Oakland, FL Homes

/26
$674,350

New Construction
- 4 Beds
- 2 Baths
- 1,882 Sq Ft
5576 Dr, Oakland, FL 34787

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.Welcome to your dream home – the Cardinal. This stunning new construction features 4 spacious

Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

5576 Dr, Oakland, FL 34787
/2
$505,000

Sold Jan 28, 2026

222 Largovista Dr, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,094 Sq Ft
- Built 2004
Last Sold Summary
- 1% Above List Price
- $241/SF
- 7 Days On Market
Current Estimated Value $498,111

Last Listing Agent Sonia Jenkins ORANGE REALTY PROFESSIONALS LLC

222 Largovista Dr, Oakland, FL 34787

/2
Est $738,611

Not Listed For Sale

3410 Buoy Cir, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,747 Sq Ft
- Built 2021
3410 Buoy Cir, Oakland, FL 34787

Last Sold Summary
- 33 Days On Market

/79
$729,900

Pending
- 4 Beds
- 3 Baths
- 2,268 Sq Ft
918 Hull Island Dr, Oakland, FL 34787

Under contract-accepting backup offers. Welcome to this beautifully designed POOL home in the highly desirable WATERFRONT community of Hull Island in Oakland, where residents enjoy a lifestyle rich in amenities, including a scenic walking dock, community park, playground, dog park, and resort-style pool. This thoughtfully designed four bedroom - 3 bath home offers a functional and private split

Ashley Boyd BHHS FLORIDA REALTY

918 Hull Island Dr, Oakland, FL 34787
/2
$375,000

Sold Aug 27, 2025

5840 Meditation Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $231/SF
- 22 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

5840 Meditation Dr, Oakland, FL 34787

/2
Est $411,089

Not Listed For Sale

16467 Prairie School Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,626 Sq Ft
- Built 2022
16467 Prairie School Dr, Oakland, FL 34787

Last Sold Summary
- 6 Days On Market

/2
$605,455

New Construction Pending
- 4 Beds
- 3.5 Baths
- 2,520 Sq Ft
17144 Ingram Hills Aly, Oakland, FL 34787

One or more photo(s) has been virtually staged. Pre-Construction. To be built. Sample Image The Carter offers a well-designed living space with 3 bedrooms, 3.5 baths, and a 2-car garage. The open-concept layout features a spacious family room, a gourmet kitchen with a large island and pantry, and a dining area. The primary suite includes a luxurious bath and walk-in closet, while additional

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

17144 Ingram Hills Aly, Oakland, FL 34787
/2
$701,270

Sold Mar 17, 2026

4732 Misty Forest Way, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 2,563 Sq Ft
- Built 2026
Last Sold Summary
- $274/SF
Current Estimated Value $700,908

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

4732 Misty Forest Way, Oakland, FL 34787

/2
Est $468,370

Not Listed For Sale

14034 Scarlet Aster Aly, Oakland, FL 34787
- 3 Beds
- 3 Baths
- 1,941 Sq Ft
- Built 2024
14034 Scarlet Aster Aly, Oakland, FL 34787

Last Sold Summary
- 256 Days On Market

/34
$560,000

$27K PRICE DROP Pending
- 4 Beds
- 3.5 Baths
- 2,477 Sq Ft
16140 Harbor Mist Aly, Oakland, FL 34787

Lock in a guaranteed 5.625% interest rate through our preferred lender and make your move. Priced to sell, this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community is ready for its next owner. 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

Jeanine Louis-Alcime EXP REALTY LLC

16140 Harbor Mist Aly, Oakland, FL 34787
/2
$900,000

Sold Jul 11, 2025

13193 Tollcross Way, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 4,041 Sq Ft
- Built 2024
Last Sold Summary
- 18% Below List Price
- $223/SF
- 232 Days On Market
Current Estimated Value $932,854

Last Listing Agent Chandra Maraj CHARLES RUTENBERG REALTY ORLANDO

13193 Tollcross Way, Oakland, FL 34787

/2
Est $586,926

Not Listed For Sale

14103 Lochend Way, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,586 Sq Ft
- Built 2024
14103 Lochend Way, Oakland, FL 34787

Last Sold Summary
- 5 Days On Market

/10
$3,200,000
- 41 Beds
- 75 Baths
- 17,021 Sq Ft
15992 W Colonial Dr, Oakland, FL 34787

15992 W Colonial Dr, Oakland, FL – 32-Unit Income Producing Multifamily OpportunityExceptional opportunity to acquire a 32-unit income-producing asset in the heart of West Orange County, ideally positioned along the high-visibility W Colonial Dr / SR-50 corridor in the Town of Oakland.Situated on approximately 2.15 acres, this unique property offers a diverse mix of duplex-style

Kyler Moreland REMAX SUNSTATE REALTY

15992 W Colonial Dr, Oakland, FL 34787
/2
$810,000

Sold Aug 01, 2025

3182 Sailing Pier Ave, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,720 Sq Ft
- Built 2024
Last Sold Summary
- 11% Below List Price
- $298/SF
- 76 Days On Market
Current Estimated Value $807,506

Last Listing Agent Ron Howell, II EXP REALTY LLC

3182 Sailing Pier Ave, Oakland, FL 34787

/2
Est $499,638

Not Listed For Sale

14407 Braemar St, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
- Built 2023
14407 Braemar St, Oakland, FL 34787

Last Sold Summary

/23
$575,000

$75K PRICE INCREASE
- Land
- 19,602 Sq Ft
- $1,277,778 per Acre
514 N Pollard St, Winter Garden, FL 34787

Briley Farm, Central Florida’s newest custom home community, sits on 111 acres of lush landscape in Oakland, Florida. Here, you’ll have the opportunity to build your dream custom home with Pioneer Builders on a .45-acre corner lot. Pioneer Builders is renowned for their commitment to craftsmanship, attention to detail, and creating homes that reflect each client’s unique style. Every residence is

Alexis Anderson REGENCY REAL ESTATE LLC

514 N Pollard St, Winter Garden, FL 34787
/2
$768,390

Sold Sep 22, 2025

16107 Honey Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,837 Sq Ft
- Built 2025
Last Sold Summary
- $271/SF
- 0 Days On Market
Current Estimated Value $767,000

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

16107 Honey Harvest St, Oakland, FL 34787

/2
Not Listed For Sale

6295 Blissful St, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,186 Sq Ft
- Built 2024
6295 Blissful St, Oakland, FL 34787

Last Sold Summary
- 5 Days On Market

/35
$514,900

$10K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,094 Sq Ft
12308 Bracco St, Oakland, FL 34787

Beautiful and nearly new home in the quiet and friendly Highland Ridge community. This home was built only two years ago and is in perfect condition, offering over 2,114 sq. ft. of air-conditioned space. The layout is open and bright, with a modern kitchen that overlooks the large living and dining areas, perfect for family time and hosting friends. A big plus for this property is the oversized

Eduardo Lopes ELITE INTERNATIONAL REALTY INC

12308 Bracco St, Oakland, FL 34787
/2
$649,000

Sold Mar 09, 2026

2169 Bay Line Rd, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,274 Sq Ft
- Built 2020
Last Sold Summary
- 2% Below List Price
- $285/SF
- 14 Days On Market
Current Estimated Value $649,260

Last Listing Agent Mariana Wartella LPT REALTY, LLC

2169 Bay Line Rd, Oakland, FL 34787

/59
Est $474,635

Not Listed For Sale

2071 White Feather Loop, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,082 Sq Ft
- Built 2019
2071 White Feather Loop, Oakland, FL 34787

Last Sold Summary
- 14 Days On Market

/30
$700,000

New Construction $4K PRICE DROP
- 4 Beds
- 4.5 Baths
- 2,441 Sq Ft
14780 Field Daisy Dr, Oakland, FL 34787

Welcome to the Baldwin at 14780 Field Daisy Drive in Harvest at Ovation! Enter the charming oasis within this thoughtfully designed bungalow floor plan that offers 2,441 sq. ft. of inviting living space. Just past the foyer and formal dining room, the great room opens to the designer kitchen for an easy flow that is perfect for entertaining and relaxation. A first-floor bedroom with a full bath

Taylor Morrison Builder

14780 Field Daisy Dr, Oakland, FL 34787
/2
$395,000

Sold Feb 19, 2026

329 E Gulley Ave, Oakland, FL 34760
- Land
- 12,196 Sq Ft
- $1,410,714 per Acre
Last Sold Summary
Current Estimated Value $514,000

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

329 E Gulley Ave, Oakland, FL 34760

/2
Est $448,537

Not Listed For Sale

2153 Standing Rock Cir, Winter Garden, FL 34787
- 3 Beds
- 2.5 Baths
- 1,904 Sq Ft
- Built 2020
2153 Standing Rock Cir, Winter Garden, FL 34787

Last Sold Summary
- 49 Days On Market

/23
$615,000
- 4 Beds
- 3.5 Baths
- 2,477 Sq Ft
9360 Mclaren Aly, Oakland, FL 34787

Welcome to this beautifully appointed, move-in-ready home located in the highly desirable, resort-style master-planned community of Waterleigh in Winter Garden. This home offers the perfect blend of modern sophistication and everyday functionality across a bright, open-concept design. From the moment you enter through the front door, the airy foyer welcomes you with elegant, durable ceramic tile

Leslie Heimer PREMIER SOTHEBYS INT'L REALTY

9360 Mclaren Aly, Oakland, FL 34787
/2
$425,990

Sold Nov 26, 2025

17496 Northlake Grove Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,577 Sq Ft
- Built 2025
Last Sold Summary
- $270/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

17496 Northlake Grove Dr, Oakland, FL 34787

/2
Est $624,229

Not Listed For Sale

15049 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,830 Sq Ft
- Built 2024
15049 Summer Harvest St, Oakland, FL 34787

Last Sold Summary
- 10 Days On Market

/3
$411,990

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
/2
$1,660,000

Sold Oct 23, 2025

102 Hammock Preserve Loop, Oakland, FL 34787
- 6 Beds
- 5 Baths
- 3,911 Sq Ft
- Built 2024
Last Sold Summary
- 8% Below List Price
- $424/SF
- 102 Days On Market
Current Estimated Value $1,681,148

Last Listing Agent Ken Pozek REAL BROKER, LLC

102 Hammock Preserve Loop, Oakland, FL 34787

/2
Est $591,006

Not Listed For Sale

15109 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
- Built 2024
15109 Summer Harvest St, Oakland, FL 34787

Last Sold Summary

/11
$2,186,921

New Construction Pending
- 3 Beds
- 6 Baths
- 3,555 Sq Ft
100 W Railway Ave, Oakland, FL 34760

Pre-Construction. To be built. Briley Farm rests comfortably on 111 acres in the beautiful Town of Oakland. The property is a seamless blend of charming Old Florida and modern-day Luxury Living at its finest. The community is thoughtfully designed to provide the ultimate retreat for our residents. Lot 15 will be custom pool home meticulously designed to complement its natural surroundings, with a

Blaine Dooley REGENCY REAL ESTATE LLC

100 W Railway Ave, Oakland, FL 34760
/2
$409,040

Sold Aug 27, 2025

5832 Meditation Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
- Built 2025
Last Sold Summary
- $233/SF
- 15 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

5832 Meditation Dr, Oakland, FL 34787

/2
Est $577,347

Not Listed For Sale

15101 Summer Harvest St, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,441 Sq Ft
- Built 2024
15101 Summer Harvest St, Oakland, FL 34787

Last Sold Summary

/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
/2
$645,954

Sold Nov 21, 2025

17579 Japonica Bloom Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,134 Sq Ft
- Built 2025
Last Sold Summary
- $303/SF
Current Estimated Value $607,000

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

17579 Japonica Bloom Dr, Oakland, FL 34787

/2
Not Listed For Sale

6271 Blissful St, Oakland, FL 34787
- 5 Beds
- 3 Baths
- 2,455 Sq Ft
- Built 2024
6271 Blissful St, Oakland, FL 34787

Last Sold Summary
- 11 Days On Market

/63
$749,000

Open Sat 11AM - 2PM $31K PRICE DROP
- 4 Beds
- 4 Baths
- 2,788 Sq Ft
1143 Hull Island Dr, Oakland, FL 34787

PRICE IMPROVMENT! Enjoy the best of Florida Living in the most popular M/I Homes Richmond floor plan with a spacious bonus room, located in the desirable Hull Island community in Oakland. Just steps from the WEST ORANGE TRAIL, you'll enjoy easy access to biking, walking, and outdoor recreation minutes from your doorstep.This exceptional 4-bedroom, 4-bathroom home offers a thoughtfully

Rema Perras CORCORAN PREMIER REALTY

1143 Hull Island Dr, Oakland, FL 34787
/2
$512,500

Sold Dec 08, 2025

1787 White Feather Loop, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,152 Sq Ft
- Built 2017
Last Sold Summary
- 8% Below List Price
- $238/SF
- 155 Days On Market
Current Estimated Value $506,809

Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

1787 White Feather Loop, Oakland, FL 34787

/2
Est $802,463

Not Listed For Sale

1191 Wilder Oaks Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
- Built 2024
1191 Wilder Oaks Way, Oakland, FL 34787

Last Sold Summary
- 96 Days On Market

/39
$796,000

$4K PRICE DROP
- 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

Showing Results 321 - 360, Page 9 of 18

Florida Orange County Oakland

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

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

Oakland, FL Homes

Real Estate & Homes