505 Gulley Avenue, FL

$865,000

505 Gulley Avenue

Oakland, FL 34787

Active
4
Beds
4
Baths
3,399
Sq Ft
0.3
Acres
2006
Built
Private poolIn-law suiteFireplace3-car garage$254/sqft
🏠Single Family Residence

Property type

🏗️2006

Year built

📐12,877 sqft

Lot size

📊$254

Price / sq ft

🏘️$73/mo

HOA dues

📅36

Days on market

🚗3

Garage spaces

🌊X

Flood zone

About this home

One or more photo(s) has been virtually staged. **$10,000 towards closing costs**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 KITCHENETTE & ADA-compliant BATHROOM—ideal for multi-generational living or guest privacy.The 2nd bedrm 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 heats water in 3 minutes,convection oven & the rare convenience of 2 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 Theme parks, 20 minutes to Downtown Orlando & 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!

Estimated monthly payment

Principal & interest$4,374
Property taxes$554
Home insurance (est.)$396
HOA dues$73

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history36 days on market

  1. Status: Active
    Apr 24, 2026
  2. Listed$899,000
    Apr 24, 2026
  3. Price reduced$865,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
36
Subdivision
Winters Lndg Ph 01 A D F & G
County
Orange
Year built
2006
Living area
3,399 sq ft
Price/sq ft
$254
Building area
4,307 sq ft (Appraiser)
Lot size
12,877 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X (12095C0215H)
Garage
3 spaces
Pool
Private pool
Annual taxes
$6,649 (2025)
Parcel #
21-22-27-9401-00-220
Zoning
R-1A
MLS #
O6400317

Interior Details

Bedrooms
4
Full bathrooms
3
Half bathrooms
1
Flooring
Carpet, Ceramic Tile
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator, Water Softener
Interior features
Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Walk-In Closet(s)
Laundry
Inside, Laundry Room
Stories / Levels
Two
Direction faces
South
Fireplace
Yes
In-law suite
Yes

Heating & Cooling

Heating
Central, Electric, Zoned
Cooling
Central Air, Zoned

Parking

Garage spaces
3
Attached garage
Yes
Parking features
Driveway, Garage Door Opener, On Street

HOA & Financial

HOA fee
$220 / Quarterly
Monthly HOA
$73/mo
Total monthly fees
$73/mo
Total annual fees
$880
HOA name
Southwest Property Management
CDD
No
Homestead exemption
Yes
Min lease term
1-2 Years
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Please verify with HOA management company

Exterior & Construction

Exterior features
Lighting, Private Mailbox, Rain Gutters, Sidewalk, Sliding Doors, Storage
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Pool
Private pool
Road surface
Asphalt, Paved

Utilities

Sewer
Septic Tank
Water source
Public
Utilities
BB/HS Internet Available, Electricity Available, Electricity Connected, Underground Utilities, Water Connected

Community

Pets allowed
Cats OK, Dogs OK

Schools

ElementaryATildenville ElemGreatSchools ↗
MiddleBLakeview MiddleGreatSchools ↗
High SchoolAWest Orange HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Primary BedroomFirst23x13
Bedroom 2First10x11
Bedroom 3First10x14
Bedroom 4First
KitchenFirst15x12
DinetteFirst11x11
Great RoomFirst17x21
Living RoomFirst11x13
Dining RoomFirst10x13
Bonus RoomSecond21x18

Listing Details

Listing date
2026-04-24
On market date
2026-04-24
Original list price
$899,000
Occupant type
Owner
MLS area
34787 - Winter Garden/Oakland
Listing AOR
Orlando Regional
Status changed
2026-04-24
Tax legal description
WINTERS LANDING PHASE 1 60/17 LOT 22

Flood risk

Minimal riskFEMA Zone XPanel 12095C0215H

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From Downtown Winter Garden Plant St, straight approximately 2 miles to Winters Landing. Right on Winters Landing Dr, Left on E Gulley. Home will be on your right. From Highway 50 to Tildenville School Rd, Left on Oakland Ave. Right on Winters Landing Drive, Left on E Gulley. Home will be on your right.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 30, 2026 at 2:06 PM ET. 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.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA