Oakland, FL homes for sale & real estate

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NEW 3 HRS AGO

ABOUT THIS HOME
Oakland, FL Homes for Sale
Welcome to the highly sought-after McKinnon Square in Oakland Park – a pristine, better-than-new Mannington floor plan that’s truly turn-key. This light-filled 3-bedroom + office, 2.5-bath corner-lot home (2,529 sq ft) is loaded with premium upgrades and ready for immediate move-in. Enjoy 8-foot doors, 3-inch plantation shutters throughout, full California Closet systems in every closet and pantry, neutral laminate wood flooring (carpet only in guest rooms), and an oversized 2-car garage with epoxy floors. The chef’s kitchen shines with a 10-foot island and upgraded GE Profile appliances. Smart-home features include Honeywell thermostats, Resideo alarm, LiftMaster garage o

$795,500

3 beds2.5 baths2,536 sq ft

934 Mckinnon Sq, Winter Garden, FL 34787

10-foot island • 3,323 sq ft lot • 2 garage spots

ABOUT THIS HOME
Oakland, FL Homes for Sale
This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an . 8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite

$1,650,000

6 beds7.5 baths5,614 sq ft

620 N Tubb St, Oakland, FL 34760

Tall windows • 10 ceilings • Florida room

3D WALKTHROUGH

ABOUT THIS HOME
Oakland, FL Homes for Sale
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. Offering over 3,500 SQUARE FEET of beautifully designed space and built in 2019, this residence combines contemporary comfort with UPSCALE UPGRADES—creating a home that truly feels “better than new. ” Step inside to an inviting OPEN-CONCEPT LAYOUT, where the chef’s kitchen overlooks the spacious living area. Recessed lighting, NEW TILE FLOORING on the main level (2023), and ceiling fans throughout (2020) elevate the home’s comfort and style. The entire home is also PREWIRED WITH CAT 6, i

$800,000

5 beds3 baths3,528 sq ft

1970 Standing Rock Cir, Oakland, FL 34787

Generous loft • Custom accent wall • Open-concept layout

ABOUT THIS HOME
Oakland, FL Homes for Sale
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 extended patio and unwind with morning coffee or evening wine, all while enjoying privacy of no rear neighbors. Upgrades abound, including a gourmet kitchen with granite countertops, stainless steel appliances and elegant luxury vinyl flooring, designed with comfort and efficiency in mind, this hom

$714,500

5 beds4 baths3,163 sq ft

2450 Standing Rock Cir, Oakland, FL 34787

No rear neighbors • Gourmet kitchen • Two story home

3D WALKTHROUGH

ABOUT THIS HOME
Oakland, FL Homes for Sale
One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 507 W Oakland Avenue, where comfort, charm, and convenience come together in one perfect location! Nestled in the heart of Oakland, this beautiful home offers one of the most desirable addresses in the area. Enjoy being just steps from the neighborhood park, a mile from the scenic Oakland Orange Bike Trail and City Hall, only 5 minutes from vibrant Downtown Winter Garden, and a quick 30-minute drive to the magic of Disney World. You’ll love living close to shopping, dining, and entertainment while still enjoying the peaceful small-town feel. Move-in ready and beautifully maintai

$364,900

3 beds2 baths1,338 sq ft

507 W Oakland Ave, Oakland, FL 34760

Flexible space • Neighborhood park • Breakfast bar

Property at 1808 Western Trailway Dr, Winter Garden, FL 34787, 3 beds, 2 baths

$615,000

3 beds2 baths1,857 sq ft

1808 Western Trailway Dr, Winter Garden, FL 34787

Property at 624 Hull Island Dr, Oakland, FL 34787, 4 beds, 2 baths

$1,000,000

4 beds2 baths2,708 sq ft

624 Hull Island Dr, Oakland, FL 34787

Property at 501 E Oakland Ave, Winter Garden, FL 34787, 4 beds, 3.5 baths

$899,000

4 beds3.5 baths3,448 sq ft

501 E Oakland Ave, Winter Garden, FL 34787

Property at 1173 Prado Ln, Winter Garden, FL 34787, 5 beds, 5.5 baths

$2,238,120

5 beds5.5 baths4,204 sq ft

1173 Prado Ln, Winter Garden, FL 34787

Property at 1101 Eagles Pass Way, Winter Garden, FL 34787, 6 beds, 5 baths

$1,850,000

6 beds5 baths4,104 sq ft

1101 Eagles Pass Way, Winter Garden, FL 34787

Property at 1096 Riverway Dr, Oakland, FL 34787, 4 beds, 3.5 baths

$1,700,000

4 beds3.5 baths4,171 sq ft

1096 Riverway Dr, Oakland, FL 34787

Property at 312 Briley Ave, Oakland, FL 34787, 6 beds, 6.5 baths

$2,995,000

6 beds6.5 baths5,144 sq ft

312 Briley Ave, Oakland, FL 34787

Property at 1146 Prado Ln, Winter Garden, FL 34787, 5 beds, 5.5 baths

$2,130,760

5 beds5.5 baths3,992 sq ft

1146 Prado Ln, Winter Garden, FL 34787

Property at 854 Tilden Oaks Trl, Winter Garden, FL 34787, 5 beds, 4.5 baths

$1,775,000

5 beds4.5 baths3,991 sq ft

854 Tilden Oaks Trl, Winter Garden, FL 34787

Property at 2690 Bobcat Chase Blvd, Oakland, FL 34787, 3 beds, 2 baths

$465,000

3 beds2 baths1,554 sq ft

2690 Bobcat Chase Blvd, Oakland, FL 34787

Property at 131 Ryan Ct, Oakland, FL 34760, 3 beds, 2 baths

$545,000

3 beds2 baths1,513 sq ft

131 Ryan Ct, Oakland, FL 34760

Property at 651 Regina Cir, Oakland, FL 34787, 4 beds, 3 baths

$499,999

4 beds3 baths2,352 sq ft

651 Regina Cir, Oakland, FL 34787

Property at 2090 Standing Rock Cir, Oakland, FL 34787, 3 beds, 2.5 baths

$585,000

3 beds2.5 baths2,010 sq ft

2090 Standing Rock Cir, Oakland, FL 34787

Property at 219 Largovista Dr, Oakland, FL 34787, 5 beds, 4 baths

$610,000

5 beds4 baths3,903 sq ft

219 Largovista Dr, Oakland, FL 34787

Property at 326 Largovista Dr, Oakland, FL 34787, 4 beds, 3 baths

$649,900

4 beds3 baths3,182 sq ft

326 Largovista Dr, Oakland, FL 34787

Property at 2606 Bobcat Chase Blvd, Oakland, FL 34787, 4 beds, 2.5 baths

$670,000

4 beds2.5 baths2,473 sq ft

2606 Bobcat Chase Blvd, Oakland, FL 34787

Property at 529 Johns Landing Way, Oakland, FL 34787, 4 beds, 3 baths

$675,000

4 beds3 baths2,650 sq ft

529 Johns Landing Way, Oakland, FL 34787

Property at 229 Largovista Dr, Oakland, FL 34787, 5 beds, 4 baths

$619,900

5 beds4 baths3,449 sq ft

229 Largovista Dr, Oakland, FL 34787

Property at 2755 Bobcat Chase Blvd, Oakland, FL 34787, 3 beds, 2.5 baths

$500,000

3 beds2.5 baths1,822 sq ft

2755 Bobcat Chase Blvd, Oakland, FL 34787

Property at 101 N Starr St, Oakland, FL 34760, 3 beds, 3.5 baths

$1,450,000

3 beds3.5 baths2,502 sq ft

101 N Starr St, Oakland, FL 34760

Property at 2435 Standing Rock Cir, Oakland, FL 34787, 4 beds, 2.5 baths

$477,500

4 beds2.5 baths2,017 sq ft

2435 Standing Rock Cir, Oakland, FL 34787

Property at 2375 Standing Rock Cir, Oakland, FL 34787, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths2,089 sq ft

2375 Standing Rock Cir, Oakland, FL 34787

Property at 1207 Ridge Lake Way, Oakland, FL 34787, 5 beds, 3.5 baths

$1,700,000

5 beds3.5 baths3,909 sq ft

1207 Ridge Lake Way, Oakland, FL 34787

Property at 1149 Prado Lane Dr, Oakland, FL 34787, 5 beds, 5.5 baths

$1,975,000

5 beds5.5 baths3,596 sq ft

1149 Prado Lane Dr, Oakland, FL 34787

Property at 1232 Water Maple Dr, Oakland, FL 34787, 5 beds, 6.5 baths

$2,175,000

5 beds6.5 baths4,433 sq ft

1232 Water Maple Dr, Oakland, FL 34787

Property at 1258 Ridge Lake Way, Oakland, FL 34787, 4 beds, 4 baths

$1,996,500

4 beds4 baths4,557 sq ft

1258 Ridge Lake Way, Oakland, FL 34787

Property at 1244 Water Maple Dr, Oakland, FL 34787, 6 beds, 5.5 baths

$2,295,000

6 beds5.5 baths4,859 sq ft

1244 Water Maple Dr, Oakland, FL 34787

Property at 166 Hammock Preserve Loop, Winter Garden, FL 34787, 4 beds, 4 baths

$1,675,000

4 beds4 baths3,186 sq ft

166 Hammock Preserve Loop, Winter Garden, FL 34787

Property at 1238 Water Maple Dr, Oakland, FL 34787, 5 beds, 5.5 baths

$2,150,000

5 beds5.5 baths4,388 sq ft

1238 Water Maple Dr, Oakland, FL 34787

Property at Lincoln Plan, Winter Garden, FL 34787, 4 beds, 3.5 baths

$789,900

4 beds3.5 baths2,693 sq ft

Lincoln Plan, Winter Garden, FL 34787

Listing provided by Zillow

Property at Jackson Plan, Winter Garden, FL 34787, 3 beds, 2.5 baths

$759,900

3 beds2.5 baths2,240 sq ft

Jackson Plan, Winter Garden, FL 34787

Listing provided by Zillow

Property at Jefferson Plan, Winter Garden, FL 34787, 3 beds, 2.5 baths

$749,900

3 beds2.5 baths2,247 sq ft

Jefferson Plan, Winter Garden, FL 34787

Listing provided by Zillow

Property at 121 S Nixon St, Oakland, FL 34760

$75,000

— beds— baths— sq ft

121 S Nixon St, Oakland, FL 34760

Property at 610 Simeon Rd, Oakland, FL 34787

$385,000

— beds— baths— sq ft

610 Simeon Rd, Oakland, FL 34787

Property at 522 N Nixon St, Oakland, FL 34787

$500,000

— beds— baths— sq ft

522 N Nixon St, Oakland, FL 34787

Property at 529 N Pollard St, Oakland, FL 34787

$895,000

— beds— baths— sq ft

529 N Pollard St, Oakland, FL 34787

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Based on information submitted to the MLS GRID as of Mon Dec 01 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Average home prices near Oakland, FL

Cities

Clermont homes for sale
$449,995
Altamonte Springs homes for sale
$208,900
Eustis homes for sale
$349,900
Windermere homes for sale
$1,717,500
Longwood homes for sale
$390,000
Celebration homes for sale
$469,500
Ocoee homes for sale
$472,995
Mount Dora homes for sale
$444,900
Leesburg homes for sale
$338,450
Maitland homes for sale
$425,000
Orlando homes for sale
$330,000
Kissimmee homes for sale
$342,450
Winter Garden homes for sale
$657,000
Apopka homes for sale
$449,900
Winter Park homes for sale
$950,000

Zip Codes

34787 homes for sale
$595,000
34760 homes for sale
$899,000

Oakland, FL real estate trends

All Home Types trends in Oakland, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$580,000

+1.8% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Oakland, FL

$580,000

+1.8%

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