5460 Chestnut Ridge Rd

Dade City, FL 33523

$414,500
Price
3
Beds
2,221 Sq. Ft.
$187 / Sq. Ft.
2,221
Sq. Ft.
$187
per Sq. Ft.
Open: 1/25 11:00AM - 02:00PMNew
Open: 1/25 11:00AM - 02:00PMNew

Description

Exceptional custom pool home designed for elevated Florida living, set on a generous—just under a quarter acre—offering ample outdoor space, privacy, and flexibility. The property backs to conservation with no rear neighbors, featuring tranquil pond views dotted with lily pads that create an almost Monet-like backdrop and a true sense of serenity. The outdoor living space is exceptional, highlighted by a heated saltwater pool and spa, pavered lanai, covered and tiled dining area, and disappearing...Exceptional custom pool home designed for elevated Florida living, set on a generous—just under a quarter acre—offering ample outdoor space, privacy, and flexibility. The property backs to conservation with no rear neighbors, featuring tranquil pond views dotted with lily pads that create an almost Monet-like backdrop and a true sense of serenity. The outdoor living space is exceptional, highlighted by a heated saltwater pool and spa, pavered lanai, covered and tiled dining area, and disappearing sliding glass doors that seamlessly connect indoor and outdoor living—ideal for entertaining or everyday relaxation. Inside, the home impresses with soaring cathedral ceilings, crown molding, recessed can lighting, 8-foot doors, and rich engineered hardwood floors throughout the main living areas. The open layout is anchored by a beautifully appointed kitchen with custom cabinetry and ample storage, complemented by an adjacent wet bar featuring custom cabinets and a wine refrigerator—perfect for hosting. A dedicated pool bath adds convenience, while custom window treatments and built-in closet systems elevate both form and function. The living room is anchored by a classic wood-burning fireplace that adds warmth and character to the space, creating a comfortable focal point for everyday living and entertaining. Additional highlights include a three-zone HVAC system, whole-house ventilation exhaust system, instant hot water, water softener, in-wall pest system, and an oversized two-car garage with built-in cabinetry and workspace. Recent upgrades include a 2022 roof and a 2018 AC system. Select furnishings convey, including the kitchen table, barstools, and artwork in the dining and living rooms. This is not an ordinary home—it’s a thoughtfully designed, feature-rich property that lives as beautifully as it looks and must be experienced in person.
  1. Listed by Frank Rogers • Brokerage DRE #1069405 • SUN CAY REAL ESTATE
    P: (518)-376-0669 C: (518)-376-0669 frankrogerssales@gmail.com
  2. Listed by Jimary Jimenez • Brokerage DRE #1069405 • SUN CAY REAL ESTATE
    P: (813)-951-6432 C: (813)-951-6432 JimaryJimenezRealtor@gmail.com

Property Details for 5460 Chestnut Ridge Road

Subdivision Name
WHISP OAKS ESTATE PH 6-A
Township
23
Garage Spaces
2
View
Golf Course, Water
Waterfront
No
Furnished
Negotiable

Open Houses

Sunday, Jan 25th

11:00 AM - 2:00 PM

Public

LISTING UPDATED: 01/23/2026 06:51 AM

Property Details for 5460 Chestnut Ridge Road

StatusActive
MLS #TB8467390
Days on Market1
Taxes$2,559 / year
HOA Fees$277 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2008
Lot Size0.22 AC / 9,375 SF
CountyHernando County

Location

Listing Courtesy of SUN CAY REAL ESTATE, Frank Rogers; SUN CAY REAL ESTATE, Jimary Jimenez
Add your commute

Building Information for 5460 Chestnut Ridge Road

Stories-Year Built2008Building Size-Lot Size0.22 AC / 9,375 SF

Payment Calculator

$2,257 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,020

Property Taxes

$213

HOA Dues

$23

The Payment Calculator is for illustrative purposes only.

Property Information for 5460 Chestnut Ridge Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 3436.0
  • Building Area Units: Square Feet
  • Direction Faces: West
  • Directions: From Treiman Blvd, turn onto Whispering Oaks Blvd, left on Beechwood Dr, left on Chestnut Ridge Rd
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 5460
  • Street Name: CHESTNUT RIDGE
  • Street Suffix: ROAD
  • State: FL
  • City: DADE CITY
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
  • Parking Features: Garage Door Opener
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Requirement: Required
  • Association Name: Whispering Oaks Estate
  • Association Phone: 3526638634
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Buyer and Buyer's agent to verify pet restrictions with HOA
  • Tax Block: 0000
  • Tax Book Number: 21-44
  • Tax Legal Description: WHISPERING OAKS EST PH VI-A LOT 152
  • Tax Lot: 152
  • Tax Year: 2025
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Lot Features: Conservation Area, Landscaped
  • Parcel Number: R0112321132400001520
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: MPUD
  • Living Area: 2221
Property and Assessments
  • Year Built Numeric: 2008
  • Flood Zone Code: X
  • Flood Zone Date: 02-02-2012
  • Flood Zone Panel: 12053C0243D
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 21
  • Public Survey Section: 01
Utilities
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Available, Phone Available, Sewer Available, Water Available
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Stucco
  • Exterior Features: Hurricane Shutters, Irrigation System
  • Fencing: Vinyl
  • Foundation Details: Slab
  • Levels: One
  • Patio And Porch Features: Screened
  • Pool Features: In Ground
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Spa Features: Above Ground
  • Spa: Yes
  • Vegetation: Trees/Landscaped
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 3
  • Bathrooms Full: 2
  • Additional Rooms: Formal Dining Room Separate
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Range Hood, Refrigerator, Washer, Water Softener, Wine Refrigerator
  • Cooling: Central Air
  • Fireplace Features: Family Room, Wood Burning
  • Fireplace: Yes
  • Flooring: Ceramic Tile, Hardwood
  • Heating: Central
  • Interior Features: Attic Fan, Attic Ventilator, Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, In Wall Pest System, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
  • Laundry Features: Laundry Room
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 3.0
  • Water View: No
  • Bathrooms Half: 0
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 5460 Chestnut Ridge Road

DateEvent & SourcePriceAppreciation
Jan 22, 2026

Listed (Active)

MFRMLS #TB8467390

$414,500—
Mar 30, 2007

Sold (Public Record)

Public Record #217916053

$39,611

+24.1% / yr

Sep 22, 2004

Sold (Public Record)

Public Record #143824084

$23,000

+97.6% / yr

Sep 22, 2004

Sold

MFRMLS #T2042721

$23,000—
Sep 3, 2004

Pending

MFRMLS #T2042721

—
Jun 26, 2004

Listed (Active)

MFRMLS #T2042721

$14,900—
Jun 6, 2003

Sold (Public Record)

Public Record #114203039

$9,500—
DateEvent & SourcePrice
01/22/2026

Listed (Active)

MFRMLS #TB8467390

$414,500
03/30/2007

Sold (Public Record)

Public Record #217916053

$39,611

+24.1% / yr

09/22/2004

Sold (Public Record)

Public Record #143824084

$23,000

+97.6% / yr

09/22/2004

Sold

MFRMLS #T2042721

$23,000
09/03/2004

Pending

MFRMLS #T2042721

—
06/26/2004

Listed (Active)

MFRMLS #T2042721

$14,900
06/06/2003

Sold (Public Record)

Public Record #114203039

$9,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5460 Chestnut Ridge Road

Taxable ValueLand-Additions-Total-
Tax Record2025$2,098 ($175 / month)
Home Facts
Beds3Total Finished SqFt2,221 SqFtAbove Grade Finished SqFt2,221 SqFtStories1Lot Size8,712 SqFtStyleSingle Family ResidenceYear Built2008Year Renovated2013CountyHERNANDOAPNR01-123-21-1324-0000-1520Fireplace TypeHas Fireplace

Schools near 5460 Chestnut Ridge Road

This home is within Hernando.
Rating
School
Type
Grades
Distance
Eastside Elementary School
Public - PK to 5
D. S. Parrott Middle School
Public - 6 to 8
Hernando High School
Public - 6 to 12
Brooksville Engineering, Science And Technology (B.E.S.T.) Academy
Charter - 6 to 8
Rating
School
Distance
Eastside Elementary School
PublicPK to 5

D. S. Parrott Middle School
Public6 to 8

Hernando High School
Public6 to 12

Brooksville Engineering, Science And Technology (B.E.S.T.) Academy
Charter6 to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5460 Chestnut Ridge Road, Dade City, FL 33523

5460 Chestnut Ridge Road is a single family home for sale in Dade City, FL 33523. This property was listed for sale on January 22, 2026 by SUN CAY REAL ESTATE, it's currently listed at $414,500. It has been on the market for a total of 1 days and was last sold on March 30, 2007. This listing's school district is Hernando. Nearby schools include Eastside Elementary School, D. S. Parrott Middle School and Hernando High School. 5460 Chestnut Ridge Road is a 3-bed, 2-bath, 2,221 sqft single family home built in 2008.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of SUN CAY REAL ESTATE, Frank Rogers; SUN CAY REAL ESTATE, Jimary Jimenez

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 01/23/2026 06:51 AM