# 280 SANTA ROSA Drive, Winter Haven, FL 33884 > **TL;DR:** 3bd/2ba single family, $415,000 ($184/sqft), built 1986, 2,251 sqft. > Pool, Fireplace, A/C, 2-car garage. Est. $2,219/mo. Listed 72 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $415,000 | | Price/sqft | $184 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 2,251 | | Year Built | 1986 | | Lot Size | 12,632 sqft (0.29 acres) | | Stories | 1 | | Garage | 2-car | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 72 | ## Why This Home Stands Out - **Pool** - Pool listed; type not specified ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,098 | | Estimated Insurance | $121 | | **Total** | **$2,219** | ## Nearby Schools - **Elementary:** Elbert Elem - **Middle:** Denison Middle - **High:** Winter Haven Senior ## Key Amenities - Pool - Fireplace - A/C - 2-car garage ## Property Highlights - Built in 1986 - 0.29 acre lot - Private pool - Fireplace ## Description ### Agent Description This property went under contract fast and it's back on the market, no fault of the owner. If you missed it the first time, here's your second chance! Welcome to the beautiful neighborhood of Overlook Estates. This 3 bedroom 2 bath + bonus room is waiting for its new owner/s to make it their own. This home is completely vacant which makes it that much easier to envision your own life here. When you first arrive you will notice the beautiful curb appeal this home offers. Upon entering you will be greeted by the stunning entrance. This home is bright and spacious with high ceilings and beautiful wood beams giving it character right off the bat. The kitchen was completely remodeled in 2022. It has floor to ceiling cabinets giving you plenty of space for storage. Use the large island with a built in cook top or move it over to a more formal dining room. Either way this home is the perfect place for entertaining. You can access the lanai/salt water pool from the primary bedroom, kitchen, living room, and even the full guest bath. The open floor plan allows for friends and family to gather while still having plenty of space to spread out. The primary bedroom with ensuite bath and walk in closet as well as that access to the lanai. The primary bathroom has a walk in shower, garden tub, dual vanity and also includes a walk in closet as well as a linen closet. The two additional bedrooms as well as a full bath are located on the opposite side of the house. A fourth room allows for the perfect office space or even a room to host your guests. This home has been wonderfully updated while still holding onto its charm and character. Schedule your showing today! ## Location - **Address:** 280 SANTA ROSA Drive, Winter Haven, FL 33884 - **County:** Polk - **Neighborhood:** OVERLOOK ESTATES - **Coordinates:** 28.007436, -81.688015 - **Google Maps:** https://www.google.com/maps?q=28.007436,-81.688015 ## Virtual Tour & Media - **Video Tour:** https://www.propertypanorama.com/instaview/stellar/L4964337 ## Listing Agent - **Name:** Ashley James - **Brokerage:** Smart Realty of Winter Haven LLC - **Broker Phone:** (863) 508-3000 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/280-Santa-Rosa-Dr_Winter-Haven_FL_33884_M50497-06414?f=listhub&s=MFRMLSFL&m=L4964337&c=propsimple) ## Photos ![280 SANTA ROSA Drive - Photo 1](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f360308737r.jpg) ![280 SANTA ROSA Drive - Photo 2](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3538696654r.jpg) ![280 SANTA ROSA Drive - Photo 3](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3627462687r.jpg) ![280 SANTA ROSA Drive - Photo 4](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f574642532r.jpg) ![280 SANTA ROSA Drive - Photo 5](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f384247450r.jpg) ![280 SANTA ROSA Drive - Photo 6](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3757372938r.jpg) ![280 SANTA ROSA Drive - Photo 7](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1202864613r.jpg) ![280 SANTA ROSA Drive - Photo 8](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1641895766r.jpg) ![280 SANTA ROSA Drive - Photo 9](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3300143367r.jpg) ![280 SANTA ROSA Drive - Photo 10](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3691293212r.jpg) ![280 SANTA ROSA Drive - Photo 11](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1016493170r.jpg) ![280 SANTA ROSA Drive - Photo 12](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2905631623r.jpg) ![280 SANTA ROSA Drive - Photo 13](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2961981496r.jpg) ![280 SANTA ROSA Drive - Photo 14](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2732387193r.jpg) ![280 SANTA ROSA Drive - Photo 15](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3657118179r.jpg) ![280 SANTA ROSA Drive - Photo 16](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3415506667r.jpg) ![280 SANTA ROSA Drive - Photo 17](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f871876740r.jpg) ![280 SANTA ROSA Drive - Photo 18](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1223447277r.jpg) ![280 SANTA ROSA Drive - Photo 19](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f4177058068r.jpg) ![280 SANTA ROSA Drive - Photo 20](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1752114675r.jpg) ![280 SANTA ROSA Drive - Photo 21](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f648542470r.jpg) ![280 SANTA ROSA Drive - Photo 22](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f4098202240r.jpg) ![280 SANTA ROSA Drive - Photo 23](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1307842835r.jpg) ![280 SANTA ROSA Drive - Photo 24](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f135057021r.jpg) ![280 SANTA ROSA Drive - Photo 25](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2759580622r.jpg) ![280 SANTA ROSA Drive - Photo 26](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f18512235r.jpg) ![280 SANTA ROSA Drive - Photo 27](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3393586250r.jpg) ![280 SANTA ROSA Drive - Photo 28](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2846426528r.jpg) ![280 SANTA ROSA Drive - Photo 29](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2788090358r.jpg) ![280 SANTA ROSA Drive - Photo 30](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f4293942269r.jpg) ![280 SANTA ROSA Drive - Photo 31](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1935091310r.jpg) ![280 SANTA ROSA Drive - Photo 32](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3739944813r.jpg) ![280 SANTA ROSA Drive - Photo 33](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3917136001r.jpg) ![280 SANTA ROSA Drive - Photo 34](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3940907450r.jpg) ![280 SANTA ROSA Drive - Photo 35](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1795086629r.jpg) ![280 SANTA ROSA Drive - Photo 36](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1866146768r.jpg) ![280 SANTA ROSA Drive - Photo 37](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2234413617r.jpg) ![280 SANTA ROSA Drive - Photo 38](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1414598760r.jpg) ![280 SANTA ROSA Drive - Photo 39](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f3021359346r.jpg) ![280 SANTA ROSA Drive - Photo 40](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f1103690922r.jpg) ![280 SANTA ROSA Drive - Photo 41](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f62137422r.jpg) ![280 SANTA ROSA Drive - Photo 42](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f4249389293r.jpg) ![280 SANTA ROSA Drive - Photo 43](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f64484538r.jpg) ![280 SANTA ROSA Drive - Photo 44](http://lh.rdcpix.com/156bbd7dd3c27cf18eb052d2ca8ff2ecl-f2266694050r.jpg) --- **MLS#:** L4964337 | **Updated:** 2026-10-27 **Source:** listhub *Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/280-santa-rosa-drive-winter-haven-fl-33884-398ee72dbcbb4de6bbf54481d9248d82) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/280-santa-rosa-drive-winter-haven-fl-33884-398ee72dbcbb4de6bbf54481d9248d82#listing", "url": "https://staging.propertysimple.ai/listing/280-santa-rosa-drive-winter-haven-fl-33884-398ee72dbcbb4de6bbf54481d9248d82", "name": "280 SANTA ROSA Drive, Winter Haven, FL 33884", "description": "This property went under contract fast and it's back on the market, no fault of the owner. If you missed it the first time, here's your second chance! Welcome to the beautiful neighborhood of Overlook Estates. This 3 bedroom 2 bath + bonus room is waiting for its new owner/s to make it their own. This home is completely vacant which makes it that much easier to envision your own life here. When you first arrive you will notice the beautiful curb appeal this home offers. Upon entering you will be greeted by the stunning entrance. This home is bright and spacious with high ceilings and beautiful wood beams giving it character right off the bat. The kitchen was completely remodeled in 2022. It has floor to ceiling cabinets giving you plenty of space for storage. Use the large island with a built in cook top or move it over to a more formal dining room. Either way this home is the perfect place for entertaining. You can access the lanai/salt water pool from the primary bedroom, kitchen, living room, and even the full guest bath. The open floor plan allows for friends and family to gather while still having plenty of space to spread out. The primary bedroom with ensuite bath and walk in closet as well as that access to the lanai. The primary bathroom has a walk in shower, garden tub, dual vanity and also includes a walk in closet as well as a linen closet. The two additional bedrooms as well as a full bath are located on the opposite side of the house. A fourth room allows for the perfect office space or even a room to host your guests. This home has been wonderfully updated while still holding onto its charm and character. 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