4044 Cypress Lndg E, Winter Haven, FL 33884
Property image
Property image
OFF MARKET

$227,800

Trulia Estimate
as of Sep 10, 2026
  • 2 Beds
  • 2 Baths
  • 1,353 sqft

4044 Cypress Lndg E, Winter Haven, FL 33884

Home Highlights

Single-Family Home
1,353 sqft
$168/sqft

Local Information

  • Map ViewExplore the area around 4044 Cypress Lndg E.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome to 4044 Cypress Landing E, a charming home featuring 2 bedrooms, 2 bathrooms, and a 2-car garage. As you enter, a long foyer leads you into the spacious great room, highlighted by a decorative brick fireplace wall. From here, and from the primary suite, you'll have direct access to a 10x26 screened lanaiideal for relaxation. The open kitchen, equipped with all appliances and a cozy small eat-in area, also provides access to another 14x8 screened lanai, perfect for enjoying your morning coffee. The home offers a split bedroom plan, with the primary suite located off the great room. The suite includes a private en-suite with a walk-in tile shower and a 5x5 walk-in closet. The second bedroom is conveniently connected to the guest bath, featuring a tile tub/shower combo, and is located off the foyer entrance. An inside laundry room is situated between the garage and kitchen, adding convenience to daily living. The fenced rear yard ensures added privacy. Residents can also delight in community amenities, including a pool, tennis court, boat ramp, dock, and clubhouse. Situated in a great Southeast Winter Haven location, the home is close to Publix, Walmart, shopping, restaurants, medical facilities, and Legoland.
4044 Cypress Lndg E, Winter Haven, FL 33884 is a 2 bedroom, 2 bathroom, 1,353 sqft single-family home. It last sold for $110,500 on Feb 8, 2005 (6,400% above the $1,700 asking price). More recently, it was listed as a rental in August 2024 with an asking price of $1,700 per month. That rental listing was removed on August 29, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $227,800, with a rent estimate of $1,760/month.

Home Details for 4044 Cypress Lndg E

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Interior Features

Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Pool
Pool

Additional Information

ClubhouseTennis Court(s)

Comparable Sales for 4044 Cypress Lndg E

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3912 CYPRESS LANDING N, Winter Haven, FL
0.09
Single-Family Home
$210,000
12/30/25
2
2
1,278 sqft
4009 CYPRESS LANDING S, Winter Haven, FL
0.09
Single-Family Home
$225,000
06/05/26
2
2
1,291 sqft
4007 CYPRESS LANDING S, Winter Haven, FL
0.09
Single-Family Home
$235,000
09/16/25
2
2
1,578 sqft
4304 LARRYS LAGOON, Winter Haven, FL
0.14
Single-Family Home
$238,000
03/06/26
2
2
1,366 sqft
4412 GLENNS LANDING, Winter Haven, FL
0.17
Single-Family Home
$227,500
02/20/26
2
2
1,394 sqft
1454 GRAND CAYMAN CIRCLE, Winter Haven, FL
0.17
Single-Family Home
$245,000
08/14/26
2
2
1,596 sqft
4118 FISHERMANS LANDING, Winter Haven, FL
0.09
Single-Family Home
$238,000
02/27/26
3
2
1,247 sqft
4118 Fishermans Land, Winter Haven, FL
0.09
Single-Family Home
$238,000
03/13/26
3
2
1,247 sqft
1447 KINGFISH LN, Winter Haven, FL
0.19
Single-Family Home
$245,000
12/01/25
2
2
1,596 sqft
3806 OSPREY POINTE CIRCLE, Winter Haven, FL
0.04
Single-Family Home
$271,000
09/29/25
3
2
1,635 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
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Rental Market Trends in Winter Haven

Last updated Sep 2026
Trulia Rent Estimate$1,760/mo
Average rent
$1.8K
$13MoM
Available listings
476
View rental market trends in Winter Haven, FL

Around this home

What Locals Say about Winter Haven

At least 800 Trulia users voted on each feature.

  • 83 % Say car is needed

  • 80 % Say parking is easy

  • 78 % Say yards are well-kept

  • 76 % Say it's dog friendly

  • 68 % Say there's holiday spirit

  • 64 % Say it's quiet

  • 61 % Say kids play outside

  • 49 % Say people would walk alone at night

  • 48 % Say there are sidewalks

  • 47 % Say they plan to stay for at least 5 years

  • 46 % Say streets are well-lit

  • 44 % Say neighbors are friendly

  • 43 % Say it's walkable to grocery stores

  • 32 % Say there's wildlife

  • 30 % Say it's walkable to restaurants

  • 24 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Cathyharris1222
    "Safe area for children and families "
    0
    Flag
  • Cocobrownie3
    "Freindly neighbors, Holloween is wonderful here, everyone loves to BBQ , and Santa Clause comes on Chismas Eve. Wonderful place to live. However, to schools are not so good. "
    0
    Flag
  • William David Evans
    "We have our personal cars have used uber a few times but not really necessary for us because we live close to most of the stores and restaurants "
    1
    Flag
  • Morgan Ivey-trask
    "Everyone is friendly and so nice. I like it here but I will be moving out soon to live in North Carolina to get my kids back and live a new life "
    2
    Flag
  • Madeline R
    "Its neighborly and quiet while still being close to the theme parks and airport. Ive lived here for 5 years and it was the best decision we made."
    0
    Flag
  • Miguel Catalano
    "Quiet neighborhood, everything you need is close by and affordable, and places of worship for everyone. Light traffic all the time and great restaurants all over town with views of the lake. Serenity is everywhere in Winter Haven."
    0
    Flag
  • Z64p52x99r
    "I don’t go to the community events in the area I solely go to work and home I enjoy this peace in the neighborhood "
    0
    Flag
  • John Van Volkenburgh
    "Quick. No issues as long as you don’t work in Orlando or Tampa. Rural and central to the state. Small town. I’m "
    0
    Flag
  • Jenna Strickler
    "Food giveaways, law enforcement always circling/passing by Security feels safe Not the best neighborhood overall, but I have not had an issue since living here. "
    0
    Flag
  • Emily Torres
    "I’ve lived close to this area for 3 years now and worked there for a year and a half. Very nice area !"
    1
    Flag
  • Anonymous
    "You can walk your dogs with no problems. Many houses are fenced. Dogs will bark but not bite. Dogs ca"
    0
    Flag
  • Bianca Nieves
    "A lot of cats on the NE side of winter haven other than that winter haven lots of parks for children good schools "
    4
    Flag
  • Nicole Horton
    "I don’t feel safe for my 13 year old son to walk to the middle school by himself. I drive him and pick him up every day."
    0
    Flag
  • Chris M
    "There is a farmers market every weekend. A lot of community activities every weekend. Christmas parade happened a few weekends ago. "
    1
    Flag
  • Yoflyboys
    "NW Winter Haven has turned into a dump site. Homeless has taken over bus stop. Inman park and the surrounding areas."
    4
    Flag
  • Oo7legend
    "Great for families to live in and feel part of a community. Needs more retailers, restaurants and higher rated schools."
    30
    Flag
  • April_stylist
    "Quiet hard working families, no issues with traffic or safety we love this area. Very friendly folks"
    5
    Flag
  • Angmartinez05
    "Not much to do in terms of attractions but safe everywhere. 45 min from either Orlando or Tampa. Friendly people "
    0
    Flag
  • Katia S.
    "I live there for 3 years ,it’s quiet,I don’t have any complaint against it.I recommend it for a start,no to stay for a long time .I live close to the park.i like it and I feel safe."
    1
    Flag
  • Atrollergirl
    "My commute is nice. I live 1 mile from Wahneta and I'm located near Bartow, Eagle Lake, Winter Haven."
    0
    Flag
  • Carly.m.williams
    "The area is a family friendly area. High traffic area also. Schools and shopping nearby. Legoland brings in a lot of traffic also"
    0
    Flag
  • Nakeem G.
    "My neighborhood in walking distance to a college, police station, farmers market, hair store, hospital/clinics and parks"
    11
    Flag
  • Joan
    "I live in this great neighborhood with great neighbors who get along. Quiet neighborhood. It feels safe."
    0
    Flag
  • Angela S.
    "Very busy front Street with big trucks daily passing by. Car speed a lot on the main road thru the area. "
    0
    Flag
  • Carly.m.williams
    "The area is very family friendly in my opinion. Never had any issues with neighbors. Quite a few stray cats but no issues."
    0
    Flag
  • Nancy F.
    "I see people walking there dogs daily. we have a dog park in the community very nice area they are allowed off the leash in the fenced in area, they can run and play freely, very friendly area for them all maintained spayed often to keep fleas away.. pet friendly area. "
    1
    Flag
  • Jennycomp
    "There are no sidewalks or places to walk your dogs. They are forced to use people’s yards and they get upset."
    0
    Flag
  • Gina K.
    "Halloween is great here!!! Trick or treating is like a giant party and there’s so much fun going on. "
    0
    Flag
  • Shelley P.
    "the downtown markets on 2and saturday, the water show @ lake howard things that go on at the church's and community centers n parks. I love Winter Haven I can go on and on just being able to walk lake"
    22
    Flag
  • Martha K.
    "My neighborhood is nice and quiet and their isn’t any crimes they maintain over here but sometimes the neighbors can be loud."
    0
    Flag
  • Shelley P.
    "traffic can be a little heavy on the main roads n have a tendency to speed thru the side streets. But overall the traffic is decent."
    5
    Flag
  • John D. B.
    "very quiet,peaceful...laid back family oriented neighborhoods... older community.... spirit lake road can get busy with traffic noice.... best to live away from spirit lake road.."
    0
    Flag
  • Basapooh81
    "Winter Haven holds a lot of community events. They have something going on mostly every weekend in downtown winter Haven. Winter Haven has Legoland park and water park also. "
    10
    Flag
  • Cdixon496
    "Dog owners would like the fact that there is plenty of open fields and place for the dogs to run around."
    0
    Flag
  • Victoria W.
    "Some people don’t pick up after their dogs and some dog parks aren’t well kept. You can walk your dog easily with a lot of sidewalks and areas to walk to"
    14
    Flag
  • Mp19601
    "I just work around the area and every time i talk to sombody there nice and no complane for nothing...maybe i move in this area one fay"
    0
    Flag
  • Solomon G. .
    "Yes it’s nice area to be in no issues what so ever I like it very much . Can’t say anything bad nor good "
    1
    Flag
  • Norma.G
    "Well the associated need to be more strict,and severe with the Owners each property, how they park at the street, not at the grass, do not allow any car on the side of street,they should park at there own driveway ,and the driving at the neighbors area should be limited speed,driving to fast can cause hitting someone."
    0
    Flag
  • DR
    "Work is minutes away. Hardly ever go anywhere but Orlando as I don’t feel theres anything to do around here."
    0
    Flag
  • Ctjohns34
    "Neighbors complain about walking dogs, dogs only recently became allowed in this community and some neighbors resist change "
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Aug 29, 2024
Source: Zillow Rentals
ListingRemoved
$1,700
Aug 28, 2024
Source: Zillow Rentals
Listed For Rent
$1,700
Feb 8, 2005
Source: N/A
Sold
$110,500
Feb 26, 2004
Source: N/A
Sold
$93,500
Jun 5, 2002
Source: N/A
Sold
$76,000

Frequently asked questions about 4044 Cypress Lndg E

  • What is 4044 Cypress Lndg E estimated to be worth?
    Trulia's estimated value for 4044 Cypress Lndg E in Winter Haven, FL is $227,800.
  • What is the price history for 4044 Cypress Lndg E?
    4044 Cypress Lndg E in Winter Haven, FL last sold for $110,500 in February 2005.
  • Is Winter Haven a buyer's or seller's market?
    Winter Haven is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Haven?
    The median sale price in Winter Haven is $260K. That is up $3.28K from the prior month.
  • Does 4044 Cypress Lndg E have a pool?
    Yes, 4044 Cypress Lndg E in Winter Haven, FL has a pool.

Homes for rent near 4044 Cypress Lndg E

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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