Homes For Sale in Winter Haven 33880 - 155 homes

Remarks: Welcome home to this beautifully maintained three-bedroom two-bathroom gem offering comfort, charm, and everyday functionality! Situated on a spacious lot with a large front yard, this home features a warm and inviting exterior with great curb appeal and plenty of room to enjoy outdoor living. Step inside to find a bright and open layout with multiple living spaces, perfect for both relaxing and entertaining. The updated kitchen showcases crisp cabinetry, ample counter space, and a cozy, modern feel that flows seamlessly into the dining and living areas. The home offers generously sized bedrooms filled with natural light, along with well-appointed bathrooms designed for both style and convenience. A dedicated laundry space and flexible bonus areas provide extra functionality for today’s lifestyle, whether you need a home office, playroom, or hobby space. Enjoy Florida living with a large backyard, ideal for gatherings, pets, or simply unwinding at the end of the day. With a spacious driveway and additional storage options, this home checks all the boxes. Conveniently located near shopping, dining, and major roadways, this one is move in ready and waiting for its next owner!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: Jamie Baker (863-258-2244)

Remarks: **$5000 towards closing costs with any reasonable offer. Seller will entertain any reasonable offer!!** Beautiful 3-bedroom, 2-bath ranch home built in 2022 offering modern design and easy one-level living. Open concept layout with spacious living areas, contemporary finishes, and abundant natural light. Well appointed kitchen and comfortable bedroom split for added privacy. Move-in ready and perfect for today's lifestyle.

Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)

Listing Agent: David Hartigan (407-955-1156)

Remarks: Attention Investors & Homeowners! Whether you’re a seasoned investor or looking for a home with built-in income, this property presents an exciting opportunity. This well-maintained 3-bedroom, 2-bath block home is located within Winter Haven city limits and offers 1,155 square feet of tile flooring throughout with no HOA. The home features a functional layout, spacious rooms, ample kitchen counter space, and a large fenced backyard. Major updates include a newer roof (2018), A/C replacement (2014), and a water heater installed in 2004. Currently tenant-occupied, making it a great income-producing option with future flexibility. Conveniently located just minutes from shopping, downtown Winter Haven, and approximately 12 minutes from LEGOLAND. Don’t miss out—schedule your showing today and see the potential for yourself.

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)

Listing Agent: Melissa Ramirez (813-956-1071)

Remarks: Welcome home to 4420 Limewood St in Winter Haven, located in the desirable 55+ co-op community of Oakwood Estates—a neighborhood known for active living, friendly neighbors, and resort-style amenities that make every day feel like a vacation.This home has been thoughtfully updated so you can move right in with confidence. One of the biggest improvements is the brand-new architectural shingle roof, designed to withstand winds up to 175 MPH—a huge value and peace-of-mind upgrade. Inside, you’ll immediately notice the refreshed, modern feel thanks to new flooring throughout, plus drywall upgrades in the kitchen and living room, replacing traditional paneling for a brighter, cleaner look.The kitchen is both functional and inviting, featuring all-new stainless steel appliances and a convenient drop-leaf table—perfect for morning coffee, casual meals, or entertaining. The home also includes a mini bar, creating the perfect space for hosting friends and family. The primary bedroom is ready for comfort from day one with a brand-new king bed and mattress included.To make ownership even easier, the seller is providing a home warranty to the buyer.Life in Oakwood Estates is all about lifestyle. Residents enjoy an incredible list of amenities including a lake for water activities, a heated community pool, clubhouse, tennis, pickleball, shuffleboard, mini golf, and a full calendar of community events and activities designed to keep you as social—or as laid back—as you’d like.Whether you’re looking for a seasonal getaway or a full-time Florida lifestyle, 4420 Limewood St offers the perfect blend of upgrades, comfort, and community living in one of Winter Haven’s most established 55+ communities.

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Chris Loschiavo (863-280-2201)

Remarks: You finally have freedom & privacy without the constraints of an HOA & it's USDA Eligible which is a rare find! This charming home is situated on a half-acre of dry, high-fenced land, providing the perfect blend of comfort, space & security. The home boasts a 2016 durable metal roof, new Pergo flooring, updated Cold AC, updated plumbing, 50 gallon 2023 water heater and fresh paint inside & out. Perfect for entertaining with open floorplan with large kitchen, breakfast bar, living room, split-bedroom layout and large, screen/window back porch with brick extended patio and outdoor brick grill. One of the highlights of this home is its prime location, backing up to over 300 acres of tranquil woods. Say goodbye to backyard neighbors and look forward to waking up to the sounds of nature, enjoying your morning coffee in a peaceful setting. But that's not all! Calling all car guys! The property comes with a Huge 24’ x 24’ x 13.6’ high garage/shed with INSULATED ceiling and walls. Constructed for 150 mph hurricane winds on a slab with every post 4 ft deep in concrete. It provides ample space & electricity for a shop to work on your cars, RV, boat, recreational toys, storage or a home business. Plus, there is a carport on slab attached to another shed for combined area 43’ x 45’ with privacy fence shielding the back yard. Irrigation system in front and back yard. Conveniently located with easy access to the Parkway & i-4, making commutes to Lakeland, Orlando or Tampa a breeze. Don't miss out on this fantastic opportunity – make this home yours and embrace a lifestyle of comfort, tranquility, and freedom with no HOA! Call today to schedule your private showing!

Listing is courtesy of: KELLER WILLIAMS HERITAGE REALTY (407-862-9700)

Listing Agent: Sheryl Manche (386-882-2121)

Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Welcome to this beautiful 3-bedroom, 2-bathroom block home perfectly positioned at the end of a quiet cul-de-sac in Winter Haven's sought-after Cypress Gardens neighborhood. With 1,400 square feet of interior living space and a layout designed for both comfort and connection, this home checks every box. Step inside and you're immediately greeted by a bright, open floor plan where the living room, dining area, and kitchen flow together seamlessly ideal for everyday living and effortless entertaining. The kitchen is generously sized, featuring an abundance of cabinetry and two lazy Susan's that maximize every inch of storage. Natural light floods the home through an impressive array of windows, and sliding glass doors in the main bedroom, middle bedroom, and living room all open directly onto the crown jewel of this property: a stunning 47 x 15 screened-in patio complete with a bar area, built-in grill, refrigerator, and cabinetry. Whether you're hosting guests or simply enjoying a quiet Florida evening, this outdoor space delivers. Both bathrooms have been tastefully updated. The guest bath features a brand-new tub and shower installed by Westshore Homes in October 2025, along with a new vanity, mirrored medicine cabinet, cabinet above the toilet, and new toilet. The main bathroom has also been refreshed with a new mirrored medicine cabinet, cabinet above the toilet, and new toilet. Major systems are all squared away brand-new roof in 2025, A/C replaced in 2021, and water heater from 2018 offering true peace of mind from day one. The home is also pre-wired for a generator, a smart bonus for Central Florida living. The attached garage includes a dedicated laundry and storage room with extensive shelving, and the washer and dryer convey with the home. Set on an 8,537 square foot lot at the end of a tucked-away cul-de-sac, this property offers the rare combination of privacy, space, and convenience. Just minutes from US-27, LEGOLAND Florida Resort, Winter Haven Hospital, Polk State College, and the renowned Chain of Lakes, everything Central Florida has to offer is right at your doorstep. Homes this move-in ready, this well-maintained, and this well-located don't stay on the market long schedule your private showing today! Offers may be entered ONLINE through Monday, April 20, 2026 at 2:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.

Listing is courtesy of: NEW HEIGHTS REALTY GROUP (407-934-0305)

Listing Agent: Daniel Rodriguez (407-934-0305)

Remarks: REDUCED!! Winter Haven Single Family Residential home, 3B/1ba offers a well landscaped Corner Lot. The Interior accommodates Electric AC & natural gas heat. This home still boasts original well maintained kitchen cabinets & oven appliances. The Exterior features are Concrete Block Detached storage/workshop 20x14’, covered carport 20x12’, exterior lighting,pvc plumbing, irrigation well/pump, pole barn for RV parking 28x20’ and outside carport laundry room, This home offers updated plumbing and abundant parking. Pride of Ownership. A must see!

Listing is courtesy of: WATSON & WATSON INC REALTORS (863-294-4149)

Listing Agent: Wendy Gibbs (863-557-5249)

Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath condominium. It's located in the highly sought-after 55+ Imperial Harbor community of Winter Haven. Convenient elevator access makes daily living effortless in this serene lakefront retreat. Start your mornings with a walk to the private community dock on Lake Howard, where fishing and boating await. Enjoy an array of resort-style amenities, including a heated pool, fitness center, shuffleboard, and billiards, all designed to support an active and relaxed lifestyle. Ideally situated just 45 minutes from both Tampa and Orlando, this central location offers the perfect balance of tranquility and accessibility. Inside, the open and airy floor plan feels inviting and relaxing. Refinished cabinets, fresh paint throughout and new double pane insulated windows make this home move-in ready! The primary suite is bright and spacious and two additional bedrooms provide flexibility for guests, hobbies, or a home office. An in-unit laundry closet with washer and dryer adds everyday convenience. HOA fees also include water, basic cable, and internet—making this an exceptional opportunity for low-maintenance, carefree living. Schedule a private tour today !

Listing is courtesy of: KELLER WILLIAMS TAMPA CENTRAL (813-865-0700)

Listing Agent: William Kilpatrick (863-669-8090)

Remarks: Auction Property. ***Auction will run April 27th 2026- May 7th 2026 *** 2 bedroom 1 bathroom house ***All property information to be verified by buyers*** Property is sold with any outstanding code violations, liens, or expired permits. Buyer to do own research prior to bidding.

Listing is courtesy of: A BETTER LIFE REALTY (727-521-7378)

Listing Agent: Tony Kelly (863-287-4672)

Remarks: BIG PRICE REDUCTION – $7,000! Recently Fully Renovated Townhouse – Move-In Ready! Seller offering $4,000 credit toward buyer’s closing costs or interest rate buydown. Don’t miss your chance to own this completely remodeled 2-bedroom, 2.5-bathroom townhouse in Park Lake, now available at an unbeatable price! This home has been beautifully updated from top to bottom, offering modern style and worry-free living: All 3 bathrooms fully renovated with fresh, modern finishes Brand-new kitchen featuring stainless steel appliances (refrigerator, gas range, range hood, microwave), new sink & faucet, New A/C system & new gas water heater for comfort and efficiency Fresh paint throughout (walls, doors, and closets), New vertical and window blinds, New ceiling fans with remote controls and stylish light fixtures in every room, balcony, and lanai, Garage floor freshly painted for a clean, polished look, Washer and dryer included. The spacious main living area is filled with natural light and opens to an extra-large screened lanai, perfect for entertaining or relaxing outdoors. Upstairs, both bedrooms are oversized with private bathrooms, and the primary suite features its own screened balcony. All 3 Bathrooms are renovated, brand new vanities. Prime Winter Haven Location! Next to the new collegiate baseball stadium and parks project, bringing $60M in growth to the city, Direct access to Lake Lulu, part of the Chain of 22 Lakes for boating, fishing, and outdoor fun, Walking distance to dining and shopping: Starbucks, Chick-fil-A, Panera, Outback, Red Lobster, Steps from the Rowdy Gaines Olympic Pool and Advent Fieldhouse, This townhouse is truly move-in ready—all major upgrades are already completed. Perfect as a primary residence, vacation home, or investment property in one of Winter Haven’s most desirable communities. Schedule your private showing today!

Listing is courtesy of: HIGDON HOMES REALTY LLC (863-209-2543)

Listing Agent: Fatma Higdon (863-209-5243)

Remarks: Under contract-accepting backup offers. Welcome to this inviting 3 bedroom, 2 bath home with 1,860 sqft of living space in one of Southeast Winter Haven’s desirable neighborhoods. Enjoy a spacious family room surrounded by large glass windows on three sides, flooding the home with natural light and providing a perfect spot to relax or entertain. The cozy living room features a fireplace with built-in bookshelves, creating a warm and welcoming atmosphere. Enjoy a fully fenced backyard, offering privacy and plenty of space for outdoor living, gardening, or pets. Located in a sought-after area, this home combines comfort, character, and convenience—close to schools, shopping, dining, Legoland and all that Winter Haven has to offer. Don’t miss the opportunity to make this beautiful property your own—schedule your showing today!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Opportunity is knocking in Winter Haven! This 2-bedroom, 1-bath single-family home offers the perfect canvas for investors, flippers, or buyers looking to build instant equity. The property needs work, which is exactly where the upside lies — bring your vision and your contractor, and turn this into a solid rental or a profitable resale. Located in a quiet, established residential neighborhood with a close-knit community feel, you're just minutes from US Hwy 17, local dining, shops, and all that Winter Haven has to offer. Winter Haven continues to grow, making this an ideal time to plant your flag in Polk County. Priced for the market it is — don't sleep on this one.

Listing is courtesy of: ENCORE INVESTMENT REALTY (407-334-8664)

Listing Agent: Desmond Pollock (407-334-8664)

Remarks: Check out this well maintained home located in Oakwood Estates, a 55+ community, located in Sunny central Florida. The home features a very open and inviting kitchen, perfect for entertaining. The cooktop and built in oven have been updated. Step into the primary bedroom to find plenty of space for a king size bed, then step into the remodeled and updated primary bathroom. The split bedroom floor plan offers privacy to guests with a bathroom conveniently located outside the door. All the flooring is a laminate with no carpeting in the home. Enjoy the peaceful screened side porch. The home is located on a corner lot with a Florida room giving views of both streets, a great place for your morning coffee. The double pane windows and window AC offers additional living space when guests arrive. Oakwood Estates offers many amenities and activities. You can be as busy as you would like or enjoy the peaceful community and watch the world go by.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Kathy Devor (573-450-1679)

Remarks: One or more photo(s) has been virtually staged. SELLERS are MOTIVATED! Just made a big price reduction! The moment you walk up you’ll discover your own private & peaceful setting under the paved Pergola area incorporated with a running fountain pond awaiting more koi fish. You’ll enjoy your shaded space with the feel & sounds of nature surrounding you. Your entire home is equipped with installed roll-up hurricane shutters (some are hardwired for a flip of a switch, and some are manual). If you love to cook, you’ll love this chef’s dream kitchen offering plenty of cooking/prepping countertop space. Kitchen has an island with electric, gas range, wide breakfast bar open to the living areas and a walk-in pantry. This home offers a split plan layout, wide hallways, ceiling fans, recessed lighting, large closets, high 10 ft ceilings throughout. You will find you have multiple uses of living/family/dining /office areas. The options are endless. Main bedroom has 2 walk-in closets and access to the nice screened-in back patio. The main bedroom bathroom offers a double sink make-up vanity, walk-in shower, and a linen closet. The 2nd full bathroom offers a shower/tub combo with access to the back screened-in patio. The half bathroom is located off the entry to bedroom #3. The inside utility room is equipped with shelving, a utility sink, a cabinet unit, and a built-in ironing board. New luxury vinyl plank flooring in the utility room and bedroom #3. If all this wasn’t enough there is more…. You will love enjoying the 11x25 covered & screened-in back patio. Your front entryway is also covered. The 2-car garage has a newer electric garage door opener, shelving on both sides & a cabinet for storage. It also provides a keyless touchpad for access from the outside. NEW A/C April 2026. Ring doorbell. You won’t want to miss the 12x14 workshop/shed equipped with electric, a work bench, storage shelving, and an access ramp. Your home is situated on a beautiful lot with mature landscaping. The lawn and landscaping is beautiful and will snap back as we just had the FL record-breaking cold front when pictures were taken so see past that. It will all green up beautifully in no time. Lawn irrigation is on a well water system equipped with a timer system. NO HOA!!! Home has been overhead plumbed. All of this conveniently located close to the 570 Toll Rd taking you to Orlando/Tampa. Be sure to check back for the virtual tour link coming soon and will be attached to the listing. Welcome Home!

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Jennifer Smith (863-559-1229)

Remarks: Price Improved! Seller is motivated... Welcome to 740 Squires Grove Dr. This beautiful 5 bedroom, 3 bath residence offers the space you've looking for, filled with natural light and and large fenced backyard ideal for gatherings, pets or relaxing outdoors. Well located near shopping, dining, hospitals, major highways, and just minutes from LEGOLAND. Book your showing today!

Listing is courtesy of: NORTHGROUP REAL ESTATE, INC (561-222-1850)

Listing Agent: Lulis Batista (407-969-2098)

Remarks: Being sold as is. Fixer upper needs a new owner willing to give it some TLC. Cash or renovation loan only.

Listing is courtesy of: SWAN CITY REALTY LLC (863-535-7271)

Listing Agent: Tonya Lockamy (863-535-7271)

Remarks: Welcome to 104 CAVALIER ROAD IN WINTER HAVEN!! This 3 Bedroom, 1 Bath offers plenty of Space and is situated on an Overzized FENCED (0.15 Acre) Lot! 21x21 Living Room, Dining Room, Cute Kitchen with little eat in area, Exterior Laundry Room located right off the Kitchen and 2 Huge Storage Bays out back! NO HOA and No Restrictions! Home needs only a small touch of TLC.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Natalie Patten (863-508-5055)

Remarks: Located in the new Residences at Winter Haven community, this home features the Everglades model floor plan, designed with an open-concept layout that maximizes natural light and functionality. The home backs directly to the community pond, offering water views and added privacy. Built with double-pane insulated windows and constructed in compliance with the current Florida Building Energy Efficiency Code, the home offers modern efficiency standards. Residences at Winter Haven is a newly developed single-family home community conveniently located near shopping, dining, major roadways, and everyday conveniences. There is a natural ease to this home, from the open layout to the thoughtful finishes. The 8-foot doors and premium flooring flow throughout the main living areas, creating a clean and consistent feel. In the kitchen, the focus is on quality and gathering, highlighted by a large waterfall island and 42” cabinetry with crown molding. It’s a home designed for both quiet mornings and hosting friends, with an open living area that leads out to a covered lanai. It’s a clean, modern space that’s ready for you to make it your own. A model home is available for on-site visits within the community.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Rodrigo Gomes De Almeida (407-837-8173)

Remarks: Short Sale. Don’t miss the opportunity to own this one-of-a-kind, 3-bedroom, 2-bathroom, 2-car garage custom home. Upon arriving at the property, you are greeted by an oversized lot and mature trees in a quiet, well-established neighborhood. Inside, the home offers an open and split floor plan, cathedral ceilings, and an indoor/outdoor pool that flows from the back patio into the living room, adding a unique feature to this property—perfect for entertaining and allowing you to take a dip in any weather. On the left side of the home are two spacious bedrooms with large closets and a shared bathroom featuring a single vanity and a shower/tub combo. Moving to the right side of the house, you’ll find the master suite, loft, and kitchen. The master suite offers ample space and direct access to the pool area. The en-suite bathroom includes a garden tub and walk-in shower. The loft overlooks the living room and pool area and also contains two large storage spaces on either side, making storage accessible while serving as a great spot to watch a show and unwind. The kitchen features tile countertops and a small bar for additional seating. Right out back, the pool is enclosed in a full-screen cage with a large deck. The yard also boasts a shed for storage and plenty of space for activities. This home has so much to offer. Don’t wait—schedule your private showing today!

Listing is courtesy of: LPT REALTY LLC (386-388-7877)

Listing Agent: Trent Shackelford (941-518-7875)

Remarks: NO HOA | NO CDD | Move-in ready! Hi there! - I’m 2519 Avenue E SW, but you can call me home. I’m a new construction block home with 3 bedrooms, 2 bathrooms, and 2,063 sq ft of thoughtfully designed living space — plus a 2-car garage and NO HOA or CDD, giving you more freedom and affordability. I was built with comfort and style in mind. My high ceilings and large windows fill every room with natural light, creating a bright and welcoming atmosphere. My open-concept layout makes it easy to gather, entertain, and enjoy everyday living. My kitchen is one of my favorite features — a beautiful island space with granite countertops, stainless steel appliances, and plenty of cabinet storage, perfect for cooking, hosting, and making memories. When it’s time to unwind, my primary suite offers a peaceful retreat with a spacious bathroom, double vanity, elegant finishes, and a walk-in closet ready for you to make your own. I also have a dedicated laundry room, ceiling fans, and wood flooring throughout for added comfort and convenience. I’m located in a growing area of Winter Haven, just minutes from shopping, dining, parks, and major highways, making everyday living easy and connected. I’m move-in ready and excited to meet my new owners. Come take a look — I think we might be the perfect fi!

Listing is courtesy of: SIVEN PREMIER REAL ESTATE (813-419-7009)

Listing Agent: Fanta Traore (863-282-9602)