240 Santa Rosa Dr

Winter Haven, FL 33884

$446,700
Price
4
Beds
2,850 Sq. Ft.
$157 / Sq. Ft.
2,850
Sq. Ft.
$157
per Sq. Ft.

Description

New price drop Discover a remarkable private home in Winter Haven’s premier Overlook Estates. This spacious 4-bedroom, 2.5 bath residence boasts 2,850 square feet of elegant living space, featuring highly desirable outdoor amenities within an established and coveted neighborhood. Built in 1988, the house combines classic style with significant modern enhancements. Inside, you’ll find soaring ceilings, generous rooms, and abundant sunlight that together create a refined yet welcoming setting, perfect...New price drop Discover a remarkable private home in Winter Haven’s premier Overlook Estates. This spacious 4-bedroom, 2.5 bath residence boasts 2,850 square feet of elegant living space, featuring highly desirable outdoor amenities within an established and coveted neighborhood. Built in 1988, the house combines classic style with significant modern enhancements. Inside, you’ll find soaring ceilings, generous rooms, and abundant sunlight that together create a refined yet welcoming setting, perfect for daily life or entertaining guests. Its open design effortlessly connects formal areas with casual ones, providing ample options for social gatherings, home offices, or multi-generational living arrangements. At the heart of the home is a well-equipped kitchen, offering plenty of cabinetry and counter area, plus direct access to the outdoor entertainment spaces. The large primary suite serves as a peaceful sanctuary with its own en-suite bath and walk-in closet, while three additional bedrooms provide flexibility for family, guests, or other uses. Step outside into your secluded backyard retreat, which includes a sparkling saltwater pool, detached hot tub, bar or pool house, and extensive patio ideal for relaxing or hosting year-round events, a true representation of Florida lifestyle. Major recent updates add both security and enduring value: a new roof (2018), updated drain field and septic system (2024), and a brand-new second-floor air conditioning system (2025) ensure ongoing comfort and reliability. Perfectly located just minutes from the Chain of Lakes, golf courses, shops, restaurants, and main routes to Tampa and Orlando, this home offers unparalleled prestige, privacy, and convenience. Don’t miss this rare chance to own a luxurious, spacious, and upgraded residence in one of Winter Haven’s top communities. Schedule your private visit today before this outstanding property is sold.
  1. Listed by Brian Surrency • Brokerage DRE #1028915 • LIVE FLORIDA REALTY
    P: (863)-204-4298 C: (863)-204-4298 brian@liveflrealty.com

Property Details for 240 Santa Rosa Drive

Architectural Style
Traditional
Subdivision Name
OVERLOOK ESTS PH 3
Township
28
Garage Spaces
2
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 02/05/2026 07:05 PM

Property Details for 240 Santa Rosa Drive

StatusActive
MLS #L4958092
Days on Market44
Taxes$2,790 / year
HOA Fees$550 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built1988
Lot Size0.28 AC / 12,350 SF
CountyPolk County

Location

Listing Courtesy of LIVE FLORIDA REALTY, Brian Surrency
Add your commute

Building Information for 240 Santa Rosa Drive

Stories-Year Built1988Building Size-Lot Size0.28 AC / 12,350 SF

Payment Calculator

$2,455 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,177

Property Taxes

$233

HOA Dues

$46

The Payment Calculator is for illustrative purposes only.

Property Information for 240 Santa Rosa Drive

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 4216.0
  • Building Area Units: Square Feet
  • Community Features: Deed Restrictions, Gated Community - No Guard
  • Direction Faces: South
  • Directions: From Hwy 27: Turn onto Dundee Rd. Follow to Carl Floyd Rd, then turn left. Follow to Overlook Dr., then veer right onto Wakulla. Overlook Estates will be the first community on the right. Once through the gates turn right and follow the road to the back of the community, and the home is on the right. From Cypress Gardens Blvd: Turn onto Overlook Dr., follow to Wakulla and turn left. Overlook Estates will be the first community on the right. Once through the gates turn right and follow the road to the back of the community, and the home is on the right.
  • Elementary School: Elbert Elem
  • Middle Or Junior School: Denison Middle
  • High School: Winter Haven Senior
  • Mls Major Change Type: Price Decrease
  • Listing Service: Full Service
  • Road Frontage Type: Street Paved
  • Senior Community: No
  • SW Subdiv Community Name: Not Applicable
  • Unit Number: No
  • Street Number: 240
  • Street Name: SANTA ROSA
  • Street Suffix: DRIVE
  • State: FL
  • City: WINTER HAVEN
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: Overlook Estates
  • Association Phone: 717-855-3110
  • Association: Yes
  • CDD: No
  • Pet Restrictions: Please verify with HOA
  • Tax Book Number: 0083/0050
  • Tax Legal Description: OVERLOOK ESTATES PHASE 3 PB 83 PG 50 LOT 22
  • Tax Lot: 22
  • Tax Year: 2023
Virtual Tour
Property
Lot Information
  • Additional Parcels: No
  • Future Land Use: 0010
  • Lot Features: In County, Landscaped
  • Lot Size Dimensions: 95.0 x 130.0
  • Parcel Number: 262835662927000220
  • Total Acreage: 1/4 to less than 1/2
  • Water Access: No
  • Water Extras: No
  • Zoning: 0
  • Living Area: 2850
  • Lot Dimensions: 95.0 x 130.0
Property and Assessments
  • Year Built Numeric: 1988
  • Association Amenities: Gated
  • Flood Zone Code: X
  • Home Warranty: No
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 26
  • Public Survey Section: 35
Utilities
  • Sewer: Septic Tank
  • Utilities: Cable Available, Electricity Connected, Fire Hydrant, Sprinkler Well
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Wood Frame, Wood Siding
  • Exterior Features: Fire Pit, Irrigation System, Outdoor Shower, Rain Gutters, Storage
  • Fencing: Fenced
  • Foundation Details: Slab
  • Levels: Two
  • Other Structures: Shed(s)
  • Patio And Porch Features: Covered, Patio, Porch
  • Pool Features: Gunite, In Ground, Salt Water
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Roof: Shingle
  • Security Features: Gated Community
  • Spa Features: Above Ground, Heated
  • Spa: Yes
  • Vegetation: Mature Landscaping, Trees/Landscaped
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 2
  • Additional Rooms: Attic, Family Room, Florida Room, Formal Dining Room Separate, Formal Living Room Separate, Inside Utility
  • Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Family Room, Living Room, Wood Burning
  • Fireplace: Yes
  • Flooring: Carpet, Ceramic Tile
  • Heating: Central
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, PrimaryBedroom Upstairs, Split Bedroom, Walk-In Closet(s)
  • Laundry Features: Inside
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 11.0
  • Water View: No
  • Window Features: Blinds, Window Treatments
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 240 Santa Rosa Drive

DateEvent & SourcePriceAppreciation
Feb 5, 2026

Price Change

MFRMLS #L4958092

$446,700—
Jan 16, 2026

Price Change

MFRMLS #L4958092

$450,000—
Jan 2, 2026

Price Change

MFRMLS #L4958092

$452,900—
Dec 24, 2025

Listed (Active)

MFRMLS #L4958092

$450,000—
Dec 24, 2025

Temporarily Off Market

MFRMLS #L4958092

—
Dec 24, 2025

Listed (Active)

MFRMLS #L4958092

$462,900—
Apr 18, 2024

Sold (Public Record)

Public Record #1531593696

$440,000

+59.0% / yr

Apr 18, 2024

Sold

MFRMLS #L4941822

$440,000—
Mar 5, 2024

Pending

MFRMLS #L4941822

—
Jan 15, 2024

Listed (Active)

MFRMLS #L4941822

$469,000—
May 11, 2018

Sold (Public Record)

Public Record #623221639

$28,000

-34.4% / yr

Jun 28, 2013

Sold (Public Record)

Public Record #356653422

$217,500—
Jun 28, 2013

Sold

MFRMLS #P4625193

$217,500—
Jun 5, 2013

Pending

MFRMLS #P4625193

—
Apr 19, 2013

Listed (Active)

MFRMLS #P4625193

$214,000—
Apr 3, 2013

Withdrawn

MFRMLS #P4619759

$210,000—
Feb 21, 2012

Listed (Active)

MFRMLS #P4619759

$245,000—
DateEvent & SourcePrice
02/05/2026

Price Change

MFRMLS #L4958092

$446,700
01/16/2026

Price Change

MFRMLS #L4958092

$450,000
01/02/2026

Price Change

MFRMLS #L4958092

$452,900
12/24/2025

Listed (Active)

MFRMLS #L4958092

$450,000
12/24/2025

Temporarily Off Market

MFRMLS #L4958092

—
12/24/2025

Listed (Active)

MFRMLS #L4958092

$462,900
04/18/2024

Sold (Public Record)

Public Record #1531593696

$440,000

+59.0% / yr

04/18/2024

Sold

MFRMLS #L4941822

$440,000
03/05/2024

Pending

MFRMLS #L4941822

—
01/15/2024

Listed (Active)

MFRMLS #L4941822

$469,000
05/11/2018

Sold (Public Record)

Public Record #623221639

$28,000

-34.4% / yr

06/28/2013

Sold (Public Record)

Public Record #356653422

$217,500
06/28/2013

Sold

MFRMLS #P4625193

$217,500
06/05/2013

Pending

MFRMLS #P4625193

—
04/19/2013

Listed (Active)

MFRMLS #P4625193

$214,000
04/03/2013

Withdrawn

MFRMLS #P4619759

$210,000
02/21/2012

Listed (Active)

MFRMLS #P4619759

$245,000

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

Public Records for 240 Santa Rosa Drive

Taxable ValueLand$60,000Additions$298,676Total$358,676
Tax Record2025$4,754 ($396 / month)
Home Facts
Beds4Total Finished SqFt2,850 SqFtAbove Grade Finished SqFt2,850 SqFtStories2Lot Size14,000 SqFtStyleSingle Family ResidenceYear Built1988CountyPOLKAPN262835662927000220Fireplace TypeHas Fireplace

Schools near 240 Santa Rosa Drive

This home is within Polk.
Rating
School
Type
Grades
Distance
Frank E. Brigham Academy
Public - PK to 5
Elbert Elementary School
Public - PK to 5
Jewett School Of The Arts
Public - PK to 8
Jewett Middle Academy Magnet
Public - 6 to 8
Rating
School
Distance
Frank E. Brigham Academy
PublicPK to 5

Elbert Elementary School
PublicPK to 5

Jewett School Of The Arts
PublicPK to 8

Jewett Middle Academy Magnet
Public6 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.

Similar Homes

Similar Sold Homes

Explore Nearby Homes

More information about 240 Santa Rosa Drive, Winter Haven, FL 33884

240 Santa Rosa Drive is a single family home for sale in Winter Haven, FL 33884. This property was listed for sale on December 24, 2025 by LIVE FLORIDA REALTY, it's currently listed at $446,700. It has been on the market for a total of 44 days and was last sold on April 18, 2024. This listing's school district is Polk. Nearby schools include Frank E. Brigham Academy, Elbert Elementary School and Jewett School Of The Arts. 240 Santa Rosa Drive is a 4-bed, 3-bath, 2,850 sqft single family home built in 1988.

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 LIVE FLORIDA REALTY, Brian Surrency

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: 02/05/2026 07:05 PM