369 Sterling Dr, Winter Haven, FL 33884
Property image
Property image
OFF MARKET

$363,500

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 2,002 sqft

369 Sterling Dr, Winter Haven, FL 33884

Est. Refi. Payment $2,419/mo*
Refinance Your Home
Currently Off Market - Sold May 19, 2020 for $48,300

Home Value

Trulia Estimate
$364K
Since last month
Increased$1K (+0.3%)
Since last year
Increased$5K (+1.3%)
Since last sale
Increased$316K (+653.8%)
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 +112% in the last 10 years
MonthEstimated value
2026
August 2026$364K
August 2026$364K
July 2026$363K
June 2026$363K
May 2026$362K
April 2026$358K
March 2026$357K
February 2026$355K
January 2026$357K
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
409 BIGSTAFF COURT, Winter Haven, FL
0.02
Single-Family Home
$290,000
10/23/25
3
2
1,756
419 BIGSTAFF COURT, Winter Haven, FL
0.08
Single-Family Home
$280,000
06/24/26
3
2
1,405
356 STERLING DRIVE, Winter Haven, FL
0.11
Single-Family Home
$330,000
06/26/26
3
2
1,535
811 W HERON PLACE, Winter Haven, FL
0.11
Single-Family Home
$278,000
10/10/25
3
2
1,459
343 STERLING DRIVE, Winter Haven, FL
0.14
Single-Family Home
$259,900
07/02/26
3
2
1,372
134 SAINT KITTS CIRCLE, Winter Haven, FL
0.23
Single-Family Home
$250,000
12/22/25
3
2
1,596
4622 CYPRESS GARDENS ROAD, Winter Haven, FL
0.11
Single-Family Home
$247,500
09/01/26
3
2
1,706
132 SAINT KITTS CIRCLE, Winter Haven, FL
0.23
Single-Family Home
$265,000
10/14/25
3
2
1,445
924 S HERON CIRCLE, Winter Haven, FL
0.16
Single-Family Home
$261,000
08/28/26
3
2.5
1,483
112 ST. KITTS CIRCLE, Winter Haven, FL
0.26
Single-Family Home
$269,900
12/29/25
3
2
1,420

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
409 BIGSTAFF COURT, Winter Haven, FL 33884
0.02
$289,400
3
2
1,756
Off Market
404 BIGSTAFF COURT, Winter Haven, FL 33884
0.06
$323,700
3
2
1,580
Off Market
419 BIGSTAFF COURT, Winter Haven, FL 33884
0.08
$280,000
3
2
1,405
Recently Sold
307 STERLING DRIVE, Winter Haven, FL 33884
0.07
$260,000
3
2
1,444
For Sale
428 BIGSTAFF COURT, Winter Haven, FL 33884
0.11
$366,600
3
2
1,703
Off Market
376 STERLING DRIVE, Winter Haven, FL 33884
0.05
$305,500
4
2
1,929
Off Market
384 STERLING DRIVE, Winter Haven, FL 33884
0.06
$367,600
3
2
1,740
Off Market
306 STERLING DRIVE, Winter Haven, FL 33884
0.10
$391,600
3
2
1,972
Off Market
356 STERLING DRIVE, Winter Haven, FL 33884
0.11
$330,000
3
2
1,535
Recently Sold
343 STERLING DRIVE, Winter Haven, FL 33884
0.14
$259,900
3
2
1,372
Recently Sold
341 STERLING DRIVE, Winter Haven, FL 33884
0.14
$380,000
4
3
2,008
Recently Sold
811 W HERON PLACE, Winter Haven, FL 33884
0.11
$277,200
3
2
1,459
Off Market

Local Information

  • Map ViewExplore the area around 369 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
1992
Living Area
2,002 sqft
Price/Sqft
$182
Parking
Garage

About this House

SPACIOUS, fully remodeled House 3 bedrooms 2 Bath - with BRAND NEW RE-SURFACED POOL located in a very WELL MAINTAINED community, this SE Winter Haven house featuring Brand NEW CERAMIC TILE in the Oversize Family room and Living room. W/ FIREPLACE, Wood Laminate throughout, an OVERSIZED master bedroom With walk-in LARGE CLOSET .walk out through A WIDE SLIDE DOOR onto the large Florida Room that led to A CLEAN n' CRYSTAL CLEAR LARGE INGROUND POOL with a decent size back yard, with BRAND NEW INSTALLED -VINYL FENCE. The eat-in kitchen has a breakfast nook and a breakfast bar with brand new GRANITE countertop, BRAND NEW bathrooms cabinets with STONE countertops. BRAND NEW stainless steel appliances,( with warranty ) freshly painted outside and inside, and epoxy on the garage floor. Close to shopping, restaurants, Churches. Schools, medical facilities, and LEGOLAND.- this is a great SE Winter Haven location house is READY TO MOVE IN! DON'T miss this opportunity - call and schedule your showing! , THIS HOUSE IS PRICED RIGHT! PRICE REDUCED!
369 Sterling Dr, Winter Haven, FL 33884 is a 3 bedroom, 2 bathroom, 2,002 sqft single-family home built in 1992. It last sold for $48,300 on May 19, 2020. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $363,500, with a rent estimate of $2,191/month.

Home Details for 369 Sterling Dr

Interior Features

Heating & Cooling
Heating: Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Laminate
Interior Details
Number of Rooms: 8Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalMicrowave
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: OtherFoundation Type: Retaining Wall
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1992Year Updated: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 8712 sqft

Price and Tax history

DateEventPrice
May 19, 2020
Source: N/A
Sold
$48,300
Mar 25, 2020
Source: Agent Provided
PriceChange
$234,500
Price decreased by 0%
Feb 20, 2020
Source: Agent Provided
PriceChange
$234,900
Price decreased by 1%
Jan 5, 2020
Source: Agent Provided
Listed For Sale
$237,900
Sep 16, 2019
Source: N/A
Sold
$165,500

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 369 Sterling Dr

  • What is 369 Sterling Dr estimated to be worth?
    Trulia's estimated value for 369 Sterling Dr in Winter Haven, FL is $363,500.
  • What is the price history for 369 Sterling Dr?
    369 Sterling Dr in Winter Haven, FL last sold for $48,300 in May 2020.
  • 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 369 Sterling Dr have air conditioning?
    Yes, 369 Sterling Dr in Winter Haven, FL has air conditioning.
  • Does 369 Sterling Dr have a pool?
    Yes, 369 Sterling Dr in Winter Haven, FL has a pool.

Explore by feature - Pet Friendly

252 pet-friendly rentals in Winter Haven, FL

Explore by feature - Garage

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Explore by feature - Outdoor Space

72 rentals with an outdoor space in Winter Haven, FL

Apartments for Rent

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Off Market Homes Near 369 Sterling Dr

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