Oakland Real Estate, Homes and Condos for sale

All Oakland homes currently listed for sale in Oakland as of 09/23/2017 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Oakland homes for sale or other Oakland real estate, please contact us and one of our knowledgeable Oakland REALTORS® would be pleased to assist you.


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$580,000
15250 SUNSET OVERLOOK CIR, Oakland FL 34787
5
BEDS
3
BATHS
3,135
SQFT
$185
$/SQFT
0.25
ACRES
"Five bedroom with little extras that makes this house feel like home. Screen pool with outside shower to rinse from a day of swimming. High ceilings that allow for chandelier of your choice. All appliance included with house included designer washer and dryer set. John Lake Pointe Community also features a resort style pool, clubhouse, playground and tennis court. A must see and ready for move in today!"
* LISTED OVER 120 DAYS 
$425,000
71 MILLHOLLAND ST, Oakland FL 34760
4
BEDS
3
BATHS
2,676
SQFT
$159
$/SQFT
0.32
ACRES
"LAKE VIEW! Come see this beautiful home in sought-after OAKAND with breathtaking VIEWS of LAKE APOPKA! Oakland speaks for itself with a reputation for its family-friendly old town character nestled among the OAKS, conveniently, just off the turnpike and Hwy 50, and just a short WEST ORANGE TRAIL bike ride to lively downtown WINTER GARDEN or CLERMONT. And this gorgeous home in the middle of it all boasts a well-thought-out custom design by the original owner... meticulously cared for. It's many features and recent upgrades include: .32 acre lot, granite counters, stainless steel appliances, tile and wood floors, Beam central vacuum, newer roof and AC, solar roof fans, surround sound, FL Keystone fireplace, tray and vaulted ceilings, custom master suite walk-in closet, exterior entrance for in-law bedroom/bath/living area (man cave or flexible space). Home is surrounded by mature citrus and palm trees. Drive to the nearby GROVE for shopping, walk to Oakland s square and parks for weekend festivals and entertainment, walk to Oakland s 128 acre NATURE PRESERVE or just sit back on your porch and enjoy. Oakland has it all, still just minutes from DISNEY, UNIVERSAL STUDIOS, and ORLANDO. . Come fall in love with this home and Oakland ..everyone does!....Also, check out more in store for the Town of Oakand by going to their website!"
$419,700
500 E GULLEY AVE, Oakland FL 34787
4
BEDS
3
BATHS
2,874
SQFT
$146
$/SQFT
0.32
ACRES
"Gorgeous Winters Landing Home. Ready to spend this Summer in one of the most sought after neighborhoods in the Winter Garden/Oakland area. Nestled among mature oaks in the quaint town of Oakland, this meticulously maintained, David Weekly, freshly painted inside and out, new carpet throughout home is a must see! Features 4 bedrooms, 3 baths, study, formal living & dining, screened Pool, 2 car garage. Open Kitchen is designed for family gatherings and entertaining. 10'2 ceilings in this perfect split floor plan includes HUGE Master with sitting room and walk in closet, master bath with garden tub and separate shower. PERFECT location with a short walk or bike ride on the West Orange Trail leads you to beautiful downtown Winter Garden with restaurants, shops, weekend farmers market, family activities galore! This home also provides preferred enrollment at Oakland Charter School which is a short walk down the sidewalk on the side of this home! Don't miss this one...It will NOT LAST!!!"
* PRICE LOWERED - $424,900 TO $419,700 
$416,000
808 CURA CT, Oakland FL 34787
5
BEDS
4
BATHS
3,305
SQFT
$126
$/SQFT
0.25
ACRES
"This gorgeous gated community is on a chain of lakes and it has a private boat ramp and dock where residents can launch their boat. The property is just as impressive as it offers elegance and beauty thanks to its architectural charm. Large 5 Bed 3.1 Bath w/ Office, Family Room, Living Room, Dining Room, Master Bath has a wonderful Garden Tub, Dual Sinks/Vanities and large Walk-in Shower. The second floor has ceramic tile and it boasts a huge bonus room which can be great for office, theater room, or play area. Johns Landing is situated on 2500 Acre Johns Lake & Chain of Lakes w/ Private Access and Private Boat Ramp, Tennis Court and Playground. Johns Lake is one of the Best Bass Fishing Lakes in ALL of Central Florida. Only a short drive to The Winter Garden Village and Historic Downtown Winter Garden. Just minutes from the FL Turn Pike, 429 and 408, just 25 minutes to Downtown Orlando, Disney, and too many wonderful amenities to mention. Do Not Wait Home won't Last Long!"
$384,900
412 MACCHI AVE, Oakland FL 34787
4
BEDS
3
BATHS
3,354
SQFT
$115
$/SQFT
0.29
ACRES
"Great Home waiting for you! 4 bedrooms plus office/3 bathrooms, family room, 3 car garage, screened in porch/overseeing bike path, laundry room under A/C. Ready to move in. BEAUTIFUL WINTER LANDINGS COMMUNITY IN OAKLAND!"
* PRICE LOWERED - $400,000 TO $384,900 
$369,000
1201 JOHNS COVE LN, Oakland FL 34787
3
BEDS
3
BATHS
2,465
SQFT
$150
$/SQFT
0.31
ACRES
"Come live the LAKE LIFE in beautiful Johns Cove of Oakland. This gated, lake access community is part of the Johns Chain of Lakes and is tucked away yet convenient to everywhere in Central Florida. Johns Lake is known for World class bass fishing and you can also enjoy water sports, paddleboarding, kayaking, etc... you decide! The home is 3 bedrooms and 3 full bathrooms Plus an Office/Den. The 3 car garage is perfect for storing your cars, equipment, and toys. Step out from the sliding glass doors onto your screen lanai to enjoy a BBQ and unwind enjoy the serenity of your backyard with no rear neighbor. The kitchen is spacious and has an island, breakfast bar and large pantry. Plenty of room to host and entertain. The gas fireplace, vaulted ceilings, and tile floors give the home an elegant and warm feel. Take advantage of this wonderful opportunity to live in the Johns Cove community and call today for your private showing."
* PRICE LOWERED - $369,900 TO $369,000 
$362,317
1823 STANDING ROCK CIR, Oakland FL 34787
3
BEDS
3
BATHS
2,088
SQFT
$174
$/SQFT
0.11
ACRES
"Under Construction Brand NEW Energy-Efficient home ready NOW! Enjoy entertaining guests in the lofty two-story dining room or move the party outdoors to the covered corner lanai of this beautiful 2-story Baldwin plan with tile roof elevation. Dedicated first-floor flex space can be configured to suite your family's needs. Walk-in closets in all of the bedrooms means everyone has plenty of storage. Upstairs balcony is the perfect place to enjoy morning coffee. Laminate floors in all main living areas of first floor and wood stairs with upgraded baluster. Additional upgrades include quartz countertops and 5 1/4 baseboards. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429 providing quick access to the Turnpike interchange and is adjacent to Killarney Station so you can enjoy leisurely bike rides and walks on the West Orange Trail. Winter Garden Village is less than 6 miles away & offers a host of shopping, dining and entertainment options. Known for their energy efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $360,767 TO $362,317 
$327,143
1787 WHITE FEATHER LOOP, Oakland FL 34787
3
BEDS
3
BATHS
2,183
SQFT
$150
$/SQFT
0.09
ACRES
"Brand NEW Energy-Efficient home ready NOW! Enjoy sitting and relaxing on the front porch or back lanai of this well-appointed 2-story Whitaker plan. Kitchen with quartz counter-tops is open to both the family and living room so you can carry on conversations with friends and family while preparing meals. Upstairs game room offers extra space for work or play. Outdoor spaces include a front porch, balcony, and back lanai. Enjoy having beautiful upgraded tile throughout the main floor. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429 providing quick access to the Turnpike interchange and is adjacent to Killarney Station so you can enjoy leisurely bike rides and walks on the West Orange Trail. Winter Garden Village is less than 6 miles away & offers a host of shopping, dining and entertainment options. Known for their energy efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $325,813 TO $327,143 
$326,331
1793 WHITE FEATHER LOOP, Oakland FL 34787
3
BEDS
4
BATHS
3,098
SQFT
$105
$/SQFT
0.09
ACRES
"Under Construction Brand NEW Energy-Efficient home ready NOW! Enjoy morning coffee on the large, covered front porch of this Whitman II plan. Spacious, open first-floor living areas and a second-floor game room offer plenty of space. Master suite has dual walk-in closets. Upgrades include tray ceilings, gourmet kitchen and tile on main floor. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429 providing quick access to the Turnpike interchange and is adjacent to Killarney Station so you can enjoy leisurely bike rides and walks on the West Orange Trail. Winter Garden Village is less than 6 miles away & offers a host of shopping, dining and entertainment options. Known for their energy efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $325,331 TO $326,331 
$325,000
829 CURA CT, Oakland FL 34787
4
BEDS
3
BATHS
2,329
SQFT
$140
$/SQFT
0.22
ACRES
"Priced to sell and willl not last long!!! A beautiful home in a fantastic gated community, lake access! This beautiful 4 bedroom 3 bath home offers the convenience of a perfect location with lake access, a playground, and tennis courts. The large kitchen is a cook s delight offering breakfast nook, breakfast bar, stainless steel appliances and granite counter tops with gorgeous cabinets. No carpet except the bedrooms. The owners retreat features walk in closets, a garden tub, and separate walk in shower. Private screened oversized pool with a spa! Located in cul-de-sac and it's quiet and safe for your family! Amenities in the gated community of Johns Landing include boat ramp, good fishing, boating and skiing on Johns Lake, playground, and tennis. Conveniently located just minutes from the Florida Turnpike, State Route 429, West Orange Trail, historic downtown Winter Garden, Winter Garden Village, downtown Orlando and theme parks. Freshly painted inside with new carpets, this home is ready for you to move right in."
$305,622
1799 STANDING ROCK CIR, Oakland FL 34787
3
BEDS
3
BATHS
2,008
SQFT
$152
$/SQFT
0.08
ACRES
"Under Construction Brand NEW energy-efficient home ready September 2017! The beautiful Kipling features an open kitchen that overlooks the dual living areas on the first floor. Upstairs, you'll find the loft that separates the master suite and secondary bedrooms for privacy. Relax and watch the Florida sunset under the covered lanai. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429 providing quick access to the Turnpike interchange and is adjacent to Killarney Station so you can enjoy leisurely bike rides and walks on the West Orange Trail. Winter Garden Village is less than 6 miles away & offers a host of shopping, dining and entertainment options. Known for their energy efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills."
$300,540
1781 WHITE FEATHER LOOP, Oakland FL 34787
3
BEDS
3
BATHS
1,892
SQFT
$159
$/SQFT
0.09
ACRES
"Under Construction Brand NEW Energy-Efficient home ready NOW! This charming two-story Angelou II plan is perfect for the family who loves to entertain everyone regardless of age. The open, spacious kitchen overlooks the living and dining areas making it perfect for a dinner party or game night with friends. The second floor loft can serve as an office area, or a play room for the youngsters. Upgrades include granite counters, 8' interior doors, and wood laminate floors. Community is convenient to Central Florida's major employment, service, and entertainment corridors including Downtown Orlando and Walt Disney World and is just miles from SR 408 and SR 429 providing quick access to the Turnpike interchange and is adjacent to Killarney Station so you can enjoy leisurely bike rides and walks on the West Orange Trail. Winter Garden Village is less than 6 miles away & offers a host of shopping, dining and entertainment options. Known for their energy efficient features, our homes help you live a healthier and quieter lifestyle while saving thousands of dollars on utility bills."
* LISTED OVER 120 DAYS  * PRICE INCREASED - $300,000 TO $300,540 
$290,000
302 EDGEGROVE LN, Oakland FL 34760
3
BEDS
2
BATHS
1,916
SQFT
$151
$/SQFT
0.29
ACRES
"This Beautiful home in Oakland has been meticulously maintained and offers an amazing in ground pool and spa to entertain guests. The pool is filtered by and over-sized Pentair salt filter system and motor to assist with the pools filtration. The backyard has a high screen and covered porch that provides lots of room under the covered area for: dining table, living room set and TV. There is plenty of room to play games, listen to music and swim in the sun area. Large side yard for endless activities play outside of the pool area. There is also a gated area to park your boat. All new plumbing, new windows, and vaulted ceilings. Well maintained lawn with sprinkler system and shade trees. There is an indoor heated Jacuzzi tub with shower. This well designed split bedroom floor plan features the master bedroom on one end and two bedrooms and bath on the other. The home is located in the beautiful, highly sought after town of Oakland, FL. The town offers a park, lake, and bike trail. This is a must see!"
* PRICE LOWERED - $310,000 TO $290,000 
$224,700
323 W HENSCHEN AVE, Oakland FL 34760
4
BEDS
2
BATHS
2,076
SQFT
$108
$/SQFT
0.14
ACRES
"UPDATED / UPGRADED 4 Bed 2 Bath Oakland Home, New Paint, Carpet, appliances, HUGE upstairs bedrooms as well as a giant living/entertainment area upstairs! Right near Lake Apopka, Situated only a few miles away from the Turnpike, Downtown Winter Garden, this location is perfect to easily access just about anywhere in the greater Orlando area! Don't miss this opportunity, inventory in Oakland is LOW, come see this house before it's taken!"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $224,800 TO $224,700 
$189,900
320 W HULL AVE, Oakland FL 34760
4
BEDS
2
BATHS
1,328
SQFT
$143
$/SQFT
0.14
ACRES
"****** NOT A SHORT SALE OR REO ******** Dont miss this solid block 4 bedroom 2 bath home in quaint Oakland neighborhood. This property has been totally renovated from top to bottom. The updates include NEW roof, HVAC, updated electrical, kitchen, flooring, bathrooms, and more! The kitchen features an open concept with custom wood cabinets, solid granite counter tops, and stainless steel appliance package. New tile flooring has been professionally installed throughout the home for that easy Florida living. The bathrooms have all new tile surrounds, toilets, and vanities. Too many upgrades to list them all here. Dont miss your chance to see this one before its gone!!!!!!"
* PRICE LOWERED - $199,900 TO $189,900 
$183,000
315 W HULL AVE, Oakland FL 34760
3
BEDS
2
BATHS
1,682
SQFT
$109
$/SQFT
0.25
ACRES
"This recently renovated 4 bedroom home has one of the most practical floor plans you can find at such an affordable price. Upon arriving you encounter a long driveway which leads to 20 x 19 carport. Go inside. New items include: kitchen cabinets and counter, upscale refrigerator, microwave and range, plumbing fixtures, ceramic flooring in kitchen, living room, dining area, laundry room and both bathrooms, carpet in all four bedrooms and the loft. There are two bedrooms on the first level. The second level offers a giant 26 x 15 loft area, a bathroom and two bedrooms. Would you like a large back yard ? There's a large fenced backyard. The entire house, inside and out, has been repainted. Energy conscious owners will appreciate the fact that the home has two A/C units; one for each level. Set the upstairs thermostat at a thriftier temperature when it's not in use ! Save even more money: this home is not part of a Homeowner's Association..... NO Dues, nor intrusive HOA Committees ! Historic Oakland is one of the prettiest towns in West Orange County. This location offers the best of small town living yet it is close to The Florida Turnpike, State Road 50, the principal East-West corridor of Central Florida, shopping, schools, restaurants, golf courses, the West Orange Trail and jobs. We know of no better value in the area."
* NEW LISTING  * PRICE LOWERED - $184,900 TO $183,000 
$179,900
501 W HERRIOTT AVE, Oakland FL 34760
4
BEDS
2
BATHS
1,650
SQFT
$109
$/SQFT
0.09
ACRES
"4 bedroom 2 bath Great Location: across the street from a beautiful new park, just 3 blocks away from West Orange Trail, and just over a mile to the Turnpike on-ramps. Mango tree and multiple orange trees in the yard with a large oak tree for shade. Don't miss this one."
 
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