Under contract-accepting backup offers. Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Pending
Price increase: $4.1K (5/18)
$439,000
240 Santa Rosa Dr, Winter Haven, FL 33884
4beds
2,850sqft
Single Family Residence
Built in 1988
0.28 Acres Lot
$-- Zestimate®
$154/sqft
$46/mo HOA
What's special
Pool home
- 192 days |
- 29 |
- 2 |
Zillow last checked:
Listing updated:
Listed by:
Brian Surrency 863-204-4298,
LIVE FLORIDA REALTY 863-868-8905
Source: Stellar MLS,MLS#: L4958092
Originating MLS: Suncoast Tampa
Originating MLS: Suncoast Tampa
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Attic, Family Room, Florida Room, Dining Room, Living Room, Utility Room
Primary bedroom
- Features: Walk-In Closet(s)
- Level: Second
- Area: 351 Square Feet
- Dimensions: 27x13
Bedroom 2
- Features: Built-in Closet
- Level: Second
- Area: 165 Square Feet
- Dimensions: 15x11
Bedroom 3
- Features: Built-in Closet
- Level: Second
- Area: 143 Square Feet
- Dimensions: 13x11
Bedroom 4
- Features: Built-in Closet
- Level: Second
- Area: 180 Square Feet
- Dimensions: 18x10
Primary bathroom
- Features: Dual Sinks, Shower No Tub
- Level: Second
- Area: 80 Square Feet
- Dimensions: 8x10
Bathroom 2
- Level: Second
- Area: 80 Square Feet
- Dimensions: 8x10
Bonus room
- Features: No Closet
- Level: First
- Area: 300 Square Feet
- Dimensions: 12x25
Dining room
- Level: First
- Area: 154 Square Feet
- Dimensions: 14x11
Family room
- Level: First
- Area: 420 Square Feet
- Dimensions: 28x15
Kitchen
- Features: Pantry
- Level: First
- Area: 221 Square Feet
- Dimensions: 17x13
Living room
- Level: First
- Area: 210 Square Feet
- Dimensions: 14x15
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
- Laundry: Inside
Features
- Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, PrimaryBedroom Upstairs, Split Bedroom, Walk-In Closet(s)
- Flooring: Carpet, Ceramic Tile
- Doors: Outdoor Shower
- Windows: Blinds, Window Treatments
- Has fireplace: Yes
- Fireplace features: Family Room, Living Room, Wood Burning
Interior area
- Total structure area: 4,216
- Total interior livable area: 2,850 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Garage Door Opener
- Attached garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Patio, Porch
- Exterior features: Fire Pit, Irrigation System, Outdoor Shower, Rain Gutters, Storage
- Has private pool: Yes
- Pool features: Gunite, In Ground, Salt Water
- Has spa: Yes
- Spa features: Above Ground, Heated
- Fencing: Fenced
Lot
- Size: 0.28 Acres
- Dimensions: 95.0 x 130.0
- Features: In County, Landscaped
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Additional structures: Shed(s)
- Parcel number: 262835662927000220
- Zoning: 0
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Siding
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1988
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
- Utilities for property: Cable Available, Electricity Connected, Fire Hydrant, Sprinkler Well
Community & HOA
Community
- Features: Deed Restrictions, Gated Community - No Guard
- Security: Gated Community
- Pet fee: $0 monthly
- Subdivision: OVERLOOK ESTS PH 3
HOA
- Has HOA: Yes
- Amenities included: Gated
- HOA fee: $46 monthly
- HOA name: Overlook Estates
- HOA phone: 717-855-3110
Location
- Region: Winter Haven
Financial & listing details
- Price per square foot: $154/sqft
- Tax assessed value: $358,676
- Annual tax amount: $2,790
- Date on market: 12/24/2025
- Cumulative days on market: 157 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/29/2026 | Pending sale | $439,000$154/sqft |
Source:  Stellar MLS #L4958092 Report a problem | ||
| 5/18/2026 | Price change | $439,000+0.9%$154/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 3/24/2026 | Price change | $434,900-2.3%$153/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 3/8/2026 | Price change | $445,000-0.4%$156/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 2/6/2026 | Price change | $446,700-0.7%$157/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 1/17/2026 | Price change | $450,000-0.6%$158/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 1/2/2026 | Price change | $452,900-2.2%$159/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 12/25/2025 | Listed for sale | $462,900+5.2%$162/sqft |
Source: Stellar MLS #L4958092 Report a problem | ||
| 4/18/2024 | Sold | $440,000-2.2%$154/sqft |
Source: Stellar MLS #L4941822 Report a problem | ||
| 3/6/2024 | Pending sale | $450,000$158/sqft |
Source: Stellar MLS #L4941822 Report a problem | ||
| 1/31/2024 | Price change | $450,000-4.1%$158/sqft |
Source: Stellar MLS #L4941822 Report a problem | ||
| 1/15/2024 | Listed for sale | $469,000+115.6%$165/sqft |
Source: Stellar MLS #L4941822 Report a problem | ||
| 6/28/2013 | Sold | $217,500+1.6%$76/sqft |
Source: Stellar MLS #P4625193 Report a problem | ||
| 4/20/2013 | Listed for sale | $214,000+1.9%$75/sqft |
Source: Keller Williams Realty of Winter Haven #P4625193 Report a problem | ||
| 11/4/2012 | Listing removed | $210,000$74/sqft |
Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem | ||
| 10/7/2012 | Price change | $210,000-10.6%$74/sqft |
Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem | ||
| 7/4/2012 | Price change | $234,900-4.1%$82/sqft |
Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem | ||
| 2/25/2012 | Listed for sale | $245,000+32.4%$86/sqft |
Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem | ||
| 10/4/1999 | Sold | $185,000$65/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $4,754 +102.1% | $358,676 +61.5% |
| 2024 | $2,353 +2.2% | $222,048 +3% |
| 2023 | $2,301 +2.2% | $215,581 +3% |
| 2022 | $2,251 -0.4% | $209,302 +3% |
| 2021 | $2,260 +0.9% | $203,206 +1.4% |
| 2020 | $2,240 +0% | $200,400 +2.3% |
| 2019 | $2,240 -15.6% | $195,894 +1.9% |
| 2018 | $2,653 +1.9% | $192,241 +2.1% |
| 2017 | $2,605 +21.5% | $188,287 +2.1% |
| 2016 | $2,144 -1.7% | $184,414 +0.7% |
| 2015 | $2,181 -8.9% | $183,132 +0.8% |
| 2014 | $2,395 -7.8% | $181,679 +12% |
| 2013 | $2,598 -0.8% | $162,185 -1.6% |
| 2012 | $2,618 +24.2% | $164,824 -2.7% |
| 2011 | $2,107 -5.6% | $169,396 -3.2% |
| 2010 | $2,232 -14.6% | $174,908 -8.2% |
| 2009 | $2,615 +7.2% | $190,445 +0.1% |
| 2008 | $2,440 | $190,255 |
| 2007 | -- | -- |
| 2006 | $2,793 | -- |
| 2005 | -- | -- |
| 2004 | $2,468 +2.2% | -- |
| 2003 | $2,414 +0.3% | $166,697 +2.4% |
| 2002 | $2,406 -14% | $162,790 +1.6% |
| 2001 | $2,796 | $160,150 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: Cypress Gardens
Nearby schools
GreatSchools rating
- 2/10Elbert Elementary SchoolGrades: PK-5Distance: 1.3 mi
- 3/10Denison Middle SchoolGrades: 6-8Distance: 2.2 mi
- 3/10Winter Haven Senior High SchoolGrades: 9-12Distance: 1.9 mi
Schools provided by the listing agent
- Elementary: Elbert Elem
- Middle: Denison Middle
- High: Winter Haven Senior
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Florida
- Polk County
- Winter Haven
- 33884
- Cypress Gardens
- 240 Santa Rosa Dr
Nearby cities
Nearby neighborhoods
Nearby zip codes
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