Recently Sold Homes in Oakland, FL

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SOLD NOV 24, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, FL:
Welcome to MAINTENANCE-FREE living in the GATED community of Tucker Oaks! This beautiful 3-bedroom, 2.5-bath end-unit townhome lives like a single-family home — complete with a private front entrance, driveway with ample parking, attached 2-car garage, and a RARE oversized cul-de-sac yard backing to peaceful conservation with no rear neighbors. Enjoy privacy, westward views, and peace of mind with a BRAND NEW ROOF (2025) and thoughtful updates throughout. Inside, the open and flexible layout features tile flooring on the first floor, a spacious living and dining area, and a stylish kitchen with solid wood cabinets, granite countertops, stainless steel appliances, and modern lighting a

$347,000 Last sold price

3 beds2.5 baths1,589 sq ft

1352 Scarlet Oak Loop, Winter Garden, FL 34787

SOLD SEP 19, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, FL:
Discover the wonderful blend of functionality, efficiency, and flexibility in this beautifully maintained two-story home nestled in the heart of Oakland, FL. Built in 2006, this 4-bedroom, 2-bathroom residence offers a rare opportunity to enjoy modern amenities, income potential, and eco-conscious living—all just minutes from the West Orange Trail and charming downtown Winter Garden. Property Highlights: - 1,680 sq ft of well-designed living space - Fully fenced in backyard - No HOA – enjoy the freedom to use your property your way - Solar-powered with a robust 15kWh system, keeping energy costs low - Dual HVAC systems for optimal comfort on both floors - Full kitchen downstairs

$480,000 Last sold price

4 beds2 baths1,681 sq ft

312 W Hull Ave, Oakland, FL 34760

SOLD OCT 27, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, FL:
One or more photo(s) has been virtually staged. Charming Renovated Home in the Heart of Historic Oakland! Welcome to 500 W Oakland Avenue, nestled in the storybook town of Oakland, which is celebrated for its Hallmark-like charm and strong sense of community. Located in the desirable 34760 zip code, this beautifully updated two-story home features an open floor plan with thoughtfully designed living space and NO HOA restrictions! You’ll fall in love with the bright, clean, and welcoming feel throughout with brand-new flooring and fresh interior paint. The heart of the home is the completely renovated chef’s kitchen, featuring all-new cabinets, sleek countertops, and modern appl

$367,500 Last sold price

3 beds2 baths1,336 sq ft

500 W Oakland Ave, Oakland, FL 34760

SOLD SEP 23, 20253D WALKTHROUGH

ABOUT THIS HOME
Recently Sold Home in Oakland, FL:
Custom Entertainer’s Dream Courtyard Home, Welcome to the charming town of Oakland, Florida—just minutes from the Florida Turnpike, Johns Lake, new hospitals, top dining options, and the convenience of the new Costco. This beautifully designed custom residence is situated on an oversized corner lot, featuring a private, screen-enclosed pool that offers comfort, functionality, and luxury living. From the moment you arrive, you’ll be captivated by the circular driveway with dual entrances, mature shade trees, and the impressive side-entry garage. Step inside to discover an open, light-filled floor plan with abundant windows and large sliding doors that seamlessly connect ind

$950,000 Last sold price

4 beds3 baths3,025 sq ft

100 Demens St, Oakland, FL 34760

SOLD SEP 19, 2025

ABOUT THIS HOME
Recently Sold Home in Oakland, FL:
Charming 1959 Gem in the Town of Oakland with In-Law Suite. Find where timeless character meets small town charm in the heart of Oakland, FL. This beautifully maintained 4-bedroom, 2-bath, plus the Multi-generational suite home offers almost 2,500 square feet of living space, blending vintage appeal with the comfort and flexibility today's buyers are seeking. Nestled on a quiet street just minutes from the West Orange Trail and the scenic beauty of Lake Apopka, this unique property is perfect for those who appreciate the warmth and personality of a home with history. This mid-century home residence showcases many of its original features—from the striking parquet style ceiling in the

$604,000 Last sold price

5 beds3 baths2,458 sq ft

410 E Gulley Ave, Oakland, FL 34760

Property at 310 E Gulley Ave, Oakland, FL 34760, 3 beds, 2 baths

$450,000 Last sold price

3 beds2 baths1,419 sq ft

310 E Gulley Ave, Oakland, FL 34760

Property at 38 Live Oak Rd, Winter Garden, FL 34787, 2 beds, 2 baths

$560,000 Last sold price

2 beds2 baths1,640 sq ft

38 Live Oak Rd, Winter Garden, FL 34787

Property at 619 Largovista Dr, Oakland, FL 34787, 5 beds, 3.5 baths

$900,000 Last sold price

5 beds3.5 baths3,728 sq ft

619 Largovista Dr, Oakland, FL 34787

Property at 530 Largovista Dr, Oakland, FL 34787, 5 beds, 4 baths

$2,275,000 Last sold price

5 beds4 baths4,798 sq ft

530 Largovista Dr, Oakland, FL 34787

Property at 829 Cura Ct, Oakland, FL 34787, 4 beds, 3 baths

$645,000 Last sold price

4 beds3 baths2,329 sq ft

829 Cura Ct, Oakland, FL 34787

Property at 1301 Johns Cove Ln, Oakland, FL 34787, 4 beds, 2 baths

$710,000 Last sold price

4 beds2 baths2,495 sq ft

1301 Johns Cove Ln, Oakland, FL 34787

Property at 812 Johns Point Dr, Oakland, FL 34787, 5 beds, 4 baths

$1,520,000 Last sold price

5 beds4 baths4,373 sq ft

812 Johns Point Dr, Oakland, FL 34787

Property at 233 Largovista Dr, Oakland, FL 34787, 4 beds, 2 baths

$525,000 Last sold price

4 beds2 baths2,176 sq ft

233 Largovista Dr, Oakland, FL 34787

Property at 1873 White Feather Loop, Oakland, FL 34787, 4 beds, 3 baths

$539,000 Last sold price

4 beds3 baths2,418 sq ft

1873 White Feather Loop, Oakland, FL 34787

Property at 2163 White Feather Loop, Oakland, FL 34787, 3 beds, 2.5 baths

$464,000 Last sold price

3 beds2.5 baths1,744 sq ft

2163 White Feather Loop, Oakland, FL 34787

Property at 2340 Standing Rock Cir, Oakland, FL 34787, 5 beds, 3 baths

$735,000 Last sold price

5 beds3 baths3,493 sq ft

2340 Standing Rock Cir, Oakland, FL 34787

Property at 1143 Bobcat Chase Blvd, Oakland, FL 34787, 3 beds, 2.5 baths

$500,000 Last sold price

3 beds2.5 baths1,811 sq ft

1143 Bobcat Chase Blvd, Oakland, FL 34787

Property at 2642 Bobcat Chase Blvd, Oakland, FL 34787, 3 beds, 2.5 baths

$580,000 Last sold price

3 beds2.5 baths1,811 sq ft

2642 Bobcat Chase Blvd, Oakland, FL 34787

Property at 1212 Civitas Way, Winter Garden, FL 34787, 4 beds, 2 baths

$785,000 Last sold price

4 beds2 baths2,260 sq ft

1212 Civitas Way, Winter Garden, FL 34787

Property at 1219 Foltz Loop, Oakland, FL 34787, 3 beds, 2 baths

$592,500 Last sold price

3 beds2 baths1,860 sq ft

1219 Foltz Loop, Oakland, FL 34787

Property at 1382 Foltz Loop, Oakland, FL 34787, 4 beds, 3 baths

$635,000 Last sold price

4 beds3 baths2,268 sq ft

1382 Foltz Loop, Oakland, FL 34787

Property at 102 Hammock Preserve Loop, Winter Garden, FL 34787, 6 beds, 5 baths

$1,660,000 Last sold price

6 beds5 baths3,911 sq ft

102 Hammock Preserve Loop, Winter Garden, FL 34787

Property at 1143 Bulwark Oaks Ln, Oakland, FL 34787, 5 beds, 4.5 baths

$1,159,532 Last sold price

5 beds4.5 baths4,436 sq ft

1143 Bulwark Oaks Ln, Oakland, FL 34787

Property at 1179 Prado Ln, Winter Garden, FL 34760, 4 beds, 4.5 baths

$2,675,000 Last sold price

4 beds4.5 baths4,561 sq ft

1179 Prado Ln, Winter Garden, FL 34760

$699,000

3 beds2 baths3,053 sq ft

302 E Oakland Ave, Oakland, FL 34760

Property at 1281 Ridge Lake Way, Oakland, FL 34787

$695,000 Last sold price

— beds— baths— sq ft

1281 Ridge Lake Way, Oakland, FL 34787

Property at 1225 Water Maple Dr, Oakland, FL 34760

$375,000 Last sold price

— beds— baths— sq ft

1225 Water Maple Dr, Oakland, FL 34760

Property at 521 N Pollard St, Oakland, FL 34787

$895,000 Last sold price

— beds— baths— sq ft

521 N Pollard St, Oakland, FL 34787

Property at N Daniels St, Oakland, FL 34760

$450,000 Last sold price

— beds— baths— sq ft

N Daniels St, Oakland, FL 34760

Property at 544 Walker, Oakland, FL 34787

$950,000 Last sold price

— beds— baths— sq ft

544 Walker, Oakland, FL 34787

$450,000

— beds— baths— sq ft

N Daniels St, Oakland, FL 34760

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Based on information submitted to the MLS GRID as of Sun Nov 30 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.

Recently Sold Homes in Oakland

There are currently 31 recently sold homes for sale in Oakland at a median listing price of $620K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Oakland stay on the market for 105 days. This map is refreshed with the newest listings in Oakland every 15 minutes.

In the past month, 11 homes have been sold in Oakland. In addition to houses in Oakland, there was also 1 condo, 3 townhouses, and 0 multi-family units for sale in Oakland last month. Find your dream home in Oakland using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Oakland are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Oakland. Our Oakland real estate stats and trends will give you more information about home buying and selling trends in Oakland. If you're looking to sell your home in the Oakland area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Oakland with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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