Refine Search
Sort by
4158 Rolling Oaks Drive, Winter Haven
$119,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Walk right in to this fully furnished home located in Oakwood Estates, a 55+ community. The kitchen is laid out perfect for entertaining and contains a large pantry for storage. The living area is open and spacious with cathedral ceilings to make it feel even more open. The area currently used for a dining area could also be used as a family room or second living area. The primary bedroom can easily accommodate a king sized bed. The walk in closet offers plenty of space for all your clothes. The air conditioner is approximately 4 years old and the roof over offers extra insulation value to the home. Oakwood Estates offers many activities and amenities to keep you as busy as you would like, or just sit back and enjoy the peaceful community.

4158 Rolling Oaks Drive, Winter Haven

4840 Old Lucerne Park Rd, Winter Haven
$400,000
3 Beds ⋅ 2 Baths ⋅ Lucerne Shores SubDv. ⋅ 33881 Zip Code
Relax and Enjoy Lakefront Living on Beautiful Lake Lucerne! Situated on 0.84 acres, this updated 3-bedroom, 2-bath home offers stunning views of Lake Lucerne from the second-floor balcony, wraparound deck, screened porch, and spacious backyard. Even better, all three bedrooms feature sliding glass doors overlooking the lake, bringing the beauty of the waterfront indoors. The inviting living room showcases a stone fireplace with cedar wood walls to accent, creating warmth and rustic charm. Numerous updates include fully remodeled bathrooms, refreshed kitchen, new flooring throughout, new interior doors, roof (2019), A/C (2017), tankless hot water heater (2024), and water softener. Whether you're relaxing on the porch, entertaining on the deck, or simply enjoying the peaceful lake views, this property offers the perfect blend of comfort, character, and waterfront living. This home is in a successful vacation rental program and is being offered turnkey and ready to go for the next home owner or an investor interested in continuing the rental opportunity. Don't forget to view the attached 3-D Interactive Tour for a virtual walkthrough of the home.

4840 Old Lucerne Park Rd, Winter Haven

151 1st Street, Winter Haven
$249,000
3 Beds ⋅ 2 Baths ⋅ Leslie J A Sub SubDv. ⋅ 33880 Zip Code
Virtually Staged. NO HOA !!!!! BUILT IN 2023 - Welcome to this beautifully maintained 3-bedroom, 2-bath home built in 2023. Situated at the end of a quiet dead-end street, this property offers a functional layout with an open-concept living area designed for comfortable everyday living and entertaining. The kitchen features granite countertops, a large breakfast bar, ample cabinet space, and a spacious pantry. The primary bedroom features en-suite and living areas are filled with natural light, creating a bright and inviting atmosphere throughout the home. Outside, enjoy a generously sized backyard with banana and mature trees providing shade and privacy, along with a storage shed for additional convenience. The attached one-car garage adds extra storage and parking flexibility. Conveniently located near shopping, dining, schools, major roadways, and the many amenities Winter Haven has to offer, this move-in-ready property presents an excellent opportunity for homeowners and investors alike.

151 1st Street, Winter Haven

3250 Dundee Road, Winter Haven
$1,550,000
33884 Zip Code
Income producing property located on 1 acre. This well-maintained commercial property on Dundee Road in Winter Haven offers an exceptional opportunity for investors and future owner-users alike. The main building encompasses approximately 7,341 square feet of office and production space and is currently leased to a printing company, providing immediate income potential. Featuring strong visibility with an estimated traffic count of 19,000 vehicles per day, the property is equipped with six central air conditioning units, serving the entire main building. The interior includes three private offices, a conference room, server room, break room, and separate men's and women's restrooms, with the remaining space dedicated to printing operations. The building is serviced by three-phase power electric service through TECO, city water and sewer, telephone & internet, making it suitable for a wide range of commercial uses. There is a John Deere powered diesel generator for back up power needs. Constructed of durable cinder block and brick, the property features ceiling heights of 10 and 12 feet, an 8-foot-wide by 7-foot-tall drive-up door, and a 10-foot-wide by 12- foot-tall dock-high loading door. Additional improvements include an 800- square-foot block storage building and a 400-square-foot storage shed. The site provides 20 designated parking spaces, with additional parking available in the rear. The roof was replaced approximately four years ago, adding to the property's value and appeal. Investors can continue to benefit from the existing tenant, while future owner-users may have the opportunity to occupy the property upon lease expiration. Please contact the listing agent for current lease terms and additional details.

3250 Dundee Road, Winter Haven

265 Majestic Gardens Lane, Winter Haven
$294,999
3 Beds ⋅ 2 Baths ⋅ Gardens Ph 01 SubDv. ⋅ 33880 Zip Code
Located in a desirable gated community on a oversized corner lot, paved driveway and low HOA fee and convenient access to everything Central Florida has to offer. 3 BEDROOM WITH OFFICE! This spacious and well-maintained home offers flexibility, comfort, and thoughtful upgrades throughout. Step inside to discover a bright and airy floor plan featuring a spacious living room with soaring vaulted ceilings and an open-concept design perfect for both everyday living and entertaining. The kitchen overlooks the main living area, creating a seamless flow, and features solid wood cabinetry, ample counter space, and plenty of storage. The versatile office can easily be converted into a fourth bedroom, providing additional space for family, guests, or a home office. The spacious primary suite is a true retreat, complete with elegant tray ceilings and a luxurious en-suite bathroom featuring dual vanities, a relaxing garden tub, walk-in shower, and a large walk-in closet. Additional highlights include a roof replaced in 2022, two AC units for enhanced comfort and efficiency, a large rear lanai perfect for outdoor relaxation, and a storage shed offering extra space for tools and equipment. Ideally situated in Winter Haven, you'll enjoy easy access to excellent shopping, dining, and entertainment options. Popular destinations include the vibrant downtown Winter Haven district, numerous waterfront restaurants along the Chain of Lakes, and shopping at nearby centers featuring national retailers and local boutiques. Outdoor enthusiasts will appreciate the area's beautiful lakes, parks, boating opportunities, and recreational amenities. Families and visitors alike will enjoy being just a short drive from LEGOLAND Florida Resort, one of Central Florida's premier attractions. Whether you're looking for a growing family home, extra space for remote work, or simply a peaceful gated community lifestyle, this exceptional property offers the perfect combination of location, value, and functionality. SELLER OFFERING A FLOORING CREDIT!

265 Majestic Gardens Lane, Winter Haven

Lake Blue Drive Nw, Winter Haven
$109,000
Inwood SubDv. ⋅ 33881 Zip Code
Build your dream home on this beautiful 0.25-acre Lakefront lot located on Lake Blue Dr NW in the established Inwood community of Winter Haven, Polk County. Offering Direct Frontage on scenic Lake Blue, this waterfront parcel presents a rare opportunity to enjoy lakefront living in the heart of Central Florida. Zoned RL-3 Residential, the property is suitable for a single-family residence or modular home. The lot features approximately 10,720 square feet, paved road frontage, electricity available at the street, nearby city water, and private septic service. With direct lake access and beautiful water views, this property is ideal for a custom home, seasonal retreat, or long-term investment. Enjoy the Florida waterfront lifestyle with opportunities for boating, fishing, kayaking, paddleboarding, and relaxing lake views right from your backyard. Located within a designated Opportunity Zone, the property offers additional long-term investment appeal while remaining conveniently situated near major transportation corridors, including Havendale Boulevard (SR 544), US Highway 92, US Highway 17, and Interstate 4, providing excellent connectivity throughout Central Florida. Conveniently located approximately 10 minutes from Downtown Winter Haven, 15 minutes from Auburndale, 20 minutes from Lakeland, 35 minutes from Walt Disney World, 50 minutes from Orlando International Airport (MCO), and approximately 1 hour from Tampa International Airport (TPA). Nearby amenities include Publix, Walgreens, Wawa, Planet Fitness, restaurants, medical facilities, shopping, entertainment, and everyday conveniences. No HOA. Direct lake frontage. Opportunity Zone location. Paved road access. City water nearby. Electricity available. Financing available with as little as 20% down for qualified buyers.

Lake Blue Drive Nw, Winter Haven

301 Terranova Boulevard, Winter Haven
$379,900
4 Beds ⋅ 2 Baths ⋅ Terranova Ph 04 SubDv. ⋅ 33884 Zip Code
Discover this spacious 4-bedroom, 2-bath, 1,960 SqFt home in the gated Terranova community of Winter Haven, offering the comfort, privacy, and location today’s buyers are looking for—all just minutes from LEGOLAND Florida Resort. Step inside to an inviting and functional layout with generous living spaces designed for everyday comfort and entertaining. Outside, enjoy your own private retreat with a fully fenced backyard and relaxing spa/jacuzzi—perfect for unwinding after a long day or enjoying Florida living year-round. Terranova offers the added benefits of gated access, NO CDD, and a low HOA, providing an attractive combination of community living and affordability. The home is conveniently located near shopping, dining, medical facilities, schools, entertainment, and major Central Florida destinations. The property is equipped with leased solar panels. The solar will be transferred to the buyer subject to the solar provider’s requirements and approval. Additional information regarding the solar is available upon request. Ask about available financing and down payment assistance options that may help make homeownership more accessible. Schedule your private showing today and discover everything 301 Terranova Blvd

301 Terranova Boulevard, Winter Haven

203 Avenue C  Ne, Winter Haven
$75,000
Winter Haven Heights SubDv. ⋅ 33881 Zip Code
Prime mixed-use redevelopment opportunity in one of Winter Haven’s most strategic growth corridors. Located directly across from Winter Haven Hospital, this vacant parcel offers exceptional potential for investors, builders, and developers seeking a highly visible location with strong future redevelopment potential. The property is situated within a Mixed-Use (MU) district that allows up to four residential dwelling units per lot and building heights of up to four stories, providing flexibility for residential, mixed-use, or income-producing projects. Its proximity to major employment centers, healthcare facilities, retail, dining, and downtown Winter Haven further enhances its long-term investment appeal. An exceptional opportunity exists to expand the development footprint through the acquisition of the adjacent parcel at 204 Ave C NE (see separate MLS#O6413665), as well as 209 Ave C NE (coming soon), creating the potential for a larger multi-parcel redevelopment project in a rapidly evolving area. Opportunities to assemble contiguous properties in such a strategic location are increasingly limited. Whether acquired individually or as part of a larger assemblage, this vacant parcel presents a compelling opportunity for developers and investors seeking density, flexibility, and a premier location directly across from one of the region’s largest healthcare campuses.

203 Avenue C Ne, Winter Haven

4132 Sprucewood Street, Winter Haven
$124,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Location! Location! Location! This beautiful fully furnished home in Oakwood Estates is located next to the pool, tennis courts, and smaller clubhouse. Walk into the lanai as you enter the home. Once inside the home you will find a cozy family room and an open and and appealing kitchen just perfect for entertaining. The living room beyond the kitchen is open and spacious. The refrigerator was new in 2025. The guest bedroom opens onto the guest bath giving your overnight guest their own bathroom. The primary bedroom is large enough for a king sized bed, plus lots of closet storage space. The laundry with new washer and dryer is located inside the home. The roof was done in 2019 and the air conditioner in 2024. And if that isn't enough, there is new carpet throughout the home. Oakwood Estates is a 55+ community offering many activities and amenities. You can stay as busy as you would like, or just sit back and watch the world go by.

4132 Sprucewood Street, Winter Haven

1302 Lake Elbert Dr Se, Winter Haven
$589,500
5 Beds ⋅ 5 Baths ⋅ Elbert Hills SubDv. ⋅ 33880 Zip Code
Come and See this Amazing Lake Front Home Located in the Water Skiing Capital of the World, on Lake Elbert in Winter Haven, FL. As you enter the front door of this beautiful Home the hardwood floors will delight your eyes as you look down the long foyer to the right that leads pass the kid's 2 Bedrooms area for them to enjoy, to a large Family room with Lake Views that will be one of your favorite places to relax. Going back down the foyer you will end up seeing the 1st floor Master King Ensuite with Lake views and a private bathroom on the left, and the Stunning Gourmet Kitchen on the right flowing into a light-filled Dining Sunroom with Lake Views, perfect for entertaining. This Home is the ideal home to Live in full time, or Enjoy it here during your favorite time of the year, or use it for a short term rental or longer term while you're at your other home. This Home easily sleeps 10 with it's 5 Bedroom, 4.5 Bathrooms, a kid's area that will sleep 4, while the Adults can appreciate 3 King Master Ensuites with their own Bathrooms. The kid's 2 bedrooms area with a bathroom circles back with a door into the Kitchen, the HUB of the home. You can go out the rear door to the nice patio and the 2 car Garage / Game Room that also has the Laundry Room and a Full Bathroom with a walk in Shower. Back inside, going up to the 2nd floor you have a door going out to the balcony in the front of the home over the 1st floor patio that allows for the peaceful Lake views. The other 2 Master King Ensuites with Walk in Closets and Private Full Bathrooms. Sitting on almost 1/2 acre on a hill up from the Lake, this AMAZING HOME with so much to love and could be Yours's to ENJOY all year or create a Great Cash Flow for your Retirement. It is only about a 10 minutes drive to LEGOLAND, and aproxamently 30 minutes or so to DISNEY WORLD, UNIVERSAL STUDIOS, SEA WORLD, and OTHER PARKS, and only about 1.5 hours to the BEAUTIFUL FLORIDA BEACHES OR EITHER SIDE OF THE STATE. Come and See this Amazing Home the is Priced to SELL.

1302 Lake Elbert Dr Se, Winter Haven

445 Talamone Drive, Winter Haven
$519,990
5 Beds ⋅ 3 Baths ⋅ Tuscany At Winterset SubDv. ⋅ 33884 Zip Code
Unfurnished and move in ready! Nestled within the exclusive gated community of Tuscany, a charming neighborhood of just 19 homes in Southeast Winter Haven, this 5 bedroom, 3 bath pool home offers over 3,300 square feet under roof on a private 0.33 acre lot. Designed for both comfortable living and entertaining, the home features a dedicated office, formal dining room, living room, and an impressive 25' x 17' poolside bedroom / bonus room complete with a custom wall-to-wall hardwood entertainment center, surround sound, upgraded lighting, tile flooring, and ceiling fan. The spacious kitchen showcases abundant Kraft Maid cabinetry, granite countertops, generous workspace, and a sunny breakfast nook overlooking the pool. A thoughtfully designed triple-split bedroom floor plan provides privacy for family and guests, while multiple access points lead to the screened pool and outdoor living areas. The spacious primary suite features a double-sink vanity, garden tub, separate shower, private water closet, and oversized walk-in closet. It also as access to the pool area. Additional highlights include hand-scraped real wood flooring throughout most of the home, including the primary suite, an outdoor summer kitchen with built-in gas grill, sink, and refrigerator, indoor laundry room, oversized two-car garage, expanded driveway with parking for up to eight vehicles, a separate entrance to the bonus room, and mature landscaping with an irrigation system on a dedicated meter. The large private backyard offers plenty of space beyond the screened pool area, creating a peaceful retreat while remaining conveniently located less than a mile from schools and Publix supermarket. Experience this exceptional property like never before with a 3D Interactive Virtual Tour or Virtual Reality featuring a 2D Floor Plan and immersive 3D Dollhouse Model, plus a 360-degree Interactive Aerial Virtual Tour showcasing the entire Tuscany community and panoramic views as far as the eye can see. The home features a stunning collection of modern gold crystal chandeliers throughout, including a 23.6" dimmable LED crystal chandelier with adjustable color temperatures in the hallways and kitchen, an elegant gold crystal flush-mount chandelier in the master bedroom, a large modern crystal LED chandelier that serves as a beautiful focal point in the living room, and a luxurious 40" gold rectangular crystal chandelier with 16 lights above the dining area, creating a cohesive, contemporary design with lighting and timeless elegance throughout the home. Meticulously maintained, this one-of-a-kind pool home is a rare opportunity to own a beautiful property in one of Southeast Winter Haven's most desirable gated communities.

445 Talamone Drive, Winter Haven

2049 San Marcos Drive Se Unit 127, Winter Haven
$149,900
1 Beds ⋅ 1 Baths ⋅ Park Lake 03 02 Amd SubDv. ⋅ 33880 Zip Code
MUST SEE! Discover this beautifully remodeled first-floor condo with NO STAIRS to climb, offering the convenience and comfort of true single-level living. Perfect for year-round residents, seasonal owners, or anyone seeking easy accessibility, this move-in-ready home combines modern updates with an exceptional lifestyle in one of Winter Haven's most desirable lakefront communities. Located just steps from the community clubhouse, pool, fitness room, mailboxes, and parking, you'll enjoy maintenance-free living with outstanding amenities right outside your door. Park Lake residents also enjoy access to a private dock, gazebo, and beautiful waterfront views of Lake Lulu, part of the world-famous Winter Haven Chain of Lakes, providing opportunities for boating, fishing, and enjoying Florida's natural beauty. The nearby Chain of Lakes Complex and baseball fields add to the recreational appeal. Inside, soaring vaulted ceilings in the living room, dining area, and primary bedroom create a bright and spacious atmosphere. The screened lanai offers dual entry points and the perfect place to enjoy your morning coffee or evening breeze. Major renovations completed in December 2022 include stylish kitchen cabinetry, granite countertops, under-counter refrigerator, induction cooktop, and ceramic tile flooring throughout. Additional upgrades include impact-resistant windows, a new A/C system with UV light, Nest security system, and a new washer and dryer. The location is hard to beat, with restaurants, shopping, banking, medical facilities, downtown Winter Haven, and LEGOLAND Florida all just minutes away, making this home ideal for both full-time living and seasonal enjoyment. Whether you're looking for a primary residence, winter retreat, or investment opportunity, this beautifully updated condo offers affordability, convenience, lakefront amenities, and a truly carefree Florida lifestyle. Seller financing and Private Financing Available! Do not wait, it will not last long!

2049 San Marcos Drive Se Unit 127, Winter Haven

217 4th Jpv Street, Winter Haven
$214,000
3 Beds ⋅ 1 Baths ⋅ Jan Phyl Village Unit 03 A SubDv. ⋅ 33880 Zip Code
Welcome to this beautifully updated 3-bedroom, 1-bath home in Winter Haven! Move-in ready and filled with recent improvements, this property offers comfort, style, and peace of mind. The kitchen was completely updated in May 2025 with new cabinets, granite countertops, and sink, creating a fresh and modern space for everyday living. Major system upgrades include a new roof with warranty (April 2025), new electrical panel with warranty (May 2025), new hot water heater (September 2024), and updated A/C coils and air handler box (January 2024). New flooring installed in October 2025 adds to the home's updated appeal. The living area features a built-in entertainment center with fireplace, added in March 2025, creating a cozy focal point for relaxing or entertaining. Step outside to enjoy the screened back patio, where you'll also find the laundry area for added convenience. Conveniently located near shopping, dining, schools, and major roadways, this well-maintained home is ready for its next owner. Schedule your private showing today!

217 4th Jpv Street, Winter Haven

3038 Thornhill Road, Winter Haven
$350,000
3 Beds ⋅ 2 Baths ⋅ Orange Hill Sub SubDv. ⋅ 33880 Zip Code
SELLER INCENTIVE – 2/1 MORTGAGE RATE BUYDOWN AVAILABLE! Buy this home and enjoy lower mortgage payments for the first two years! The seller is offering help toward a temporary mortgage rate buydown that may lower your monthly payments. This offer is subject to buyer qualification, lender approval, loan guidelines, and agreed-upon terms. This new construction build sits on almost an acre (.72) and is a comfortable and cozy home with 3 bedrooms, 2 bathrooms and 1,467 square feet of living space. The foyer opens to the spacious dining and great rooms, with raised ceilings throughout the home, and there's convenient access to the outdoor patio from the living space. The kitchen features a large island. The primary bathroom boasts a separate shower and tub, and this home comes equipped with ample storage space including two oversized primary walk-in closets, a pantry in the kitchen, a linen closet and a coat closet. The 2-car garage provides additional storage and laundry space. This home is located in a quiet neighborhood off Winter Lake Rd, close to all of the amenities Lakeland or Winter Haven have to offer! With no HOA, there's room for your boat, RV, or other outdoor vehicles. USDA FINANCING AVAILABLE FOR ELIGIBLE BUYERS, WITH NO MONEY DOWN. CALL TODAY FOR MORE DETAILS.

3038 Thornhill Road, Winter Haven

996 Summer Glen Drive, Winter Haven
$289,900
4 Beds ⋅ 2 Baths ⋅ Coventry Cove Ph Il SubDv. ⋅ 33880 Zip Code
Come and see this move-in ready four-bedroom, two-bathroom home in the lovely Coventry Cove neighborhood. This home features a spacious open floor plan that seamlessly connects the living spaces for a highly functional and airy feel. The updated kitchen boasts beautiful granite countertops and stainless steel appliances, keeping the chef of the family engaged with the rest of the home. A well-appointed bathroom includes the convenience of a double vanity. Step outside to enjoy a private, fully fenced-in backyard that serves as a perfect space for outdoor entertaining or relaxing. Ideally located in Winter Haven, this home offers easy access to excellent shopping, dining, and vibrant local attractions. One or more photos in this listing have been virtually staged. Schedule your private showing today!

996 Summer Glen Drive, Winter Haven

1716 Terry Circle Ne, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Buckeye Haven SubDv. ⋅ 33881 Zip Code
Beautifully maintained, fully furnished home in Winter Haven offering a move-in-ready opportunity for a primary residence, seasonal home, or investment property. The home features ceramic tile flooring throughout, updated bathrooms, and an open floor plan with spacious living and dining areas. The kitchen offers breakfast bar seating and stainless steel appliances. The split-bedroom layout provides added privacy for the primary bedroom. Furnishings and décor are included, creating a convenient turnkey opportunity. The roof is approximately five years old. No HOA fees or restrictions. Conveniently located near LEGOLAND Florida Resort, Peppa Pig Theme Park Florida, the Winter Haven Chain of Lakes, shopping, dining, schools, medical facilities, and downtown Winter Haven. Easy access to major highways connecting to Orlando and Tampa. Make your move just in time for the holidays and enjoy all that Central Florida has to offer. Showings begin next week. Schedule your private tour today!

1716 Terry Circle Ne, Winter Haven

132 Duval Road, Winter Haven
$290,000
2 Beds ⋅ 2 Baths ⋅ Eloise Woods East Lake Mariam Unit SubDv. ⋅ 33884 Zip Code
This 2-bedroom, 2-bathroom home features a private, screened-in backyard pool. Enjoy nearly non-existent electric bills thanks to a fully paid-off SolarEdge solar system, complemented by a whole-house 22 kW Generac generator with a 250-gallon propane tank, hurricane-rated windows, a 5-year-old architectural shingle roof, and a Rinnai tankless water heater. The spacious interior boasts a large galley kitchen with stainless steel appliances and a gas stove, a convenient indoor laundry room with extra storage, a 2-car garage, and a versatile 16x12 climate-controlled Florida room. This property has been an Airbnb and can be purchased fully furnished, making it a turnkey investment or a move-in-ready retreat!

132 Duval Road, Winter Haven

3097 Buckeye Pointe Drive, Winter Haven
$419,000
5 Beds ⋅ 3 Baths ⋅ Buckeye Pointe SubDv. ⋅ 33881 Zip Code
A luxury-updated 5-bedroom pool home with short-term rental potential for $419,000? This is a Winter Haven opportunity worth exploring! Welcome to 3097 Buckeye Pointe Drive, where beautiful upgrades, spacious living, and investment flexibility come together in the established Buckeye Pointe community. Offering 2,577 square feet, 5 bedrooms, and 2.5 bathrooms, this impressive two-story home is designed for comfort, entertaining, and the Florida lifestyle. Inside, you'll find oversized 24x36 porcelain tile flooring, a beautifully updated kitchen with newer appliances, upgraded bathrooms, and luxury finishes throughout. A convenient first-floor bedroom and bathroom provide additional flexibility for guests, a home office, or multigenerational living. Step outside and discover one of this home's most desirable features: a stunning screened-in, heated pool and spa. Imagine relaxing poolside, entertaining friends, or enjoying your own private Florida retreat year-round. The fenced backyard also features established fruit trees and additional outdoor space. Major improvements include a 2023 roof and 2020 water heater, offering added peace of mind. Located in Flood Zone X, this property combines beautiful living spaces with practical upgrades. What makes this home even more appealing? Buckeye Pointe has no community rental restrictions, creating exciting possibilities for investors interested in short-term rentals, Airbnb, vacation rentals, or long-term rental opportunities. Whether you're searching for a primary residence, second home, vacation getaway, or potential income-producing property, this home offers exceptional versatility. Situated in Winter Haven, Florida, you'll enjoy access to Polk County's famous Chain of Lakes, boating, fishing, waterfront dining, downtown Winter Haven, shopping, LEGOLAND Florida Resort, Peppa Pig Theme Park, and Central Florida attractions. Finding a 5-bedroom home with luxury updates, a private heated pool and spa, a newer roof, and flexible rental possibilities at $419,000 is an opportunity worth a closer look. Why compromise on space, lifestyle, or potential when you could have all three? Schedule your private showing of 3097 Buckeye Pointe Drive today and discover everything this Winter Haven pool home has to offer.

3097 Buckeye Pointe Drive, Winter Haven

419 Greenfield Road, Winter Haven
$334,990
3 Beds ⋅ 2 Baths ⋅ Cypresswood Mdws SubDv. ⋅ 33884 Zip Code
Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.

419 Greenfield Road, Winter Haven

700 Mirror Terrace Nw Unit 507, Winter Haven
$159,900
2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code
Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the famous 17-lake Winter Haven Chain of Lakes. Be the first to enjoy this beautiful extensively remodeled and upgraded 5th floor corner Deluxe unit directly off of the elevators. Lots of natural light through the expansive windows looking out to Lake Spring and over the pool area. Lots of storage closets and an extra storage locker. Its turn-key & ready to move into. Exquisitely maintained building and has passed the newly required Florida State Milestone Inspection & Reserves Study. Many amenities including an owner covered assigned parking space plus guest parking, boat slips & fishing pier, paver brick pool area, large work-out room, library and community room w/ kitchen. Outdoor grills for your use, shuffle board & patio furniture on the huge pool deck overlooking Lake Spring. Publix shopping center by walking across the side street is a great convenience. Close to downtown No pets or smoking. Owner will consider different leasing and/or purchase & financing options. Short term seasonal or long term lease. Tenants and/or buyers have to be approved and interviewed by the HOA as this is a 98% owner occupied building. Nicest condominium building in Polk County with full-time maintenance and management on-site daily.

700 Mirror Terrace Nw Unit 507, Winter Haven

5312 Nicklaus Drive, Winter Haven
$334,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to resort-style living in the highly sought-after Lake Ashton Golf Club Community! This impeccably maintained home is nestled on a quiet and secluded street, offering the perfect combination of privacy, comfort, and an active Florida lifestyle. From the moment you arrive, you will appreciate the pride of ownership and pristine condition of this beautiful residence. Designed for both everyday living and entertaining, the home offers spacious living areas, abundant natural light, and a floor plan that flows effortlessly throughout. One of the most valuable features of this property is that the CDD bond has been fully paid off, providing significant long-term savings and added value for the new owner. Lake Ashton is one of Central Florida's premier gated 55+ communities, offering an unmatched array of amenities and activities. Residents enjoy access to two private 18-hole championship golf courses, including one of the most challenging and highly regarded courses in the region, making it a favorite among golf enthusiasts. The community also features two expansive clubhouses, a state-of-the-art health and fitness center, resort-style pools, tennis and pickleball courts, bowling lanes, movie theater, ballroom, restaurant and lounge, arts and crafts facilities, numerous social clubs, and a private marina with access to beautiful Lake Ashton. Whether you are looking for an active retirement, a seasonal retreat, or your forever home, this exceptional property offers the perfect opportunity to enjoy the Florida lifestyle at its finest. Schedule your private showing today and discover why so many residents proudly call Lake Ashton home.

5312 Nicklaus Drive, Winter Haven

4519 Rapallo Avenue, Winter Haven
$329,900
4 Beds ⋅ 3 Baths ⋅ Villamar Ph 6 & Ph 6d SubDv. ⋅ 33884 Zip Code
**JUST REDUCED** Welcome home to this beautifully designed 4-bedroom, 2.5-bath residence nestled on a desirable corner lot in the heart of Central Florida! From the moment you step inside, you’ll love the bright and open feel, complemented by stylish luxury vinyl plank flooring throughout the main living areas. The spacious kitchen is truly the heart of the home, featuring a large center island perfect for entertaining, meal prep, or gathering with family and friends, along with an oversized walk-in pantry offering an incredible amount of storage. The open-concept layout flows seamlessly into the living and dining spaces, creating an inviting atmosphere for both everyday living and hosting guests. Designed with functionality in mind, this home features a convenient guest half bath, while the secondary bedrooms are connected by a thoughtfully designed Jack-and-Jill bathroom layout. Step outside to enjoy the covered, screened-in lanai and partially fenced backyard, creating a private space to relax and enjoy Florida living. The corner lot adds extra curb appeal and a welcoming presence within the community. Located in a sought-after community with a resort-style pool and fantastic amenities, this home combines comfort, style, and convenience all in one. With easy access to shopping, dining, attractions, and everything Central Florida has to offer, this one checks all the boxes!

4519 Rapallo Avenue, Winter Haven

3408 Costello Circle, Winter Haven
$315,000
4 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 & Ph 6d SubDv. ⋅ 33884 Zip Code
4-bedroom, 2-bathroom home, you'll find 1,713 square fee of comfortable living. A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting quartz countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. The four generously sized bedrooms are flexible for various lifestyles. The primary suite is a tranquil retreat, featuring a private ensuite bathroom with dual sinks, a separate shower, and a walk-in closet. The remaining three bedrooms share one well-appointed bathroom, making morning routines a breeze. Like all homes in Villamar, the Harper includes all concrete block and also smart home technology, which allows you to control your home anytime with your smart device while near or away. Whether you're seeking a peaceful family retreat or a stylish place to call your own, this home is sure to meet your every need. Priced to Sell !!

3408 Costello Circle, Winter Haven

820 Avenue Z  Nw, Winter Haven
$197,500
3 Beds ⋅ 2 Baths ⋅ Hartridge Manor SubDv. ⋅ 33881 Zip Code
Short Sale. Discover a wonderful opportunity in the desirable Winter Haven area. This inviting residence offers comfortable living with a practical and welcoming layout. Bright natural light enhances the interior, creating a warm and airy feel throughout. The living areas flow seamlessly, making everyday living and entertaining effortless. A functional kitchen provides plenty of space for cooking and gathering. Spacious bedrooms showcase relaxing retreats for rest and privacy. The home sits on a generous lot with room to enjoy outdoor living. The backyard is perfect for relaxing evenings, gardening, or weekend gatherings. With no HOA, you’ll enjoy added flexibility and freedom. Ample parking adds convenience for residents and guests alike. The location provides easy access to shopping, dining, and daily essentials. Nearby parks and lakes fit outdoor recreation opportunities year-round. Major roadways are just a short drive away for easy commuting. This property is a great fit for homeowners or investors seeking value and potential. Come explore the possibilities this home has to show for.

820 Avenue Z Nw, Winter Haven

215 Kilmer Lane, Winter Haven
$379,998
4 Beds ⋅ 3 Baths ⋅ Fla Highlands Co Sub SubDv. ⋅ 33884 Zip Code
Fully Occupied Income Property | 3 Units | $4,300/mo Gross Rent | No Vacancy | Winter Haven Rare turnkey income property generating $4,300/month in gross rent — fully occupied with zero vacancy. This versatile multi-income single-family property features two interior apartments plus a separate rear cabin, each independently rented with established tenants in place. Landlord expenses are minimal: owner covers water (~$25/mo) and basic WiFi ($50/mo). Tenants handle electricity, lawn maintenance, and all other utilities — maximizing net cash flow from day one. 4 bedrooms | 2 bathrooms | 1,680 sq ft | Built 1965 | Polk County | Minutes from US-27, downtown Winter Haven, and Legoland Florida. Ideal for the buy-and-hold investor seeking immediate cash flow with low management overhead. Current leases transfer at closing. All financing welcome: Conventional | DSCR Loan | Cash.

215 Kilmer Lane, Winter Haven

7350 Cypress Gardens Boulevard, Winter Haven
$2,400,000
33884 Zip Code
Presenting a rare investment and owner-user opportunity along one of Central Florida’s most prominent commercial corridors. This fully renovated restaurant property offers approximately 2,200 square feet of thoughtfully updated space situated on nearly one acre with extensive on-site parking and exceptional visibility. Recent capital improvements include a new roof, new HVAC system, and comprehensive interior and exterior renovations, creating a true turnkey asset ready for immediate operation. Strategically positioned on highly traveled Cypress Gardens Boulevard, the property benefits from strong daily traffic counts, excellent accessibility, and proximity to major retail, entertainment destinations, residential communities, and tourism-driven demand. The generous site size provides flexibility for future expansion, redevelopment opportunities, outdoor dining enhancements, or additional revenue-generating uses, subject to local approvals. Whether acquired as a flagship restaurant location, long-term investment, or redevelopment play, this offering combines a premier location, significant recent upgrades, strong market fundamentals, and exceptional visibility in one of Winter Haven’s most desirable commercial corridors. Opportunities of this caliber and location are increasingly rare in today’s market.

7350 Cypress Gardens Boulevard, Winter Haven

4130 Bedford Avenue, Winter Haven
$309,900
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code
WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT "TRADITIONS OF RUBY LAKE". This home is MOVE IN READY and is situated withing very close proximity to the clubhouse and Lake Ruby!!! NEW ROOF and NEW HOT WATER HEATER both installed in 2023. With nearly (1,820 Sqft.) of heated and cooled space, this OPEN-CONCEPT SPLIT PLAN with SOARING CEILINGS will not disappoint. There is plenty of room for the chef in the family with your OVERSIZED KITCHEN that has an ABUNDANCE of cabinetry and GRANITE COUNTERTOPS! The kitchen also has 2 windows, giving you a pleasant view along with plenty of extra natural light. Just off the kitchen sits the great room leading into 2 bedrooms and another room (11 x 10) that would be perfect for an office, craft room, or out of town guests. You'll love the (21 x 9) BONUS ROOM that has its own AC and gives you so much extra cooled living space. As if this wasn't enough, the bonus room also overlooks a (21 x 9) SCREENED, PAVERED PATIO for outside grilling or just relaxing. The large primary en-suite has a WALK-IN-SHOWER WITH BUILT-IN BENCH and GLASS SLIDERS, DUAL SINKS, and OVERSIZED WALK-IN-CLOSET. You have direct access to the bonus room from the primary bedroom. Cleaning is a breeze in this home featuring NO CARPET!!! The clubhouse is beautiful and boasts amazing views beyond the pool of 2 lakes (Ruby and Bess). The clubhouse also features an oversized pool and spa, dock, boat ramp, boat slips, tennis courts, pickle ball, basketball, shuffleboard, ball room, billiards, library, craft room, fitness center, dog park and much more! Golf carts are allowed in the community for ease of navigating. Traditions is centrally located in close proximity to medical, shopping, restaurants, 2 major international airports (Tampa/Orlando) and the up and coming airline Avelo in Lakeland, FL. LEGOLAND, FL is just minutes away!

4130 Bedford Avenue, Winter Haven

How much is your home worth?

Get instant property value now!