Oakland, FL Homes

/2
Est $1,217,450 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,803 Sq Ft
914 Tilden Oaks Trail, Winter Garden, FL 34787

914 Tilden Oaks Trail, Winter Garden, FL 34787

/40
$580,000
- 2 Beds
- 2 Baths
- 1,889 Sq Ft
13732 Fresh Ivy St, Oakland, FL 34787

Not your average Del Webb home—this nearly new, designer-upgraded retreat offers rare touches and nightly neighborhood Disney fireworks views. Why wait to build? This home is just under a year old and move-in ready, located in the vibrant 55+ community of Del Webb Oasis, where resort-style amenities include a clubhouse, zero-entry pool with cabanas, tennis, pickleball, and more. The open-concept

Ken Pozek REAL BROKER, LLC.

13732 Fresh Ivy St, Oakland, FL 34787
/2
$980,000 Sold Apr 14, 2025

210 Hammock Preserve Loop, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 3,070 Sq Ft
- Built 2023
Last Sold Summary
- 18% Below List Price
- $319/SF
- 47 Days On Market
Current Estimated Value $1,001,350

Last Listing Agent Matthew Sutton BERGER REALTY & INVESTMENTS

210 Hammock Preserve Loop, Oakland, FL 34787

/2
Est $1,221,659 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,115 Sq Ft
15281 Arcadia Bluff Loop, Oakland, FL 34787

15281 Arcadia Bluff Loop, Oakland, FL 34787

/43
$704,500
- 5 Beds
- 4 Baths
- 3,163 Sq Ft
2450 Standing Rock Cir, Oakland, FL 34787

Come tour this stunning two-story Meritage Home thoughtfully designed for modern living and effortless entertaining! The open-concept floor plan features a spacious kitchen that seamlessly overlooks the living and dining areas, creating a setting for family gatherings or dinner parties. Upstairs, enjoy a versatile loft ideal for movie nights, game days or relaxing with friends. Go outside to your

Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

2450 Standing Rock Cir, Oakland, FL 34787
/2
$444,590 Sold Jul 29, 2025

6678 Juneberry Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,846 Sq Ft
- Built 2025
Last Sold Summary
- $241/SF
- 39 Days On Market
Current Estimated Value $447,515

Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

6678 Juneberry Way, Oakland, FL 34787

/9
Est $429,731 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
10665 Words Dr, Oakland, FL 34787

10665 Words Dr, Oakland, FL 34787

/86
$645,900
- 4 Beds
- 2.5 Baths
- 2,473 Sq Ft
2606 Bobcat Chase Blvd, Oakland, FL 34787

*** Back on market after being temporarily off while the Seller moved (~45 days). *** Stunning former MODEL HOME on a premium CORNER lot – loaded with custom upgrades and just footsteps to the community POOL! Welcome to this beautifully appointed and lushly landscaped 4-bedroom, 2.5-bath home filled with high-end designer touches and thoughtful upgrades throughout, offering both comfort and

Ashley Boyd BHHS FLORIDA REALTY

2606 Bobcat Chase Blvd, Oakland, FL 34787
/2
$688,000 Sold Aug 28, 2025

2901 Haze Rd, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,385 Sq Ft
- Built 2025
Last Sold Summary
- $203/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

2901 Haze Rd, Oakland, FL 34787

/2
Est $439,993 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,818 Sq Ft
6519 Glory Bower Dr, Oakland, FL 34787

6519 Glory Bower Dr, Oakland, FL 34787

/39
$600,000 Pending
- 4 Beds
- 2.5 Baths
- 1,811 Sq Ft
1119 Bobcat Chase Blvd, Oakland, FL 34760

Prepare to be captivated by this enchanting 4-bedroom, 2.5-bath pool home, nestled amidst mature oaks that lend an air of timeless charm. Located in the idyllic community of Long Leaf, this home boasts the best lot in the neighborhood—complete with a cozy fire pit that begs for evening gatherings under the stars.Step inside to discover a kitchen adorned with tasteful taupe cabinetry,

Erica Diaz HOMEVEST REALTY

1119 Bobcat Chase Blvd, Oakland, FL 34760
/2
$387,900 Sold Jul 17, 2025

1509 Sweet Apple St, Oakland, FL 34787
- 3 Beds
- 3 Baths
- 1,809 Sq Ft
- Built 2019
Last Sold Summary
- 8% Below List Price
- $214/SF
- 144 Days On Market
Current Estimated Value $395,242

Last Listing Agent Robert Jones OFFERPAD BROKERAGE FL, LLC

1509 Sweet Apple St, Oakland, FL 34787

/2
Est $714,983 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,346 Sq Ft
13234 Spring Grove Way, Oakland, FL 34787

13234 Spring Grove Way, Oakland, FL 34787

/50
$409,000
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
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
$585,000 Sold Aug 20, 2025

15114 Field Daisy Dr, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,142 Sq Ft
- Built 2025
Last Sold Summary
- $273/SF
Current Estimated Value $582,985

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

15114 Field Daisy Dr, Oakland, FL 34787

/2
Est $521,088 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
14086 Frasier St, Oakland, FL 34787

14086 Frasier St, Oakland, FL 34787

/4
$508,990 New Construction
- 4 Beds
- 3 Baths
- 2,083 Sq Ft
Newbury Plan at Serenade at Ovation, Oakland, FL 34787

Discover the Newbury - our largest bungalow! This expansive home is designed to accommodate a variety of lifestyles with its 4 bedrooms, 3 bathrooms, a loft, and a 2-car garage. The extended kitchen is a standout feature, offering more cabinet space than you'll ever need, perfect for those who love to cook and entertain. Each bedroom in the Newbury is generously sized ensuring that everyone in

Dream Finders Homes Builder

14229 Lanyard Way Unit 36490206, Oakland, FL 34787
/2
$800,000 Sold Feb 24, 2025

16261 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 2,587 Sq Ft
- Built 2023
Last Sold Summary
- 11% Below List Price
- $309/SF
- 229 Days On Market
Current Estimated Value $790,088

Last Listing Agent Jose Fernandes CELEBRITY GLOBAL REALTY LLC

16261 Point Rock Dr, Oakland, FL 34787

/2
Est $906,388 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,334 Sq Ft
9122 Sonoma Coast Dr, Oakland, FL 34787

9122 Sonoma Coast Dr, Oakland, FL 34787

/21
$445,999
- 3 Beds
- 2.5 Baths
- 1,796 Sq Ft
12748 Brodlove Ln, Oakland, FL 34787

MOTIVATED SELLER — MUST SELL! — PRICED BELOW MARKET. Exceptionally maintained 2022 M/I Homes Baldwin floorplan in sought-after Encore at Ovation (Horizon West/Winter Garden). 3BD/2.5BA bungalow-style, move-in ready and turnkey with smart-home features (smart appliances/thermostat). Bright open-concept living with abundant natural light. Modern kitchen with quartz countertops, quality cabinetry,

Mayra Rivas Acevedo CASA SOL REALTY LLC

12748 Brodlove Ln, Oakland, FL 34787
/2
$455,000 Sold Jun 11, 2025

13418 Princess St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,579 Sq Ft
- Built 2024
Last Sold Summary
- 1% Above List Price
- $288/SF
- 185 Days On Market
Current Estimated Value $456,427

Last Listing Agent Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC

13418 Princess St, Oakland, FL 34787

/2
Est $431,369 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,579 Sq Ft
15169 Aqua Sol Ln, Oakland, FL 34787

15169 Aqua Sol Ln, Oakland, FL 34787

/49
$639,500
- 4 Beds
- 3 Baths
- 3,000 Sq Ft
847 Cura Ct, Oakland, FL 34787

Located within the exclusive gated waterfront community of John’s Landing, this residence offers the perfect balance of Florida lifestyle, privacy, and everyday convenience, just minutes from Downtown Winter Garden and the scenic John’s Lake Chain. Set on an oversized lot at the end of a quiet cul-de-sac, the home features multiple living spaces, a bonus room / optional 5th bedroom, and a Florida

Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

847 Cura Ct, Oakland, FL 34787
/2
$954,900 Sold Oct 09, 2025

4637 Golden Birch Ave, Oakland, FL 34787
- 5 Beds
- 5 Baths
- 4,272 Sq Ft
- Built 2025
Last Sold Summary
- $224/SF
- 0 Days On Market
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

4637 Golden Birch Ave, Oakland, FL 34787

/2
Est $791,512 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,076 Sq Ft
14229 Lanyard Way, Oakland, FL 34787

14229 Lanyard Way, Oakland, FL 34787

/57
$649,000 Pending
- 4 Beds
- 3 Baths
- 2,281 Sq Ft
2139 Bay Line Rd, Oakland, FL 34787

Located at 2139 Bay Line in Oakland, this well-maintained residence offers a clean, modern interior and a peaceful conservation setting with no rear neighbors. The open living area features light tile flooring, recessed lighting, and sliding glass doors that lead to a screened covered patio overlooking natural greenery, creating a comfortable indoor outdoor flow. The kitchen is designed with a

Ryan Barnett MARKET CONNECT REALTY LLC

2139 Bay Line Rd, Oakland, FL 34787
/2
$430,000 Sold Jul 16, 2025

1113 Prado Ln, Oakland, FL 34787
- Land
- 0.37 Acre
- $1,162,162 per Acre
Last Sold Summary
- 0 Days On Market
Last Listing Agent Alexis Anderson REGENCY REAL ESTATE LLC

1113 Prado Ln, Oakland, FL 34787

/2
Est $380,045 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
9145 Mellow Coral St, Oakland, FL 34787

9145 Mellow Coral St, Oakland, FL 34787

/62
$1,799,000
- 6 Beds
- 5 Baths
- 4,104 Sq Ft
1101 Eagles Pass Way, Oakland, FL 34787

One or more photo(s) has been virtually staged. Modern Luxury in the Heart of Winter Garden’s Golf Cart District! Welcome to 1101 Eagles Pass Way, an exquisite 6-bedroom, 5-bathroom home situated on a desirable corner lot in the sought-after Oakland Park community—one of the few neighborhoods within Winter Garden’s beloved golf cart district. Just one block from Lake Apopka and less than two

Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

1101 Eagles Pass Way, Oakland, FL 34787
/2
$449,490 Sold Jul 22, 2025

2915 Transformation Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,795 Sq Ft
- Built 2025
Last Sold Summary
- $250/SF
- 4 Days On Market
Last Listing Agent Ben Goldstein LENNAR REALTY

2915 Transformation Way, Oakland, FL 34787

/2
Est $538,555 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,114 Sq Ft
14115 Frasier St, Oakland, FL 34787

14115 Frasier St, Oakland, FL 34787

$1,675,000 New Construction
- 5 Beds
- 5 Baths
- 3,895 Sq Ft
Custom Carrabelle Plan at Oakland Park, Winter Garden, FL 34787

AR Homes Builder

884 Tilden Oaks Trail Unit 37615294, Winter Garden, FL 34787
/2
$380,000 Sold Jul 25, 2025

2203 Gopher Tortoise Terrace, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
- Built 2020
Last Sold Summary
- 8% Below List Price
- $235/SF
- 57 Days On Market
Current Estimated Value $382,591

Last Listing Agent Dawn Thomas KELLER WILLIAMS REALTY AT THE LAKES

2203 Gopher Tortoise Terrace, Oakland, FL 34787

/2
Est $453,174 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,032 Sq Ft
8149 Mosaic Ln, Oakland, FL 34787

8149 Mosaic Ln, Oakland, FL 34787

/3
$568,000 New Construction
- 3 Beds
- 2.5 Baths
- 2,062 Sq Ft
13121 Tollcross Way, Oakland, FL 34787

Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion July 2025. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master

Alicea Salgado ORLANDO TBI REALTY LLC

13121 Tollcross Way, Oakland, FL 34787
/2
$525,000 Sold Oct 22, 2025

233 Largovista Dr, Oakland, FL 34787
- 4 Beds
- 2 Baths
- 2,176 Sq Ft
- Built 2004
Last Sold Summary
- 2% Below List Price
- $241/SF
- 93 Days On Market
Current Estimated Value $519,931

Last Listing Agent Rachael Segarra EXP REALTY LLC

233 Largovista Dr, Oakland, FL 34787

/2
Est $824,723 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,254 Sq Ft
1197 Wilder Oaks Way, Oakland, FL 34787

1197 Wilder Oaks Way, Oakland, FL 34787

/3
$70,000
- Land
- 0.11 Acre
- $636,364 per Acre
121 S Nixon St, Oakland, FL 34760

If you're looking for land in Oakland, you have certainly found it! Located in the most picturesque neighborhood in central Florida, this beautiful lot could be the site of your next home. Oakland is quaintly situated in between Winter Garden and Clermont, blending small town feel with activity brimming everywhere you turn.

Ramon Morales SANCTUM REALTY PROFESSIONALS LLC

121 S Nixon St, Oakland, FL 34760
/2
$719,000 Sold Jun 05, 2025

17858 Adrift Rd, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,113 Sq Ft
- Built 2022
Last Sold Summary
- 10% Below List Price
- $340/SF
- 97 Days On Market
Current Estimated Value $706,671

Last Listing Agent John R. Gordon EXP REALTY LLC

17858 Adrift Rd, Oakland, FL 34787

/2
Est $833,314 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,247 Sq Ft
1210 Oak Fort Ln, Oakland, FL 34787

1210 Oak Fort Ln, Oakland, FL 34787

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