8 E CYPRESS STREET, Winter Garden, FL 34787
OFF MARKET

$295,400

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 832 sqft

8 E CYPRESS STREET, Winter Garden, FL 34787

Est. Refi. Payment $2,108/mo*
Refinance Your Home
Currently Off Market - Sold Dec 12, 2023 for $270,000

Home Value

Trulia Estimate
$295K
Since last month
Decreased$14K (-4.4%)
Since last year
Increased$7K (+2.5%)
Since last sale
Increased$26K (+9.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +159% in the last 10 years
MonthEstimated value
2026
August 2026$296K
August 2026$295K
July 2026$310K
June 2026$293K
May 2026$296K
April 2026$294K
March 2026$297K
February 2026$297K
January 2026$295K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
135 E STORY ROAD, Winter Garden, FL
0.25
Single-Family Home
$280,000
09/12/25
2
1
957
345 WINTER STREET, Winter Garden, FL
0.37
Single-Family Home
$285,000
06/08/26
2
1
700
18 W VINING STREET, Winter Garden, FL
0.24
Single-Family Home
$435,000
02/17/26
2
1
948
330 E STORY ROAD, Winter Garden, FL
0.41
Single-Family Home
$285,000
04/20/26
2
1
760
143 W MORGAN STREET, Winter Garden, FL
0.28
Single-Family Home
$150,001
11/17/25
2
1
780
341 E LAFAYETTE STREET, Winter Garden, FL
0.42
Single-Family Home
$162,500
07/31/26
2
1
1,106
422 CHARLOTTE STREET, Winter Garden, FL
0.55
Single-Family Home
$290,000
04/23/26
3
1
858
243 FLORIDA AVENUE, Winter Garden, FL
0.48
Single-Family Home
$335,000
07/29/26
2
2
1,100
329 W BAY STREET, Winter Garden, FL
0.77
Single-Family Home
$375,000
02/02/26
2
1
1,004

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
721 S WOODLAND STREET, Winter Garden, FL 34787
0.08
$440,000
2
1
1,034
For Sale
641 S BOYD STREET, Winter Garden, FL 34787
0.08
$170,000
2
1
912
Recently Sold
30 E PALMETTO STREET, Winter Garden, FL 34787
0.13
$298,300
2
1
880
Off Market
617 S BOYD STREET, Winter Garden, FL 34787
0.12
$227,200
1
1
550
Off Market
27 W PALMETTO STREET, Winter Garden, FL 34787
0.16
$418,400
2
2
1,004
Off Market
636 SIGLER DRIVE, Winter Garden, FL 34787
0.17
$611,610
3
2.5
1,634
For Sale
642 MEDORA WAY, Winter Garden, FL 34787
0.18
$1,137,150
4
3.5
2,995
For Sale
522 S WOODLAND STREET, Winter Garden, FL 34787
0.18
$396,600
3
1.5
1,412
Off Market
50 W STORY ROAD, Winter Garden, FL 34787
0.18
$683,900
3
2
2,040
Off Market
608 S Lakeview Ave, Winter Garden, FL 34787
0.21
$256,300
3
2
-
Off Market
611 SIGLER DRIVE, Winter Garden, FL 34787
0.21
$899,760
4
3.5
2,432
For Sale

Local Information

  • Map ViewExplore the area around 8 E CYPRESS STREET.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1957
832 sqft
$355/sqft
1 Carport Spaces

About this House

OPPORTUNITY AWAITS !!!! Located in the sought-after GOLF CART DISTRICT of DOWNTOWN WINTER GARDEN. NO HOA! This 2 Bedroom, 1 bath bungalow with spacious kitchen and living room has a lot of potential!!! No carpet! The master bedroom offers sliders that lead out to a large open patio. Private oversized back yard provides opportunity to expand onto the existing home. ** ROOF 2016! ** HVAC 2019! ** Just a short golf cart ride to charming Downtown Winter Garden offering plenty of Restaurants, Shops, Saturday Farmer's Market, The Plant Street Market, The West Orange Bike Trail or explore Lake Apopka's Newton Park! Public boat ramp at Newton Park on Lake Apopka offers access to the Dora Chain of Lakes. Easy access to major highways, downtown Orlando, International Airport, area beaches and so much more.
8 E CYPRESS STREET, Winter Garden, FL 34787 is a 2 bedroom, 1 bathroom, 832 sqft single-family home built in 1957. It last sold for $270,000 on Dec 12, 2023 (5% below the $285,000 asking price). More recently, it was listed as a rental in July 2026 with an asking price of $2,200 per month. That rental listing was removed on August 1, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $295,400, with a rent estimate of $2,121/month.
Last check for updates: about 20 hours ago
Listed by Erica Sadelfeld, (407) 427-0398
THE REAL ESTATE COLLECTION LLC, (407) 656-7814
Kimberly Beach Byerly, (407) 516-7780
THE REAL ESTATE COLLECTION LLC, (407) 656-7814
Bought with: Kimberly Beach Byerly, (407) 516-7780, THE REAL ESTATE COLLECTION LLC, (407) 656-7814
Co-Buyer's Agent: Erica Sadelfeld, (407) 427-0398, THE REAL ESTATE COLLECTION LLC, (407) 656-7814
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6149240
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

Home Details for 8 E CYPRESS STREET

Interior Features

Interior Details
Number of Rooms: 5Types of Rooms: Master Bedroom, Bedroom 2, Bathroom 1, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout
Living Area: 832 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Natural Gas Available, Public, Sewer Connected, Street Lights, Water ConnectedAppliances: Electric Water Heater, Range, RefrigeratorLaundry: Laundry Closet,OutsideRefrigerator
Heating & Cooling
Heating: Central,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: Sliding DoorsFlooring: Laminate, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Laminate, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: MembranePatio / Porch: Patio, Rear PorchFencing: WoodVegetation: Mature LandscapingExterior: LightingFoundation: SlabNo Private Pool
Parking & Garage
Number of Carport Spaces: 1Number of Covered Spaces: 1Has a CarportNo GarageParking Spaces: 1Parking: Carport
Frontage
Waterfront: Lake PrivilegesResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: LAKE APOPKA

Days on Market

Cumulative Days on Market: 14

Property Information

Year Built
Year Built: 1957
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, ConcreteNot a New ConstructionAttached To Another StructureNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 232227806000020

Price & Status

Price
List Price: $285,000
Status Change & Dates
Off Market Date: Sat Nov 11 2023Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Location

Direction & Address
City: WINTER GARDENCommunity: SIMMONS SUB
School Information
Elementary School: Dillard Street ElemJr High / Middle School: Lakeview MiddleHigh School: West Orange High

Building

Building Area
Building Area: 1220 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 8031 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6149240Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-232227806000020-R-N

Price and Tax history

DateEventPrice
Aug 1, 2026
Source: Stellar MLS #O6427158
ListingRemoved
$2,200
Jul 29, 2026
Source: Stellar MLS #O6427158
Listed For Rent
$2,200
Jul 29, 2026
Source: Zillow Rentals
ListingRemoved
$2,200
Jul 23, 2026
Source: Zillow Rentals
Listed For Rent
$2,200
Dec 12, 2023
Source: Stellar MLS #O6149240
Sold
$270,000

Market trends in Winter Garden

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$583K
$3.33KMoM
Sale-to-List Price
98.3%
0.2%MoM
Price per sq ft
$254
$3MoM
Available listings
760
4MoM

Around this home

What Locals Say about Winter Garden

At least 513 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

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • jhp331
    "A rated schools and lots to do for families "
    0
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  • 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
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  • 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 ."
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
  • 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
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  • 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"
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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
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  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
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  • 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."
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  • 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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LGBTQ Local Legal Protections

Frequently asked questions about 8 E CYPRESS STREET

  • What is 8 E CYPRESS STREET estimated to be worth?
    Trulia's estimated value for 8 E CYPRESS STREET in Winter Garden, FL is $295,400.
  • What is the price history for 8 E CYPRESS STREET?
    8 E CYPRESS STREET in Winter Garden, FL last sold for $270,000 in December 2023.
  • Is Winter Garden a buyer's or seller's market?
    Winter Garden is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Garden?
    The median sale price in Winter Garden is $583K. That is down $3.33K from the prior month.
  • Does 8 E CYPRESS STREET have air conditioning?
    Yes, 8 E CYPRESS STREET in Winter Garden, FL has air conditioning.
  • Does 8 E CYPRESS STREET have laundry facilities?
    Yes, 8 E CYPRESS STREET in Winter Garden, FL has laundry facilities.

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Off Market Homes Near 8 E CYPRESS STREET

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