Oakland, FL Homes

/77
Est $846,020 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,440 Sq Ft
3367 Hanging Tide St, Oakland, FL 34787

3367 Hanging Tide St, Oakland, FL 34787

/15
$2,150,000 New Construction
- 5 Beds
- 5.5 Baths
- 4,388 Sq Ft
1250 Water Maple Dr, Oakland, FL 34787

Pre-Construction. To be built. Welcome to the Blossom home plan by Element Home Builders, where elegance meets functionality in a spacious, open layout. Boasting soaring ceilings and an expansive 12-foot kitchen island with abundant storage, this home is designed for both family living and entertaining. Enjoy seamless transitions between the gourmet kitchen, dining, and living areas, perfect for

Heather Spirazza REGENCY REAL ESTATE LLC

1250 Water Maple Dr, Oakland, FL 34787
/2
$837,500 Sold Mar 20, 2025
- 2,362 Sq Ft
- $355/SF
- 6 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2021
932 Tilden Oaks Trail, Winter Garden, FL 34787

This David Weekley Home is in the heart of Model Home Row at Oakland Park. Oakland Park was Voted the “No.1 Community to Live In” by Orlando Style Magazine… The Lifestyle is designed so that residents can engage in social interaction while enjoying the picturesque streetscapes and the natural environment. Our Energy Saver Home, built in 2021, features 3-bedroom, 2.5 bathrooms, a loft, a spacious

Tony Marino REAL LIVING R E SOLUTIONS

932 Tilden Oaks Trail, Winter Garden, FL 34787

/34
Est $711,662 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,314 Sq Ft
2042 South Old Killarney St, Winter Garden, FL 34787

2042 South Old Killarney St, Winter Garden, FL 34787

/3
$655,990 New Construction
- 4 Beds
- 3.5 Baths
- 2,843 Sq Ft
Captiva, Oakland, FL 34787

The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

Dream Finders Homes

Captiva, Oakland, FL 34787
/2
$624,000 Sold Mar 20, 2025
- 2,449 Sq Ft
- $255/SF
- 133 Days On Market
- 4 Beds
- 3 Baths
- Built 2015
15116 Dragon Fly Ct, Oakland, FL 34787

One or more photo(s) has been virtually staged. Welcome to your future home, where elegance meets comfort. The neutral paint scheme gives the property timeless appeal. The kitchen is equipped with stainless steel appliances for a modern touch. The primary bathroom features double sinks and a separate tub and shower for added convenience, while the primary bedroom offers a spacious walk-in closet.

GREGORY BLACKALL VERANDA REALTY GROUP

15116 Dragon Fly Ct, Oakland, FL 34787

/21
Est $659,224 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,787 Sq Ft
2025 South Old Killarney St, Winter Garden, FL 34787

2025 South Old Killarney St, Winter Garden, FL 34787

/27
$645,990 New Construction
- 5 Beds
- 3.5 Baths
- 2,688 Sq Ft
Anna Maria w/ Bonus, 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

Anna Maria w/ Bonus, Oakland, FL 34787
/8
$1,259,910 Sold Mar 20, 2025
- 3,852 Sq Ft
- $327/SF
- 15 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2024
1080 Canyon Creek Trail, Oakland, FL 34787

Nestled in the picturesque Oakland Park community, this stunning home is surrounded by beautiful oaks, located in the Winter Garden golf cart district and just steps from the West Orange Trail. The Crabtree floor plan welcomes you with an inviting wrap-around porch that overlooks the lush oak trees. This spacious residence includes 4 bedrooms, 3.5 baths, a study, and a bonus room, offering ample

Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

1080 Canyon Creek Trail, Oakland, FL 34787

/38
Est $600,298 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,108 Sq Ft
2021 South Old Killarney St, Winter Garden, FL 34787

2021 South Old Killarney St, Winter Garden, FL 34787

/2
$617,990 New Construction
- 3 Beds
- 2 Baths
- 2,278 Sq Ft
Lexington w/ Bonus, Oakland, FL 34787

The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 2 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

Dream Finders Homes

Lexington w/ Bonus, Oakland, FL 34787
/2
$445,000 Sold Mar 18, 2025
- 1,814 Sq Ft
- $245/SF
- 12 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2023
13311 Pontoon Rd, Oakland, FL 34787

Welcome to your stunning new corner unit townhome at 13311 Pontoon Street, nestled in the highly coveted Waterleigh community! More than just a neighborhood, Waterleigh offers a lifestyle of luxury with resort-style amenities, including sparkling pools, playgrounds, sports fields, a state-of-the-art fitness center, scenic lakes, and beautiful community gardens. The highly-rated Water Spring

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

13311 Pontoon Rd, Oakland, FL 34787

/55
Est $532,146 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,029 Sq Ft
15926 Moonlight Bay St, Oakland, FL 34787

15926 Moonlight Bay St, Oakland, FL 34787

/3
$577,990 New Construction
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
Lexington, 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, café, and kitchen, creating a welcoming atmosphere for entertaining and everyday

Dream Finders Homes

Lexington, Oakland, FL 34787
/2
$1,100,000 Sold Mar 17, 2025
- 3,333 Sq Ft
- $330/SF
- 7 Days On Market
- 4 Beds
- 3 Baths
- Built 2001
111 Millholland St, Oakland, FL 34760

** Ask your lender about RATE BUY DOWN options. Did you know some lenders have minimal closing costs? Inquire for more information. ** Discover the beauty of lakefront living on the shores of Lake Apopka with this 4-bedroom, 3-bath, 3 CAR garage home with an air-conditioned BONUS space (~ 400 sqft) over the garage. Lake Apopka is the headwaters of the Ocklawaha Chain of Lakes, which connects to

Ashley Boyd BHHS FLORIDA REALTY

111 Millholland St, Oakland, FL 34760

/34
Est $694,678 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,345 Sq Ft
2037 South Old Killarney St, Winter Garden, FL 34787

2037 South Old Killarney St, Winter Garden, FL 34787

/4
$505,990 New Construction
- 3 Beds
- 2.5 Baths
- 2,078 Sq Ft
Cooper, 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

Cooper, Oakland, FL 34787
/2
$980,000 Sold Mar 17, 2025
- 2,811 Sq Ft
- $349/SF
- 19 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2023
126 Hammock Preserve Loop, Oakland, FL 34787

Welcome to 126 Hammock Preserve Loop in the highly coveted Oakland Park community. This four bedroom, three and a half bathroom home sits on a tranquil lot with sweeping views of beautiful trees from your private, oversized front porch. Once stepping into this specious open floorplan, you'll be greeted with upgraded touches throughout such as custom window treatments, designer light fixtures,

Jenna Palmero COLDWELL BANKER REALTY

126 Hammock Preserve Loop, Oakland, FL 34787

/26
Est $557,682 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,128 Sq Ft
5977 Painted Leaf Dr, Oakland, FL 34787

5977 Painted Leaf Dr, Oakland, FL 34787

/3
$649,990 New Construction
- 4 Beds
- 3 Baths
- 2,689 Sq Ft
Biscayne, 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

Biscayne, Oakland, FL 34787
/2
$695,000 Sold Mar 13, 2025
- 1,943 Sq Ft
- $358/SF
- 3 Days On Market
- 2 Beds
- 2 Baths
- Built 2024
13636 Fresh Ivy St, Oakland, FL 34787

Under Construction. All photos and videos shown are of model homes. All homes are sold unfurnished. Del Webb Oasis offers the famous 55+ lifestyle and a location just minutes away from world-famous Orlando attractions! This world-class, resort-style luxurious boutique community features natural gas single-family and villa homes nestled in wooded conservation. Del Webb Oasis will offer an

Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

13636 Fresh Ivy St, Oakland, FL 34787

/28
Est $466,087 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,032 Sq Ft
7718 Bowery Dr, Oakland, FL 34787

7718 Bowery Dr, Oakland, FL 34787

/3
$407,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,715 Sq Ft
Porter, 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

Porter, Oakland, FL 34787
/21
$446,000 Sold Mar 13, 2025
- 1,753 Sq Ft
- $254/SF
- 136 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2019
2261 Standing Rock Cir, Oakland, FL 34787

Check out this charming two-story Chandler Floor Plan from Meritage Homes, perfect for families who enjoy hosting guests of all ages! The open, spacious kitchen overlooks the living and dining areas, making it ideal for hosting dinner parties or game nights with friends! For your privacy, all bedrooms are located on the second floor, along with a loft that can be used as an office area or a

Fernando Orsini CT HOMES REALTY CORPORATION

2261 Standing Rock Cir, Oakland, FL 34787

/57
Est $627,821 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,449 Sq Ft
2511 Sky Stone Ct, Winter Garden, FL 34787

2511 Sky Stone Ct, Winter Garden, FL 34787

/3
$603,990 New Construction
- 4 Beds
- 2.5 Baths
- 2,235 Sq Ft
Anna Maria, 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

Anna Maria, Oakland, FL 34787
/11
$900,000 Sold Mar 07, 2025
- 3,318 Sq Ft
- $271/SF
- 25 Days On Market
- 5 Beds
- 4 Baths
- Built 2025
13259 Tollcross Way, Oakland, FL 34787

Under Construction. Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. This 5 bedroom 4 bath home an has oversized first floor primary suite overlooking the water. The two story foyer creates an impressive entry into this home. This is a very open floor plan that has a casual dining area and great room adjacent to each other. The well-equipped kitchen features

Dayene S. Grubert ORLANDO TBI REALTY LLC

13259 Tollcross Way, Oakland, FL 34787

/21
Est $464,403 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,744 Sq Ft
2093 Standing Rock Cir, Winter Garden, FL 34787

2093 Standing Rock Cir, Winter Garden, FL 34787

/99
$1,675,000 New Construction
- 4 Beds
- 4 Baths
- 3,186 Sq Ft
166 Hammock Preserve Loop, Oakland, FL 34787

Under Construction. UPDATE: Ahead of schedule with an estimated completion in Sept.–Oct. 2025, 166 Hammock Preserve Loop offers one of the finest new construction custom homes in Winter Garden, FL. Built by AR Homes—celebrating over 40 years of luxury homebuilding—this Carrabelle model sits in the highly sought-after Oakland Park community. Boasting 3,186 sq ft of impeccably crafted living space,

AJ Lash CORCORAN PREMIER REALTY

166 Hammock Preserve Loop, Oakland, FL 34787
/2
$650,000 Sold Mar 07, 2025
- 3,074 Sq Ft
- $211/SF
- 628 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2022
13737 Werrington Dr, Oakland, FL 34787

BACK TO MARKET DUE DO BUYER'S DEFAULT - HERE'S YOUR CHANCE! Welcome to your dream lakefront retreat in the exclusive and newly built Encore at Ovation community, nestled in the charming Winter Garden area just a few minutes from Disney. This stunning almost new 4 bedroom, 3.5 bath home offers a truly elevated living experience, combining luxury, modern comforts, and picturesque views. With no

Patricia Alvares FLORIDA REALTY INVESTMENTS

13737 Werrington Dr, Oakland, FL 34787

/2
Est $482,959 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,992 Sq Ft
Unlisted Address

Unlisted Address

/5
$1,996,500 New Construction
- 4 Beds
- 4 Baths
- 4,557 Sq Ft
1258 Ridge Lake Way, Winter Garden, FL 34787

Pre-Construction. To be built. Welcome 1258 Ridge Lake Way, nestled in the final phase of the sought-after Oakland Park community. This custom-built modern farmhouse by RCB Homes offers a perfect blend of style and comfort. Spanning just under 6,280 square feet, this two-story residence features four spacious bedrooms and four luxurious bathrooms, providing ample space for relaxation and

Matt McKee COMPASS FLORIDA LLC

1258 Ridge Lake Way, Winter Garden, FL 34787
/2
$537,500 Sold Mar 06, 2025
- 2,160 Sq Ft
- $249/SF
- 189 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
13037 Tollcross Way, Oakland, FL 34787

Don't miss out on this opportunity to have this new home at an incredible price.Discover this stunning home for sale in Winter Garden, blending comfort and elegance. Featuring 4 bedrooms and 3 full bathrooms, this spacious and well-lit residence offers ceramic tile flooring in common areas and plush carpeting in the bedrooms.The kitchen is a true highlight, boasting granite

Michele Drebes Weiand WRA BUSINESS & REAL ESTATE

13037 Tollcross Way, Oakland, FL 34787

/35
Est $742,663 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,652 Sq Ft
50 Demens St, Oakland, FL 34760

50 Demens St, Oakland, FL 34760

/36
$2,200,000 New Construction
- 5 Beds
- 4.5 Baths
- 3,876 Sq Ft
110 W Railway Ave, Oakland, FL 34760

Under Construction. Welcome to your dream retreat in the Central Florida's most coveted new community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. This custom-built masterpiece by Pioneer Builders blends timeless elegance with modern convenience, offering a quintessential French farmhouse style that exudes warmth and charm. Step inside this 5-bedroom,

Heather Spirazza REGENCY REAL ESTATE LLC

110 W Railway Ave, Oakland, FL 34760
/2
$869,900 Sold Feb 28, 2025
- 2,260 Sq Ft
- $385/SF
- 4 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2023
1102 Eagles Pass Way, Oakland, FL 34787

Timeless luxuries, countless upgrades and quality craftsmanship come together to make this Laroca II model an impressive dream home. Located just off the west orange trail and minutes from downtown winter garden in the highly sought after community of Oakland Park, this 3 bedroom 3 bathroom plus office home is proudly offered for sale. Prepare to be “wowed” by the gorgeous Interior design

Jayme Taylor SAGE REALTY FLORIDA, INC.

1102 Eagles Pass Way, Oakland, FL 34787

/28
Est $515,676 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,680 Sq Ft
3295 Hanging Tide St, Oakland, FL 34787

3295 Hanging Tide St, Oakland, FL 34787

/46
$1,895,000 Open Sun 12PM - 5PM
- 5 Beds
- 4.5 Baths
- 3,862 Sq Ft
511 Briley Ave, Oakland, FL 34787

Pre-Construction. To be built. Introducing Briley Farm, an exquisite 111-acre sanctuary nestled in the historic charm of Oakland, Florida. Designed by renowned Element Home Builders, this brand-new architectural design evokes a Modern Farmhouse vibe, epitomizing luxury with a touch of heritage. A welcoming front porch creates small-town charm. The open kitchen connects to the family gathering

Matthew Burks CORCORAN PREMIER REALTY

511 Briley Ave, Oakland, FL 34787
/2
$484,990 Sold Feb 28, 2025
- 1,835 Sq Ft
- $264/SF
- 82 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2024
9267 Gran Teatro Dr, Oakland, FL 34787

Under Construction. Welcome to this inviting 3-bedroom, 2.5-bathroom townhome nestled in the scenic neighborhood of Winter Garden, FL. Upon entering, you are greeted by a bright and airy atmosphere that flows throughout the home. The main floor features a cozy living area, perfect for relaxation or entertaining guests. The kitchen is a focal point of the townhome, equipped with modern appliances

Stacie Brown Kelly KELLER WILLIAMS ADVANTAGE REALTY

9267 Gran Teatro Dr, Oakland, FL 34787

/49
Est $788,824 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,909 Sq Ft
9611 Lost Creek Dr, Oakland, FL 34787

9611 Lost Creek Dr, Oakland, FL 34787

Showing Results 241 - 280, Page 7 of 18

Florida Oakland

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

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Homes in Nearby Neighborhoods

Homes in Nearby Cities

Homes in Nearby Counties

Homes in Nearby Zip Codes

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage