Oakland, FL Homes

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$730,000 Pending
- 4 Beds
- 3 Baths
- 2,240 Sq Ft
5715 Orange Orchard Dr, Oakland, FL 34787

Under contract-accepting backup offers. More pictures coming soom! Located in one of Hamlin's most sought-after master-planned communities, this beautifully maintained 4-bedroom, 3 full-bath home delivers the kind of lifestyle that's rarely available at this price point — with the upgrades, the location, and the details that actually matter.The open floor plan flows naturally from a

Caroline De Castro Marcellini COMPASS FLORIDA, LLC

5715 Orange Orchard Dr, Oakland, FL 34787
/2
$470,000 Sold Feb 14, 2026

17562 Northlake Grove Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,726 Sq Ft
- Built 2025
Last Sold Summary
- $272/SF
Current Estimated Value $474,000

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

17562 Northlake Grove Dr, Oakland, FL 34787

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Est $451,590 Not Listed For Sale

9109 Legado Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,687 Sq Ft
- Built 2020
9109 Legado Dr, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $266/SF
- 126 Days On Market
- Last Sold Price $448,750
- Apr 28, 2025
Last Listing Agent Jessica Garcon DIAMOND REAL ESTATE GROUP

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$749,900
- 4 Beds
- 4 Baths
- 2,852 Sq Ft
2017 Boss Hewett St, Oakland, FL 34787

One or more photo(s) has been virtually staged. This meticulously maintained 2,852 sq ft, 4-bedroom, 4-bath home, built in 2022, is situated on a quiet street in the lakefront community of Hull Island in Oakland, with direct access to the West Orange Trail and just minutes from historic downtown Winter Garden’s shops and Saturday farmers market.Designed for primarily single-level living, all

Peter Biskup CHARLES RUTENBERG REALTY ORLANDO

2017 Boss Hewett St, Oakland, FL 34787
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$395,000 Sold Nov 21, 2025

13322 Pontoon Rd, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 2023
Last Sold Summary
- 1% Below List Price
- $252/SF
- 46 Days On Market
Current Estimated Value $392,317

Last Listing Agent Denise Gregorie CLOCK TOWER REALTY

13322 Pontoon Rd, Oakland, FL 34787

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Est $1,700,456 Not Listed For Sale

1243 Civitas Way, Winter Garden, FL 34787
- 5 Beds
- 4.5 Baths
- 4,020 Sq Ft
- Built 2023
1243 Civitas Way, Winter Garden, FL 34787

Last Sold Summary
- 8% Below List Price
- $460/SF
- 4 Days On Market
- Last Sold Price $1,850,000
- Dec 06, 2024
Last Listing Agent Ronald Ziolkowski RE/MAX

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$759,000 Pending
- 5 Beds
- 4.5 Baths
- 3,682 Sq Ft
3351 Current Ave, Oakland, FL 34787

Under contract-accepting backup offers. Welcome to this stunning two-story Tortola floor plan by Taylor Morrison, ideally located in the gated community of Lakeview Preserve in Winter Garden. Perfectly positioned on an oversized 75-foot-wide corner homesite with no rear neighbors, this home offers exceptional privacy, beautiful rear views, and a welcoming front porch that sets the tone from the

Amy Kidwell PA PREFERRED REAL ESTATE BROKERS

3351 Current Ave, Oakland, FL 34787
/2
$522,000 Sold May 23, 2025

15657 Pelican Cay Dr, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,685 Sq Ft
- Built 2021
Last Sold Summary
- 1% Above List Price
- $310/SF
- 5 Days On Market
Current Estimated Value $508,811

Last Listing Agent Kevin Pribell ACRES INC

15657 Pelican Cay Dr, Oakland, FL 34787

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Est $512,069 Not Listed For Sale

14091 Frasier St, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,112 Sq Ft
- Built 2024
14091 Frasier St, Oakland, FL 34787

Last Sold Summary
Last Listing Agent Erika Gao RC GROUP REALTY LLC

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$795,000
- 4 Beds
- 3 Baths
- 2,909 Sq Ft
9611 Lost Creek Dr, Oakland, FL 34787

No rear neighbors! Situated on a premium conservation lot with lake views, this fully furnished 4-bedroom, 3-bathroom two-story home in the desirable Waterleigh community offers privacy, upgrades, and true move-in-ready convenience. Exceptional curb appeal features a brick paver driveway and welcoming front porch. Inside, enjoy wood-look tile throughout the main living areas, a flexible formal

Patricia Mendonca Garcia Cunha M2M REALTY

9611 Lost Creek Dr, Oakland, FL 34787
/2
$1,260,826 Sold Sep 26, 2025

1143 Bulwark Oaks Ln, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,046 Sq Ft
- Built 2025
Last Sold Summary
- $414/SF
Current Estimated Value $1,165,023

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

1143 Bulwark Oaks Ln, Oakland, FL 34787

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Est $486,716 Not Listed For Sale

9231 Gran Teatro Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,833 Sq Ft
- Built 2024
9231 Gran Teatro Dr, Oakland, FL 34787

Last Sold Summary
- 7% Below List Price
- $286/SF
- Last Sold Price $523,835
- Oct 29, 2024
Last Listing Agent Eusebio Salas LA ROSA REALTY LLC

/79
$729,900
- 4 Beds
- 3 Baths
- 2,268 Sq Ft
918 Hull Island Dr, Oakland, FL 34787

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 floor plan ideal for both everyday living

Ashley Boyd BHHS FLORIDA REALTY

918 Hull Island Dr, Oakland, FL 34787
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$537,000 Sold Feb 24, 2026

326 Largovista Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 3,182 Sq Ft
- Built 2004
Last Sold Summary
- 23% Below List Price
- $169/SF
- 135 Days On Market
Current Estimated Value $614,163

Last Listing Agent Chris Sanford EXP REALTY LLC

326 Largovista Dr, Oakland, FL 34787

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Est $364,144 Not Listed For Sale

2226 Gopher Tortoise Terrace, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,472 Sq Ft
- Built 2020
2226 Gopher Tortoise Terrace, Oakland, FL 34760

Last Sold Summary
- 4% Below List Price
- $258/SF
- 1 Day On Market
- Last Sold Price $380,000
- Dec 18, 2024
Last Listing Agent Cristina Ireland THE SIMON SIMAAN GROUP

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$785,000 Pending
- 4 Beds
- 3 Baths
- 2,909 Sq Ft
9062 Sonoma Coast Dr, Oakland, FL 34787

Under contract-accepting backup offers. 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

Asher Chen AAA GLOBAL VENTURES PA

9062 Sonoma Coast Dr, Oakland, FL 34787
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$642,120 Sold Oct 16, 2025

5810 Fabry St, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 2,563 Sq Ft
- Built 2025
Last Sold Summary
- $251/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

5810 Fabry St, Oakland, FL 34787

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Est $630,501 Not Listed For Sale

12742 Lavender Bloom Aly, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 2,743 Sq Ft
- Built 2024
12742 Lavender Bloom Aly, Oakland, FL 34787

Last Sold Summary
- 4% Below List Price
- $238/SF
- Last Sold Price $653,836
- Oct 22, 2024
Last Listing Agent Nicole Duque Estrada Almeida Per TALENT REALTY SOLUTIONS

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$796,000
- 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
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$826,850 Sold Jan 27, 2026

4684 Golden Birch Ave, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,810 Sq Ft
- Built 2026
Last Sold Summary
- $217/SF
Current Estimated Value $825,471

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

4684 Golden Birch Ave, Oakland, FL 34787

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Est $491,072 Not Listed For Sale

6672 Juneberry Way, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,846 Sq Ft
- Built 2025
6672 Juneberry Way, Oakland, FL 34787

Last Sold Summary
- $265/SF
- 155 Days On Market
- Last Sold Price $489,990
- Apr 14, 2025
Last Listing Agent Adam Schott DRB GROUP REALTY, LLC

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$401,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,644 Sq Ft
Harbor Plan at Serenade at Ovation - Townhomes, Oakland, FL 34787

The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath,

Dream Finders Homes Builder

14229 Lanyard Way Unit 36477638, Oakland, FL 34787
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$635,000 Sold Dec 01, 2025

546 Egret Place Dr, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 3,156 Sq Ft
- Built 2014
Last Sold Summary
- 2% Below List Price
- $201/SF
- 44 Days On Market
Current Estimated Value $641,442

Last Listing Agent Matthew Blanco MARK SPAIN REAL ESTATE

546 Egret Place Dr, Oakland, FL 34787

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Est $496,933 Not Listed For Sale

14015 Lochend Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 1,996 Sq Ft
- Built 2024
14015 Lochend Way, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $245/SF
- Last Sold Price $490,000
- Oct 16, 2024
Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/3
$778,206 Pending
- 5 Beds
- 3.5 Baths
- 3,076 Sq Ft
14014 Lanyard Way, Oakland, FL 34787

One or more photo(s) has been virtually staged. Under Construction. Images shown are for illustrative purposes only and will differ from the actual home. Anna Maria Bonus C with Stone on Lot114 offers 5 Bedrooms: 3 baths and a 2 Car Garage. Discover the allure of the Horizon West area and the vibrant pulse of Downtown Orlando,where Dream Finders Homes proudly present Serenade at Ovation.

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14014 Lanyard Way, Oakland, FL 34787
/2
$787,000 Sold Feb 23, 2026

3375 Hanging Tide St, Oakland, FL 34787
- 4 Beds
- 4.5 Baths
- 2,741 Sq Ft
- Built 2021
Last Sold Summary
- 9% Below List Price
- $287/SF
- 62 Days On Market
Current Estimated Value $797,191

Last Listing Agent Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

3375 Hanging Tide St, Oakland, FL 34787

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Not Listed For Sale

6343 Blissful St, Oakland, FL 34787
- 3 Beds
- 3 Baths
- 1,685 Sq Ft
- Built 2024
6343 Blissful St, Oakland, FL 34787

Last Sold Summary
Last Listing Agent Eduardo Pavone ON ME REALTY

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$1,195,000
- 4 Beds
- 2.5 Baths
- 2,469 Sq Ft
250 N Walker St, Oakland, FL 34760

Nestled in the heart of downtown Oakland, FL, this newly renovated two-story home features 4 bedrooms and 2.5 bathrooms. Situated on an oversized lot of nearly 1/2 acre, the property includes a resort-style pool, screened patio, shed, and a 3-car garage. Perfectly positioned between Clermont and Winter Garden, this rare property sits on quiet, charming dirt roads, surrounded by mature LIVE oak

Alaina Edmondson COAST TO COAST REAL ESTATE PRO

250 N Walker St, Oakland, FL 34760
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$575,000 Sold May 01, 2026

13732 Fresh Ivy St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,889 Sq Ft
- Built 2024
Last Sold Summary
- 8% Below List Price
- $304/SF
- 222 Days On Market
Current Estimated Value $577,748

Last Listing Agent Ken Pozek REAL BROKER, LLC

13732 Fresh Ivy St, Oakland, FL 34787

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Not Listed For Sale

13437 Princess St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,579 Sq Ft
- Built 2024
13437 Princess St, Oakland, FL 34787

Last Sold Summary
- $285/SF
- 5 Days On Market
- Last Sold Price $449,530
- Dec 20, 2024
Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

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$1,295,000
- Land
- 1.26 Acres
- $1,027,778 per Acre
556 Walker St, Oakland, FL 34760

Welcome to Briley Farm, a picturesque community nestled along the serene shores of Lake Apopka. This premium lot offers the perfect opportunity to design and build your custom dream home in one of Central Florida’s most sought-after lakefront neighborhoods. With plenty of space and stunning views, this homesite is ideal for creating your oasis—a timeless farmhouse, a classic Southern estate, or a

Matthew Burks CORCORAN PREMIER REALTY

556 Walker St, Oakland, FL 34760
/2
$395,000 Sold Feb 19, 2026

321 E Gulley Ave, Oakland, FL 34760
- Land
- 12,196 Sq Ft
- $1,410,714 per Acre
Last Sold Summary
- 8 Days On Market
Current Estimated Value $411,807

Last Listing Agent Deanna Meredith LUXE PROPERTIES LLC

321 E Gulley Ave, Oakland, FL 34760

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Not Listed For Sale

17971 Hither Hills Cir, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,097 Sq Ft
- Built 2022
17971 Hither Hills Cir, Winter Garden, FL 34787

Last Sold Summary
- $283/SF
- 10 Days On Market
- Last Sold Price $594,000
- Dec 04, 2024
Last Listing Agent Jay Love DR HORTON REALTY OF CENTRAL FLORIDA LLC

/3
$655,990 New Construction
- 4 Beds
- 3.5 Baths
- 2,843 Sq Ft
Captiva Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

The Captiva floorplan offers a spacious two-story design with 4 bedrooms, 2.5 bathrooms, and plenty of extra room for customization. This thoughtfully laid-out home includes a flex space on the first floor, which can be transformed into a guest suite or home office, adding versatility to the design. A bonus room on the second floor provides additional living space, perfect for a media room or

Dream Finders Homes Builder

14229 Lanyard Way Unit 36490537, 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 $833,100 Not Listed For Sale

14384 Wabasso Loop, Oakland, FL 34787
- 5 Beds
- 3 Baths
- 3,562 Sq Ft
- Built 2022
14384 Wabasso Loop, Oakland, FL 34787

Last Sold Summary
- 1% Below List Price
- $236/SF
- 7 Days On Market
- Last Sold Price $839,000
- Nov 12, 2024
Last Listing Agent Viviane Rocha WRA BUSINESS & REAL ESTATE

/48
$574,000 Pending
- 5 Beds
- 3.5 Baths
- 3,248 Sq Ft
1490 Stone Arrow Ct, Oakland, FL 34787

This stunning 5 BEDROOM + LOFT + DEN, 3.5 BATH home is situated on a spacious CONSERVATION LOT in the all-new Oakland Trail community. Once you step inside you will immediately appreciate the modern open first floor feat NEW VINYL PLANK flooring int the living room/ dining room. The spacious kitchen feat stainless steel appliance package, lots of cabinet storage under beautiful granite counters,

Eric Jia NUMBER 1 BROKER, LLC

1490 Stone Arrow Ct, Oakland, FL 34787
/2
$680,000 Sold Mar 31, 2026

2450 Standing Rock Cir, Oakland, FL 34787
- 5 Beds
- 4 Baths
- 3,163 Sq Ft
- Built 2019
Last Sold Summary
- 5% Below List Price
- $215/SF
- 120 Days On Market
Current Estimated Value $695,200

Last Listing Agent Anamaria Marquez PREMIER SOTHEBYS INT'L REALTY

2450 Standing Rock Cir, Oakland, FL 34787

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Est $485,560 Not Listed For Sale

14011 Lochend Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 1,996 Sq Ft
- Built 2024
14011 Lochend Way, Oakland, FL 34787

Last Sold Summary
- $244/SF
- Last Sold Price $487,365
- Oct 01, 2024
Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

/2
$617,990 New Construction
- 3 Beds
- 2 Baths
- 2,278 Sq Ft
Lexington w/ Bonus Plan at Serenade at Ovation - Single Family Homes, Oakland, FL 34787

The Lexington with Bonus floorplan offers a versatile layout perfect for both comfort and functionality. This one-story design includes 3 bedrooms and 2 bathrooms, complemented by a spacious three-car garage, providing ample storage and parking options. What sets this plan apart is the large bonus room on the second floor, ideal for creating a personalized space, whether it be a media room, home

Dream Finders Homes Builder

14229 Lanyard Way Unit 36473362, Oakland, FL 34787

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