Oakland, FL Homes for Sale

/79
$3,575,000 New Construction
- 5 Beds
- 7 Baths
- 5,478 Sq Ft
510 Briley Ave, Oakland, FL 34787

Stunning J&J Model Home in Briley Farm – Leaseback Opportunity! Step into unmatched luxury at this impeccably crafted J&J Building model home, perfectly positioned on a premier corner lot in the sought-after Briley Farm community of Oakland, FL. Designed with exceptional attention to detail, this residence offers 4 bedrooms, 4 full baths, 2 powder baths, a loft, bonus room, private office, two

Alexis Anderson REGENCY REAL ESTATE LLC

510 Briley Ave, Oakland, FL 34787
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/62
$1,650,000
- 6 Beds
- 7.5 Baths
- 5,614 Sq Ft
620 N Tubb St, Oakland, FL 34760

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 with abundant

Jennifer Wilson OAKSTRAND REALTY

620 N Tubb St, Oakland, FL 34760
/56
$900,000 Pre-Foreclosure
- 7 Beds
- 4.5 Baths
- 4,720 Sq Ft
5074 Breezy Acres St, Oakland, FL 34787

MOVE-IN READY | EASY OWNER FINANCING AVAILABLE | FURNITURE NEGOTIABLE WITH PURCHASE Welcome to an exceptional opportunity in the heart of Winter Garden’s highly sought-after Wincey Groves community. This beautifully upgraded Sweetwater model by Dream Finders Homes, built in 2021, offers over 4,700 square feet of refined living space with 7 bedrooms and 4.5 bathrooms, plus two additional flex

Daniel Rodriguez NEW HEIGHTS REALTY GROUP

5074 Breezy Acres St, Oakland, FL 34787
/35
$585,000
- 3 Beds
- 2.5 Baths
- 2,010 Sq Ft
2090 Standing Rock Cir, Oakland, FL 34787

Price reduced to $585,000 on this Stunning Home in Oakland Trails!This immaculate 3-bedroom, 2.5 bath home blends thoughtful upgrades with a warm, inviting layout. From the moment you walk in, pride of ownership is evident. The bright, open living area features built-in HEOS speakers, perfect for entertainment. The chef’s kitchen will impress with 42" wood cabinetry, granite countertops,

Tim Boon CREEGAN GROUP

2090 Standing Rock Cir, Oakland, FL 34787
/24
$1,250,000
- Land
- 0.82 Acre
- $1,524,390 per Acre
552 Walker St, Oakland, FL 34760

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

Alexis Anderson REGENCY REAL ESTATE LLC

552 Walker St, Oakland, FL 34760
/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
/33
$569,990 New Construction
- 4 Beds
- 3 Baths
- 2,175 Sq Ft
2934 Good Vibes Way, Oakland, FL 34787

Under Construction. This popular new Hendrix is a four-bedroom home with convenient single-story living. Three secondary bedrooms are located near the front of the home off the foyer, near a versatile flex space ready to be used as an office or studio. An open-concept floorplan blends the kitchen, living and dining areas with easy access to a covered patio, while a luxe owner’s suite is nestled

Ben Goldstein LENNAR REALTY

2934 Good Vibes Way, Oakland, FL 34787
/3
$449,900
- Land
- 0.23 Acre
- $1,956,087 per Acre
1203 Ridge Lake Way, Winter Garden, FL 34787

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

Tracey McFadden OAK AVENUE REAL ESTATE LLC

1203 Ridge Lake Way, Winter Garden, FL 34787
/4
$498,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,836 Sq Ft
Brantley Plan at Serenade at Ovation, 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
/17
$2,238,120 New Construction
- 5 Beds
- 5.5 Baths
- 4,204 Sq Ft
1173 Prado Ln, Oakland, FL 34787

Pre-Construction. To be built. Introducing the Sunburst Model by Davila HomesDiscover the perfect blend of modern luxury and everyday comfort in the Sunburst, a beautifully designed 4,204-square-foot residence by Davila Homes. With 5 spacious bedrooms and 5.5 elegantly finished bathrooms, this home offers the ideal balance of open living and private retreat—crafted to meet the needs of

Alexis Anderson REGENCY REAL ESTATE LLC

1173 Prado Ln, Oakland, FL 34787
/4
$800,000 New Construction
- 5 Beds
- 4.5 Baths
- 3,101 Sq Ft
16029 Honey Harvest St, Oakland, FL 34787

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

Michelle Campbell TAYLOR MORRISON REALTY OF FLORIDA INC

16029 Honey Harvest St, Oakland, FL 34787
/32
$480,000
- 4 Beds
- 2 Baths
- 2,065 Sq Ft
717 Strihal Loop, Oakland, FL 34787

Welcome Home to Johns Landing! Discover this beautifully maintained 4-bedroom, 2-bath residence located in the gated community of Johns Landing, offering private boat access to scenic Johns Lake. From the moment you step into the foyer, you’ll appreciate the soaring volume ceilings, tile flooring throughout the main living areas, and an abundance of natural light that creates a bright and

Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

717 Strihal Loop, Oakland, FL 34787
/38
$395,000
- 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 offers

Ruth Santos Blystone WRA BUSINESS & REAL ESTATE

12043 Holystone St, Oakland, FL 34787
/7
$1,700,000 New Construction
- 5 Beds
- 3.5 Baths
- 3,909 Sq Ft
1207 Ridge Lake Way, Winter Garden, FL 34787

Pre-Construction. To be built. This is a pre-construction, to be built, custom home located in the final phase (The Reserve) of the Oakland Park community. This two-story custom RCB home can be customized! All finish selections can be made by the buyer; even change/customize the floor plan! This two story floor plan offers 5 bedrooms, 3.5 baths, an office and 3-car garage. This home can be yours

Chris Herlihy NEW HOMES REAL ESTATE, INC.

1207 Ridge Lake Way, Winter Garden, FL 34787
/38
$499,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,675 Sq Ft
17490 Northlake Grove Dr, Oakland, FL 34787

Enjoy convenient, low-maintenance living in this two-story townhome featuring a two-car garage, perfectly located in the heart of Winter Garden. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Ideally situated, you’re just 37 minutes from Orlando International Airport, 20 minutes from world-famous Disney theme parks, and 30

Reed Williams ASHTON WOODS FLORIDA REALTY LLC

17490 Northlake Grove Dr, Oakland, FL 34787
/33
$700,000
- 5 Beds
- 3.5 Baths
- 3,381 Sq Ft
729 Strihal Loop, Oakland, FL 34787

One or more photo(s) has been virtually staged. Experience the height of Florida luxury in this stunningly renovated 5-bedroom pool home, nestled within an exclusive gated community featuring a private boat ramp and lake access. Boasting soaring ceilings, quartz countertops, and a striking panoramic landing, this residence blends architectural elegance with modern sophistication. Peace of mind is

Dylan Stanley MARK SPAIN REAL ESTATE

729 Strihal Loop, Oakland, FL 34787
/35
$587,000
- 4 Beds
- 3.5 Baths
- 2,477 Sq Ft
16140 Harbor Mist Aly, Oakland, FL 34787

Welcome to your dream home in Winter Garden! This stunning 2018-built residence offers 2,477 square feet of thoughtfully designed living space with four bedrooms and three and a half bathrooms. The open floor plan creates an inviting atmosphere perfect for both daily living and entertaining guests who might "accidentally" extend their stay. The first floor showcases beautiful tile flooring

Jeanine Louis-Alcime EXP REALTY LLC

16140 Harbor Mist Aly, Oakland, FL 34787
/84
$599,000
- 3 Beds
- 2 Baths
- 1,857 Sq Ft
1808 Western Trailway Dr, Oakland, FL 34787

Welcome to this stunning, like-new 3-bedroom, 2-bath home in the charming Hull Island community of Oakland, just 0.5 miles from the West Orange Trail, 1.5 miles to Costco, and only 10 minutes from historic downtown Winter Garden. Recently updated and truly move-in ready, this split-plan residence shines with beautiful wood-look tile flooring throughout (no carpet anywhere!), fresh backyard turf

Daniel McGrath UNLOCK REALTY GROUP INC

1808 Western Trailway Dr, 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
/39
$800,000
- 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
/17
$460,000 New Construction
- 4 Beds
- 3 Baths
- 1,847 Sq Ft
4580 Maple Waltz, Oakland, FL 34787

Exceptional investment opportunity! This stunning new townhome built by Pulte Homes is located in the desirable Park Side Trails community in Clermont, FL. The property is already leased starting November 28th with a 12-month contract at $2,800/month, offering immediate rental income and a great return potential.Featuring a bright and open floor plan with abundant natural light throughout,

Marta Faustino DTB FLORIDA REALTY, INC.

4580 Maple Waltz, 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
/100
$958,000
- 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
/6
$2,995,000 New Construction
- 6 Beds
- 6.5 Baths
- 5,144 Sq Ft
312 Briley Ave, Oakland, FL 34760

Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully

Carolina Dumit CORCORAN PREMIER REALTY

312 Briley Ave, Oakland, FL 34760
/17
$459,000 New Construction
- 3 Beds
- 2.5 Baths
- 1,730 Sq Ft
8937 Matriarca Aly, Oakland, FL 34787

Price adjustment! Move in ready! Freshly painted last year in “North Star” inside, and luxury vinyl plank flooring (no carpets) in this end townhouse just minutes away from theme parks and great shopping at Legado community in Windermere. 3 spacious bedrooms, and 2.5 bathrooms combine with generous living space in this 2-story townhome. Designed for entertaining, the "Minneola" features a large

Tony Wong, LLC SANCTUM REALTY PROFESSIONALS LLC

8937 Matriarca Aly, Oakland, FL 34787
/33
$607,990 New Construction
- 4 Beds
- 3 Baths
- 2,692 Sq Ft
2930 Good Vibes Way, Oakland, FL 34787

Under Construction. The Jagger has it all! This sleek new two-story home features a convenient game room on the second level, perfect for entertaining, relaxation and more. The first floor is host to an inviting open-concept layout shared between a modern kitchen, elegant dining room and comfortable family room. Three secondary bedrooms boast a private space near the front of the home off the

Ben Goldstein LENNAR REALTY

2930 Good Vibes Way, Oakland, FL 34787
/2
$852,342 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
/17
$399,990 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 - Single Family Homes, 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
/14
$420,000
- Land
- 0.26 Acre
- $1,615,385 per Acre
1161 Prado Ln, Oakland, FL 34787

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

Alexis Anderson REGENCY REAL ESTATE LLC

1161 Prado Ln, Oakland, FL 34787
/44
$655,000
- 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
/3
$374,900
- Land
- 0.24 Acre
- $1,562,083 per Acre
1215 Ridge Lake Way, Winter Garden, FL 34787

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

Tracey McFadden OAK AVENUE REAL ESTATE LLC

1215 Ridge Lake Way, Winter Garden, FL 34787
/36
$268,900
- 3 Beds
- 2 Baths
- 1,747 Sq Ft
651 J W Jones Rd, Winter Garden, FL 34787

*****Sellers motivated! Sellers will consider closing assistance to Buyer(s).***** Welcome Home! Bicyclists and nature lovers will appreciate being just minutes from West Orange Trail. Let the stresses of the day melt away as you step into this beautiful residence in the highly sought-after Winter Garden. Relax on the screened front porch as you soak in the peaceful atmosphere. Inside, the

David Seeley EXIT REALTY TRI-COUNTY

651 J W Jones Rd, Winter Garden, FL 34787
/3
$475,000
- Land
- 0.51 Acre
- $931,373 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

Chris Kaminski SMART SOLUTIONS REALTY LLC

17858 Hither Hills Cir, Winter Garden, FL 34787
/8
$69,999
- Land
- 0.28 Acre
- $249,996 per Acre
0 Killarney Cove Dr, Winter Garden, FL 34787

This is a group of 3 lots for sale; they can all be purchased or sold individually. They're side by side. The lots have canal access to Lake Apopka. They will need to be cleaned out due to the overgrowth. Right off of highway 50 just minutes to the turnpike onramp for quick access anywhere in the Orlando area. Tax ID 19 22 27 0000 00 043 is first on the left, middle Lot is Tax ID 19 22 27 0000 00

Carl Mataushek REAL ESTATE FIRM OF ORLANDO

0 Killarney Cove Dr, Winter Garden, FL 34787

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