1024 Prosperity Dr, Winter Garden, FL 34787
OFF MARKET

1024 Prosperity Dr
Winter Garden, FL 34787

  • 3 Beds
  • 2.5 Baths
  • 2,260 sqft

$859,900

Trulia Estimate
as of Jun 14, 2026
Est. Refi. Payment $5,841/mo*
Refinance Your Home

$859,900

Trulia Estimate
as of Jun 14, 2026
Est. Refi. Payment $5,841/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,260 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

BEST DEAL IN OAKLAND PARK!! Welcome to 1024 Prosperity Dr, Winter Garden, FL! This stunning 3 bedroom 2.5 bathroom home in the desirable Oakland Park neighborhood has an open floorplan and large windows that fill it with natural light. The heart of the home is the chef's kitchen, featuring stainless steel appliances, a large island with plenty of counter space, and sleek cabinetry – perfect for cooking and entertaining. The study/den is perfect for working from home or a hobby area, because it has a stylish barn door that keeps it nice and private. And there's a downstairs powder room for your guest's convenience. Upstairs you will find the spacious primary suite and two additional bedrooms, the laundry room and also a bonus loft area that could be your second TV room, play room, exercise room or whatever you can imagine. Entertain a crowd or enjoy a peaceful beverage on both the large front porch and the screened back porch. The expansive backyard is fully fenced and perfect for creating your dream outdoor retreat, with plenty of room to add a pool. (additional pool renderings available) This home is equipped with a full-home water filtration system, and an electric car charger in the garage. Not to mention that it's in the golf cart district and just a short ride to charming Downtown Winter Garden and the West Orange hike and bike trail! Don’t miss the opportunity to make this your forever home- Schedule a showing today!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from June 21, 2025

Home Highlights

Parking
Garage
Outdoor
Porch
View
No Info
HOA
$201/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 1024 Prosperity Dr

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 2, Bathroom 3, Den, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2260 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights, Water ConnectedAppliances: Oven, Dishwasher, Disposal, Electric Water Heater, Microwave, Range, RefrigeratorDishwasherDisposalLaundry: Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Luxury Vinyl
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Luxury Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Front Porch, Rear Porch, ScreenedVegetation: Trees/LandscapedExterior: LightingFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Electric Vehicle Charging Station(s),Garage Door Opener,Garage Faces Rear
Frontage
Waterfront: LakeRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 12

Property Information

Year Built
Year Built: 2021
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod
Building
Construction Materials: HardiPlank TypeNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 212227610005060

Price & Status

Price
List Price: $879,000
Status Change & Dates
Off Market Date: Thu May 01 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER GARDENCommunity: OAKLAND PARK
School Information
Elementary School: Tildenville ElemJr High / Middle School: Lakeview MiddleHigh School: West Orange High

Building

Building Area
Building Area: 3264 Square Feet

Community

Community Features: Lake, Clubhouse, Community Mailbox, Deed Restrictions, Dog Park, Golf Carts OK, Park, Playground, Pool, SidewalksNot Senior Community
Other
Playground

HOA

HOA Fee Includes: Community Pool, Pool MaintenanceHOA Name: Edward RiosHOA Phone: 407-409-8594Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $201/Monthly

Lot Information

Lot Area: 6812 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6285139Back On Market Date: Wed Apr 23 2025Showing Considerations: Pet(s) on PremisesShowing Requirements: Appointment Only, Call Before Showing, Call Listing Agent, Combination Lock BoxUniversal Property Id: US-12095-N-212227610005060-R-N

Additional Information

LakeClubhouseCommunity MailboxDeed RestrictionsDog ParkGolf Carts OKParkPlaygroundPoolSidewalks
Last check for updates: about 9 hours ago
Listed by Tracey McFadden, (321) 217-7808
OAK AVENUE REAL ESTATE LLC, (407) 720-5000
Bought with: Tracey McFadden, (321) 217-7808, OAK AVENUE REAL ESTATE LLC, (407) 720-5000
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6285139
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Price History for 1024 Prosperity Dr

DatePriceEventSource
06/18/2025$870,000Sold
Stellar MLS #O6285139
05/01/2025$879,000PendingStellar MLS #O6285139
04/23/2025$879,000PendingToActiveStellar MLS #O6285139
03/05/2025$879,000PendingStellar MLS #O6285139
02/28/2025$879,000PriceChange
Stellar MLS #O6285139
02/18/2025$869,000Listed For SaleN/A
02/25/2021$536,600Sold
N/A

Market trends in Winter Garden

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$592K
$1.67KMoM
Sale-to-List Price
98.3%
0.3%MoM
Price per sq ft
$248
$3MoM
Available listings
744
17MoM
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Property Tax and Assessment

Year2024
Tax$7,891
Assessment$695,551
Home facts updated by county records

Homeowner tools

Estimated monthly rent$3,309/mo
List your home for rent

Comparable Sales for 1024 Prosperity Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
908 Tilden Oaks Trl, Winter Garden, FL
0.05
Single-Family Home
$915,000
08/15/25
4
3.5
2,683
936 Allendale Ln, Winter Garden, FL
0.17
Single-Family Home
$1,025,000
07/21/25
4
3
2,711
1016 Huntspoint St, Winter Garden, FL
0.30
Single-Family Home
$850,000
01/05/26
3
2.5
2,421
855 Oakland Park Blvd, Winter Garden, FL
0.25
Single-Family Home
$875,000
03/26/26
4
2.5
2,553
883 Tilden Oaks Trl, Winter Garden, FL
0.08
Single-Family Home
$1,075,000
04/30/26
4
3.5
2,811
836 Gayle Mill Dr, Winter Garden, FL
0.19
Single-Family Home
$770,000
11/03/25
3
2
2,022
1212 Civitas Way, Oakland, FL
0.28
Single-Family Home
$785,000
10/24/25
4
2
2,260
862 Oakland Park Blvd, Winter Garden, FL
0.21
Single-Family Home
$915,000
11/26/25
4
2.5
3,095
1120 Civitas Way, Oakland, FL
0.27
Single-Family Home
$1,200,000
03/10/26
4
3
2,563

Nearby homes

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Assigned Schools

These are the assigned schools for 1024 Prosperity Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Garden

At least 510 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say there are sidewalks

  • 86 % Say car is needed

  • 83 % Say parking is easy

  • 81 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 76 % Say it's quiet

  • 75 % Say streets are well-lit

  • 74 % Say people would walk alone at night

  • 72 % Say yards are well-kept

  • 61 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 54 % Say there's wildlife

  • 50 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 42 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Its great to live this area we have market and restauran near us . We can walk when we want in our neighboorhood. We have parks schools near us …"
    0
    Flag
  • Amanda
    "Great safe area for all ages and diversity. Good schools, lots of shopping, dining, nearby and more coming."
    0
    Flag
  • Ypgs9v7hpd
    "It is a nice area and the schools are nice. It is good area to raise children away from the tourists area and the city ."
    0
    Flag
  • Ypgs9v7hpd
    "The only thing that is unique about this neighborhood is the people that are friendly and the kids get along great. The only downside of living here in Wintergarden is it’s not enough places to go out to eat and it is not enough places for kids to hang out or teenagers to hang out and the closest place for teenagers to hang out is at the Wintergarden Grove area where you have to take off the exit 9, which I think that’s a bit too far for them to hang out when they can remain closer, it would be better if they had a place to hang out within the neighborhood. Also, Price is over here for a living is very high so if you’re not making a decent amount of money, it is expensive even the apartments that are surrounding it. It’s expensive.."
    0
    Flag
  • Emilye Chasen
    "Downtown events occur all the time. Christmas, Halloween, 4th of July etc. Santa comes down my street"
    1
    Flag
  • Ypgs9v7hpd
    "I’ve living here for the last 3 yrs. It’s nice area, people are nice. It’s nice area to raise your family there."
    0
    Flag
  • Heather Kotyk
    "I work near the airport and the commute using the turnpike and I4 is about 25-30 minutes. Traffic is usually manageable and continuously is moving "
    0
    Flag
  • Erin
    "There are many families in the neighborhood, a great playground and an A rated school nearby. There’s also a grocery store and pharmacy conveniently within a mile. "
    0
    Flag
  • Maria Rojas
    "Great place to have a family, lots of parks and activities for kids. Amazing schools and the community is very united. Most communities have hoa "
    0
    Flag
  • Rosa Aguilar
    "There’s lots of places, activities, parks, trails to take kids. There’s also lots of churches with daycare and city programs for children to take part in."
    0
    Flag
  • Andres.toro
    "Mostly all good schools. A lot of parks (and a few others upcoming) and services are increasing in availability. "
    0
    Flag
  • Logan Mahalek
    "The historic area of downtown winter garden boasts local shops and restaurants and also hosts a farmers market every weekend. There is also plenty of name brands within 15 minutes "
    0
    Flag
  • Cfbranf3rd
    "I’m don’t have a commute, as I’m retired. I’m in Cypress Reserve, and Avalon Road can be a nightmare at school drop off/pick up times."
    0
    Flag
  • Kelly
    "Beautiful, safe & friendly area. Winter Garden is a great place to raise a family! This is a very active area with tons of activities. Lots of wildlife & opportunities to get in touch with nature. Big, beautiful Florida birds and animals all around. Great restaurants too! "
    0
    Flag
  • Geisha
    "In Winter Garden for the area's of Horizon West, Hamlin, Summerlake, Waterleight, The Grove is amazing is like living in a perfect community bubble completely recomend"
    0
    Flag
  • Catherine Law
    "There is a private lake side park and a bbq area. Dogs poop trash and bags available. Dogs need to be on leash all the time. No many houses are fenced. "
    0
    Flag
  • Dawnddavidson1
    "Great little town if you live in the north side near old Winter Garden. Quaint small town feel with plenty to do. Surrounding area is overdeveloped like everywhere in central Florida. Schools could be better. Real estate is inflated, but the town is desirable. Everything you need is close; no need to go to Orlando for much. "
    0
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  • Vanessaasantini
    "Wonderful , Safe, beatiful, peaceful, very good, clean, good school, nice and bog city Close to supermarket, gas station "
    2
    Flag
  • Aj2636
    "Halloween costume parties for kids. Community Easter egg hunts. Santa Claus visits on a fire truck. Community watch parties for football games. A soccer field, tennis courts, pickleball courts and basketball courts that allow the neighborhood to enjoy each other’s company. During COVID, we had live music performances in the park."
    0
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  • Cara Conley
    "The area is established and offers. Great amenities within 15 minutes. Clean and safe and welcoming."
    1
    Flag
  • Isaac Peterson
    "Very friendly and helpful neighbors, and the schools are awesome. Very safe "
    2
    Flag
  • Aj2636
    "I’ve lived here for 11 years. It’s close to shopping. The neighborhood feels comfortable with homes far apart from each other. Nice lakes nearby that most neighborhoods have access to. Hospital close-by for emergencies."
    1
    Flag
  • Felton.amanda
    "I lived here for 10 years and just now moving this month. The neighborhood is safe not a lot of crime just a few thieves here and there that steal packages from ppls door steps occasionally."
    1
    Flag
  • Dismiki24
    "Lots of dogs in our neighborhood but many don’t pick up after their dogs. There is a dog park nearby "
    0
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  • Jason M.
    "We see people walk their dogs all the time. The neighborhood has dog stations for easy to dispose of waste. "
    0
    Flag
  • Megan E.
    "You will love it! Lots of dog owners and very kind. Lots of doggy poop bag stations as we all know! Great dog parks and trails to go on lovely long walks. "
    13
    Flag
  • Zimmiac
    "Everything is very nice ,and the persons are very nice ,very quite area and the schools are good also,parks and events as well very nice"
    0
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  • Lil D.
    "The people and shops are great. Love all the bike tails as well. Every Saturday they have the farmers market and quite enjoyable to go to and walk around. "
    0
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  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
    0
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  • Hollister M.
    "Lots of dogs. Most people are very polite about their dogs. People with cats do not keep them indoors and they roam the streets a lot. Most people pick up after their dogs and keep them on leashes."
    0
    Flag
  • Jim
    "It’s an amazing place to love. Doesn’t feel like living in Florida. I love living the country and still being close to Disney"
    6
    Flag
  • Cathy
    "Great it is safe and very homey the people are friendly and irs all clean. Very close to shopping places to eat and nice bars "
    5
    Flag
  • Jonathancrespo21
    "We have a neighborhood Facebook page open to everyone and we use this to communicate with each other regularly. We participate in food drives, raise money for special causes, and even sponsor dinners for our local police, firefighters, and nurses."
    0
    Flag
  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
    0
    Flag
  • Valerie
    "Weekend Farmers Market. Beautiful downtown area. Older historic feeling. Very convenient with shops food and stores. Best city I've lived in since being here in Florida."
    0
    Flag
  • jay j
    "People love dogs. They are loving animals that make everyone happy when they see them. Most people now a days have dogs"
    0
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  • Nicola O.
    "Some neighbors don’t clean up after their pets or leave their pets on the balcony barking all night long, but there is a lot of open grass fields and dog stations all throughout. "
    0
    Flag
  • Candy H.
    "Winter Garden Farmer’s Market and shows going on at the Garden Theatre, along with more dog friendly mom and pop places."
    0
    Flag
  • Ryanm1995
    "They will love this neighborhood. Bright open space to walk around. We also have a lot of friendly dog in our neighborhood. "
    0
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Homes for sale near 1024 Prosperity Dr

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Off Market Homes Near 1024 Prosperity Dr

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1024 Prosperity Dr, Winter Garden, FL 34787 is a 3 bedroom, 3 bathroom, 2,260 sqft single-family home built in 2021. This property is not currently available for sale. 1024 Prosperity Dr was last sold on Jun 18, 2025 for $870,000 (1% lower than the asking price of $879,000). The current Trulia Estimate for 1024 Prosperity Dr is $859,900.