Oakland, FL Homes

$829,346 New Construction
- 3 Beds
- 2.5 Baths
- 2,718 Sq Ft
15075 Tea Tree Dr, 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

15075 Tea Tree Dr, Oakland, FL 34787
/29
$3,600 per month
- 5 Beds
- 3.5 Baths
- 2,563 Sq Ft
- House for Rent
5816 Dancing Willow St, Oakland, FL 34787

Step into comfort and convenience in this beautifully designed 2026 5-bedroom, 3.5-bath home located in the desirable Parkside Trails community. With over 2,562 square feet of living space, this home offers a bright, open layout ideal for everyday living, entertaining, and relaxing. Parkside Trails is a growing community with resort-style amenities coming soon, including two pools, a clubhouse,

Tisa Sa Barreto SELECTA REALTY LLC

5816 Dancing Willow St, Oakland, FL 34787
/2
$404,990 Sold Jul 29, 2025

2907 Transformation Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,647 Sq Ft
- Built 2025
Last Sold Summary
- 4% Below List Price
- $246/SF
- 18 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

2907 Transformation Way, Oakland, FL 34787

/2
Est $517,247 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,112 Sq Ft
14091 Frasier St, Oakland, FL 34787

14091 Frasier St, 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
/80
$2,700 per month
- 3 Beds
- 2.5 Baths
- 1,635 Sq Ft
- Townhouse for Rent
17538 Northlake Grove Dr, Oakland, FL 34787

Lakefront Luxury Living in Winter Garden - Brand New 3BR Townhome at Northlake at Ovation Discover the perfect blend of comfort, style, and convenience in this brand-new, lakefront townhome located in the highly desirable Northlake at Ovation community. Nestled in the heart of Winter Garden and just a short drive from Downtown Orlando, this beautifully designed residence offers modern living in

Leo Martins Silva THE FLORIDA LOUNGE REALTY LLC

17538 Northlake Grove Dr, Oakland, FL 34787
/2
$455,000 Sold Dec 23, 2025

2023 White Feather Loop, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,089 Sq Ft
- Built 2018
Last Sold Summary
- 6% Below List Price
- $218/SF
- 123 Days On Market
Last Listing Agent Karen Albright OPENDOOR BROKERAGE LLC

2023 White Feather Loop, Oakland, FL 34787

/2
Est $622,762 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 2,861 Sq Ft
15030 Summer Harvest St, Oakland, FL 34787

15030 Summer Harvest St, 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
/42
$2,800 per month
- 4 Beds
- 3 Baths
- 1,809 Sq Ft
- Townhouse for Rent
2202 Gopher Tortoise Terrace, Oakland, FL 34787

Welcome to your dream townhome in the heart of Oakland, FL! This spacious 4-bedroom 3-bathroom residence combines comfort, style, and convenience in one beautiful package. Thoughtfully designed with an open layout and ample natural light, this home offers room for everyone-perfect for families, professionals, or anyone looking for space to grow.Enjoy easy living with walking trails just steps

Johna Jennings Coastal Life Properties LLC

2202 Gopher Tortoise Terrace, Oakland, FL 34787
/2
$465,597 Sold Dec 22, 2025

17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,696 Sq Ft
- Built 2025
Last Sold Summary
- $275/SF
- 20 Days On Market
Last Listing Agent Reed Williams ASHTON WOODS FLORIDA REALTY LLC

17687 Japonica Bloom Dr Unit 221, Oakland, FL 34787

/2
Est $483,675 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,833 Sq Ft
9231 Gran Teatro Dr, Oakland, FL 34787

9231 Gran Teatro Dr, 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
/41
$3,700 per month
- 4 Beds
- 4.5 Baths
- 2,931 Sq Ft
- House for Rent
15070 Summer Harvest St, Oakland, FL 34787

Modern Fenced Corner-Lot Home with Multigenerational Suite This spacious single-family home offers a thoughtful layout designed for comfort and flexibility. Located on a desirable fenced corner lot, the property includes 4 bedrooms and 4.5 bathrooms in the main home, PLUS a private multigenerational suite above the garage with its own bedroom, kitchenette, and full bath—ideal for guests, extended

Robert Benenati 365 REALTY, INC.

15070 Summer Harvest St, Oakland, FL 34787
/2
$768,700 Sold Oct 28, 2025

5780 Dancing Willow St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,575 Sq Ft
- Built 2025
Last Sold Summary
- $215/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

5780 Dancing Willow St, Oakland, FL 34787

/2
Est $371,893 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,472 Sq Ft
2226 Gopher Tortoise Terrace, Oakland, FL 34760

2226 Gopher Tortoise Terrace, Oakland, FL 34760

/57
$990,000
- 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
/14
$2,149 per month
- 3 Beds
- 2.5 Baths
- 1,689 Sq Ft
- Townhouse for Rent
3075 Mindfullness Dr, Oakland, FL 34787

***BRAND NEW TOWNHOME FOR RENT**INTERNET INCLUDED! Enjoy resort-style amenities at Wellness Ridge, including a clubhouse, pool, fitness center, playgrounds, and scenic walking trails. Conveniently located near shopping, dining, top-rated schools, and just minutes from Disney and major highways. Ready for immediate move-in – schedule your showing today!

Frederico Hexsel KARDOSH REALTY

3075 Mindfullness Dr, Oakland, FL 34787
/2
$1,224,660 Sold Feb 10, 2025

15252 Canopy Cover Dr, Oakland, FL 34787
- 4 Beds
- 5 Baths
- 3,653 Sq Ft
- Built 2024
Last Sold Summary
- $335/SF
- 0 Days On Market
Current Estimated Value $1,224,353

Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

15252 Canopy Cover Dr, Oakland, FL 34787

/2
Est $657,066 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,743 Sq Ft
12742 Lavender Bloom Aly, Oakland, FL 34787

12742 Lavender Bloom Aly, Oakland, FL 34787

/54
$999,300 New Construction
- 4 Beds
- 4 Baths
- 4,271 Sq Ft
4608 Golden Birch Ave, 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!Introducing the exquisite

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

4608 Golden Birch Ave, Oakland, FL 34787
/20
$3,380 per month
- 4 Beds
- 2.5 Baths
- 2,441 Sq Ft
- House for Rent
12767 Harvest Rain Ave, Oakland, FL 34787

Be the first to live in this brand-new home just delivered by the builder!Located in one of Winter Garden’s most desirable areas, surrounded by top-rated A schools, this property offers luxury, comfort, and flexibility. This beautiful residence features 4 bedrooms, including one room on the first floor that can serve as a bedroom, office, playroom, or whatever best fits your family’s needs.

Natalia Romanelli Mourao MS LAND & BUILDING LLC

12767 Harvest Rain Ave, Oakland, FL 34787
/2
$620,000 Sold May 12, 2025

1215 Johns Cove Ln, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,811 Sq Ft
- Built 2003
Last Sold Summary
- 5% Below List Price
- $221/SF
- 124 Days On Market
Current Estimated Value $637,216

Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

1215 Johns Cove Ln, Oakland, FL 34787

/2
Est $514,706 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,996 Sq Ft
14015 Lochend Way, Oakland, FL 34787

14015 Lochend Way, Oakland, FL 34787

/51
$839,950
- 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
/20
$2,750 per month
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
- House for Rent
12295 Bracco St, Oakland, FL 34787

Brand New 3-Bed 2.5-Bath Home For Rent in Winter Garden!Brand new, energy-efficient home for rent in the desirable Highland Ridge community! This stunning 3 bedroom, 2.5 bathroom house offers 1,788 square feet of modern living space. The open kitchen boasts a large island that seamlessly flows into the spacious dining and family room, perfect for entertaining. Upstairs, you'll find a

Eileen Scates SCATES REALTY & INVESTMENT PRO

12295 Bracco St, Oakland, FL 34787
/2
$710,000 Sold Nov 04, 2025

1301 Johns Cove Ln, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,495 Sq Ft
- Built 2003
Last Sold Summary
- 14% Below List Price
- $285/SF
- 124 Days On Market
Current Estimated Value $684,578

Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

1301 Johns Cove Ln, Oakland, FL 34787

/2
Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,685 Sq Ft
6343 Blissful St, Oakland, FL 34787

6343 Blissful St, Oakland, FL 34787

/51
$849,000 Pending
- 4 Beds
- 4.5 Baths
- 2,741 Sq Ft
3375 Hanging Tide St, Oakland, FL 34787

Under contract-accepting backup offers. 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

Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

3375 Hanging Tide St, Oakland, FL 34787
/41
$3,000 per month
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
- House for Rent
9588 Jacques Aly, Oakland, FL 34787

Welcome to Waterleigh in the desirable area of Horizon West located in Winter Garden, FL. “Come Here and Stay” in this stunning community situated on over 1,400 acres of land with over a dozen lakes and ponds. Check out one of Waterleigh’s most popular bungalow floor-plans the Cordale offering 4 bedrooms, 2.5 bathrooms, and an attached 2 car garage. Enjoy the water view, while sitting on the

Teresa Valdes VALSTAR REALTY LLC

9588 Jacques Aly, Oakland, FL 34787
/2
$990,900 Sold Jul 09, 2025

1180 Riverway Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,796 Sq Ft
- Built 2025
Last Sold Summary
- $354/SF
Current Estimated Value $968,196

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

1180 Riverway Dr, Oakland, FL 34787

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,579 Sq Ft
13437 Princess St, Oakland, FL 34787

13437 Princess St, Oakland, FL 34787

/42
$780,000 New Construction
- 4 Beds
- 3 Baths
- 3,076 Sq Ft
5808 Dancing Willow St, Oakland, FL 34787

Take full advantage of this great opportunity! Enjoy life in the award-winning Coral Grand home design by Pulte Homes, located on a very special lot with no rear neighbors, in a highly desirable area of the community where no more lots are available. This beautiful new home is part of the first phase of the Parkside Trails development, so it features over $110,000 in upgrades and is for sale at a

Tisa Sa Barreto SELECTA REALTY LLC

5808 Dancing Willow St, Oakland, FL 34787
/76
$5,500 per month
- 5 Beds
- 4.5 Baths
- 3,653 Sq Ft
- House for Rent
15511 Shorebird Ln, Oakland, FL 34787

Welcome to this open plan 5 Bedroom, 4 and a half bathroom water front home including a 3 car garage.Flooring includes tile, laminate and carpet. You will never run out of storage with the abundance of cabinets. Chef's kitchen include upgraded appliances and wall oven. Large sliders allow plenty of light and gorgeous water view and open to a covered lanai. Some of the amenities include a

Mark Volchko REALTY WORLD PREFERRED

15511 Shorebird Ln, Oakland, FL 34787
/37
$449,990 Sold Nov 13, 2025

17687 Japonica Bloom Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,696 Sq Ft
- Built 2025
Move in Ready Sold Summary
- $265/SF
- 15 Days On Market
Ashton Woods Northlake at Ovation - Townhomes

17687 Japonica Bloom Dr, Oakland, FL 34787

/2
Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,097 Sq Ft
17971 Hither Hills Cir, Winter Garden, FL 34787

17971 Hither Hills Cir, Winter Garden, FL 34787

/55
$997,790 New Construction
- 5 Beds
- 4.5 Baths
- 4,313 Sq Ft
4632 Golden Birch Ave, 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!Introducing the exquisite

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

4632 Golden Birch Ave, Oakland, FL 34787
/2
$1,050,000 Sold Feb 14, 2025

1056 Sadler Oaks Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,711 Sq Ft
- Built 2024
Last Sold Summary
- 4% Below List Price
- $387/SF
- 129 Days On Market
Current Estimated Value $1,048,196

Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

1056 Sadler Oaks Way, Oakland, FL 34787

/2
Est $838,835 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,562 Sq Ft
14384 Wabasso Loop, Oakland, FL 34787

14384 Wabasso Loop, Oakland, FL 34787

/39
$875,000
- 4 Beds
- 3.5 Baths
- 3,448 Sq Ft
501 E Oakland Ave, Winter Garden, FL 34787

One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue

Erica Diaz HOMEVEST REALTY

501 E Oakland Ave, Winter Garden, FL 34787

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