Oakland, FL Homes

/2
$2,675,000 Sold Oct 30, 2025

1179 Prado Ln, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 4,561 Sq Ft
- Built 2026
Last Sold Summary
- $586/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

1179 Prado Ln, Oakland, FL 34787

/2
Est $504,563 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,788 Sq Ft
14122 Frasier St, Oakland, FL 34787

14122 Frasier St, 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
/37
$449,990 Sold Nov 07, 2025
- 1,577 Sq Ft
- $285/SF
- 3 Beds
- 2.5 Baths
- Built 2025
17681 Japonica Bloom Dr, Oakland, FL 34787

Welcome to The Kendall II, a beautifully designed home in the highly sought-after Northlake at Ovation community of Winter Garden. This spacious two-story floorplan combines modern design with everyday functionality, offering open-concept living spaces filled with natural light. The stylish kitchen features 42” cabinets, quartz countertops, and stainless steel appliances, perfect for both

Ashton Woods

17681 Japonica Bloom Dr, Oakland, FL 34787

/2
Est $493,095 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,992 Sq Ft
11361 Great Rock St, Oakland, FL 34787

11361 Great Rock St, 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
/2
$390,000 Sold Jul 31, 2025

121 W Oakland Ave, Oakland, FL 34760
- 3 Beds
- 1 Bath
- 1,159 Sq Ft
- Built 1935
Last Sold Summary
- $336/SF
- 7 Days On Market
Current Estimated Value $383,756

Last Listing Agent Sheri Loiacono WINDSOR REALTY GROUP INC

121 W Oakland Ave, Oakland, FL 34760

/2
Est $835,785 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,038 Sq Ft
14211 Lanyard Way, Oakland, FL 34787

14211 Lanyard Way, 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
/2
$620,000 Sold Mar 24, 2025

13648 Fresh Ivy St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,707 Sq Ft
- Built 2024
Last Sold Summary
- 6% Below List Price
- $363/SF
- 13 Days On Market
Current Estimated Value $622,673

Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

13648 Fresh Ivy St, Oakland, FL 34787

/2
Est $757,155 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,065 Sq Ft
14199 Lanyard Way, Oakland, FL 34787

14199 Lanyard Way, 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
/2
$583,380 Sold Nov 18, 2025

4652 Golden Birch Ave, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 2,199 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $265/SF
- 7 Days On Market
Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

4652 Golden Birch Ave, Oakland, FL 34787

/69
Est $750,459 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,332 Sq Ft
11168 Robert Frost Dr, Oakland, FL 34787

11168 Robert Frost Dr, 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
/2
$840,000 Sold Aug 29, 2025

413 MacChi Ave, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 3,290 Sq Ft
- Built 2006
Last Sold Summary
- 7% Below List Price
- $255/SF
- 80 Days On Market
Current Estimated Value $816,718

Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

413 MacChi Ave, Oakland, FL 34787

/2
Est $608,756 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,338 Sq Ft
15129 Summer Harvest St, Oakland, FL 34787

15129 Summer Harvest St, Oakland, FL 34787

/25
$649,000 Pending
- 5 Beds
- 4 Baths
- 4,246 Sq Ft
207 Largovista Dr, Oakland, FL 34787

Under contract-accepting backup offers. ACT FAST! HOMES OF THIS SIZE AND STYLE WITH A PRIVATE POOL RARELY STAY ON THE MARKET. SCHEDULE YOUR SHOWING TODAY BEFORE IT IS GONE. WITH INTEREST RATES DROPPING MORE BUYERS WILL BE ENTERING THE MARKET AND COMPETITION WILL INCREASE. NOW IS THE TIME TO MAKE YOUR MOVE! LISTED UNDER MARKET VALUE!!!!!!!! This impressive 5 bedroom 4 bathroom home features a

Lindsay Seibert COLDWELL BANKER REALTY

207 Largovista Dr, Oakland, FL 34787
/2
$950,000 Sold Sep 23, 2025

100 Demens St, Oakland, FL 34760
- 4 Beds
- 3 Baths
- 3,025 Sq Ft
- Built 1999
Last Sold Summary
- 14% Below List Price
- $314/SF
- 100 Days On Market
Current Estimated Value $946,861

Last Listing Agent David Dorman CENTURY 21 CARIOTI

100 Demens St, Oakland, FL 34760

/2
Est $600,382 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,450 Sq Ft
15141 Summer Harvest St, Oakland, FL 34787

15141 Summer Harvest St, 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
/2
$660,000 Sold Jun 12, 2025

13672 Fresh Ivy St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,889 Sq Ft
- Built 2024
Last Sold Summary
- 8% Below List Price
- $349/SF
- 96 Days On Market
Current Estimated Value $661,660

Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

13672 Fresh Ivy St, Oakland, FL 34787

/2
Est $852,349 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,247 Sq Ft
1215 Wilder Oaks Way, Oakland, FL 34787

1215 Wilder Oaks Way, 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
/2
$460,000 Sold Sep 23, 2025

17055 Wynford Ln, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 2,345 Sq Ft
- Built 2021
Last Sold Summary
- 16% Below List Price
- $196/SF
- 160 Days On Market
Current Estimated Value $479,006

Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

17055 Wynford Ln, Oakland, FL 34787

/2
Est $519,265 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,985 Sq Ft
14114 Frasier St, Oakland, FL 34787

14114 Frasier St, Oakland, FL 34787

/21
$610,000 Pending
- 5 Beds
- 4 Baths
- 3,903 Sq Ft
219 Largovista Dr, Oakland, FL 34787

Investor Special! Located in the highly desirable, gated lakefront community of Johns Landing. This spacious 5-bedroom, 4-bathroom pool home offers nearly 4,000 sq. ft. of living space (excluding garage) and features two upstairs primary suites, additional bedrooms with a loft and bathroom, plus a downstairs guest/in-law suite. The layout also includes formal living and dining rooms, an open

Gnesa Fray INTERMIX REAL ESTATE INC

219 Largovista Dr, Oakland, FL 34787
/2
$835,050 Sold Dec 27, 2024

Unlisted Address
- 5 Beds
- 4.5 Baths
- 3,860 Sq Ft
- Built 2024
Last Sold Summary
- $216/SF
Current Estimated Value $908,516

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

Unlisted Address

/2
Est $529,276 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,114 Sq Ft
14078 Frasier St, Oakland, FL 34787

14078 Frasier St, 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
/2
$500,000 Sold Apr 08, 2025

16257 Prairie School Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,070 Sq Ft
- Built 2021
Last Sold Summary
- 3% Below List Price
- $242/SF
- 54 Days On Market
Current Estimated Value $499,885

Last Listing Agent Sue Vasquez FLORIDA REALTY RESULTS LLC

16257 Prairie School Dr, Oakland, FL 34787

/2
Est $1,398,565 Not Listed For Sale
- 5 Beds
- 5 Baths
- 3,747 Sq Ft
100 Millholland St, Oakland, FL 34760

100 Millholland St, 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
/2
$785,000 Sold Oct 24, 2025

16152 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 2,866 Sq Ft
- Built 2025
Last Sold Summary
- 6% Below List Price
- $274/SF
- 48 Days On Market
Last Listing Agent Stephen Cline DR HORTON REALTY OF CENTRAL FLORIDA LLC

16152 Point Rock Dr, Oakland, FL 34787

/2
Est $536,695 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,094 Sq Ft
14387 Braemar St, Oakland, FL 34787

14387 Braemar St, 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
/52
$580,000 Sold Oct 31, 2025

2642 Bobcat Chase Blvd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,811 Sq Ft
- Built 2019
Last Sold Summary
- 6% Below List Price
- $320/SF
- 38 Days On Market
Last Listing Agent Johna Jennings Coastal Life Properties LLC

2642 Bobcat Chase Blvd, Oakland, FL 34787

/2
Est $816,576 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
1221 Wilder Oaks Way, Oakland, FL 34787

1221 Wilder Oaks Way, Oakland, FL 34787

/2
$908,676 Pending
- 4 Beds
- 3.5 Baths
- 2,688 Sq Ft
15099 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

15099 Tea Tree Dr, Oakland, FL 34787
/2
$900,000 Sold Sep 12, 2025

619 Largovista Dr, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,728 Sq Ft
- Built 2005
Last Sold Summary
- 9% Below List Price
- $241/SF
- 52 Days On Market
Current Estimated Value $890,917

Last Listing Agent Farhad Haniff EXP REALTY LLC

619 Largovista Dr, Oakland, FL 34787

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