Refine Search
Sort by
1525 Oakview Circle Se, Winter Haven
$193,000
2 Beds ⋅ 2 Baths ⋅ Oakview SubDv. ⋅ 33880 Zip Code
Turn-Key Elegance & Low-Maintenance Living in Oakview! Welcome home to Oakview, an immaculate, highly sought-after hidden jewel in the heart of Winter Haven. This smoke-free, move-in ready 2-bedroom, 2-bathroom villa delivers the perfect balance of relaxation and functionality. Seller is offering a generous price reduction, giving you the immediate opportunity to install a brand-new AC system of your choice! For added peace of mind, this home also includes a one-year whole-house warranty. The heart of the home features a bright, open-concept living and dining area that flows seamlessly into a well-appointed kitchen boasting abundant cabinetry and full appliances. Guests will appreciate the privacy of the split-bedroom layout, while the owner enjoys a serene primary suite complete with a large walk-in shower. Need extra space? The flexible rear den is ideal for a home office, library, or hobby room. Enjoy true carefree living: the low $180/month HOA fee covers roof replacement, exterior painting, and complete lawn care! Spend your days exploring local dining, shopping, and Legoland Florida Resort, or travel effortlessly via nearby Orlando and Tampa international airports. Schedule your showing today and move right in

1525 Oakview Circle Se, Winter Haven

1700 6th Street Nw Unit C21, Winter Haven
$92,000
2 Beds ⋅ 2 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code
Easy Florida living starts here in Winter Haven Harbour, a centrally located 55+ condominium community close to shopping, dining, medical facilities, public transportation, and downtown Winter Haven. This 2-bedroom, 1.5-bath end-unit condo offers 840 square feet of functional living space and a smart opportunity for a buyer looking to downsize, simplify, or create a comfortable seasonal Florida retreat. The end-unit placement provides added privacy, while the half bath gives the floor plan extra everyday convenience compared to many smaller or single-bath options. Enjoy the low-maintenance lifestyle Winter Haven Harbour is known for, with community amenities that include a heated pool, clubhouse, shuffleboard, grilling area, fitness/community space, car wash area, elevator access, assigned/covered parking, and storage/laundry conveniences. Whether you are a full-time resident or a snowbird looking for a manageable Florida home base, this condo puts convenience, community, and value in one package. Buyer approval required. Buyer and buyer’s agent to verify association rules, fees, leasing restrictions, measurements, and all community information. **Some photos are AI enhanced**

1700 6th Street Nw Unit C21, Winter Haven

4146 Sprucewood Street, Winter Haven
$135,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
You won't want to miss this opportunity. This 1344 sf home located in Oakwood Estates, a 55+ community. From the carport walk into the lanai, perfect for entertaining. From there step through the French doors into the open and inviting home with an open and updated kitchen with newer appliances including a cooktop, built in double ovens, built in microwave, and nice sized refrigerator. Past the kitchen you will see the comfortable dining area with built in cabinetry. Then follow through to the spacious living room with more built in cabinets. Returning back through the kitchen you will find the family room area which is open to the kitchen, just perfect for those family and friends get togethers. The main bathroom has been updated with a beautiful shower and updated stool. The guest bedroom is attached to this bath. At the back of the home you will find the primary bedroom complete with two built in closets and a nice sized bathroom attached. The shingled room was installed in 2025 and the air conditioner and water heater were installed in 2021. Oakwood Estates offers many amenities as well as activities. You can join in on the activities or just sit back and watch the world go by.

4146 Sprucewood Street, Winter Haven

664 Clubhouse Road, Winter Haven
$229,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Villas/Green Bldg SubDv. ⋅ 33884 Zip Code
Situated in the desirable golfing community of Cypresswood Golf & Country Club, this lovely 2-bedroom, 2-bath townhome offers comfort, style, and beautiful golf course views. Upon arrival, you'll be welcomed by a charming courtyard adorned with pavers, creating a warm and inviting entrance. A glass storm door and smart lock entry provide both convenience and security. Inside, luxury vinyl plank flooring flows throughout the main living areas, enhancing the home's modern appeal and ease of maintenance. The open-concept floor plan features an updated kitchen with maple wood cabinetry embellished with brushed nickel hardware and soft-close hinges. Corian countertops beautifully complement the tile backsplash, while the custom center island serves as the heart of the home. Additional features include a stainless steel appliance package, recessed lighting, and a closet pantry for ample storage. The adjacent dining area is filled with natural light from an overhead solar tube skylight, creating a bright and cheerful space for meals and gatherings. The spacious living room features a convenient dry bar and oversized sliding glass doors that showcase peaceful views of the golf course. The primary bedroom suite serves as a relaxing retreat, offering dual closets and sliding glass doors leading to the Florida Room. The remodeled en-suite bathroom features a comfort-height vanity with Corian countertops, bronze fixtures, and a walk-in shower with a frameless glass enclosure and safety grab bars. The guest bedroom includes luxury vinyl plank flooring, a custom closet organizer system, and views of the private courtyard. The spacious Florida Room provides the perfect place to relax and unwind while enjoying tranquil golf course views through two oversized sliding glass doors. Additional Features: Laundry room with washer and dryer, Comfort-height toilets, Exterior lighting, Metal roof, Gutters with gutter guards. Conveniently located within walking distance of the community clubhouse, restaurant, pub, swimming pool, and tennis courts, this property offers exceptional accessibility to Cypresswood's amenities. The monthly HOA fee of $320 includes: Exterior painting Roof maintenance Lawn care Additional memberships are available for golf and fitness center access. The picturesque Cypresswood Golf & Country Club features beautifully maintained grounds, a 24-hour manned gated entrance, and a welcoming lifestyle centered around golf, recreation, and community living. This home can be offered turnkey and fully furnished the choice is up to you.

664 Clubhouse Road, Winter Haven

2500 21st Street Nw Unit 22, Winter Haven
$178,490
2 Beds ⋅ 3 Baths ⋅ Casa Del Sol Condo Village Ph 02 SubDv. ⋅ 33881 Zip Code
PRICE DROP! Welcome to easy Florida living at this beautifully updated 2-bedroom, 2.5-bath townhome with a rare 2 CAR GARAGE in the desirable Casa Del Sol community of Winter Haven. Offering direct views of the community pool and multiple outdoor living spaces, this home combines comfort, convenience, and a low-maintenance lifestyle in one attractive package. As you enter, you'll find a versatile flex space that can easily serve as a dining room, home office, reading nook, or additional sitting area. This inviting space features access to a private front patio, creating the perfect setting to enjoy your morning coffee. The updated galley-style kitchen showcases modern white cabinetry, granite countertops, stainless steel appliances, and ample storage, providing both style and functionality. The spacious living room features attractive laminate flooring and sliding glass doors that lead to the screened rear patio, creating a seamless indoor-outdoor flow ideal for entertaining or everyday living. A convenient half bath and a full laundry room add functionality and convenience to the first floor. Upstairs, both bedrooms provide privacy and comfort. The spacious primary suite serves as a relaxing retreat, complete with a large walk-in closet, a private bathroom with a tub, and access to a PRIVATE BALCONY overlooking the sparkling community pool. Enjoy peaceful mornings or unwind in the evenings while taking in the tranquil pool views from your own bedroom. The second bedroom offers flexibility for guests, family members, or additional workspace. The screened rear patio provides another wonderful outdoor living area and is perfectly positioned just steps from the community pool. Whether you're entertaining guests or simply enjoying Florida's beautiful weather, this space offers the ideal place to relax. Additional peace of mind comes from the 2020 air conditioning system. Residents enjoy access to community amenities including a swimming pool, shuffleboard courts, exterior maintenance services, sewer, trash service, and beautifully maintained grounds. Conveniently located in the heart of Winter Haven, this home is just minutes from downtown Winter Haven, the Chain of Lakes, shopping, dining, medical facilities, and LEGOLAND Florida Resort. Whether you're looking for a primary residence, seasonal getaway, or investment opportunity, this move-in-ready townhome offers an exceptional combination of location, lifestyle, and value.

2500 21st Street Nw Unit 22, Winter Haven

1620 17th Street Nw, Winter Haven
$449,000
2 Beds ⋅ 3 Baths ⋅ Hendersons Ext Kenilworth Park SubDv. ⋅ 33881 Zip Code
New Lake Life listing, two houses one price. Must see lake property with no HOA. Airbnb allowed. Chain of lakes property on Lake Mirror with generator, gas, irrigation, and whole house water system. Main house has beautiful kitchen, big living/dining combo. Kitchen has extra-large refrigerator, island, wall tile, and entry to garage. Large living room has fireplace, storage, and muti doors to sunroom. Primary bedroom has walk in closet, ensuite bathroom, and doors to sunroom. Sunroom faces lake has storage and hurricane windows. Laundry room has washer, gas dryer, and storage. gas tankless water heater. Covered back porch overlooks pineapple garden. Separate cottage comes fully furnished and has full bath, kitchen, pantry and closet. Cottage overlooks banana and avocado trees. Covered dock overlooks lake with a swing for relaxation. Each house has one bedroom. Main house has space to build a second bedroom. 23 chain lakes are connected by canals. All information is deemed reliable but not guaranteed. Buyer must verify all information and measurements. No seller financing.

1620 17th Street Nw, Winter Haven

105 Laurel Cove Way Unit 105, Winter Haven
$189,000
2 Beds ⋅ 2 Baths ⋅ Winterset 01 A Condo 02 Amd SubDv. ⋅ 33884 Zip Code
Beautiful lake-view condo in Winterset! This ground-floor 2-bedroom, 2-bath residence offers amazing views of Lake Winterset, part of the renowned Winter Haven Chain of Lakes. The spacious great room features tile flooring, sliding glass doors to the screened porch, and stunning lakefront vistas. Just off the kitchen is a comfortable dining area, creating an inviting space for everyday living and entertaining. The kitchen is beautifully appointed with custom Kraft Maid wood cabinetry, granite countertops, a breakfast bar, and a complete appliance package. The primary bedroom enjoys peaceful lake views and includes plush carpeting with a gel pad, a large 11' X 7' walk-in closet, a ceiling fan, sliding doors to the patio, and an en-suite bath featuring dual sinks, quartz countertops, and an oversized walk-in shower with a seamless glass door. The guest bedroom is generously sized at 13' x 10', offering ample closet space and convenient access to the guest bathroom, which features quartz countertops and tile flooring. The screened porch is the perfect place to relax and enjoy breathtaking lakefront views and spectacular sunsets. Residents enjoy true resort-style living with access to a community clubhouse, pool, spa, shuffleboard courts, tennis & Pickleball courts. The highly desirable location offers close proximity to shopping, dining, schools, medical facilities, and LEGOLAND Florida Resort. Additional features include a private storage room off the patio, inside laundry, a tile roof, air conditioning, 24-hour security, meticulously maintained grounds, assigned parking, and ample guest parking. This is Florida lakefront living at its finest.

105 Laurel Cove Way Unit 105, Winter Haven

700 Mirror Terrace Nw Unit 506, Winter Haven
$119,000
2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code
PRICED TO SELL!! **GORGEOUS VIEWS FROM THIS FURNISHED DIRECT LAKEFRONT CONDO** THE 2ND BEDROOM EXTENDS THE LIVING AREA AND CAN BE CLOSED FOR GUEST BEDROOM USE. THIS BEAUTIFUL CONDO IS ON THE SOUTH "CHAIN OF LAKES" IN WINTER HAVEN, FLORIDA (CENTER OF THE STATE LOCATION). THE NICE QUALITY FURNITURE IS INCLUDED. The monthly fee includes cable, internet, water, sewer, trash removal, roof, building insurance, ground maintenance, use of the pool, recreational room, exercise room, and library. The custom design features in this condominium are; raised panel wood cabinets in the kitchen, beautiful granite countertops, custom tile backsplash, stainless steel appliances, and up to date paint selections. Spring Lake Towers Condominium is an (age 55+) NON-SMOKING, NO PETS complex. BOAT SLIPS are currently available for a reasonable yearly fee. This condo complex is immaculate and conveniently located to grocery, shopping, movie theater, medical, places of worship, restaurants, bus line & downtown Winter Haven. Spring Lake Towers holds occasional social events and planned group activities if you wish to participate. This is truly living the Florida lifestyle with a gorgeous lakefront setting. Make this your full-time residence or a winter home. All information is believed to be accurate but not guaranteed. Make your showing appointment today as it is sure to sell quickly. Measurements are approximate.

700 Mirror Terrace Nw Unit 506, Winter Haven

1549 Drexel Ave Ne, Winter Haven
$400,000
2 Beds ⋅ 2 Baths ⋅ Lake Elbert Heights Unit 01 02 Rep SubDv. ⋅ 33881 Zip Code
This architecturally significant residence offers a rare blend of iconic mid-century design and historical provenance. One of only a few remaining original 1957 Craney Spec homes, the home was designed by celebrated architect Gene Leedy. Regarded as a legend and an icon, Leedy’s importance in history is prominent as a pioneering architect of the Sarasota School of Architecture movement, famous for integrating mid-century modernism with Florida’s climate. This historic residence showcases Leedy’s signature aesthetic, seamlessly merging natural surroundings with interior and exterior living spaces. Meticulously maintained landscaping and fig vines accent the perimeter walls, adding to the property's quintessential style. Clean lines and a seamless connection between interior and exterior spaces define the home’s architectural character. Floor-to-ceiling sliding glass walls, Ocala block creating the illusion of mixing an interior and exterior boarder, highlighted with exposed structural beams. This definitely details his talent for displaying the beauty of raw materials rather than covering them up. Drexel Avenue remains a celebrated example of Leedy's Florida climate-responsive Mid-Century Modern homes. In 1989, the home was remodeled by Leedy himself. The redesign improved functionality by extending the primary bedroom and primary bathroom walls, adding depth while creating additional storage and a more versatile living space. Other interior highlights include rich tongue-and-groove wood ceilings, a floating gas fireplace, and wide unobstructed views of the peaceful landscape. The kitchen and both bathrooms have been gutted, providing a blank canvas for a personalized restoration, allowing you to blend historic character with modern convenience. The dining area overlooks the courtyard, creating a stronger connection to the outdoors. The guest bedroom can also serve as an office, with a sliding glass wall that opens to the backyard. Other features include interior and exterior post-and-beam construction, an enclosed garage, original wrought-iron front gate, outdoor shower, tankless water heater, ample storage, track lighting throughout, central air conditioning, lush gardens, a relaxing courtyard for enjoying Florida's cooler days and evenings, and an eight-foot perimeter wall with ambient downlighting throughout. Gene Leedy chose to bring his modernist vision to Winter Haven, a city uniquely shaped by his work. Winter Haven is situated between Orlando and Tampa and surrounded by lakes and year-round pleasant weather. The Lake Elbert Trail is just two blocks away, and downtown is an easy bike ride or enjoyable walk. Polk State College and other everyday conveniences are only minutes from Drexel Avenue. One or more photos have been virtually staged to recreating the landscape of what was lost during the severe winter freeze. The home’s remodel (after interior cosmetic demolition) is complete, with the goal of preserving the home’s key historic mid-century elements. Key areas of improvement are: New electric wiring throughout the home; all new CPVC plumbing replaced original galvanized plumbing; non-tempered sliding glass door glass is replaced with modern tempered safety glass and new sliding glass door track glides--so the walls of glass slide easily. The original frames from the sliding glass doors are preserved, thus maintaining the home’s historic integrity. Come and be part of the few who enjoy living in a Gene Leedy Home!

1549 Drexel Ave Ne, Winter Haven

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

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

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

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

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

150 El Dorado Unit 105, Winter Haven
$94,900
2 Beds ⋅ 2 Baths ⋅ Hawaiian A Condo SubDv. ⋅ 33884 Zip Code
Discover this charming first-floor corner unit condo in the highly sought after Orchid Springs community in SE WInter Haven. This 2 bedroom 2 bathroom condo features a desirable split floor plan with an oversized living area perfect for entertaining or relaxing. Both bedrooms boast generous walk-in closets , and offers abundant storage throughout. Enjoy the convenience of a first floor corner location with a covered parking spot. The nice open layout makes every day maintenance free living easy and comfortable. Residents of Orchid Springs love the prime location minutes from shopping,dining, medical facilities, and Legoland, while being centrally situated between Tampa and Orlando for easy access to everything Central Florida has to provide. The HOA takes care of the details including grounds maintenance, water , sewer and gas giving you more time to enjoy the Florida Lifestyle. Whether you are looking for a primary residence or a winter retreat , this first floor corner unit is a fantastic opportunity in a desirable community. Schedule your showing today and make this condo your new home!

150 El Dorado Unit 105, Winter Haven

154 2nd Street  Sw Unit Unit 7, Winter Haven
$495,000
2 Beds ⋅ 3 Baths ⋅ Raingarden SubDv. ⋅ 33880 Zip Code
Discover your dream residence at RainGarden Condominiums in Downtown Winter Haven! Designed by renowned architect Max Strang, this stunning townhouse embodies a modern design within a tropical landscape that provides an atmosphere of serenity in the heart of a lively downtown. Prepare to be wowed by the blend of contemporary aesthetics and organic elements, transforming this two-bedroom, two-and-a-half-bathroom residence into a unique piece of architecture! This interior unit is one of nine townhomes that make up the RainGarden Condominium. Upon entering the secured gate into your private courtyard, you’ll immediately notice the lush landscaping and shady tree canopies that provide a peaceful place to relax or entertain guests. Step inside and enjoy a spacious and airy layout that effortlessly connects the living, dining, and kitchen areas. The large custom windows bathe the space in natural light, while the randomized, vertical fins on the front facade provide generous shading and privacy to the outside. The living room dazzles with 9'9" ceilings, elegant concrete floors, dining area, and expansive floor-to-ceiling windows. The gourmet kitchen features a breakfast bar, high-end GE appliances, granite countertops, and ample cabinet space, blending functionality with style. Access your second story via an integrated wooden stairway situated in a clerestory expanse that opens to a skylighted landing. Upstairs, the lofted master bedroom beckons with floor-to-ceiling windows, refined wood floors, an en-suite bathroom, and abundant closet space. The master bath features a double vanity, a large walk-in shower with elegant finishes, and a spacious walk-in closet. The second bedroom boasts a similar en-suite bathroom with a walk-in closet and plenty of storage. Enjoy the convenience of a second-floor washer and dryer as well as an ample storage closet. Located in the heart of Downtown Winter Haven, this home offers an urban lifestyle where you can “live, work, and play” all within a few blocks. You can leave your vehicles in the attached two-car garage and enjoy the vibrant neighborhood with new restaurants, coffee shops, retailers, and other entertainment just steps away. There are also additional visitor parking spots in the rear and ample street parking available on Ave A. This location cannot be beaten! Centrally located between Tampa & Orlando and within 1 1/2 hours of both east-coast and west-coast beaches. Or take your family out on the coveted Chain of Lakes where you can boat or swim between 22 different lakes! Don’t miss out on the opportunity to purchase this architectural gem! HOA provides for trash pickup, sewer, common electric and water expenses, exterior maintenance and landscaping.

154 2nd Street Sw Unit Unit 7, Winter Haven

75 Sunset View Drive Unit 75, Winter Haven
$405,000
2 Beds ⋅ 2 Baths ⋅ Winterset 04 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Beautiful lakefront living awaits in the gated community of Winterset! This beautifully maintained 2-bedroom, 2-bathroom condo with an attached one-car garage offers stunning lake views, abundant natural light, and unique architectural details throughout. Inside, you’ll find beautiful cork flooring, specialty tray ceilings, and a cozy library area complete with custom built-in shelving. The spacious enclosed Florida room is a true showstopper, featuring floor-to-ceiling windows overlooking the lake, creating the perfect space to relax and enjoy breathtaking water views year-round. The oversized primary suite offers a spacious layout with dual sinks, a walk-in closet, and a peaceful retreat-like feel. The large custom kitchen is a chef’s dream, complete with a gas stove, ample cabinetry, generous counter space, and plenty of storage for all your culinary needs. Enjoy the beautiful community amenities that include a pool, tennis courts, and the security and privacy of this sought-after gated neighborhood. Conveniently located near Legoland, shopping, dining, and everyday conveniences. This lakefront condo perfectly blends comfort, elegance, and Florida lifestyle living.

75 Sunset View Drive Unit 75, Winter Haven

10 Enclave Drive, Winter Haven
$214,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood Enclave Ph 01 SubDv. ⋅ 33884 Zip Code
Under contract-accepting backup offers. WELCOME TO THIS CHARMING TOWNHOUSE located in the sought-after Cypresswood Golf & Country Club community in beautiful Winter Haven! This inviting 2 BD / 2 BA home offers comfortable Florida living with a spacious open-concept living and dining room combination, abundant natural light, and a thoughtfully designed layout perfect for both relaxing and entertaining. The kitchen features beautiful granite countertops, handsome cabinetry, and a cozy eat-in space ideal for casual dining. The primary suite is generously sized and includes a custom walk-in closet, dual sink vanity, skylight, and an attractive walk-in shower creating a bright and airy retreat. The guest bedroom also offers a custom closet for added organization and convenience. Additional features include skylights that fill the home with natural light, spacious living areas, and a warm, welcoming atmosphere throughout. Residents of Cypresswood enjoy a gated golf course community with beautifully maintained grounds, scenic surroundings, clubhouse amenities, tennis courts, community pool, restaurant access, and an 18-hole championship golf course, all conveniently located near shopping, dining, medical facilities, and easy access to both Orlando and Tampa. Come experience the peaceful lifestyle and exceptional community setting this lovely townhouse has to offer!

10 Enclave Drive, Winter Haven

1004 Medinah Drive, Winter Haven
$165,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Tennis Vls SubDv. ⋅ 33884 Zip Code
Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous primary suite features a walk-in shower, and the guest bath includes a tub/shower combo. Why this is a steal: Priced well below comparable properties in the community, Resort-style amenities INCLUDED — 18-hole golf course, tennis, pickleball, pool, fitness center, clubhouse & restaurant, 24-hour manned gate for peace of mind, Pets welcome, Flexible for investors — 6-month minimum lease allowed. Whether you’re looking for your Florida dream home, a seasonal getaway, or a smart rental investment, this property checks every box at a price that won’t last long. Act fast — opportunities like this don’t stay on the market!

1004 Medinah Drive, Winter Haven

3023 Caneel Street, Winter Haven
$235,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 2a SubDv. ⋅ 33884 Zip Code
Welcome to the vibrant lifestyle of Traditions, one of Winter Haven’s most desirable gated 55+ communities! Built in 2020, this impeccably maintained villa offers 2 bedrooms, 2 bathrooms, and 1,385 sq. ft. of beautifully designed living space that perfectly blends comfort, elegance, and low-maintenance Florida living. Step inside to an inviting open-concept floor plan filled with natural light, high ceilings, and stylish ceramic tile flooring throughout the main living areas. The spacious living and dining areas are ideal for entertaining guests or simply relaxing in comfort. The modern kitchen is a standout feature, showcasing solid wood cabinetry, granite countertops, stainless steel appliances, and generous prep space for everyday living and special gatherings alike. The spacious primary suite offers a large walk-in closet and a private en-suite bath designed for comfort and convenience. Sliding glass doors lead to a screened-in porch where you can unwind and enjoy Florida’s beautiful weather year-round. Living in Traditions means enjoying an exceptional array of resort-style amenities, including a lakeside heated pool, elegant clubhouse, fitness center, tennis, pickleball, and shuffleboard courts, plus private access to Lake Ruby with a community boat ramp and dock. Even better, the HOA covers exterior maintenance, lawn care, and high-speed internet, allowing you to truly enjoy a carefree lifestyle. Ideally located near shopping, dining, hospitals, and Legoland, this stunning villa offers the perfect opportunity to enjoy the best of Central Florida living. Don’t miss your chance to own a beautiful home in one of Winter Haven’s premier active adult communities!

3023 Caneel Street, Winter Haven

4212 Cedarwood Street, Winter Haven
$129,900
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Spacious living plan and Luxurious Kitchen just updated for the top Chef status. As you come in through the covered carport you'll notice the Newly installed flooring that really shines. There are 2 Living Room areas one of which you could close off for a 3rd bedroom. Large Master Bedroom and Bath. Skirting around the home has just been replaced for a new look. Not to mention all of the amenities offered with the community swimming pool, pickleball, tennis courts and putt putt golf course. This property is located on the dog approved residence street, so Fido is in luck. New AC unit was replaced in 2026. You're in close proximity to all the Central Florida attractions. Hurricane/ Tie Down Straps Replaced 2023. Ceiling fans have been updated w/ remotes. UPDATE: New Linoleum flooring has just been professionally installed throughout the entire home to match the kitchen, along with new baseboards.

4212 Cedarwood Street, Winter Haven

1108 Sawgrass Drive, Winter Haven
$422,999
2 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
This is a must see charming oasis located behind the secure gates of Lake Ashton, you don’t want to miss this opportunity of becoming an homeowner in this Exclusive 55+ community in Florida, comes with a upgraded custom13’6 x 28’ saltwater pool with propane heater and expanded screened enclosure that measures 44’ x 24’ tankless propane water heater, and gas hookup for an outdoor kitchen in Lake Ashton! If you are seeking a stunning 2-bedroom, 2-bath property this is the one it sits on the Lake Ashton West golf course and this environment for Living certified Green home features several builder upgrades PLUS extensive builder and owner upgrades Inside, you’ll find tile flooring throughout (no carpet), upgraded kitchen cabinetry with roll-out shelving, Calcatta Silestone countertops with beveled edge; custom kitchen pantry cabinet with roll-outs; under-cabinet lighting, custom closets in both bedrooms and laundry room plus a custom pantry storage. Additional features include custom closets, updated bathrooms with a walk-in shower and glass doors, remote-controlled blinds, upgraded lighting and fans, epoxy garage flooring, and enhanced landscaping Located in Lake Ashton, a premier 55+ community offering two 18-hole golf courses, a 26,000 + sq ft Health and Fitness Center, pickleball courts , a bowling alley, a restaurant and much more, activities are abundant in this exceptional community . Don’t miss this very special pool home. Schedule your showing today.

1108 Sawgrass Drive, Winter Haven

612 Morgan Road, Winter Haven
$524,900
2 Beds ⋅ 2 Baths ⋅ Peace River Development SubDv. ⋅ 33880 Zip Code
Turnkey opportunity to own a fully equipped nursery on 5 acres! This versatile property is currently functioning as a citrus nursery, with the infrastructure already in place to support expansion into a variety of other agricultural uses. Featuring four greenhouses (one greenhouse has 3 domes) totaling in approximately 16,000 square feet, each equipped with electricity and water. This property has two 4-inch wells with 5-inch submersible pumps, fertilizer injectors, a commercial-grade chemical/fertilizer sprayer, overhead irrigation, greenhouse benches, 150,000 citrus grow pots, and much much more. Everything you need to hit the ground running. There is additional space for in-ground planting, that has an existing irrigation system with timer already installed. On-site structures include a 12x12 air-conditioned office shed, a 8x8 dedicated chemical storage shed, and a 16x20 workshop with an attached lean-to for additional workspace and storage. Also included is a 2006 single-wide mobile home offering 2 bedrooms and 2 bathrooms, with a split floor plan. The home features a rear covered porch, a private storage shed, and a full-home water purification system that also services the workshop and ice machine. Perfect for on-site living or staff housing. This property is fully set up and ready for continued operation. All measurements to be verified by buyer.

612 Morgan Road, Winter Haven

1213 8th Street Nw, Winter Haven
$189,000
2 Beds ⋅ 2 Baths ⋅ North Gate Village SubDv. ⋅ 33881 Zip Code
One or more photo(s) has been virtually staged. SELLER NOW OFFERING 2/1 INTEREST BUY DOWN RATE WITH APPROVED FINANCING! NEW ROOF JUST INSTALLED, BRINGING BUYER PIECE OF MIND. Beautiful, well-cared-for 2BR/2BA villa in a maintenance-free 55+ community — ready for a new owner. Single-level, move-in ready home with a bright, open floorplan, remodeled kitchen and stainless steel appliances. Durable LVP flooring (2021) throughout the main living areas and new carpet in the bedrooms. Laundry includes washer/dryer 2021; refrigerator 2025. Security system installed. Major recent system and structural upgrades for worry-free ownership: HVAC 2023; 40-gal water heater 2023; PEX water lines 2024; new carport roof 2024; new power panel & upgraded wiring 2021; attic insulation & interior paint 2021. Ease of living: Enjoy true low-maintenance, single-level living with HOA exterior care, complete lawn service and irrigation, Enjoy easy parking under the new carport roof, and modern systems that minimize upkeep and unexpected expenses. The thoughtful updates and security system provide peace of mind and allow you to spend more time enjoying community amenities, such as the community clubhouse, nearby lakes, dining, and shopping rather than home maintenance. Location and lifestyle: Conveniently close to Publix, dining, and scenic lakes — ideal for active adults seeking convenience and leisure.

1213 8th Street Nw, Winter Haven

6114 Grand Oaks Drive Se, Winter Haven
$159,900
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Virtually Staged. YOU OWN THE LAND – NO LOT RENT! Welcome to 6114 Grand Oaks Dr SE, a well-maintained 2-bedroom, 2-bath home with 1,288 sq. ft. of living space in the Garden Grove Oaks 55+ active community of Winter Haven. With a pond view, oversized lot, low $65/month HOA, no CDD, and no land lease, this home offers an appealing combination of affordability, comfort, and Florida lifestyle. Step inside to an open, comfortable floor plan with plenty of natural light and a spacious living area. The updated kitchen features granite countertops, luxury vinyl flooring, generous cabinet and counter space, and a pantry designed for practical storage—the deep side of the pantry includes pull-out shelves, making it much easier to reach and organize items stored toward the back. The kitchen opens to the main living area, creating an easy flow for everyday living and entertaining. The primary bedroom is conveniently located on the main level and includes an en-suite bath with walk-in shower and walk-in closet. A second bedroom and full guest bath provide comfortable space for visitors, a home office, hobbies, or additional living needs. The guest bathroom includes space for the inside laundry. The home features ceiling fans, skylights, window treatments, and a combination of luxury vinyl and carpet flooring. Appliances are included, along with the washer and dryer, and the home is being offered partially furnished. Outside, enjoy the water and garden views, covered parking with room for two vehicles plus golf cart parking, and additional storage in the exterior shed. The paved driveway provides extra parking flexibility, while the outdoor living area gives you a place to relax and enjoy Florida's year-round climate. Garden Grove Oaks is an established 55+ community with a clubhouse, community pool and fishing opportunities, with ground and pool maintenance included among the association benefits. And unlike communities where homeowners pay hundreds of dollars each month in lot rent, you own the land here, helping keep ongoing expenses manageable. Conveniently located in Winter Haven, this home combines an updated interior, water view, covered parking, storage, community amenities and land ownership with a low monthly HOA—all at an attractive price point.

6114 Grand Oaks Drive Se, Winter Haven

323 Orange Blossom Drive Unit 323, Winter Haven
$205,000
2 Beds ⋅ 3 Baths ⋅ Waters Edge Unit 1 Replat SubDv. ⋅ 33880 Zip Code
Under contract-accepting backup offers. WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location!. Primary bedroom with ensuite and screened-in balcony, one car garage and open concrete patio. The screened patio is perfect for enjoying views of boaters and paddle boarders passing between the lakes. Focusing on recreation, this home is in the perfect spot for a multitude of outdoor activities. Community features include a sparkling pool . Fish from your backyard at the bank of Lake Lulu! This residence is convenient to Great restaurants, medical, shopping, entertainment, and LEGOLAND! Check us out today to see what Florida waterfront living is all about!

323 Orange Blossom Drive Unit 323, Winter Haven

How much is your home worth?

Get instant property value now!