One or more photo(s) has been virtually staged. Welcome to this truly exceptional home offering space,flexibility, & an unbeatable location!This beautiful,expansive residence features 4 spacious bedrooms,3.5 bathrooms,plus a versatile upstairs BONUS ROOM that can easily serve as a 5th bedrm—complete with closet & half bath already pre-plumbed for a full bathroom conversion.Enjoy breathtaking sunset views right from this elevated retreat.This home features a rare & highly desirable MOTHER-IN-LAW SUITE,complete with its own KITCHENETTE & ADA-compliant BATHROOM—ideal for multi-generational living or guest privacy.The 2nd bedroom conveniently connects to the kitchenette,enhancing the suite’s functionality.A 3rd bedrm,currently used as a home office,located near an adjacent bathroom that also provides direct access to the pool area.SPACIOUS PRIMARY suite serves as a private retreat,featuring an ensuite bathroom with dual sinks,a relaxing soaking tub& large walk-in closet.At the front of the home,a formal living & dining area offers versatile space that can easily serve as a den,library, or flex rm to suit your needs.The kitchen has 42″ SOLID WOOD cabinets,granite counter tops & is equipped with NEW APPLIANCES 2025,including induction cooktop that heats water in 3 minutes,convection oven & the rare convenience of TWO dishwashers—one being a quiet Bosch,ideal for large families or entertaining.The great rm features a cozy WOOD BURNING FIREPLACE & opens to your own private Florida oasis.Step outside to a HEATED, screen-enclosed POOL & SPA(pool heater installed in 2025, screen enclosure 2020),creating the perfect setting for year-round enjoyment.The expansive pool deck extends your living space outdoors,ideal for relaxing or entertaining.Beyond the pool,the private,partially fenced backyard offers additional space to unwind,accented by tranquil bamboo that sways in the breeze creating a peaceful atmosphere.The home backs to a State of Florida wildlife ravine,providing serene views of native birds,lush greenery& natural surroundings—your own quiet retreat right at home!The home boasts 2 AC zones for superior energy conservation:Both AC units are new in the last 5 years & maintained twice a year.NEW, OVERSIZED DOUBLE PANE WINDOWS throughout lower level are only a few months old, allowing for gorgeous VIEWS.NEW ROOF 2022.NEW, LARGE HYBRID WATER HEATER installed 2024,water Softener included.Complete with a 3 CAR GARAGE.LOCATION,LOCATION truly sets this home apart. Situated in a GOLF CART- FRIENDLY community,you’ll have direct access to the vibrant charm of DOWNTOWN WINTER GARDEN,just 2 miles away. Enjoy the award-winning Winter Garden Farmers Market,along with popular dining,shopping, & year-round events.Outdoor enthusiasts will love being just steps from the scenic 22-mile West Orange Trail,perfect for biking, jogging or leisurely strolls.Nearby,the quaint & historic charm of Downtown Oakland,the scenic waterfront dock on Tubb Street & nearby Oakland Nature Preserve,offer even more to explore.Publix,Aldi,Winter Garden Village Mall,MAJOR ROADWAYS & highways are all nearby.The Turnpike is minutes away.EASY ACCESS to the Theme parks, 20 minutes to Downtown Orlando and Orlando Intl Airport 30 minutes away.With only 58 homes,this quiet street offers a true sense of community.Residents enjoy friendly neighbors,regular patrols from the nearby police department & proximity to the fire station & Oakland Charter School(priority enrollment for Oakland residents).This is more than a home—it’s a lifestyle!
Property Details
Price:
$899,000
MLS #:
O6400317
Status:
Active
Beds:
4
Baths:
3.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINTERS LNDG PH 01 A D F & G
Neighborhood:
34787wintergardenoakland
Listed Date:
Apr 24, 2026
Finished Sq Ft:
3,399
Total Sq Ft:
4,307
Lot Size:
12,877 sqft / 0.30 acres (approx)
Year Built:
2006
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator, Water Softener
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Zoned
Flooring
Carpet, Ceramic Tile
Heating
Central, Electric, Zoned
Interior Features
Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s)
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Attached Garage YN
1
Community Features
Deed Restrictions, Playground, Sidewalks
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
South
Exterior Features
Irrigation System, Lighting, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors, Storage
Fencing
Fenced, Vinyl
Garage Spaces
3
Lot Features
City Lot, In County, Landscaped, Oversized Lot, Sidewalk
Open Parking YN
1
Other Structures
Shed(s)
Parking Features
Driveway, Garage Door Opener, On Street
Patio And Porch Features
Covered, Deck, Enclosed, Front Porch, Porch, Rear Porch, Screened
Roof
Shingle
Security Features
Smoke Detector(s)
Spa Features
Heated
View
Garden, Pool, Trees/Woods
Window Features
Double Pane Windows
Financial
HOA Fee
$220
HOA Fee Frequency
Quarterly
HOA Includes
Manager
HOA Name
Southwest Property Management
HOA Phone
407-656-1081
Tax Year
2025
Taxes
$6,649
Map
Community
- Address505 E GULLEY AVENUE OAKLAND FL
- SubdivisionWINTERS LNDG PH 01 A D F & G
- CityOAKLAND
- CountyOrange
- Zip Code34787
Subdivisions in OAKLAND
- BRILEY FARM
- GROVE AT THE HARVEST DISTRICT
- HULL ISLAND ESTATES FIRST ADD
- JOHNS LANDING
- JOHNS LANDING PH 01 44/47
- JOHNS LANDING PH 02 48 138
- JOHNS LANDING PHASE 1
- LONGLEAF
- LONGLEAF AT OAKLAND
- LONGLEAF/OAKLAND
- LONGLEAF/OAKLAND REP
- OAKLAND PARK
- OAKLAND PK UN 7 NORTH
- OAKLAND TOWN
- OAKLAND TRAILS
- OAKLAND TRAILS PH 1
- OAKLAND TRLS PH 1
- OAKLAND TRLS PH 2
- RYAN COURT
- THE GROVE AT OAKLAND
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in OAKLAND as of Apr 30, 2026
29
Single Family Listed
71
Avg DOM
346
Avg $ / SqFt
$1,094,585
Avg List Price
Property Summary
- Located in the WINTERS LNDG PH 01 A D F & G subdivision, 505 E GULLEY AVENUE OAKLAND FL is a Single Family for sale in OAKLAND, FL, 34787. It is listed for $899,000 and features 4 beds, 4 baths, and has approximately 3,399 square feet of living space, and was originally constructed in 2006. The current price per square foot is $264. The average price per square foot for Single Family listings in OAKLAND is $346. The average listing price for Single Family in OAKLAND is $1,094,585. To schedule a showing of MLS#o6400317 at 505 E GULLEY AVENUE in OAKLAND, FL, contact your Charles Rutenberg Realty agent at (407) 619-0129.
Similar Listings Nearby
Courtesy of CLOCK TOWER REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than Charles Rutenberg Realty include the name of the listing broker. Neither the listing company nor Charles Rutenberg Realty shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 505 E GULLEY AVENUE
OAKLAND, FL

