Oakland, FL Houses for Sale

/24
$894,000
- 4 Beds
- 2 Baths
- 2,708 Sq Ft
624 Hull Island Dr, Oakland, FL 34787

Discover a rare opportunity to own a private estate property in one of West Orange County’s most desirable corridors. Situated in Oakland, this 2.55-acre parcel offers space, privacy, and future potential just minutes from the conveniences of West Colonial Drive, Florida Turnpike (Exit 275), Clermont, and the vibrant districts of Oakland and Downtown Winter Garden. Properties like this are

Carmelo Nuccio

RE/MAX EXCLUSIVE COLLECTION

(321) 449-7661

624 Hull Island Dr, Oakland, FL 34787
/34
$635,000 New Construction
- 4 Beds
- 3.5 Baths
- 2,445 Sq Ft
16186 Honey Harvest St, Oakland, FL 34787

Move-In Ready Luxury in Harvest at Ovation — Taylor Morrison Popular Baldwin Floor Plan. Sellers had change of plans. Brand new home available for immediate move-in! Why wait months to build when this stunning, just-completed Taylor Morrison Baldwin floor plan is ready for you right now? Located in the highly sought-after Harvest at Ovation community in Orlando, this exceptional 4-bedroom,

Nicole Rader

MAINFRAME REAL ESTATE

(689) 303-5944

16186 Honey Harvest St, Oakland, FL 34787
/4
$505,990 New Construction
- 3 Beds
- 2.5 Baths
- 2,078 Sq Ft
Cooper Plan at Serenade at Ovation - Bungalow, 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
/45
$549,900
- 3 Beds
- 2.5 Baths
- 2,089 Sq Ft
2065 White Feather Loop, Oakland, FL 34787

Welcome to the highly desirable Oakland Trails community, where this beautifully designed 2019 Meritage Home offers an exceptional blend of modern comfort, energy efficiency, and everyday convenience. Ideally located just approximately 30 minutes from Disney, Universal, and Downtown Orlando, the home provides easy access to major attractions while preserving a peaceful residential

Denis Bochkov PINK MIAMI

2065 White Feather Loop, Oakland, 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
/30
$489,000
- 4 Beds
- 3 Baths
- 2,120 Sq Ft
1051 Stationside Dr, Oakland, FL 34787

Welcome to this beautifully maintained 4-bedroom, 3-bath home in the heart of Oakland, where everyday living feels connected, convenient, and just a little more elevated. This home enjoys amazing views of the Oakland Nature Preserve. Ideally located within walking distance to the West Orange Trail and just minutes from the charm of downtown Oakland and Winter Garden’s vibrant shops, dining, and

Steve Healy CORCORAN PREMIER REALTY

1051 Stationside Dr, Oakland, FL 34787
/38
$729,900
- 5 Beds
- 4.5 Baths
- 2,931 Sq Ft
15070 Summer Harvest St, Oakland, FL 34787

PRICED TO SELL! 5BR Corner Lot + Private In-Law Suite + Soaring Ceilings Near Amenities Rare opportunity to own a spacious 5-bedroom home with a private in-law suite above the garage. Located on a premium corner lot just steps from the amenity center, this home offers flexibility, privacy, and modern upgrades. Priced aggressively for a quick sale—this one will not last. Welcome to this

Robert Benenati 365 REALTY, INC.

15070 Summer Harvest St, Oakland, FL 34787
/30
$874,900
- 4 Beds
- 4.5 Baths
- 3,134 Sq Ft
1231 Foltz Loop, Oakland, FL 34787

Nestled in the serene, lakefront community of Hull Island, this meticulously maintained corner-lot home offers 4 bedrooms, 4.5 bathrooms, and a spacious bonus/game room. The Dorchester floor plan delivers a modern layout designed for both comfort and functionality. Upon entering the elegant foyer, you are welcomed by a formal dining room or flex space that leads into a bright, open-concept living

Elisabeth Rusnak SOUTHERN REALTY GROUP LLC

1231 Foltz Loop, Oakland, FL 34787
/78
$2,750,000
- 5 Beds
- 6 Baths
- 4,373 Sq Ft
812 Johns Point Dr, Oakland, FL 34787

Experience unparalleled lakefront living in this fully renovated Mediterranean-style estate located in the exclusive gated community of John’s Cove on Johns Lake. A grand driveway and manicured landscaping welcome you into a striking modern entry and elegant interior featuring high-end flooring and designer finishes throughout.Designed for effortless entertaining, the open-concept layout

Any Alves WRA BUSINESS & REAL ESTATE

812 Johns Point Dr, Oakland, FL 34787
/76
$1,299,500
- 5 Beds
- 3.5 Baths
- 3,911 Sq Ft
8978 Sonoma Coast Dr, Oakland, FL 34787

LUXURY POOL HOME on PREMIUM LAKE FRONT LOT! Unique Opportunity to Enjoy an Outdoor PARADISE with STUNNING LAKE, CONSERVATION & SUNSET Views! The HOA is Allowing Docks on these Special Lots – Relax, Fish or Kayak! Most POPULAR Floor Plan – North Haven – has 5 Bedrooms, 3.5 Baths, Gourmet Kitchen, First Floor Primary Suite, TONS OF STORAGE, Tile Roof and 3 Car Garage. The OUTDOOR LIVING Space is

JoAnn Best CHARLES RUTENBERG REALTY ORLANDO

8978 Sonoma Coast Dr, Oakland, FL 34787
/60
$675,000
- 3 Beds
- 2.5 Baths
- 1,772 Sq Ft
936 Kylee Aly, Winter Garden, FL 34787

Move-in ready 3-bedroom, 2.5-bathroom single-family home in the Oakland Park community of Winter Garden, Florida. Built in 2022, turnkey condition, full appliance package included, and a low-maintenance 0.05-acre homesite designed for connected daily living without the upkeep. Oakland Park is one of those Winter Garden communities people move to on purpose. Tree-lined streets, walkable sidewalks,

Nelson Cruz REAL BROKER, LLC

936 Kylee Aly, Winter Garden, FL 34787
/47
$885,000
- 4 Beds
- 3 Baths
- 2,850 Sq Ft
8 Winters Landing Dr, Oakland, FL 34787

One or more photo(s) has been virtually staged. Welcome to your own private retreat in one of West Orange County’s most sought-after areas. This completely renovated 4-bedroom, 3-bathroom home offering 2,850 square feet of beautifully updated living space, with a new roof (2025), located in the heart of Oakland is just minutes from downtown Winter Garden.From the moment you step inside,

Danielle Norvell REGENCY REAL ESTATE LLC

8 Winters Landing Dr, Oakland, FL 34787
/78
$1,588,000
- 4 Beds
- 4.5 Baths
- 3,613 Sq Ft
1412 Johns Cove Ln, Oakland, FL 34787

Welcome to your ideal lakeside sanctuary in the highly sought-after gated community of Johns Cove! This home features a split bedroom layout with over 3600 s/f of easy, relaxing living complemented by a pool area that boasts stunning views of Johns Lake. The property has been completely reinvented since the current owners purchased it. Renovations include, a kitchen with all new appliances

Betsey West NEXT RESIDENCE REALTY LLC

1412 Johns Cove Ln, Oakland, FL 34787
/51
$649,900
- 4 Beds
- 2.5 Baths
- 2,235 Sq Ft
5679 Orange Orchard Dr, Oakland, FL 34787

Move-In Ready Home Near Hamlin Town Center with Open Layout and Private Backyard. Built in 2021 and located in the sought-after Wincey Groves community of Winter Garden, this beautifully maintained energy efficient 4-bedroom, 2.5-bath home offers thoughtfully designed living space with modern finishes and a functional open layout. The spacious main living area is filled with natural light and

Helen Thompson RE/MAX SELECT GROUP

5679 Orange Orchard Dr, Oakland, FL 34787
/55
$819,000
- 5 Beds
- 4 Baths
- 2,840 Sq Ft
8807 Sonoma Coast Dr, Oakland, FL 34787

Welcome to the beautiful community of Waterleigh in Winter Garden! This meticulously maintained home features 5 bedrooms, 4 bathrooms, and a second floor laundry and bonus/game room. This thoughtfully designed open-concept home offers functionality and space for all. The spacious foyer invites you into the great room filled with natural light and overlooks the pond. The kitchen features stainless

Teresa Stewart SOUTHERN REALTY GROUP LLC

8807 Sonoma Coast Dr, Oakland, FL 34787
/44
$725,000
- 4 Beds
- 3 Baths
- 2,113 Sq Ft
17936 Adrift Rd, Oakland, FL 34787

This is an amazing one-story 4-bedroom, 3 bath lakeview, conservation area home with elegant exteriors and high end features in Waterleigh, Horizon West’s Premier Community! Desirable Horizon West, featuring resort-style amenities and thoughtful design minutes from Disney World Parks and resorts. Elegant 4 bedroom, 3-bath home offers 2,113 sq. ft. of single-story comfort, ideal for families or

Stephen Hachey FLAT FEE MLS REALTY

17936 Adrift Rd, Oakland, FL 34787
/53
$875,000
- 4 Beds
- 4 Baths
- 2,831 Sq Ft
931 Kylee Aly, Winter Garden, FL 34787

There is a specific frequency to life in Oakland Park that exists nowhere else in Central Florida. It is a rare, rhythmic harmony between the nostalgia of Old Florida and the crisp, clean lines of modern luxury. As you cross into the community, the atmosphere shifts. The air feels lighter, filtered through the canopy of ancient oaks and manicured greenery of a village designed for connection.

Barbara Vance PA PREMIER SOTHEBYS INT'L REALTY

931 Kylee Aly, Winter Garden, FL 34787
/46
$875,000
- 4 Beds
- 3.5 Baths
- 2,923 Sq Ft
9409 Emerald Berry Dr, Oakland, FL 34787

Nestled on a premium homesite with no rear neighbors in the exclusive Summerlake Reserve enclave, this beautifully designed home blends comfort, functionality, and thoughtful upgrades throughout. The home offers 4 bedrooms, 3.5 bathrooms, a private office with barn doors, a spacious loft, and an extended covered lanai ideal for indoor-outdoor living. The gourmet kitchen is both elegant and

Manuella Espinosa LA ROSA REALTY LLC

9409 Emerald Berry Dr, Oakland, FL 34787
/76
$1,275,000
- 4 Beds
- 2.5 Baths
- 2,710 Sq Ft
1156 Civitas Way, Winter Garden, FL 34787

Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's most desirable communities. Ideally positioned on a premium corner lot with a view of Apopka Lake, from the second story balcony and no onward facing front neighbors, this residence embodies the front-porch lifestyle that defines Oakland Park's appeal. Located near the scenic West Orange Trail and minutes

Heidi Pfeffer-Morgan DALTON WADE INC

1156 Civitas Way, Winter Garden, FL 34787
/19
$519,000
- 4 Beds
- 2 Baths
- 2,046 Sq Ft
1270 Stationside Dr, Oakland, FL 34787

Nested right along the scenic West Orange Trail, this spacious 4 bedroom, 2 bath home offers the perfect balance of recreation and relaxation. The open interior flows seamlessly to private pool, creating an ideal oasis for Florida living. Located for ultimate convenience, just 15 mins from Downtown Winter Garden with The Turnpike nearby for an easy commute. Enjoy being 30 mins of Orlando's world

Ky Lam HOME INVEST REALTY INC

1270 Stationside Dr, Oakland, FL 34787
/59
$525,000
- 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
/49
$679,900
- 4 Beds
- 3.5 Baths
- 3,583 Sq Ft
729 Strihal Loop, Oakland, FL 34787

Prince drastically reduced for quick sale !!! Luxury, Location, and Lake Access !! This elegant 5 bedrooms, 3.5 baths home is located in an exclusive gated community on Johns Lake, offering privacy and luxury lifestyle. Home boasts vaulted ceilings and designer quartz counter tops. Step outside to your private pool or take advantage of the community's private boat ramp with direct lake access to

Subhas C Sawh LIBERTY HOME SALES INC

729 Strihal Loop, Oakland, FL 34787
/49
$899,900
- 3 Beds
- 2 Baths
- 2,214 Sq Ft
13343 Sunny Retreat Ln, Oakland, FL 34787

The neighbors call this home the best kept secrets in Oasis. Sip your coffee from from the comfort of your backyard facing due east and enjoy the gorgeous sunrise, every morning!In the evening, you'll find great views of the Disney fireworks! You won't be able to find these beautiful views and gorgeous Pergola/Patio set up anywhere in the community! The seller spared no expense in making the

John Hart ENGEL & VOLKERS ORLANDO DR PHILLIPS

13343 Sunny Retreat Ln, Oakland, FL 34787
/58
$1,765,000
- 5 Beds
- 4 Baths
- 3,784 Sq Ft
906 Allendale Ln, Winter Garden, FL 34787

Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for

Jurgita Blake CENTURY 21 CARIOTI

906 Allendale Ln, Winter Garden, FL 34787
/57
$795,000
- 4 Beds
- 3 Baths
- 2,909 Sq Ft
9611 Lost Creek Dr, Oakland, FL 34787

No rear neighbors! Situated on a premium conservation lot with lake views, this fully furnished 4-bedroom, 3-bathroom two-story home in the desirable Waterleigh community offers privacy, upgrades, and true move-in-ready convenience. Exceptional curb appeal features a brick paver driveway and welcoming front porch. Inside, enjoy wood-look tile throughout the main living areas, a flexible formal

Mariana Micheti M2M REALTY

9611 Lost Creek Dr, Oakland, FL 34787
/64
$599,000
- 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
/48
$574,000
- 5 Beds
- 3.5 Baths
- 3,248 Sq Ft
1490 Stone Arrow Ct, Oakland, FL 34787

This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters,

Eric Jia NUMBER 1 BROKER, LLC

1490 Stone Arrow Ct, Oakland, FL 34787
/55
$2,190,000
- 5 Beds
- 4.5 Baths
- 4,436 Sq Ft
9014 Morgana Ct, Oakland, FL 34787

This is more than a house ~ Lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare “water-on-water” moment – breathtaking

Jennifer Wemert WEMERT GROUP REALTY LLC

9014 Morgana Ct, Oakland, FL 34787
/34
$565,000 Open Sat 12PM - 2PM
- 4 Beds
- 3.5 Baths
- 2,477 Sq Ft
16140 Harbor Mist Aly, Oakland, FL 34787

Priced to sell — don't miss this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community. Offering 2,477 sq ft, 4 bedrooms, and 3.5 bathrooms, this home is move-in ready with major updates already done. The open-concept main floor features a chef-ready kitchen with granite countertops, wood cabinetry, and stainless steel appliances, flowing into spacious

Jeanine Louis-Alcime EXP REALTY LLC

16140 Harbor Mist Aly, Oakland, FL 34787
/62
$1,499,000
- 6 Beds
- 7.5 Baths
- 5,614 Sq Ft
620 N Tubb St, Oakland, FL 34760

PRICE IMPROVEMENT! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an .8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty

Jennifer Wilson OAKSTRAND REALTY

620 N Tubb St, Oakland, FL 34760
/39
$796,000
- 5 Beds
- 3 Baths
- 3,528 Sq Ft
1970 Standing Rock Cir, Oakland, FL 34787

Discover expansive living and modern sophistication in this STUNNING 5-bedroom, 3-bath home with a Spacious, Peaceful backyard in the highly desirable Oakland Trails community, minutes from the West Orange Trail and the Winter Garden Plant Street Market. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE

Jennifer Wemert WEMERT GROUP REALTY LLC

1970 Standing Rock Cir, 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
/42
$599,000
- 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 PL Franzoi WRA BUSINESS & REAL ESTATE

12554 Westhaven Oak Dr, Oakland, FL 34787
/51
$824,950
- 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 + Office, 2 1/2 Bath 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
/57
$990,000 Open Sun 12PM - 3PM
- 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. Big Price Reduction!!!!!! 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,

Jennifer Ibarra REAL BROKER, LLC

9849 Lost Creek Dr, Oakland, FL 34787
/13
$550,000 New Construction
- 3 Beds
- 3.5 Baths
- 2,149 Sq Ft
14736 Field Daisy Dr, Oakland, FL 34787

Welcome to the Newberry at 14736 Field Daisy Drive in Harvest at Ovation! The Newberry bungalow floor plan is a true representation of modern living and the perfect space for all of your entertainment needs and desires. The 2149 sq. ft. two-story home with 3 bedrooms, 3.5 bathrooms and a 2-car detached garage presents prospective homebuyers with both the basic features and intricate details that

Taylor Morrison Builder

14736 Field Daisy Dr, Oakland, FL 34787
/24
$607,990 New Construction
- 4 Beds
- 3 Baths
- 2,650 Sq Ft
3160 Namaste Dr, Oakland, FL 34787

One or more photo(s) has been virtually staged. Under Construction. This lovely Riviera Next Gen® single-story home features an attached private suite with its own living room, kitchenette, bedroom and bathroom. In the main home is an open space layout in the kitchen, nook and family room, which extends to the covered patio through sliding glass doors for outdoor living. There is a flex space to

Ben Goldstein LENNAR REALTY

3160 Namaste Dr, Oakland, FL 34787
/21
$647,690 New Construction
- 4 Beds
- 3.5 Baths
- 2,911 Sq Ft
3128 Namaste Dr, Oakland, FL 34787

Under Construction. The Inverness is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s suite

Ben Goldstein LENNAR REALTY

3128 Namaste Dr, Oakland, FL 34787

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Florida Orange County Oakland

Why Live in Oakland

Between Lake Apopka and Johns Lake, Oakland, Florida is a small Orange County town with a strong connection to nature and lake access. About 18 miles west of downtown Orlando and 15 miles north of Walt Disney World, it sits close to major attractions while keeping a quiet, low-key feel. Residential streets feature coastal cottages, Colonial Revival homes, and modern traditional builds, many constructed in the 1970s or later, with a large share built in the past decade. Lots are generally a quarter-acre or smaller, shaded by mature oaks and Spanish moss, and many homes include in-ground pools; lakefront properties often add private docks and direct water access. Local students may attend Tildenville Elementary School, which has a high rating, and West Orange High School, also highly rated and known for its dual enrollment options and more than 50 extracurricular activities. Outdoor life centers on the 150-acre Oakland Nature Preserve with wooded trails and regular programs, Speer Park’s playground and sports courts, and the paved West Orange Trail, which runs over 22 miles and links to nearby Winter Garden businesses. The town center along Tubb Street includes the historic Oakland Town Hall and the Healthy West Orange Arts and Heritage Center, which hosts rotating exhibits, classes, and the Oakland Farmers Market, while everyday errands are handled at nearby ALDI and Publix and regional travel relies on Florida’s Turnpike, Route 408, and LYNX bus routes.

Learn more about living in Oakland

Home Trends in Oakland, FL

On average, homes in Oakland, FL sell after 59 days on the market compared to the national average of 55 days. The median sale price for homes in Oakland, FL over the last 12 months is $635,000, up 7% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$635,000

Median Single Family Sale Price

$738,750

Median Townhouse Sale Price

$447,368

Average Price Per Sq Ft

$296

Number of Homes for Sale

Last 12 months Home Sales

172

Months of Supply

3.40

Median List Price

$663,655

Median Change From 1st List Price

Median Home Sale Price YoY Change

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

In Oakland, there are currently 62 houses for sale, offering an array of options for potential buyers. With houses priced between $489,000 to $2,750,000, there's a range to accomodate every budget. As of April, 2026 the median home price in Oakland is $663,655, while the average sale price is $777,599, offering insights into the local housing market. On average, houses spend 59 days listed before being sold. Whether you're searching for a single-family residence, exploring single-family detached houses for sale, or considering new construction houses for sale, there are options to cater to different lifestyles. Explore the listings and houses for sale in Oakland, FL and find the perfect place to call home.

Oakland Types of Homes for Sale

Oakland Townhouses for Sale

Oakland Real Estate Listings

More About Living in Oakland

Single-family Homes for Sale in Nearby Neighborhoods

Single-family Homes for Sale in Nearby Cities

Single-family Homes for Sale in Nearby Counties

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