205 Cunningham Rd, Winter Haven, FL 33884
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Property image
OFF MARKET

205 Cunningham Rd
Winter Haven, FL 33884

  • 4 Beds
  • 2 Baths
  • 6,825 sqft

$821,400

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,295/mo*
Refinance Your Home

$821,400

Trulia Estimate
as of Aug 18, 2026
Est. Refi. Payment $5,295/mo*
Refinance Your Home
4 Beds
2 Baths
6,825 sqft

Home Value

Trulia Estimate
$821K
Since last month
Decreased$30K (-3.6%)
Since last year
Increased$144K (+21.6%)
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 +22% in the last 10 years
MonthEstimated value
2026
August 2026$808K
July 2026$839K
June 2026$768K
May 2026$665K

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
308 Corso Loop, Winter Haven, FL
0.08
Single-Family Home
$304,290
09/16/25
4
2
1,867
521 VITTORIO DRIVE, Winter Haven, FL
0.12
Single-Family Home
$329,782
05/04/26
4
2
2,005
6594 Crescent Loop, Winter Haven, FL
0.16
Single-Family Home
$424,600
01/28/26
3
2
2,492
6654 CRESCENT LOOP, Winter Haven, FL
0.18
Single-Family Home
$280,000
03/05/26
4
2
1,820
5543 Taverna Loop, Winter Haven, FL
0.06
Single-Family Home
$267,290
05/26/26
3
2
1,504
4157 Giorgio Dr, Winter Haven, FL
0.06
Single-Family Home
$275,490
03/16/26
3
2
1,504
4659 Ostero St, Winter Haven, FL
0.06
Single-Family Home
$325,990
11/06/25
5
3
2,447
124 EMANUELLE DRIVE, Winter Haven, FL
0.10
Single-Family Home
$250,000
04/29/26
3
2
1,672
6626 CRESCENT LOOP, Winter Haven, FL
0.10
Single-Family Home
$277,000
11/05/25
3
2
1,251
6610 Crescent Loop, Winter Haven, FL
0.10
Single-Family Home
$259,900
01/21/26
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
309 CORSO LOOP, Winter Haven, FL 33884
0.05
$341,000
5
3
2,601
Off Market
313 CORSO LOOP, Winter Haven, FL 33884
0.05
$342,300
5
3
2,601
Off Market
305 CORSO LOOP, Winter Haven, FL 33884
0.05
$291,500
4
2
1,828
Off Market
108 EMANUELLE DRIVE, Winter Haven, FL 33884
0.06
$296,600
4
2
1,828
Off Market
4631 Ostero St, Winter Haven, FL 33884
0.06
$246,900
3
2
1,504
Off Market
ROBIE, Winter Haven, FL 33884
0.06
$323,990+
5
3
2,447
-
ARIA, Winter Haven, FL 33884
0.06
$296,490+
3
2
1,672
-
CALI, Winter Haven, FL 33884
0.06
$311,490+
4
2
1,828
-
HARPER, Winter Haven, FL 33884
0.06
$288,990+
4
2
1,665
-
ALLEX 2, Winter Haven, FL 33884
0.06
$273,990+
3
2
1,504
-
4157 Giorgio Dr, Winter Haven, FL 33884
0.06
$275,490
3
2
1,504
Recently Sold
ELSTON II, Winter Haven, FL 33884
0.06
$311,990+
4
2.5
2,305
-

Local Information

  • Map ViewExplore the area around 205 Cunningham Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
6,825 sqft
Price/Sqft
$120
Parking
Attached Garage

About this House

Beautiful and well-maintained home located in a quiet and desirable neighborhood in Winter Haven, FL. This spacious property offers a comfortable and functional layout, perfect for families or professionals looking for a peaceful place to call home.
The home features bright natural light throughout, an open living area, and a clean, modern feel. The kitchen is fully equipped with ample cabinet space and flows seamlessly into the dining and living areas, making it ideal for everyday living and entertaining.
Bedrooms are generously sized with plenty of closet space. The home also includes a shared/private bathroom (adjust as needed), in-unit laundry, and access to outdoor space where you can relax and enjoy Florida weather.
Conveniently located near shopping centers, restaurants, schools, and major highways, making commuting easy while still enjoying a quiet residential setting.

Lease Duration:
Minimum 12-month lease required.
Rent & Payments:
Monthly rent is due on the 1st of each month. Late payments may be subject to additional fees.
Security Deposit:
A security deposit equivalent to one month's rent is required prior to move-in.
Utilities:
Tenant is responsible for all utilities except electricity, which is included in the rent.
Pets Policy:
Small pets are allowed (subject to approval). Additional pet deposit or monthly pet fee may apply. Aggressive breeds are not permitted.
Smoking Policy:
No smoking allowed inside the property.
Occupancy:
Maximum occupancy limits apply in accordance with local regulations.
Maintenance:
Tenant is responsible for keeping the property clean and in good condition. Any damages beyond normal wear and tear will be the tenant's responsibility.
Parking:
Designated parking available (adjust if needed).
Background Check:
All applicants are subject to background, credit, and rental history screening
205 Cunningham Rd, Winter Haven, FL 33884 is a 4 bedroom, 2 bathroom, 6,825 sqft single-family home. More recently, it was listed as a rental in May 2026 with an asking price of $2,100 per month. That rental listing was removed on July 18, 2026. It is currently off market. The Trulia Estimate is $821,400, with a rent estimate of $1,969/month.

Home Details for 205 Cunningham Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 6 MonthAvailable: now

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached, On Site

Price and Tax history

DateEventPrice
Jul 18, 2026
Source: Zillow Rentals
ListingRemoved
$2,000
Jul 16, 2026
Source: Zillow Rentals
PriceChange
$2,000
Price decreased by 7%
Jul 14, 2026
Source: Zillow Rentals
PriceChange
$2,150
Price decreased by 2%
Jun 4, 2026
Source: Zillow Rentals
PriceChange
$2,200
Price increased by 5%
May 1, 2026
Source: Zillow Rentals
Listed For Rent
$2,100

Market trends in Winter Haven

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$260K
$3.28KMoM
Sale-to-List Price
98.4%
0.2%MoM
Price per sq ft
$161
$4MoM
Available listings
778
10MoM
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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

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Apartments for Rent

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Explore by feature - Pet Friendly

236 pet-friendly rentals in Winter Haven, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Washer/dryer

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Explore by feature - Outdoor Space

65 rentals with an outdoor space in Winter Haven, FL

Homes for sale near 205 Cunningham Rd

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Off Market Homes Near 205 Cunningham Rd

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Frequently asked questions about 205 Cunningham Rd

  • What is 205 Cunningham Rd estimated to be worth?
    Trulia's estimated value for 205 Cunningham Rd in Winter Haven, FL is $821,400.
  • 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.
  • What do residents say about Winter Haven?
    Residents describe Winter Haven, FL as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Winter Haven, FL.
  • Does 205 Cunningham Rd have air conditioning?
    Yes, 205 Cunningham Rd in Winter Haven, FL has air conditioning.
  • Does 205 Cunningham Rd have a pool?
    Yes, 205 Cunningham Rd in Winter Haven, FL has a pool.