102 Overlook Dr, Winter Haven, FL 33884
OFF MARKET

102 Overlook Dr
Winter Haven, FL 33884

Cypress Gardens
  • 3 Beds
  • 2 Baths
  • 2,070 sqft (on 0.85 acres)

$372,700

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $2,420/mo*

$372,700

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $2,420/mo*
3 Beds
2 Baths
2,070 sqft
(on 0.85 acres)

Local Information

  • Map ViewExplore the area around 102 Overlook Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

READY IF YOU ARE ~ GREAT LOCATION ~ IMMEDIATE OCCUPANCY ~ CHARMING KEY WEST STYLING includes a covered front porch and a 25ft. lanai. This 3BD, (could be 4), 2BA home, on a ¾ (+) acre professionally landscaped site, is shaded by 6 Live Oaks. The REALLY BIG back yard, [fenced], provides plenty of privacy for little ones and pets or a pool if you'd prefer. Featuring a NEW septic system, NEW maintenance free vinyl siding, NEW Anderson thermo pane windows; NEW interior trim throughout, NEW Stainless Steel > refrigerator > range > dishwasher > micro wave, NEW, upscale, kitchen cabinets, NEW granite counters with counter-to-cabinet granite backsplashes, NEW, bathroom vanities and sinks, NEW toilets, NEW ceiling fans and lights, NEW wall-to-wall carpet in all BR's, and is NEWLY painted throughout. Are you tired of looking at 'cookie cutter' houses? Would you prefer something that isn't? Would you also like a yard that lets you breeeeeeath? If so, you should consider this really pretty Winter Haven property. Brokered And Advertised By: BY DESIGN REAL ESTATE SERVICES (255000565) Listing Agent: RHONDA MARTIN
102 Overlook Dr, Winter Haven, FL 33884 is a 3 bedroom, 2 bathroom, 2,070 sqft single-family home in Cypress Gardens, built in 1939. It last sold for $166,500 on Mar 23, 2015. It is currently off market. The Trulia Estimate is $372,700, with a rent estimate of $2,264/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 102 Overlook Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Laminate
Interior Details
Number of Rooms: 8Types of Rooms: Dining Room, Family Room
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Heating & Cooling
Air ConditioningCooling System: Central

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: WoodFoundation Type: Retaining WallPatioPorch
Parking & Garage
GarageParking Space: 1Parking: Garage Detached

Property Information

Year Built
Year Built: 1939Year Updated: 1939
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.85 acres

Price History for 102 Overlook Dr

DatePriceEventSource
03/23/2015$166,500Sold
N/A
10/05/2014$169,900Listed For SaleAgent Provided
09/01/2014$164,900ListingRemovedAgent Provided
08/17/2014$164,900PriceChange
Agent Provided
05/10/2014$179,900PriceChange
Agent Provided
02/28/2014$199,900Listed For SaleAgent Provided
06/21/2013$72,000Sold
N/A
05/31/2013$72,900Listed For SaleAgent Provided
04/13/2013$72,900ListingRemovedAgent Provided
03/26/2013$72,900PriceChange
Agent Provided
02/26/2013$74,900PriceChange
Agent Provided
01/25/2013$79,900Listed For SaleAgent Provided
11/07/2012$128,000ListingRemovedAgent Provided
09/19/2012$128,000Listed For SaleAgent Provided
03/23/2005$161,500Sold
N/A

Market trends in Winter Haven

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$257K
Sale-to-List Price
98.2%
Price per sq ft
$158
$2
MoM
Available listings
767
3
MoM
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Property Tax and Assessment

Year2025
Tax$3,741
Assessment$298,979
Home facts updated by county records

Comparable Sales for 102 Overlook Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.08
Single-Family Home
$326,000
10/21/25
3
2
1,858
0.27
Single-Family Home
$300,000
06/18/26
3
2.5
1,573
0.12
Single-Family Home
$333,000
10/10/25
3
2
1,601
0.12
Single-Family Home
$333,000
10/20/25
3
2
1,601
0.22
Single-Family Home
$377,000
11/26/25
3
2
2,054
0.24
Single-Family Home
$295,000
11/07/25
3
2
1,747
0.27
Single-Family Home
$300,000
06/22/26
3
2
1,573
0.44
Single-Family Home
$170,000
04/06/26
3
2
1,465
0.28
Single-Family Home
$270,000
07/30/25
3
2
1,628
0.17
Single-Family Home
$280,000
05/04/26
4
3
1,900

Nearby homes

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Assigned Schools

These are the assigned schools for 102 Overlook Dr.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Neighborhood stats provided by third party data sources.

What Locals Say about Cypress Gardens

At least 62 Trulia users voted on each feature.
  • 88 % Say it's dog friendly

  • 84 % Say parking is easy

  • 81 % Say car is needed

  • 76 % Say yards are well-kept

  • 76 % Say it's quiet

  • 75 % Say there's holiday spirit

  • 56 % Say people would walk alone at night

  • 50 % Say kids play outside

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

  • 45 % Say neighbors are friendly

  • 42 % Say streets are well-lit

  • 35 % Say there are sidewalks

  • 30 % Say it's walkable to grocery stores

  • 30 % Say there's wildlife

  • 27 % Say there are community events

  • 26 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • 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 "
  • 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."
  • 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"
  • 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."
  • 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."
  • Jessica S.
    "Very family friendly and a great place to raise kids. Neighbors have always been great and little to no criminal activity."
  • Trulia User
    "I lived here my entire life. Love this area and all amenities available. People are friendly and it still has a small town feel. "
  • Whmidas
    "Neighbors watch out for each other’s property when anyone is out of town. Good neighborhood watch with Ring."
  • Timothy H.
    "Good restaurants and bars always something to do like bowl or mall or enjoy the downtown lifestyle. Lake everywhere get on a boat and enjoy"
  • Tyler S.
    "Nothing special. It's quiet, and safe with the occasional police car for small disturbances. Generally nice neighbors, not a lot of families moving in and out every other day. "
  • Eichhorst1986
    "looks good great neighbors and closer to most ever sour toy need. w are closer to Legoland and tough can see fireworks at night."
  • Wilmatoes66
    "It’s an older neighborhood and it’s quiet. It’s centrally located near restaurants And shopping. We have a charming neighborhood "
  • nreina1
    "i live here nd it's a beautiful area, convenient to everything and everywhere."
  • eliska o.
    "this has got to be the best of both worlds! country lake setting only one block from everything - everthing. "
  • S
    "Beautiful, Serene, Private and alot of greenery. Close to everything but far enough away from nonsense.....Safe, NO crime and very desirable for the family or couple looking for a peace of mind. "

LGBTQ Local Legal Protections

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Homes for sale near 102 Overlook Dr

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Off Market Homes Near 102 Overlook Dr

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