337 Sterling Dr, Winter Haven, FL 33884
OFF MARKET

$275,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,429 sqft

337 Sterling Dr, Winter Haven, FL 33884

Est. Refi. Payment $1,825/mo*
Refinance Your Home
Currently Off Market - Sold Jul 2, 2014 for $144,900

Home Value

Trulia Estimate
$276K
Since last month
Decreased$2K (-0.8%)
Since last year
Decreased$6K (-2%)
Since last sale
Increased$130K (+89.4%)
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 +66% in the last 10 years
MonthEstimated value
2026
August 2026$275K
August 2026$274K
July 2026$277K
June 2026$276K
May 2026$277K
April 2026$277K
March 2026$274K
February 2026$274K
January 2026$274K
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
343 STERLING DRIVE, Winter Haven, FL
0.04
Single-Family Home
$259,900
07/02/26
3
2
1,372
419 BIGSTAFF COURT, Winter Haven, FL
0.07
Single-Family Home
$280,000
06/24/26
3
2
1,405
356 STERLING DRIVE, Winter Haven, FL
0.09
Single-Family Home
$330,000
06/26/26
3
2
1,535
409 BIGSTAFF COURT, Winter Haven, FL
0.14
Single-Family Home
$290,000
10/23/25
3
2
1,756
112 ST. KITTS CIRCLE, Winter Haven, FL
0.17
Single-Family Home
$269,900
12/29/25
3
2
1,420
132 SAINT KITTS CIRCLE, Winter Haven, FL
0.22
Single-Family Home
$265,000
10/14/25
3
2
1,445
134 SAINT KITTS CIRCLE, Winter Haven, FL
0.22
Single-Family Home
$250,000
12/22/25
3
2
1,596
811 W HERON PLACE, Winter Haven, FL
0.25
Single-Family Home
$278,000
10/10/25
3
2
1,459
4622 CYPRESS GARDENS ROAD, Winter Haven, FL
0.24
Single-Family Home
$163,300
05/29/26
3
2
1,706
403 SAINT ANNS DRIVE, Winter Haven, FL
0.36
Single-Family Home
$265,000
12/12/25
3
2
1,596

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
330 Sterling Dr, Winter Haven, FL 33884
0.06
$295,000
3
2
1,426
For Sale
4032 DORAL, Winter Haven, FL 33884
0.09
$357,200
3
2
1,692
Off Market
341 STERLING DRIVE, Winter Haven, FL 33884
0.03
$380,000
4
3
2,008
Recently Sold
4034 DORAL, Winter Haven, FL 33884
0.10
$375,000
4
3
2,674
Recently Sold
343 STERLING DRIVE, Winter Haven, FL 33884
0.04
$259,900
3
2
1,372
Recently Sold
4803 WILLOWBROOK CIRCLE, Winter Haven, FL 33884
0.09
$328,100
3
2
2,059
Off Market
428 BIGSTAFF COURT, Winter Haven, FL 33884
0.05
$367,800
3
2
1,703
Off Market
346 STERLING DRIVE, Winter Haven, FL 33884
0.07
$337,700
3
2
1,929
Off Market
4904 WILLOWBROOK CIRCLE, Winter Haven, FL 33884
0.09
$390,600
3
2
2,106
Off Market
419 BIGSTAFF COURT, Winter Haven, FL 33884
0.07
$280,000
3
2
1,405
Recently Sold
3029 PINETREE, Winter Haven, FL 33884
0.14
$311,900
3
3
1,942
Off Market
356 STERLING DRIVE, Winter Haven, FL 33884
0.09
$330,000
3
2
1,535
Recently Sold

Local Information

  • Map ViewExplore the area around 337 Sterling Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1998
Living Area
1,429 sqft
Price/Sqft
$193
Parking
Garage

About this House

Only one owner of this totally remodeled home in S.E. Winter Haven. The dream kitchen has spiced-colored wooden cabinets with crown moulding and easy close cabinets and drawers. Countertops are quartz with a coordinated backsplash with glass tiles and the cabinets have under-counter lighting. The breakfast bar and dining room close by make entertaining easy. This three bedroom two bath home has a great room, volume ceilings and a split floorplan. The kitchen, both bathrooms and all flooring has been redone. The majority of the flooring is Amtico which provides a rich wood look to the property. There is new neutral paint throughout. New thermal windows provide energy efficiency to the home. Relax on the 15x14 tiled and screened porch. There is also a 29x12 pavered open area perfect for gatherings and grilling. The large, manicured lawn is privacy fenced with white PVC fencing. This is a truly move-in condition gem close to shopping, I-4, LEGOLAND and much more. Mature landscaping adds the final touch. Brokered And Advertised By: QUINN & COMPANY REALTORS, LLC Listing Agent: BRENDA J QUINN
337 Sterling Dr, Winter Haven, FL 33884 is a 3 bedroom, 2 bathroom, 1,429 sqft single-family home built in 1998. It last sold for $144,900 on Jul 2, 2014. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $275,800, with a rent estimate of $1,944/month.

Home Details for 337 Sterling Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Interior Details
Number of Rooms: 7Types of Rooms: Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other, StuccoFoundation Type: Retaining WallPatioPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1998Year Updated: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 7405 sqft

Price and Tax history

DateEventPrice
Jul 2, 2014
Source: N/A
Sold
$144,900
May 22, 2014
Source: Agent Provided
Pending
$144,900
May 6, 2014
Source: Agent Provided
Listed For Sale
$144,900
Apr 21, 1998
Source: N/A
Sold
$87,900

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

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

Frequently asked questions about 337 Sterling Dr

  • What is 337 Sterling Dr estimated to be worth?
    Trulia's estimated value for 337 Sterling Dr in Winter Haven, FL is $275,800.
  • What is the price history for 337 Sterling Dr?
    337 Sterling Dr in Winter Haven, FL last sold for $144,900 in July 2014.
  • 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 337 Sterling Dr have air conditioning?
    Yes, 337 Sterling Dr in Winter Haven, FL has air conditioning.
  • How big is the lot at 337 Sterling Dr?
    The lot at 337 Sterling Dr in Winter Haven, FL is about 0.17 acres (7,405 sq ft).

Explore by feature - Pet Friendly

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