Oakland, FL Homes

/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 REAL ESTATE

2065 White Feather Loop, Oakland, FL 34787
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/17
$3,800 Per Month
- 4 Beds
- 3.5 Baths
- 2,861 Sq Ft
- House for Rent
15030 Summer Harvest St, Oakland, FL 34787

Nestled in the sought-after Harvest at Ovation community in Horizon West/Winter Garden, this beautifully appointed single-family home offers the perfect combination of comfort, style, and location. Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, the home includes a desirable first-floor suite—ideal for guests or multi-generational living. Enjoy the convenience of being just minutes from

Cristiane Leon KICANTO REALTY

15030 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
Not Listed For Sale

3119 Armstrong Ave, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 1,867 Sq Ft
- Built 2025
3119 Armstrong Ave, Oakland, FL 34787

Last Sold Summary
- $233/SF
- Last Sold Price $435,000
- Jan 14, 2025
Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/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
/13
$2,595 Per Month
- 4 Beds
- 2 Baths
- 1,778 Sq Ft
- House for Rent
17802 Jefferson St, Oakland, FL 34787

Spacious 4 Bedroom, 2 Bath Split Plan Lake View House with Oversized Corner Lot. Owner has recently updated Home. New Paint on Interior. Tile throughout Home. Fireplace has Granite Hearth and Travertine Facing. Newer Custom Kitchen with granite tops, tumbled marble back splash with decorative tiles. Newer Stainless Steel Appliances. Master bath has Frameless Shower Door. No Sewer Bill. No Water

Barry Stephens MAINFRAME REAL ESTATE

17802 Jefferson St, 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 $641,818

Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

1215 Johns Cove Ln, Oakland, FL 34787

/2
Est $446,525 Not Listed For Sale

13311 Pontoon Rd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,814 Sq Ft
- Built 2023
13311 Pontoon Rd, Oakland, FL 34787

Last Sold Summary
- $245/SF
- 12 Days On Market
- Last Sold Price $445,000
- Mar 18, 2025
Last Listing Agent Ken Pozek REAL BROKER, LLC

/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
/50
$2,795 Per Month
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Townhouse for Rent
2208 Gopher Tortoise Terrace, Oakland, FL 34760

Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere. The large open kitchen offers a large island with seating for four, granite

Fred Mansfield ORLANDO PROP MGMNT RLTY LLC

2208 Gopher Tortoise Terrace, Oakland, FL 34760
/2
$430,000 Sold Mar 23, 2026

2201 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,753 Sq Ft
- Built 2020
Last Sold Summary
- 2% Below List Price
- $245/SF
- 6 Days On Market
Current Estimated Value $434,580

Last Listing Agent Christine Anthony CHARLES RUTENBERG REALTY ORLANDO

2201 Standing Rock Cir, Oakland, FL 34787

/2
Est $998,571 Not Listed For Sale

210 Hammock Preserve Loop, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 3,070 Sq Ft
- Built 2023
210 Hammock Preserve Loop, Oakland, FL 34787

Last Sold Summary
- 2% Above List Price
- $319/SF
- 47 Days On Market
- Last Sold Price $980,000
- Apr 14, 2025
Last Listing Agent Matthew Sutton BERGER REALTY & INVESTMENTS

/3
$919,000 Pending
- 5 Beds
- 4.5 Baths
- 3,894 Sq Ft
12940 Westhaven Oak Dr, Oakland, FL 34787

Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. The wide and elongated foyer create an impressive entry into this home, with large formal dining room and spacious kitchen. The well-equipped kitchen features a walk-in pantry and an open view of the breakfast area and great room. The great room opens out to a

Dayene Grubert ORLANDO TBI REALTY LLC

12940 Westhaven Oak Dr, Oakland, FL 34787
/23
$2,900 Per Month
- 3 Beds
- 2 Baths
- 1,788 Sq Ft
- House for Rent
17651 Japonica Bloom Dr, Oakland, FL 34787

Beautiful, brand-new 3-bedroom, 2-bath single-family home situated on a desirable corner lot, offering 1,788 sq ft of living space. This modern home features an open-concept layout with a contemporary kitchen equipped with stainless steel appliances, granite countertops, and a spacious island. Tile flooring runs throughout the entire home, including all bedrooms, providing a clean and cohesive

Leidy Sanquiz ROMAN'S PRO REALTY LLC

17651 Japonica Bloom Dr, 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 $686,888

Last Listing Agent Heidi Pfeffer-Morgan DALTON WADE INC

1301 Johns Cove Ln, Oakland, FL 34787

/2
Est $499,882 Not Listed For Sale

16257 Prairie School Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,070 Sq Ft
- Built 2021
16257 Prairie School Dr, Oakland, FL 34787

Last Sold Summary
- $242/SF
- 54 Days On Market
- Last Sold Price $500,000
- Apr 08, 2025
Last Listing Agent Sue Vasquez FLORIDA REALTY RESULTS LLC

/53
$974,300 Pending
- 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
/28
$2,600 Per Month
- 3 Beds
- 2.5 Baths
- 1,451 Sq Ft
- House for Rent
13323 Pontoon Rd, Oakland, FL 34787

Beautiful and well maintained 3bedroom, 2.5 bath townhouse located in the highly sought-after WaterLeigh community in Winter Garden. This property offers an open-concept layout with abundant natural light, a modern kitchen with all appliances included, and spacious living and dining areas ideal for comfortable everyday living. All bedrooms are located upstairs, including a generous primary suite

Monica Paz LA ROSA REALTY INTERNACIONAL L

13323 Pontoon Rd, 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 $960,902

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

1180 Riverway Dr, Oakland, FL 34787

/2
Est $845,489 Not Listed For Sale

1102 Eagles Pass Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,260 Sq Ft
- Built 2023
1102 Eagles Pass Way, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $385/SF
- 4 Days On Market
- Last Sold Price $869,900
- Feb 28, 2025
Last Listing Agent Jayme Taylor SAGE REALTY FLORIDA, INC.

/2
$925,990 Pending
- 4 Beds
- 3.5 Baths
- 3,498 Sq Ft
15184 Tea Tree Dr, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

15184 Tea Tree Dr, Oakland, FL 34787
/12
$2,600 Per Month
- 3 Beds
- 2 Baths
- 1,858 Sq Ft
- House for Rent
1010 Stationside Dr, Oakland, FL 34787

Charming 3 bedroom, 2 bath home located in Historic Oakland, just minutes from the Florida Turnpike, West Orange Bike Trail, and Downtown Winter Garden. A split-plan layout includes a formal dining room, formal living room or den that's also perfect for an office space and an open kitchen and dinette that flows seamlessly into a spacious family room, perfect for entertaining. The master bedroom

Jeffrey Petch GECKO REALTY, INC

1010 Stationside Dr, 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
Est $701,104 Not Listed For Sale

13636 Fresh Ivy St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,943 Sq Ft
- Built 2024
13636 Fresh Ivy St, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $358/SF
- 3 Days On Market
- Last Sold Price $695,000
- Mar 13, 2025
Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

/51
$809,900
- 3 Beds
- 2.5 Baths
- 2,348 Sq Ft
9008 Sonoma Coast Dr, Oakland, FL 34787

WELCOME TO WATERLEIGH LAKEFRONT LIVING at its finest! Now offered at an INCREDIBLE NEW PRICE of $809,900 — recently reduced from $824,950 for immediate value and opportunity! Experience breathtaking waterfront views and resort-style living at 9008 Sonoma Coast located in the highly desirable community of Waterleigh in Winter Garden. This stunning lakefront residence combines elegant design,

Gary Berkson RE/MAX CENTRAL REALTY

9008 Sonoma Coast Dr, Oakland, FL 34787
/47
$2,600 Per Month
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Townhouse for Rent
12032 Holystone St, Oakland, FL 34787

Experience the charm of Waterleigh Community with this stunning 3 bedroom, 2.5 bathroom townhome available for rent. The open-concept main floor features a seamless living room, dining area, and kitchen with stainless steel appliances, including a modern refrigerator. Located in Waterleigh Phase 4 near both the Elementary and Middle School, this home welcomes you with granite countertops, a large

Marcelo Lopes Santana FLORIDA CONNEXION PROPERTIES

12032 Holystone St, Oakland, FL 34787
/2
$446,340 Sold Feb 25, 2026

Unlisted Address
- 3 Beds
- 2.5 Baths
- 2,186 Sq Ft
- Built 2026
Last Sold Summary
- $204/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

Unlisted Address

/2
Est $626,890 Not Listed For Sale

13648 Fresh Ivy St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,707 Sq Ft
- Built 2024
13648 Fresh Ivy St, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $363/SF
- 13 Days On Market
- Last Sold Price $620,000
- Mar 24, 2025
Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

/56
$759,000
- 5 Beds
- 3 Baths
- 3,284 Sq Ft
8114 Sayings Dr, Winter Garden, FL 34787

Price Improvement! Welcome to this beautifully maintained 5-bedroom, 3-bathroom single-family home located in the highly desirable Story Grove community in Winter Garden. Offering approximately 3,300 sq ft of living space, this home features a functional open-concept layout ideal for both everyday living and entertaining. Situated on a premium lot with conservation and water views, the property

Anna Shi LPT REALTY, LLC

8114 Sayings Dr, Winter Garden, FL 34787
/14
$2,650 Per Month
- 3 Beds
- 2.5 Baths
- 1,654 Sq Ft
- Townhouse for Rent
12067 Holystone St, Oakland, FL 34787

Beautiful corner-unit home for rent in the highly sought-after Waterleigh community in Winter Garden. This spacious property features 3 bedrooms, 2.5 bathrooms, and an open, functional layout filled with natural light thanks to its premium corner location.Enjoy the convenience of being short distance to Atwater Bay Elementary, making daily routines effortless for families. Located in a true

Aura Ruiz LA ROSA REALTY LLC

12067 Holystone St, Oakland, FL 34787
/2
$1,400,000 Sold Jun 27, 2025

141 Millholland St, Oakland, FL 34760
- 4 Beds
- 3.5 Baths
- 3,497 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $400/SF
- 72 Days On Market
Current Estimated Value $1,370,836

Last Listing Agent Matthew Matin CLOCK TOWER REALTY

141 Millholland St, Oakland, FL 34760

/20
Est $711,687 Not Listed For Sale

13714 Fresh Ivy St, Oakland, FL 34787
- 2 Beds
- 2.5 Baths
- 2,080 Sq Ft
- Built 2024
13714 Fresh Ivy St, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $339/SF
- 65 Days On Market
- Last Sold Price $705,000
- Mar 31, 2025
Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

/55
$949,790 Pending
- 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
/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
/2
$735,000 Sold Oct 30, 2025

2340 Standing Rock Cir, Winter Garden, FL 34787
- 5 Beds
- 3 Baths
- 3,493 Sq Ft
- Built 2019
Last Sold Summary
- 3% Below List Price
- $210/SF
- 112 Days On Market
Current Estimated Value $729,956

Last Listing Agent Jennifer Coon LAKESIDE REALTY WINDERMERE INC

2340 Standing Rock Cir, Winter Garden, FL 34787

/2
Est $628,129 Not Listed For Sale

15191 Blue Peacock Ln, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 2,584 Sq Ft
- Built 2023
15191 Blue Peacock Ln, Oakland, FL 34787

Last Sold Summary
- 7% Below List Price
- $262/SF
- Last Sold Price $676,128
- Nov 27, 2024
Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/55
$799,900
- 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! ** POND VIEW** 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

Teresa Stewart SOUTHERN REALTY GROUP LLC

8807 Sonoma Coast Dr, Oakland, FL 34787
/35
$2,550 Per Month
- 3 Beds
- 2.5 Baths
- 1,652 Sq Ft
- Townhouse for Rent
4576 Maple Waltz, Oakland, FL 34787

Corner Townhouse for Rent in Clermont, FL. Experience modern living near the highly anticipated Olympus Stadium project! This spacious corner townhome features 3 bedrooms, 2 full bathrooms, and a half bathroom (2.5 total baths), a convenient 2-car rear-facing garage, and a private, fenced rear courtyard perfect for entertaining. The open-concept first floor is ideal, boasting a gourmet kitchen

Alessandra Oliveira FLORIDA CONNEXION PROPERTIES

4576 Maple Waltz, Oakland, FL 34787
/2
$690,000 Sold May 13, 2025

2157 Bay Line Rd, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,274 Sq Ft
- Built 2020
Last Sold Summary
- 10% Below List Price
- $303/SF
- 69 Days On Market
Current Estimated Value $689,180

Last Listing Agent Jamie Stolinas Crame CENTURY 21 CARIOTI

2157 Bay Line Rd, Oakland, FL 34787

/2
Est $644,453 Not Listed For Sale

15014 Summer Harvest St, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 2,861 Sq Ft
- Built 2024
15014 Summer Harvest St, Oakland, FL 34787

Last Sold Summary
- 4% Above List Price
- $216/SF
- Last Sold Price $619,040
- Dec 09, 2024
Last Listing Agent Dimerson Almeida TALENT REALTY SOLUTIONS

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