RENTED OCT 16, 2025

2956 Whispering Trails Dr Winter Haven, FL 33884

Cypresswood Neighborhood

Estimated Value: $233,000 - $255,279

3 Beds
2 Baths
1,500 Sq Ft
$163/Sq Ft Est. Value

Sale Details

Date Sold: June 16, 2025

Last sale price $242,500 $162 Per Sq Ft

Est. 1% increase in value since last sale

Current estimated payment $1,532 / mo

Highlights

  • Gated Community
  • Open Floorplan
  • High Ceiling
  • Frank E. Brigham Academy Rated 9+
  • Main Floor Primary Bedroom
  • Community Pool

About This Home

As of October 2025

NEW IMPROVED PRICE for this 3 Bedroom, 2 Bathroom Home for rent in a Gated Community, just minutes from Legoland!
This 1,500 sq. ft. rental home is ready for its new tenant(s)! Nestled in the highly desirable Whispering Trails community, this property offers a spacious open layout with a split floorplan, spacious living room, and a large kitchen featuring an oversized island and breakfast bar with plenty of room to gather and unwind. But wait, there's more! You'll find this cozy living space comes with polished concrete floors, helping it to stay cool in the FLorida heat. This home includes a two-car attached garage (418 sq. ft.) and is conveniently located near schools, shopping, and dining. Have weekend plans? If not, how does a leisure day at the community pool sound? Come take a look!
Could it get any better? Yes! Pets (upon pre-approval) are welcomed and lawn care is included!

Please note: We do NOT advertise our properties for rent on Craigslist. If you find this property listed there, please flag the post and notify our office. We also do NOT accept rental applications via Zillow.

Last Agent to Rent the Property

Kim Connahey

HOUSE OF GLASS REAL ESTATE PM Brokerage Phone: 863-940-3756 License #3375017 Listed on: 07/21/2025

Last Renter's Agent

Kim Connahey

HOUSE OF GLASS REAL ESTATE PM Brokerage Phone: 863-940-3756 License #3375017 Listed on: 07/21/2025

Range of Values:

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Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Average Value
Not Available
List Price
Sold Price
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Home Details

Home Type

  • Single Family

Year Built

  • Built in 2018

Lot Details

  • 4,600

Parking

  • 2 Car Attached Garage
  • 2 Carport Spaces

Interior Spaces

  • 1,500 Sq Ft Home
  • Open Floorplan
  • High Ceiling
  • Ceiling Fan
  • Blinds
  • Living Room
  • Concrete Flooring
  • Fire and Smoke Detector

Kitchen

  • Cooktop
  • Microwave
  • Freezer
  • Ice Maker

Bedrooms and Bathrooms

  • 3 Bedrooms
  • Primary Bedroom on Main
  • Walk-In Closet
  • 2 Full Bathrooms

Laundry

  • Laundry Room
  • Dryer
  • Washer

Schools

  • Elbert Elementary School
  • Winter Haven Senior High School

Utilities

  • Central Heating and Cooling System
  • Phone Available
  • Cable TV Available

Additional Features

  • Covered Patio or Porch
  • 4,600 Sq Ft Lot

Listing and Financial Details

  • Residential Lease
  • Security Deposit $1,600
  • Property Available on 8/1/25
  • 12-Month Minimum Lease Term
  • $75 Application Fee
  • 8 to 12-Month Minimum Lease Term
  • Assessor Parcel Number 27-28-30-850002-002000

Community Details

Overview

  • Property has a Home Owners Association
  • Whispering Trails Hoa/ Jr Krisanda (Cam) Association, Phone Number (407) 647-2622
  • Whispering Trails Ph 02 Subdivision

Recreation

  • Community Pool

Security

  • Gated Community

Home Details

Home Type

Single Family

Year Built

Built in 2018

Lot Details

4,600 Sq Ft Lot

Parking

2

Rental Info

  • Furnished: Unfurnished
  • Lease Amount Frequency: Monthly
  • Pets Allowed: Breed Restrictions, Cats OK, Dogs OK, Pet Deposit
  • Available Date: 2025-08-01
  • Terms Of Lease: No Smoking
  • Long Term YN: 1
  • Security Deposit: 1600
  • Pet Deposit Fee: 250
  • Pet Fee Non Refundable: 250
  • Additional Pet Fees: Pets are allowed with pre-approval and at the owner's discretion. There is a non-refundable pet fee per animal, with no more than two pets.

Listing Details

  • Property Type: Residential Lease
  • Property Sub Type: Single Family Residence
  • Fireplace: No
  • Living Area: 1500
  • Lot Size Acres: 0.11
  • New Construction: No
  • Year Built: 2018
  • Building Area Total: 2104
  • Lease Term: Twelve Months
  • Lot Size Sq Ft: 4600
  • Owner Pays: None
  • Status: Leased
  • Building Area Total Srch Sq M: 195.47
  • Minimum Lease: 8-12 Months
  • Number Of Pets: 2
  • RATIO Current Price By Calculate: 1.07
  • Water Access YN: 0
  • MFR_InLawSuiteYN: 0
  • Attribution Contact: 863-940-3756
  • Special Features: VirtualTour

Interior Features

  • Living Area Units: Square Feet
  • Flooring: Concrete
  • Full Bathrooms: 2
  • Interior Amenities: Ceiling Fans(s), High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Walk-In Closet(s), Window Treatments
  • Appliances Included: Cooktop, Dryer, Freezer, Ice Maker, Microwave, Range, Refrigerator, Washer
  • Total Bedrooms: 3
  • Levels: One
  • Window Features: Blinds
  • Living Area Meters: 139.35

Exterior Features

  • Pool Private: No
  • Waterfront: No
  • Patio and Porch Features: Covered, Patio, Rear Porch
  • Road Surface Type: Asphalt
  • Water View YN: 0
  • Waterfront Feet Total: 0

Garage/Parking

  • Attached Garage: Yes
  • Carport Spaces: 2
  • Carport Y N: Yes
  • Garage Spaces: 2
  • Garage Yn: Yes

Utilities

  • Utilities: Cable Available, Electricity Connected, Phone Available, Sewer Connected, Water Connected
  • Cooling: Central Air
  • Heating: Central
  • Laundry Features: Inside, Laundry Room
  • Sewer: Public Sewer
  • Water Source: Public

Condo/Co-op/Association

  • Community Features: Gated Community - No Guard, Pool
  • Association Name: Whispering Trails HOA/ JR Krisanda (CAM)
  • Phone: 407-647-2622
  • Association: Yes
  • Security: Fire Alarm
  • Senior Community: No
  • Pet Restrictions: Breed restrictions apply and all pets must be pre-approved at the discretion of the owner. Non-refundable $250 for the first pet and $100-$200 for the second pet (depends on size of pet).
  • Association Fee Requirement: None
  • Pet Size: Medium (36-60 Lbs.)
  • Management: Full Time

Fee Information

  • Total Annual Fees: 0.00
  • Total Monthly Fees: 0.00
  • Application Fee: 75

Schools

  • Elementary School: Elbert Elem
  • High School: Winter Haven Senior

Lot Info

  • Parcel Number: 27-28-30-850002-002000

Ownership History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Name Owned For Owner Type

Purchase Details

Listed on
Mar 17, 2025
Closed on
Jun 10, 2025
Sold by
Purchasing Fund 2023-2 Llc
Bought by
Seller's Agent
Charles Watson
MARK SPAIN REAL ESTATE
Buyer's Agent
Lisa Anderson
LA ROSA REALTY PRESTIGE
List Price
$260,000
Sold Price
$242,500
Premium/Discount to List
-$17,500
-6.73%
Views
38
Current Estimated Value
$243,820

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$1,320
Avg. Annual Appreciation
0.46%
Original Mortgage
$230,375
Outstanding Balance
$227,985
Interest Rate
6.89%
Mortgage Type
New Conventional
Estimated Equity
$15,835

Purchase Details

Closed on
Feb 26, 2025
Sold by
Powell Jordan Talmage and Powell Cassandra Beth
Bought by
Purchasing Fund 2023-2 Llc

Purchase Details

Closed on
Oct 3, 2018
Sold by
Whispering Trails Holdings Llc
Bought by
Powell Cassandra Beth and Powell Jordan Talmage

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$181,145
Interest Rate
4.5%
Mortgage Type
VA
Source: Public Records

Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Agents Specializing in Cypresswood, FL

  • Ginger Diedrich Real Estate Agent - EPIC REALTY GROUP INTERNATIONAL

    Ginger Diedrich

    EPIC REALTY GROUP INTERNATIONAL

    (689) 407-6426

    13 Total Sales

    1 in Cypresswood

    $345,000 Price

    Ginger Diedrich
     Section Image
  • Heather Unger, PA Real Estate Agent - Acme Real Estate Florida LLC

    Heather Unger, PA

    Acme Real Estate Florida LLC

    (321) 340-7550

    294 Total Sales

    2 in Cypresswood

    $263K - $305K Price Range

    Heather Unger, PA
     Section Image
  • Stephen Novak Real Estate Agent - LIVE FLORIDA REALTY

    Stephen Novak

    Responds Quickly

    LIVE FLORIDA REALTY

    (863) 267-9310

    104 Total Sales

    1 in Cypresswood

    $460,000 Price

    Stephen Novak
     Section Image
  • Anne Leon Real Estate Agent - COLDWELL BANKER PREMIER PROPERTIES

    Anne Leon

    COLDWELL BANKER PREMIER PROPERTIES

    (386) 388-6637

    32 Total Sales

    1 in Cypresswood

    $413,065 Price

    Anne Leon
     Section Image
  • Bianca Janice Williams Real Estate Agent - RAYNESHIRE REALTY LLC

    Bianca Janice Williams

    RAYNESHIRE REALTY LLC

    (866) 611-9499

    21 Total Sales

    1 in Cypresswood

    $328,990 Price

    Bianca Janice Williams
     Section Image
  • Shelley Davis Real Estate Agent - REMI EMERSON RESIDENTIAL

    Shelley Davis

    REMI EMERSON RESIDENTIAL

    (689) 220-2214

    76 Total Sales

    1 in Cypresswood

    $325,000 Price

    Shelley Davis
     Section Image
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Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Buyer Sale Price Title Company
$242,500 None Listed On Document
Purchasing Fund 2023-2 Llc $260,000 Homeward Title
Powell Cassandra Beth $176,900 Attorney
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Borrower Loan Amount
Open $230,375
Previous Owner Powell Cassandra Beth $181,145
Source: Public Records

Property History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Event Price List to Sale Price per Sq Ft Prior Sale
10/16/2025 10/16/25 Rented $1,600 0.0% --
10/15/2025 10/15/25 Price Changed $1,600 -5.9% $1 / Sq Ft
08/16/2025 08/16/25 Price Changed $1,700 -2.9% $1 / Sq Ft
08/07/2025 08/07/25 Price Changed $1,750 -2.8% $1 / Sq Ft
07/21/2025 07/21/25 For Rent $1,800 0.0% --
06/16/2025 06/16/25 Sold $242,500 +1.0% $162 / Sq Ft View Prior Sale
05/09/2025 05/09/25 Pending -- -- --
04/29/2025 04/29/25 Price Changed $240,000 -4.0% $160 / Sq Ft
04/21/2025 04/21/25 Price Changed $250,000 -3.8% $167 / Sq Ft
03/17/2025 03/17/25 For Sale $260,000 -- $173 / Sq Ft
Source: Stellar MLS

Tax History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $2,325 $167,784
2024 $2,181 $163,055
2023 $2,181 $158,306
2022 $2,111 $153,695 $0 $0
2021 $2,107 $149,218 $0 $0
2020 $2,081 $147,158 $0 $0
2018 $338 $16,500 $16,500 $0
2017 $291 $15,000 $0 $0
2016 $296 $15,000 $0 $0
2015 $198 $9,860 $0 $0
2014 $1 $58 $0 $0
Source: Public Records

Agents Affiliated with this Home

  • CW

    Seller's Agent in 2025

    Charles Watson

    Mark Spain

    (818) 321-6494

    1 in this area

    21 Total Sales

    Charles Watson
    Section Image

  • KC

    Landlord's Agent in 2025

    Kim Connahey

    HOUSE OF GLASS REAL ESTATE PM

    (863) 940-3756

    6 Total Sales

    Kim Connahey
    Section Image

  • LA

    Buyer's Agent in 2025

    Lisa Anderson

    LA ROSA REALTY PRESTIGE

    (256) 443-0544

    3 in this area

    40 Total Sales

    Lisa Anderson
    Section Image
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Map

Source: Stellar MLS

MLS Number: L4954592

Stellar MLS

APN: 27-28-30-850002-002000

Florida Polk County Winter Haven 33884 Cypresswood

2956 Whispering Trails Dr, Winter Haven, FL

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Stellar MLS All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Listings courtesy of Stellar MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID
Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393

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