALTY

    9988 Beach Port Dr, Oakland, FL 34787
  • /51

    $995,000

    • 4 Beds
    • 3.5 Baths
    • 2,758 Sq Ft

    8708 Sonoma Coast Dr, Oakland, FL 34787

    Nestled in Phase 3 of Waterleigh in Horizon West, this stunning single-story home offers 4 bedrooms and 3.5 bathrooms on a premium .41-acre lot with no rear neighbors, providing both privacy and tranquility. Situated on a quiet cul-de-sac, the home features beautiful views and a peaceful setting, just a short stroll from a charming community green space with a pavilion and picnic area. Inside,

    Linda Sirois LONDON FOSTER REALTY

    8708 Sonoma Coast Dr, Oakland, FL 34787
  • /60

    $1,035,000

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

    9549 Bolero Rd, Oakland, FL 34787

    The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home water softener, reverse osmosis kitchen

    Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

    9549 Bolero Rd, Oakland, FL 34787
  • /60

    $990,000

    • 5 Beds
    • 3 Baths
    • 3,275 Sq Ft

    8162 Sayings Dr, Oakland, FL 34787

    Excellent opportunity for investors!Stunning home for sale in the coveted Storey Grove community, currently renting for $4,950 per month, guaranteeing excellent passive income from day one!Located in a prime area, close to top-notch schools and with easy access to Disney parks, this charming 5-bedroom, 3-bathroom residence offers the perfect balance of comfort, sophistication, and

    Adriana Franzoi WRA BUSINESS & REAL ESTATE

    8162 Sayings Dr, Oakland, FL 34787
  • /51

    $839,900

    • 3 Beds
    • 2.5 Baths
    • 2,348 Sq Ft

    9008 Sonoma Coast Dr, Oakland, FL 34787

    Welcome to your dream home! This beautifully decorated 3 Bedroom, 2 1/2 Bath + Office home where comfort meets style offers stunning lake views and a sleek tile roof. Upon entering you'll be greeted by architectural arches and a wide foyer entry. To your left, you will be greeted by architectural arches and a wide foyer entry. On your left you will find a Den/Study/Office with glass entry doors &

    Gary Berkson RE/MAX CENTRAL REALTY

    9008 Sonoma Coast Dr, Oakland, FL 34787
  • /52

    $410,000

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

    13293 Pontoon Rd, Oakland, FL 34787

    Sometimes the right home just feels easy. This 3-bedroom, 3-bath corner unit townhome was built in 2023 and sits in one of Winter Garden’s most sought-after neighborhoods, Waterleigh. From the moment you pull into the driveway, you’ll notice how clean, simple, and ready it feels. No projects. No waiting. Just move in and enjoy.Inside, natural light pours through every room, highlighting

    Mark Raumaker SERHANT

    13293 Pontoon Rd, Oakland, FL 34787
  • /42

    $848,690 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,810 Sq Ft

    5812 Dancing Willow St, Oakland, FL 34787

    Under Construction. Welcome to Parkside Trails! Explore the charm of this premier Clermont location, offering exclusive amenities and quick access to shopping, dining, and entertainment. With a mix of new construction, single-family and townhomes, plus a variety of exclusive amenities, families will love coming home. Now Selling Onsite with 4 Models Open Daily!Step into the Scarlett by Pulte

    Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

    5812 Dancing Willow St, Oakland, FL 34787
  • /2

    $799,135 New Construction

    • 6 Beds
    • 4.5 Baths
    • 3,412 Sq Ft

    15093 Tea Tree Dr, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Pre-Construction. To be built. Opportunity in Avalon Woods! Discover the newest community by Dream Finders Homes in highly sought-after Hamlin, Winter Garden. Welcome to the Anna Maria w/ Bonus, an award-winning open-concept home designed for modern living and effortless entertaining. The thoughtfully designed layout flows seamlessly from the great

    Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

    15093 Tea Tree Dr, Oakland, FL 34787
  • /3

    $407,990 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
  • /3

    $409,990 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
  • /82

    $1,050,000

    • 5 Beds
    • 4 Baths
    • 3,084 Sq Ft

    877 Tilden Oaks Trail, Winter Garden, FL 34787

    Modern Craftsman Charmer in Oakland Park – Corner Lot, No Rear Neighbors, and Steps from the West Orange Trail!Welcome to 877 Tilden Oaks Trail, a beautifully designed David Weekley Modern Craftsman home in the heart of Oakland Park—one of Winter Garden’s most sought-after communities. Featuring 5 bedrooms, 4 bathrooms, 3,084 sq. ft., and stunning curb appeal, this move-in ready home offers

    Matthew Matin CLOCK TOWER REALTY

    877 Tilden Oaks Trail, Winter Garden, FL 34787
  • /44

    $714,500

    • 5 Beds
    • 4 Baths
    • 3,163 Sq Ft

    2450 Standing Rock Cir, Oakland, FL 34787

    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 the perfect setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days, or relaxing with friends. Step

    Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

    2450 Standing Rock Cir, Oakland, FL 34787
  • /48

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,338 Sq Ft

    507 W Oakland Ave, Oakland, FL 34760

    One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location!Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland

    Jennifer Ibarra REAL BROKER, LLC

    507 W Oakland Ave, Oakland, FL 34760
  • /62

    $1,850,000

    • 6 Beds
    • 5 Baths
    • 4,104 Sq Ft

    1101 Eagles Pass Way, Oakland, FL 34787

    One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two

    Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

    1101 Eagles Pass Way, Oakland, FL 34787
  • /53

    $749,000

    • 5 Beds
    • 3 Baths
    • 3,493 Sq Ft

    1751 Standing Rock Cir, Oakland, FL 34787

    Nestled in the highly desirable Oakland Trails community, this beautifully designed 5-bed, 3-bath "Montclair" former model home spans nearly 3,500 square feet of thoughtfully planned living space. The first floor opens with a spacious family room, separate formal living and dining areas, and a fifth bedroom with adjacent bath. The open-concept kitchen boasts an oversized island, double ovens,

    Julie Bettosini STOCKWORTH REALTY GROUP

    1751 Standing Rock Cir, Oakland, FL 34787
  • /39

    $389,000

    • 2 Beds
    • 2.5 Baths
    • 1,472 Sq Ft

    2218 Gopher Tortoise Terrace, Oakland, FL 34760

    Enjoy low-maintenance living in this beautifully kept 2-bedroom, 2.5-bathroom townhome. The open main level offers seamless flow with plank flooring and thoughtfully designed spaces for everyday living. The kitchen showcases quartz countertops, an upgraded backsplash, stainless steel appliances, and bar seating that opens to the living area. A dedicated nook provides the perfect spot for a home

    Chelsea Eckert CAM REALTY & PROPERTY MANAGEME

    2218 Gopher Tortoise Terrace, Oakland, FL 34760
  • /46

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,554 Sq Ft

    2690 Bobcat Chase Blvd, Oakland, FL 34787

    Love Where You Live — in Longleaf at Oakland! ? Welcome to Longleaf at Oakland, one of Central Florida’s most sought-after communities near Winter Garden, where modern living meets natural serenity. This immaculate 3-bedroom, 2-bath home with a 2-car garage backs to peaceful conservation land—so you’ll enjoy privacy, stunning views, and no rear neighbors. Built in 2019 and cared for like new,

    Marnetta Arnett LPT REALTY, LLC

    2690 Bobcat Chase Blvd, Oakland, FL 34787
  • /3

    $75,000

    • Land
    • 0.11 Acre
    • $681,818 per Acre

    121 S Nixon St, Oakland, FL 34760

    If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

    Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

    121 S Nixon St, Oakland, FL 34760
  • /86

    $670,000

    • 4 Beds
    • 2.5 Baths
    • 2,473 Sq Ft

    2606 Bobcat Chase Blvd, Oakland, FL 34787

    Stunning former MODEL HOME on a premium CORNER lot – loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both comfort and style. Step inside to discover a bright, open floor plan featuring elegant luxury plank

    Ashley Boyd BHHS FLORIDA REALTY

    2606 Bobcat Chase Blvd, Oakland, FL 34787
  • /42

    $649,000

    • 4 Beds
    • 3.5 Baths
    • 2,743 Sq Ft

    12554 Westhaven Oak Dr, Oakland, FL 34787

    This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

    Adriana Franzoi WRA BUSINESS & REAL ESTATE

    12554 Westhaven Oak Dr, Oakland, FL 34787
  • /44

    $675,000

    • 4 Beds
    • 3 Baths
    • 2,650 Sq Ft

    529 Johns Landing Way, Oakland, FL 34787

    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

    Denise Pellegrino REAL BROKER, LLC

    529 Johns Landing Way, Oakland, FL 34787
  • /52

    $375,000

    • 2 Beds
    • 2.5 Baths
    • 1,472 Sq Ft

    2217 Gopher Tortoise Terrace, Oakland, FL 34787

    Priced aggressively! Welcome to 2217 Gopher Tortoise Terrace, an exquisite townhome nestled in the heart of charming Oakland, Florida. This modern residence boasts 1,497 square feet of contemporary living space, offering a harmonious blend of style and functionality. Step inside to discover a thoughtfully designed living area, featuring elegant Luxury Vinyl Plank (LVP) flooring that flows

    Matt McKee COMPASS FLORIDA LLC

    2217 Gopher Tortoise Terrace, Oakland, FL 34787
  • /38

    $399,000

    • 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 for $2500 monthly, 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

    Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

    12043 Holystone St, Oakland, FL 34787
  • /14

    $385,000

    • Land
    • 0.29 Acre
    • $1,327,586 per Acre

    610 Simeon Rd, Oakland, FL 34787

    Presenting a rare opportunity to purchase a 0.29-acre residential lot in the highly sought-after Town of Oakland. This unincorporated property offers exceptional flexibility, no HOA restrictions and agricultural zoning. Conveniently located just steps from the scenic West Orange Trail, the Oakland Nature Preserve, and downtown Oakland. Enjoy the peaceful surroundings amongst the oak trees and

    Blaine Dooley REGENCY REAL ESTATE LLC

    610 Simeon Rd, Oakland, FL 34787
  • /26

    $649,900

    • 4 Beds
    • 3 Baths
    • 3,182 Sq Ft

    326 Largovista Dr, Oakland, FL 34787

    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

    Chris Sanford EXP REALTY LLC

    326 Largovista Dr, Oakland, FL 34787
  • /28

    $1,775,000

    • 5 Beds
    • 4.5 Baths
    • 3,991 Sq Ft

    854 Tilden Oaks Trail, Winter Garden, FL 34787

    This former J & J Building model home has never been lived in and has been carefully cared for. With 3,453 sq. ft. in the main house, it offers 4 bedrooms, 3.5 baths, and an oversized 2.5-car garage with extra space for a golf cart. A detached 538 sq. ft. pool house adds valuable flexibility, offering a fifth bedroom, full bath, wet bar, office, and walk-in closet—an ideal setup for extended

    Tracey McFadden OAK AVENUE REAL ESTATE LLC

    854 Tilden Oaks Trail, Winter Garden, FL 34787
  • /40

    $610,000

    • 2 Beds
    • 2 Baths
    • 1,889 Sq Ft

    13732 Fresh Ivy St, Oakland, FL 34787

    Not your average Del Webb home—this nearly new, designer-upgraded retreat offers rare touches and nightly neighborhood Disney fireworks views. Why wait to build? This home is just under a year old and move-in ready, located in the vibrant 55+ community of Del Webb Oasis, where resort-style amenities include a clubhouse, zero-entry pool with cabanas, tennis, pickleball, and more. The open-concept

    Ken Pozek REAL BROKER, LLC

    13732 Fresh Ivy St, Oakland, FL 34787

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Why Live in Oakland

Between the scenic Lake Apopka and Johns Lake, Oakland is a small, Orange County town with an established, nature-oriented feel. Around 18 miles west of downtown Orlando and 15 miles north of Walt Disney World, the town lies in the heart of ...

Frequently Asked Questions

What is the average home price in Oakland, FL?
Homes for sale in Oakland, FL have an average home price of $851,501.
How many homes have sold over the last 12 months in Oakland, FL?
185 homes have sold in Oakland, FL over the last 12 months.
What are the most popular zip codes in Oakland, FL?
The most popular zip codes in Oakland, FL include 34760, 34787, 34756, 34711 and 34715.
How much do you need to make to afford a house in Oakland?
The median home price in Oakland is $721,231. If you put a 20% down payment of $144,200 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $3,550 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $152K a year to afford the median home price in Oakland.
How are the schools in Oakland, FL?
Oakland, FL has highly rated public and private schools. Some of the best schools in Oakland based on Niche Grades are Oakland Avenue Charter School, Tildenville Elementary and West Orange High School. Browse all the schools in Oakland, FL to learn more.

Home Trends in Oakland, FL

Housing Trends

Median Sale Price
$690,000
Median Single Family Sale Price
$780,000
Median Townhouse Sale Price
$440,000
Average Price Per Sq Ft
$300
Number of Homes for Sale
52
Last 12 months Home Sales
185
Months of Supply
3.40
Median List Price
$721,231
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
25%
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