Oakland, FL Homes

/55
$1,949,000 Open Sat 12PM - 4PM
- 5 Beds
- 4.5 Baths
- 3,862 Sq Ft
511 Briley Ave, Oakland, FL 34787

Welcome to this stunning custom residence by Element Home Builders, located in the highly sought-after community of Briley Farm. Thoughtfully designed with both elegance and functionality in mind, this expansive 5-bedroom, 4.5-bathroom home offers approximately 3,862 square feet of refined living space.Step inside to a dramatic two-story foyer that sets the tone for the home’s open and airy

Carolina Dumit CORCORAN PREMIER REALTY

511 Briley Ave, Oakland, FL 34787
/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 $697,871

Last Listing Agent John R. Gordon EXP REALTY LLC

17858 Adrift Rd, Oakland, FL 34787

/2
Est $1,194,740 Not Listed For Sale

914 Tilden Oaks Trail, Winter Garden, FL 34787
- 5 Beds
- 3.5 Baths
- 3,803 Sq Ft
- Built 2022
914 Tilden Oaks Trail, Winter Garden, FL 34787

Last Sold Summary
- $316/SF
- 114 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Matt McKee COMPASS FLORIDA LLC

/4
$508,990 New Construction
- 4 Beds
- 3 Baths
- 2,083 Sq Ft
Newbury Plan at Serenade at Ovation - Bungalow, 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
$852,105 Sold Jul 02, 2025

5307 Citrus Leaf Blvd, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,300 Sq Ft
- Built 2025
Last Sold Summary
- 1% Below List Price
- $258/SF
- 33 Days On Market
Last Listing Agent Tatiana Souza FLORIDA CONNEXION PROPERTIES

5307 Citrus Leaf Blvd, Oakland, FL 34787

/2
Est $667,931 Not Listed For Sale

14219 Spring Garden Dr, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,179 Sq Ft
- Built 2024
14219 Spring Garden Dr, Oakland, FL 34787

Last Sold Summary
- 4% Below List Price
- $319/SF
- 48 Days On Market
Last Sold Price $695,000

Last Listing Agent George Weiss CHARLES RUTENBERG REALTY ORLANDO

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

Under contract-accepting backup offers. 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

Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

847 Cura Ct, Oakland, FL 34787
/2
$448,750 Sold Apr 28, 2025

9109 Legado Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,687 Sq Ft
- Built 2020
Last Sold Summary
- 6% Below List Price
- $266/SF
- 126 Days On Market
Current Estimated Value $446,597

Last Listing Agent Jay Stewart SOUTHERN REALTY GROUP LLC

9109 Legado Dr, Oakland, FL 34787

/2
Est $1,241,223 Not Listed For Sale

15281 Arcadia Bluff Loop, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 4,115 Sq Ft
- Built 2020
15281 Arcadia Bluff Loop, Oakland, FL 34787

Last Sold Summary
- 10% Below List Price
- $337/SF
- 80 Days On Market
Last Sold Price $1,385,000

Last Listing Agent Tiago Martins LA ROSA REALTY LLC

/39
$875,000 Pending
- 4 Beds
- 3.5 Baths
- 3,448 Sq Ft
501 E Oakland Ave, Winter Garden, FL 34787

One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue

Erica Diaz HOMEVEST REALTY

501 E Oakland Ave, Winter Garden, FL 34787
/2
$445,999 Sold Mar 23, 2026

12748 Brodlove Ln, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,796 Sq Ft
- Built 2022
Last Sold Summary
- $248/SF
- 30 Days On Market
Current Estimated Value $444,644

Last Listing Agent Mayra Rivas Acevedo CASA SOL REALTY LLC

12748 Brodlove Ln, Oakland, FL 34787

/9
Est $410,573 Not Listed For Sale

10665 Words Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,755 Sq Ft
- Built 2023
10665 Words Dr, Oakland, FL 34787

Last Sold Summary
- 2% Below List Price
- $239/SF
- 26 Days On Market
Last Sold Price $418,605

Last Listing Agent Ben Goldstein LENNAR REALTY

$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
$828,296 Sold Sep 29, 2025

16146 Point Rock Dr, Oakland, FL 34787
- 5 Beds
- 4.5 Baths
- 3,225 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $257/SF
- 48 Days On Market
Current Estimated Value $822,000

Last Listing Agent Paul King DR HORTON REALTY OF CENTRAL FLORIDA LLC

16146 Point Rock Dr, Oakland, FL 34787

/2
Est $420,052 Not Listed For Sale

6519 Glory Bower Dr, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,818 Sq Ft
- Built 2021
6519 Glory Bower Dr, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $239/SF
- 10 Days On Market
Last Sold Price $435,000

Last Listing Agent Michael McCourt EPOCH HOMES

/3
$844,000 Pending
- 4 Beds
- 3.5 Baths
- 3,005 Sq Ft
12916 Westhaven Oak Dr, Oakland, FL 34787

Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion Summer 2026- Welcome home to this beautifully designed open-concept residence featuring a sought-after primary suite on the main level. The light-filled two-story foyer creates an impressive first impression and flows seamlessly into spacious living and entertaining areas. Thoughtful layout,

Dayene Grubert ORLANDO TBI REALTY LLC

12916 Westhaven Oak Dr, Oakland, FL 34787
/2
$900,000 Sold Jun 25, 2025

13202 Spring Grove Way, Oakland, FL 34787
- 4 Beds
- 4 Baths
- 2,930 Sq Ft
- Built 2020
Last Sold Summary
- 5% Below List Price
- $307/SF
- 54 Days On Market
Current Estimated Value $892,268

Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

13202 Spring Grove Way, Oakland, FL 34787

/2
Est $701,018 Not Listed For Sale

13234 Spring Grove Way, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,346 Sq Ft
- Built 2021
13234 Spring Grove Way, Oakland, FL 34787

Last Sold Summary
- 8% Below List Price
- $326/SF
- 18 Days On Market
Last Sold Price $765,000

Last Listing Agent Erica Diaz HOMEVEST REALTY

/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
$389,000 Sold Dec 23, 2025

2218 Gopher Tortoise Terrace, Oakland, FL 34760
- 2 Beds
- 2.5 Baths
- 1,472 Sq Ft
- Built 2020
Last Sold Summary
- $264/SF
- 36 Days On Market
Last Listing Agent Chelsea Eckert CAM REALTY AND PROPERTY MANAGE

2218 Gopher Tortoise Terrace, Oakland, FL 34760

/2
Est $516,655 Not Listed For Sale

14086 Frasier St, Oakland, FL 34787
- 4 Beds
- 2.5 Baths
- 2,082 Sq Ft
- Built 2024
14086 Frasier St, Oakland, FL 34787

Last Sold Summary
- 4% Below List Price
- $258/SF
Last Sold Price $538,000

Last Listing Agent Erika Gao RC GROUP REALTY LLC

/42
$599,000
- 4 Beds
- 3.5 Baths
- 2,743 Sq Ft
12554 Westhaven Oak Dr, Oakland, FL 34787

This tenant-occupied home, rented for $3,400/month until June 30, 2026, presents an excellent investment opportunity with immediate income. Located in the desirable Osprey Ranch community of Winter Garden, the property features 4 bedrooms, 3.5 bathrooms, and 2,743 heated square feet of living space. The functional floor plan includes a modern kitchen with all appliances and a laundry room with

Adriana PL Franzoi WRA BUSINESS & REAL ESTATE

12554 Westhaven Oak Dr, Oakland, FL 34787
/2
$520,000 Sold Aug 29, 2025

1877 Standing Rock Cir, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 2,008 Sq Ft
- Built 2018
Last Sold Summary
- $259/SF
- 9 Days On Market
Current Estimated Value $499,053

Last Listing Agent James Goodyear COMPASS FLORIDA LLC

1877 Standing Rock Cir, Oakland, FL 34787

/2
Est $884,813 Not Listed For Sale

9122 Sonoma Coast Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,334 Sq Ft
- Built 2021
9122 Sonoma Coast Dr, Oakland, FL 34787

Last Sold Summary
- 3% Below List Price
- $273/SF
- 6 Days On Market
Last Sold Price $910,000

Last Listing Agent Carla Trine MAINFRAME REAL ESTATE

/21
$610,690 Pending
- 4 Beds
- 3.5 Baths
- 2,911 Sq Ft
3088 Namaste Dr, Oakland, FL 34787

Under Construction. The Inverness II is an expansive single-story design that exudes luxury and features two extra rooms for versatile needs. An open-concept kitchen merges effortlessly into an intimate dining room and a spacious family room ideal for entertaining, with glass-sliders extending to the lanai for outdoor living. There is a total of four bedrooms, including the luxurious owner’s

Ben Goldstein LENNAR REALTY

3088 Namaste Dr, Oakland, FL 34787
/2
$455,000 Sold Apr 25, 2025

13885 Title Way, Winter Garden, FL 34787
- 4 Beds
- 3 Baths
- 2,042 Sq Ft
- Built 2022
Last Sold Summary
- 1% Above List Price
- $223/SF
- 2 Days On Market
Current Estimated Value $463,623

Last Listing Agent Iris Lee SPRUCE QUALITY RENTALS

13885 Title Way, Winter Garden, FL 34787

/2
Est $471,371 Not Listed For Sale

13460 Princess St, Oakland, FL 34787
- 2 Beds
- 2 Baths
- 1,579 Sq Ft
- Built 2024
13460 Princess St, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $296/SF
- 159 Days On Market
Last Sold Price $468,000

Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

/55
$2,350,000
- 5 Beds
- 4.5 Baths
- 4,436 Sq Ft
9014 Morgana Ct, Oakland, FL 34787

This is more than a house ~ it is a fully furnished, turnkey lakefront retreat designed to stop you in your tracks the moment you walk through the door! Perfectly positioned on Hickorynut Lake within the exclusive Avalon Cove, this custom Jones Homes residence was built in 2022 and is one of only 49 homes in this intimate luxury enclave. From the instant you enter, you are met with a rare

Jennifer Wemert WEMERT GROUP REALTY LLC

9014 Morgana Ct, Oakland, FL 34787
/2
$645,000 Sold Feb 28, 2026

2139 Bay Line Rd, Oakland, FL 34787
- 4 Beds
- 3 Baths
- 2,281 Sq Ft
- Built 2020
Last Sold Summary
- 1% Below List Price
- $283/SF
- 17 Days On Market
Current Estimated Value $643,292

Last Listing Agent Ryan Barnett MARKET CONNECT REALTY LLC

2139 Bay Line Rd, Oakland, FL 34787

/2
Est $425,858 Not Listed For Sale

15169 Aqua Sol Ln, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,579 Sq Ft
- Built 2024
15169 Aqua Sol Ln, Oakland, FL 34787

Last Sold Summary
- 1% Above List Price
- $267/SF
- 71 Days On Market
Last Sold Price $421,990

Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

/60
$997,000 Pending
- 5 Beds
- 3.5 Baths
- 3,910 Sq Ft
9549 Bolero Rd, Oakland, FL 34787

Under contract-accepting backup offers. The lakefront life of grandeur awaits you in this stunningly enhanced North Haven model by DR Horton's luxury line, Emerald Homes! Structural enhancements are plentiful and include a Control4 Smart Home Automation System, custom designed closets in nearly every closet throughout the home, security system, technology operated window treatment, entire home

Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

9549 Bolero Rd, Oakland, FL 34787
/2
$530,000 Sold Oct 15, 2025

8001 Sayings Dr, Winter Garden, FL 34787
- 4 Beds
- 3.5 Baths
- 2,552 Sq Ft
- Built 2022
Last Sold Summary
- 8% Below List Price
- $208/SF
- 66 Days On Market
Current Estimated Value $524,252

Last Listing Agent Shanta Navarro KELLER WILLIAMS ADVANTAGE III

8001 Sayings Dr, Winter Garden, FL 34787

/2
Not Listed For Sale

14229 Lanyard Way, Oakland, FL 34787
- 5 Beds
- 3.5 Baths
- 3,076 Sq Ft
- Built 2024
14229 Lanyard Way, Oakland, FL 34787

Last Sold Summary
- $282/SF
- 0 Days On Market
Last Sold Price $866,683

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

/41
$633,990 Pending
- 5 Beds
- 4 Baths
- 3,011 Sq Ft
2982 Good Vibes Way, Oakland, FL 34787

Under Construction. The Dylan is all the rage! This stylish two-story home features a first-floor owner’s suite, offering a private retreat with a full bathroom and walk-in closet. An additional bedroom is located near the front of the home, steps from a full bathroom. A spacious and flexible open-concept layout blends the kitchen, living and dining areas, while a nearby flex space provides the

Ben Goldstein LENNAR REALTY

2982 Good Vibes Way, Oakland, FL 34787
/2
$1,272,000 Sold Apr 29, 2025

1112 Hull Island Dr, Oakland, FL 34787
- 4 Beds
- 3.5 Baths
- 3,562 Sq Ft
- Built 2021
Last Sold Summary
- 2% Below List Price
- $357/SF
- 49 Days On Market
Current Estimated Value $1,262,600

Last Listing Agent Kelly Zannini HOMEVEST REALTY

1112 Hull Island Dr, Oakland, FL 34787

/2
Est $367,867 Not Listed For Sale

9145 Mellow Coral St, Oakland, FL 34787
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 2020
9145 Mellow Coral St, Oakland, FL 34787

Last Sold Summary
- 7% Below List Price
- $252/SF
- 66 Days On Market
Last Sold Price $395,000

Last Listing Agent Maximiliano Angel AP REALTY GROUP LLC

/65
$1,495,000 Pending
- 3 Beds
- 2 Baths
- 3,340 Sq Ft
15722 E Oakland Ave, Oakland, FL 34760

Only two owners since 1952 have called this Oakland mansion home, will you be the third? Set on over an acre, surrounded by majestic oaks, and multi-million dollar homes this elegant home is time capsule of yesteryear. The long paver driveway, with ample parking for all, eventually leads to the oversized two car garage. A spacious front porch is perfect for languishing about over coffee in the

Matt Erickson RE/MAX PRIME PROPERTIES

15722 E Oakland Ave, Oakland, FL 34760
/2
$599,200 Sold Sep 25, 2025

4727 Forest Haven Way, Oakland, FL 34787
- 3 Beds
- 2 Baths
- 1,935 Sq Ft
- Built 2025
Last Sold Summary
- $310/SF
Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

4727 Forest Haven Way, Oakland, FL 34787

/2
Est $439,647 Not Listed For Sale

8149 Mosaic Ln, Oakland, FL 34787
- 3 Beds
- 3 Baths
- 2,032 Sq Ft
- Built 2020
8149 Mosaic Ln, Oakland, FL 34787

Last Sold Summary
- $217/SF
- 44 Days On Market
Last Sold Price $440,000

Last Listing Agent Andrew Hess DON HARKINS REALTY LLC

/2
$97,000
- Land
- 0.09 Acre
- $1,077,778 per Acre
406 W Herriott Ave, Oakland, FL 34760

An exceptional opportunity to build your dream residence in the charming and highly desirable Town of Oakland, Florida. This beautiful homesite offers the perfect canvas for a custom home surrounded by the character, tranquility, and small-town elegance that Oakland is known for.Ideally positioned near the scenic West Orange Trail, residents enjoy easy access to miles of biking and walking

Migdalia Ramos V PROPERTIES INC

406 W Herriott Ave, Oakland, FL 34760

Showing Results 161 - 200, Page 5 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