420 E CYPRESS STREET, Winter Garden, FL 34787
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Property image
FOR SALE
3D VIEW

$410,000

Original price: $420,000
  • 3 Beds
  • 2 Baths
  • 1,616 sqft

420 E CYPRESS STREET, Winter Garden, FL 34787

Est. Mortgage $2,990/mo*
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Home Highlights

Single-Family Home
Built in 1950
$254/sqft

Local Information

  • Map ViewExplore the area around 420 E CYPRESS STREET.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.
Last check for updates: about 9 hours ago
Listing Provided by: Trevor Zwick, (863) 303-6114
KELLER WILLIAMS ELITE PARTNERS III REALTY, (321) 527-5111
Originating MLS: Lake and Sumter
Source: Stellar MLS, MLS#O6412414
Also Listed on Stellar MLS.
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 420 E CYPRESS STREET

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Primary Bedroom, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1616 Square Feet
Appliances & Utilities
Utilities: Electricity AvailableAppliances: Dishwasher, Microwave, Range, RefrigeratorDishwasherLaundry: OtherMicrowaveRefrigerator
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: 1Number of Stories: 1Levels: OneFloors: Luxury Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleFencing: Fenced, VinylExterior: Lighting, OtherFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo Garage
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 100Days on Market: 105

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Stucco, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 122227649620028

Price & Status

Price
List Price: $410,000Price Per Sqft: $254

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINTER GARDENCommunity: OVERSTREET CRATE
School Information
Elementary School: Maxey ElemJr High / Middle School: Lakeview MiddleHigh School: West Orange High

Agent Information

Listing Agent
Listing ID: O6412414

Building

Building Area
Building Area: 1616 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Lake and SumterNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 8440 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6412414Back On Market Date: Wed Aug 19 2026Showing Requirements: ShowingTimeUniversal Property Id: US-12095-N-122227649620028-R-N

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
    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 ."
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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
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  • 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
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  • 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
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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
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  • 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
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  • 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
    Flag
  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
    0
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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."
    0
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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
    Flag

Market trends in Winter Garden

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$585K
$1.67KMoM
Sale-to-List Price
98.1%
0.2%MoM
Price per sq ft
$251
$4MoM
Available listings
742
21MoM

Home Value

Trulia Estimate
$406K
Since last month
Increased$4K (+0.9%)
Since last year
Increased$14K (+3.5%)
Since last sale
Increased$6K (+1.6%)
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 +285% in the last 10 years
MonthEstimated value
2026
September 2026$406K
August 2026$403K
July 2026$403K
June 2026$414K
May 2026$418K
April 2026$415K
March 2026$417K
February 2026$412K
January 2026$410K
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
307 GRAND ROYAL CIRCLE, Winter Garden, FL
0.17
Single-Family Home
$410,000
10/10/25
3
2
1,868
837 GRANDE REGAL POINT, Winter Garden, FL
0.15
Single-Family Home
$455,000
07/02/26
3
2
1,874
375 REGAL DOWNS CIRCLE, Winter Garden, FL
0.16
Single-Family Home
$340,000
06/03/26
3
2
1,464
320 PENNSYLVANIA AVENUE, Winter Garden, FL
0.29
Single-Family Home
$445,000
10/17/25
4
2
1,922
446 REGAL DOWNS CIRCLE, Winter Garden, FL
0.25
Single-Family Home
$315,000
01/07/26
2
2
1,508
308 Florida Avenue, Winter Garden, FL
0.35
Single-Family Home
$315,000
02/20/26
3
2
1,050
343 GRAND ROYAL CIRCLE, Winter Garden, FL
0.21
Single-Family Home
$429,000
09/30/25
4
2.5
2,260
823 MAGNOLIA AVENUE, Winter Garden, FL
0.43
Single-Family Home
$330,000
04/17/26
3
2
1,210

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
645 SUMMER STREET, Winter Garden, FL 34787
0.04
$351,000
3
2
1,038
Off Market
441 E CYPRESS STREET LOT 29, Winter Garden, FL 34787
0.04
$200,000
-
-
-
For Sale
631 GRAND ROYAL CIRCLE, Winter Garden, FL 34787
0.06
$413,300
3
2
1,632
Off Market
703 GRAND ROYAL CIRCLE, Winter Garden, FL 34787
0.08
$448,700
4
2
1,779
Off Market
316 E LAFAYETTE STREET, Winter Garden, FL 34787
0.10
$300,300
4
2
1,440
Off Market
212 E CYPRESS STREET, Winter Garden, FL 34787
0.13
$354,000
2
1
1,144
Off Market
341 E LAFAYETTE STREET, Winter Garden, FL 34787
0.13
$162,500
2
1
1,106
Recently Sold
231 E LAFAYETTE STREET, Winter Garden, FL 34787
0.15
$479,900
4
3
1,608
For Sale
330 E STORY ROAD, Winter Garden, FL 34787
0.16
$285,000
2
1
760
Recently Sold
837 GRANDE REGAL POINT, Winter Garden, FL 34787
0.15
$455,000
3
2
1,874
Recently Sold
307 GRAND ROYAL CIRCLE, Winter Garden, FL 34787
0.17
$408,100
3
2
1,868
Off Market

Price and Tax history

DateEventPrice
Jul 17, 2026
Source: Stellar MLS #O6412414
PriceChange
$410,000
Price decreased by 2%
Jun 18, 2026
Source: Stellar MLS #O6412414
PriceChange
$420,000
Price decreased by 1%
Jun 1, 2026
Source: Stellar MLS #O6412414
Listed For Sale
$425,000
Apr 11, 2024
Source: Stellar MLS #O6171645
Sold
$399,900
Mar 13, 2024
Source: Stellar MLS #O6171645
Pending
$399,900

LGBTQ Local Legal Protections

Trevor Zwick, KELLER WILLIAMS ELITE PARTNERS III REALTY, (321) 527-5111
Agent Phone: (863) 303-6114

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Frequently asked questions about 420 E CYPRESS STREET

  • What is the estimated monthly payment for 420 E CYPRESS STREET?
    Based on a $410,000 list price with 20% down at today's rates, the estimated monthly payment for 420 E CYPRESS STREET in Winter Garden, FL is approximately $3,021 (about $2,218 principal & interest, $728 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 420 E CYPRESS STREET compare to homes in Winter Garden?
    420 E CYPRESS STREET in Winter Garden, FL is listed at $410,000, about 30% below the $585K median sale price in Winter Garden.
  • What do residents say about Winter Garden?
    Residents describe Winter Garden, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Garden, FL.
  • What are the closest schools to 420 E CYPRESS STREET?
    The closest schools to 420 E CYPRESS STREET in Winter Garden, FL are Lakeview Middle School (rated 4/10), West Orange High School (rated 7/10), William S Maxey Elementary School (Pre-K, rated 8/10).
  • Does 420 E CYPRESS STREET have air conditioning?
    Yes, 420 E CYPRESS STREET in Winter Garden, FL has air conditioning.
  • Does 420 E CYPRESS STREET have laundry facilities?
    Yes, 420 E CYPRESS STREET in Winter Garden, FL has laundry facilities.
420 E CYPRESS STREET, Winter Garden, FL 34787 is a 3 bedroom, 2 bathroom, 1,616 sqft single-family home built in 1950. This property is currently available for sale and was listed by Stellar MLS on Jun 1, 2026. The MLS # for this home is MLS# O6412414.