Oakland, FL Homes

/19
Est $761,203 Not Listed For Sale
- 5 Beds
- 4 Baths
- 2,281 Sq Ft
1111 Simeon Rd, Oakland, FL 34787

1111 Simeon Rd, Oakland, FL 34787

/2
$650,000 Sold Aug 05, 2024
- 2,182 Sq Ft
- $298/SF
- 42 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
13109 Tollcross Way, Oakland, FL 34787

Under Construction. Toll Brothers New Construction at Winter Garden Horizonwest. Estimate completion July 2024. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is

Dayene S. Grubert ORLANDO TBI REALTY LLC

13109 Tollcross Way, Oakland, FL 34787

/14
Est $472,125 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,000 Sq Ft
15585 Water Spring Blvd, Winter Garden, FL 34787

15585 Water Spring Blvd, Winter Garden, FL 34787

/2
$590,000 Sold Aug 02, 2024
- 3,248 Sq Ft
- $182/SF
- 44 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2018
1540 Stone Arrow Ct, Winter Garden, FL 34787

his 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

1540 Stone Arrow Ct, Winter Garden, FL 34787

/18
Est $900,885 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,442 Sq Ft
1249 Civitas Way, Winter Garden, FL 34787

1249 Civitas Way, Winter Garden, FL 34787

/2
$455,000 Sold Aug 02, 2024
- 1,904 Sq Ft
- $239/SF
- 49 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2020
2153 Standing Rock Cir, Winter Garden, FL 34787

Welcome to 2153 Standing Rock Circle, a beautifully designed 3-bedroom, 2.5 bathroom, 2-car garage home nestled in the heart of Oakland. As you enter the home, you’re greeted with lots of natural sunlight and an open floor plan with lots of natural sunlight, where the kitchen, dining area, and living room seamlessly blend together, creating a warm and inviting atmosphere. The modern kitchen

Chad Vaughan REAL BROKER, LLC

2153 Standing Rock Cir, Winter Garden, FL 34787

/16
Est $878,741 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,219 Sq Ft
1260 Civitas Way, Winter Garden, FL 34787

1260 Civitas Way, Winter Garden, FL 34787

/2
$910,000 Sold Aug 01, 2024
- 3,334 Sq Ft
- $273/SF
- 6 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2021
9122 Sonoma Coast Dr, Oakland, FL 34787

Welcome to your dream home in the Waterleigh Community near Horizons West! This immaculate 4-bedroom, 3.5-bathroom residence showcases custom upgrades and impeccable condition throughout. From the inviting front porch to the luxurious pool area, every detail exudes elegance and comfort. Meticulously cared for and upgraded, this home is a rare gem offering the ultimate in luxury living. Upon

Carla Trine MAINFRAME REAL ESTATE

9122 Sonoma Coast Dr, Oakland, FL 34787

/16
Est $853,373 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,254 Sq Ft
1061 Sadler Oaks Way, Winter Garden, FL 34787

1061 Sadler Oaks Way, Winter Garden, FL 34787

/2
$575,000 Sold Jul 31, 2024
- 2,473 Sq Ft
- $233/SF
- 15 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2020
1113 Bobcat Chase Blvd, Oakland, FL 34760

Nestled quietly in Oakland, Florida, 1113 Bobcat Chase Blvd offers a cozy retreat for those seeking comfort and convenience.The beautiful kitchen features stainless appliances, quartz countertops and a classic subway tile backsplash. The primary suite boasts a spacious closet with built-in organizers. Step onto the screened-in patio to enjoy the scenic views of mature oaks and a fenced

Jorge Zea BLUE LIGHTHOUSE REALTY INC

1113 Bobcat Chase Blvd, Oakland, FL 34760

/50
Est $613,185 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,975 Sq Ft
2518 Stone Creek Ct, Oakland, FL 34787

2518 Stone Creek Ct, Oakland, FL 34787

/2
$1,783,268 Sold Jul 30, 2024
- 3,794 Sq Ft
- $470/SF
- 4 Beds
- 5 Baths
- Built 2025
Unlisted Address

Pre-Construction. To be built. SOLD DATA ENTRY ONLY/ Uniquely designed home in Oakland Park being built to suit the buyers. Complete with all the extras you'd desire in a custom home. Large covered clay paver front porch as well as a brick paver lanai with remote automated screens. The 3 car garage has 12 ft ceilings, brick paver driveway & there is a back entrance with mudroom. Courtyard open

Stellar Non-Member Agent Stellar Non-Member Office

Unlisted Address

/14
Est $731,543 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,333 Sq Ft
935 Honeywood Alley, Winter Garden, FL 34787

935 Honeywood Alley, Winter Garden, FL 34787

/2
$755,000 Sold Jul 30, 2024
- 3,747 Sq Ft
- $201/SF
- 33 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2021
3410 Buoy Cir, Oakland, FL 34787

Gorgeous, move in ready 5/4.5 Taylor Morrison, Tortola home in the sought after Lakeview Preserve neighborhood! VA ASSUMABLE LOAN AT RATE OF 2.375%! This beautiful 2 story home features over 3700 sq. ft of living space plus a 3 car garage overlooking John's Lake in Winter Garden. Upon entering, you step into a grand foyer with soaring ceilings, setting the tone for the luxurious living space

Kaley Hansen COLDWELL BANKER HUBBARD HANSEN

3410 Buoy Cir, Oakland, FL 34787

/13
Est $959,781 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,653 Sq Ft
1255 Civitas Way, Winter Garden, FL 34787

1255 Civitas Way, Winter Garden, FL 34787

/2
$465,000 Sold Jul 29, 2024
- 1,904 Sq Ft
- $244/SF
- 40 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2020
2165 Standing Rock Cir, Winter Garden, FL 34787

Discover this meticulously upgraded Bungalow nestled in the charming town of Oakland, Florida situated between Winter Garden and Clermont near all of the necessities of life and zoned for great schools. Conveniently located within 10 - 15 minutes from popular shopping and restaurant areas such as Winter Garden Village, Downtown Winter Garden, and Downtown Clermont. The Oakland Trails

Chad Purcell LPT REALTY, LLC

2165 Standing Rock Cir, Winter Garden, FL 34787

/40
Est $488,902 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,029 Sq Ft
1879 White Feather Loop, Oakland, FL 34787

1879 White Feather Loop, Oakland, FL 34787

/2
$600,000 Sold Jul 25, 2025
- 2,832 Sq Ft
- $212/SF
- 52 Days On Market
- 4 Beds
- 3 Baths
- Built 2003
714 Regina Cir, Oakland, FL 34787

A home in Oakland

Jeffrey Eddowes CENTURY 21 CARIOTI

714 Regina Cir, Oakland, FL 34787

/38
Est $495,699 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
2255 Standing Rock Cir, Oakland, FL 34787

2255 Standing Rock Cir, Oakland, FL 34787

/2
$1,000,000 Sold Jul 15, 2025
- 2,711 Sq Ft
- $369/SF
- 4 Beds
- 3 Baths
- Built 2025
1126 Riverway Dr, Oakland, FL 34787

Oakland Park, New Construction built by David Weekly Homes

Stellar Non-Member Agent Stellar Non-Member Office

1126 Riverway Dr, Oakland, FL 34787

/33
Est $621,349 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,674 Sq Ft
936 Beldonshire Ln, Winter Garden, FL 34787

936 Beldonshire Ln, Winter Garden, FL 34787

/2
$930,000 Sold Jul 09, 2025
- 2,796 Sq Ft
- $333/SF
- 4 Beds
- 3.5 Baths
- Built 2025
1180 Riverway Dr, Oakland, FL 34787

Sold Data entry only

Stellar Non-Member Agent Stellar Non-Member Office

1180 Riverway Dr, Oakland, FL 34787

/38
Est $749,541 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,858 Sq Ft
1372 Southern Sun Dr, Oakland, FL 34787

1372 Southern Sun Dr, Oakland, FL 34787

/2
$800,000 Sold Jul 09, 2025
- Land
- 1.17 Acres
- $683,761 per Acre
- 0 Days On Market
533 N Pollard St, Oakland, FL 34760

As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

Heather Spirazza REGENCY REAL ESTATE LLC

533 N Pollard St, Oakland, FL 34760

/24
Est $390,079 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,620 Sq Ft
1511 Sweet Apple St, Oakland, FL 34787

1511 Sweet Apple St, Oakland, FL 34787

/2
$875,000 Sold Jun 30, 2025
- 3,871 Sq Ft
- $226/SF
- 47 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2025
5319 Citrus Leaf Blvd, Oakland, FL 34787

Under Construction. Brand new, energy-efficient home available by Apr 2025! Enjoy cooking meals in the open kitchen overlooking the family room. Each secondary bedroom features a walk-in closet and there’s plenty of storage in the oversized garage. Use the first-floor study for working or relaxation. Now selling from the mid $500's, Silverleaf Reserve offers spacious open floorplan concepts fit

Tatiana Souza MERITAGE HOMES OF FL REALTY

5319 Citrus Leaf Blvd, Oakland, FL 34787

/32
Est $469,508 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,838 Sq Ft
1961 Standing Rock Cir, Oakland, FL 34787

1961 Standing Rock Cir, Oakland, FL 34787

/2
$300,000 Sold Jun 24, 2025
- Land
- 0.27 Acre
- $1,111,111 per Acre
380 Jefferson St, Oakland, FL 34760

As Central Florida newest custom home community, Briley Farm rests comfortably on 111 acres of lush landscape in Oakland, Florida. The property is a seamless blend of charming Old Florida and modern-day luxury living, designed to provide the ultimate retreat for you, your family, and friends. Welcome to a world of luxury, craftsmanship, and design excellence! At Briley Farm you will have to

Stellar Non-Member Agent Stellar Non-Member Office

380 Jefferson St, Oakland, FL 34760

/61
Est $807,136 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,717 Sq Ft
947 Honeywood Alley, Winter Garden, FL 34787

947 Honeywood Alley, Winter Garden, FL 34787

/2
$865,000 Sold Jun 05, 2025
- 2,916 Sq Ft
- $297/SF
- 0 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2021
9554 Bolero Rd, Oakland, FL 34787

Sold data only

Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

9554 Bolero Rd, Oakland, FL 34787

/15
Est $1,023,629 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,763 Sq Ft
1254 Civitas Way, Winter Garden, FL 34787

1254 Civitas Way, Winter Garden, FL 34787

/2
$419,990 Sold May 28, 2025
- 1,647 Sq Ft
- $255/SF
- 0 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2025
2895 Transformation Way, Oakland, FL 34787

Under Construction. The Westwood is timeless and built to last. The Great Room and kitchen share a convenient open floorplan on the first floor of this two-story home, with sliding glass doors that lead to the lanai. All three bedrooms occupy the second level, including the owner’s suite which is comprised of a restful bedroom, en-suite bathroom and walk-in closet. With “Everything’s Included”,

Stellar Non-Member Agent Stellar Non-Member Office

2895 Transformation Way, Oakland, FL 34787

/22
Est $862,069 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,247 Sq Ft
142 Hammock Preserve Loop, Winter Garden, FL 34787

142 Hammock Preserve Loop, Winter Garden, FL 34787

/2
$1,284,682 Sold May 08, 2025
- 3,852 Sq Ft
- $334/SF
- 5 Beds
- 4.5 Baths
- Built 2025
1245 Wilder Oaks Way, Oakland, FL 34787

The Crabtree by David Weekley Homes is a beautifully designed two-story home featuring an open-concept layout, a main-level owner’s suite, elegant finishes, and a detached garage apartment ideal for guests, family members, or a private office. Located in Oakland Park, a walkable, green-certified community in Winter Garden, residents enjoy resort-style amenities, scenic trails, and close proximity

Stellar Non-Member Agent Stellar Non-Member Office

1245 Wilder Oaks Way, Oakland, FL 34787

/14
Est $832,197 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,219 Sq Ft
1119 Eagle Pass Way, Winter Garden, FL 34787

1119 Eagle Pass Way, Winter Garden, FL 34787

/2
$849,628 Sold Mar 31, 2025
- 2,837 Sq Ft
- $299/SF
- 4 Beds
- 4.5 Baths
- Built 2025
16193 Honey Harvest St, Oakland, FL 34787

SOLD DATA ONLY

Stellar Non-Member Agent Stellar Non-Member Office

16193 Honey Harvest St, Oakland, FL 34787

/15
Est $896,953 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,442 Sq Ft
1207 Saddleback Dr, Winter Garden, FL 34787

1207 Saddleback Dr, Winter Garden, FL 34787

/2
$937,239 Sold Mar 26, 2025
- 2,773 Sq Ft
- $338/SF
- 4 Beds
- 3.5 Baths
- Built 2025
1179 Wilder Oaks Way, Oakland, FL 34787

Charming new construction home located in the beautiful neighborhood of Oakland Park. Golf cart to downtown Winter Garden!

Stellar Non-Member Agent Stellar Non-Member Office

1179 Wilder Oaks Way, Oakland, FL 34787

/2
Est $428,434 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,620 Sq Ft
13902 Title Way, Winter Garden, FL 34787

13902 Title Way, Winter Garden, FL 34787

/2
$717,583 Sold Mar 14, 2025
- 2,693 Sq Ft
- $266/SF
- 4 Beds
- 3.5 Baths
- Built 2025
15180 Field Daisy Dr, Oakland, FL 34787

SOLD DATA ENTRY ONLY/HARVEST AT OVATIONS

Stellar Non-Member Agent Stellar Non-Member Office

15180 Field Daisy Dr, Oakland, FL 34787

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