$440,000
240 Santa Rosa DriveWinter Haven, FL 33884
Listing updated: October 26, 2026 at 8:33 PM ET
Listing courtesy of Live Florida Realty · Brian Surrency · MLS #L4958092 · Active · 863-868-8905Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About this home
Short Sale. Back on the market! 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.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history181 days on market
- Status: ActiveSep 30, 2026
- Listed$462,900Dec 24, 2025
- Price reduced$440,000
Property Documents
Documents the listing agent has made public for this property. Free to view and download.
Facts & features
- Property type
- Residential
- Sub type
- Single Family Residence
- Status
- Active
- Days on market
- 181
- Subdivision
- Overlook Ests Ph 3
- County
- Polk
- Year built
- 1988
- Living area
- 2,850 sq ft
- Price/sq ft
- $154
- Building area
- 4,216 sq ft (Public Records)
- Lot size
- 12,350 sq ft
- Lot category
- 1/4 to less than 1/2
- Flood zone
- X
- Garage
- 2 spaces
- Pool
- Private pool
- Annual taxes
- $2,790 (2023)
- Parcel #
- 26-28-35-662927-000220
- Zoning
- 0
- MLS #
- L4958092
Ask about this home
Have a question? Ask the broker directly.
Ryan Solberg answers personally — no call center, no spam. Your question goes straight to him.
Interior Details
- Bedrooms
- 4
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Carpet, Ceramic Tile
- Appliances
- Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
- Interior features
- Cathedral Ceiling(s), Ceiling Fans(s), Crown Molding, High Ceilings, PrimaryBedroom Upstairs, Split Bedroom, Walk-In Closet(s)
- Laundry
- Inside
- Stories / Levels
- Two
- Direction faces
- South
- Fireplace
- Yes
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Garage Door Opener
HOA & Financial
- HOA fee
- $550 / Annually
- Monthly HOA
- $46/mo
- Total monthly fees
- $46/mo
- Total annual fees
- $550
- HOA name
- Overlook Estates
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- No Minimum
- Listing terms
- Cash, Conventional, FHA, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- No
- Additional lease restrictions
- Please verify with HOA
Exterior & Construction
- Exterior features
- Fire Pit, Outdoor Shower, Rain Gutters, Storage
- Construction materials
- Frame, Wood Siding
- Roof
- Shingle
- Foundation
- Slab
- Pool
- Private pool
- Road surface
- Paved
Utilities
- Sewer
- Septic Tank
- Water source
- Public
- Utilities
- Cable Available, Electricity Connected, Fire Hydrant, Sprinkler Well
Community
- Pets allowed
- Yes
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Bedroom 2 | 15x11 | |
| Bedroom 3 | 13x11 | |
| Bedroom 4 | 18x10 | |
| Bonus Room | 12x25 | |
| Dining Room | 14x11 | |
| Family Room | 28x15 | |
| Kitchen | 17x13 | |
| Living Room | 14x15 | |
| Primary Bathroom | 8x10 | |
| Primary Bedroom | 27x13 | |
| Bathroom 2 | 8x10 |
Listing Details
- Listing date
- 2025-12-24
- On market date
- 2025-12-24
- Original list price
- $462,900
- Occupant type
- Owner
- Special conditions
- Short Sale
- MLS area
- 33884 - Winter Haven / Cypress Gardens
- Listing AOR
- Suncoast Tampa
- Status changed
- 2026-09-30
- Tax legal description
- OVERLOOK ESTATES PHASE 3 PB 83 PG 50 LOT 22
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
Property sale history
Public records240 SANTA ROSA DR, WINTER HAVEN 33884
- Apr 2024$440,000
2,850 sq ft · Built 1988 · 0.3214 acres
Sale data from Florida public records (Department of Revenue / county property appraiser). Deemed reliable but not guaranteed; may not reflect current market or MLS status. Not Stellar MLS data.
More homes like this
$350,000
1281 Deepwater Cir
Eagle Lake, FL 33839
4 bd · 3 ba · 2,150 sqft
Ranches/Lk Mcleod Ii
MLS ID #S5160237, NONA LEGACY POWERED BY LA ROSA.
Listing provided by Stellar MLS
$320,990
2766 Adeline Ave
Winter Haven, FL 33881
4 bd · 2 ba · 1,828 sqft
Willowbrook South
MLS ID #O6452454, DR HORTON REALTY OF CENTRAL FLORIDA LLC.
Listing provided by Stellar MLS
$439,900
425 Pearl St
Lake Hamilton, FL 33851
4 bd · 4 ba · 2,215 sqft
Miller J T Sub
MLS ID #O6451995, LA ROSA REALTY LLC.
Listing provided by Stellar MLS
$344,900
693 Crown Rose Dr
Eagle Lake, FL 33839
4 bd · 3 ba · 2,236 sqft
Village At Windsor Reserve
MLS ID #S5142913, LA ROSA REALTY KISSIMMEE.
Listing provided by Stellar MLS
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of October 26, 2026 at 8:33 PM ET. 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA