Homes For Sale in Winter Haven 33884 - 389 homes

Remarks: Welcome to this modern residence at 6212 Pinehurst Loop Winter Haven, Fl. 33884, designed with 3 Bedrooms and 2 full bathrooms PLUS an additional room that could be used as a Den/Office. This delightful Sebastian home, with screened entry was BUILT in 2022 and features a spacious living area with abundant natural light, an upgraded kitchen paired with a Large Island (Great for additional seating and entertaining), Upgraded Lighting, Stainless Steel appliances and Silestone countertop. The inviting living and dining areas blend seamlessly together with newly installed carpet. The open-concept layout is beautifully enhanced by new tile plank flooring in the kitchen, laundry, guest bathroom/hall, entry and perimeter of the Living Room, offering a sleek and modern feel. Bedroom 1 and Bedroom 2 are located to the right of the front entry and the guest bathroom with comfort height vanity and shower/tub combo is conveniently located between Bedroom 1 and 2. The guest bath has a glass block above the shower/tub combo. The primary suite with newly installed carpet offers a private retreat on the back of the home, complete with a generously sized bathroom, walk-in closet, separate comfort height vanities, and an oversized shower. Step outside and enjoy the lanai, perfect for entertaining and equipped with an extended birdcage. The flooring on the lanai has been beautifully painted and it adds a touch of class to the space. The laundry room is spacious and is accessible from the garage and kitchen. The garage floor has an epoxy coating. This home blends style and functionality, making it an exceptional choice! The exterior of the home has been well maintained with beautiful landscaped flower beds and the double car garage and the separate golf cart entry is a bonus. Don't miss the opportunity to explore this wonderful property! Lake Ashton is a Florida Retirement Community that offers a Florida Retirement Lifestyle with resort style amenities and activities for 55+ in Florida. The main clubhouse offers a movie theater, bowling lanes, grand ballroom, card, craft and billiards, Restaurant (Charm City), outdoor temperature controlled swimming pool, Bocce Courts, tennis courts, 1/2 court basketball, shuffleboard courts and MORE. The Health and Fitness Center has a large indoor temperature controlled pool, fitness center, indoor 1/2 court basketball, indoor racquetball, large multi-purpose room, card, craft, billiards, pickle ball courts and tennis courts. 2 -18 hole golf courses are located in Lake Ashton (memberships are optional). Tour this well maintained home today! You'll be glad you did!

Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)

Listing Agent: Lori Raath (863-409-6899)

Remarks: Under contract-accepting backup offers. Welcome to 4504 Riviera Drive. This is a unique custom home, built by renowned builder, Bob Coons. This is one of only two homes ever constructed with this exclusive floor plan and was proudly featured in the 1985 Parade of Homes. This beautiful updated home offers a remodeled kitchen and bathrooms, hardwood floors throughout, and a spacious upstairs bonus room that could make the perfect home office, media room or guest space. There is even a striking coral rock fireplace that serves as a stunning focal point of the living room which adds warmth and character. Major upgrades provide peace of mind, including a brand-new roof (November 2025) and all new hurricane rated, energy efficient windows throughout the home. With its custom design, thoughtful updates, and timeless charm, this exceptional property offers outstanding value. Do not miss the opportunity to make this home yours.

Listing is courtesy of: ALLSTATE REALTY SERVICES (863-965-0207)

Listing Agent: Renard Ellis (863-412-8820)

Remarks: One or more photo(s) has been virtually staged. WATERFRONT CUSTOM St. John floor plan with CDD bond debt PAID IN FULL! Recent Upgrades: Kinetico whole-house water softener, refrigerator (2025), New roof (2024), AC, dishwasher, stove, additional screened room with pavers, and upgraded landscaping (2022). Experience Florida living at its finest in this beautifully upgraded 3-bedroom + den, 2-bath home, complete with an enclosed Florida room and extended screened lanai. From the moment you arrive, you’ll notice the attention to detail: custom stacked stone accents, a power screen on the garage door, golf cart garage entrance, upgraded landscaping, a front paver patio, screened entry, and elegant beveled double glass doors. Inside, round columns frame the dining area, while raised stone archways lead to the kitchen and breakfast nook. The great room features coffered ceilings with recessed lighting, a ceiling fan, and double crown molding that flows throughout the home. The kitchen boasts a bank of drawers, 42" raised-panel custom cabinets with crown molding, stainless steel appliances, a large prep island with extra storage, granite countertops, pendant lighting, and a breakfast bar. Wake up to serene views from your primary bedroom, complete with sliding doors to the lanai. The en-suite bath features two walk-in closets, a walk-in shower, double vanities, a soaking tub, and a linen closet. Enjoy two clubhouses, two 18-hole golf courses, bowling, a movie theatre, craft & card rooms, billiards, pickleball, tennis, bocce, and so much more.

Listing is courtesy of: A+ REALTY LLC (863-293-1141)

Listing Agent: Emily Muscarella (863-978-7180)

Remarks: NO LOT RENT! Live the retired life you worked so hard for. Whether you are a snowbird or looking to enjoy full-time residency, Orange Manor West welcomes you. This highly sought-after 55+ gated community in Winter Haven, secondary resident(s) must be 40+. This fully furnished 2-bedroom, 2-bath home offers a functional layout with recent updates including a 2018 roof, 2022 HVAC, 2021 water heater, newer vinyl flooring, and updated appliances. The home features a spacious layout with walk-in closets in both bedrooms, a private primary suite with a step-in shower, and an enclosed Florida room that is perfect for relaxing mornings or unwinding in the evening. Enjoy an active, low-maintenance lifestyle with monthly fees that include cable, internet, and trash, in a community that allows only service and emotional support animals. Residents have access to a wide range of amenities including a community pool, clubhouse, billiards, shuffleboard, horseshoes, mini golf, fishing, lake access, and a full calendar of social activities such as bingo, cards, sports tournaments, quilting, and much more. Additional features include onsite management, 24-hour emergency service, extra storage for boats and recreational vehicles, and boat slips. Located in Southeast Winter Haven, you are just minutes from shopping, dining, and everyday conveniences, with Legoland ad Peppa Pig theme parks nearby for visiting guests. This is a great opportunity to enjoy comfort, convenience, and community all in one place.

Listing is courtesy of: FLORIDA REALTY MARKETPLACE (863-877-1915)

Listing Agent: Jenn Manzella (863-866-0335)

Remarks: One or more photo(s) has been virtually staged. Welcome to this beautiful home in peace creek reserve! this thoughtfully designed single-story residence offers 4 bedrooms and 2.5 bathrooms, combining comfort and functionality. The open-concept floor plan seamlessly connects the family room, dining area, and kitchen—complete with a central island—creating the perfect space for everyday living and entertaining. Located in the desirable peace creek reserve community, residents enjoy a serene setting surrounded by nature, including a picturesque creek. situated in winter haven—known as the chain of lakes city with over 26 connected lakes—this area offers a variety of shopping, dining, and outdoor activities such as biking and water recreation. Peace creek reserve provides the perfect balance of a peaceful, small-town atmosphere with everyday convenience—an ideal place to call home.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Barbara Cunha De Freitas (617-458-0838)

Remarks: Located in the highly sought-after gated community of Lakewood, this beautifully maintained home offers 4 bedrooms and 3.5 bathrooms, set on a lush, manicured lot with mature trees and attractive landscaping. Inside, you’ll find rich wood flooring throughout the spacious living and dining areas, as well as the kitchen and family room—perfect for both everyday living and entertaining. A standout feature is the expansive 480 sq ft detached game room, included in the total living area, complete with a full bathroom and generous closet space—ideal for conversion into a private guest house, in-law suite, or home office. The primary suite boasts a recently renovated en-suite bathroom and direct access to the large screened lanai and pool area, creating a relaxing retreat. Major updates include a roof replacement in 2017. This exceptional property offers space, flexibility, and charm—don’t miss your opportunity to make it yours!

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

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

Remarks: This move-in-ready 3-bedroom, 2-bathroom home is located in the desirable Planters Walk neighborhood. The interior features a functional open-concept layout where the kitchen overlooks the main living areas, creating an inviting flow for daily living and entertaining. The updated kitchen is equipped with sleek granite countertops and stainless steel appliances. The primary suite serves as a private retreat, complete with a dedicated primary bathroom and a large walk-in closet. Practical features include an attached 2-car garage, a separate laundry room, and a combination of carpet and tile flooring throughout.

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: BEAUTIFUL home built in 2025, featuring 3 bedrooms, 2 baths, and an open living area. The kitchen boasts an open and airy design, with a spacious center island perfect for entertaining, complemented by new stainless-steel appliances,and a walk-in pantry. The dining room is perfectly placed near the kitchen, providing the ideal setting for meals and celebrations of any kind. The family room serves as the natural gathering space of the home, perfect for entertaining friends and family or relaxing with a favorite book or movie. The living area, laundry room, and baths texture luxury wood vinyl plank flooring, with stain-resistant carpet in the bedrooms. The owner's suite includes a walk-in wardrobe and a private en-suite bath with dual vanities, a tiled shower, and a closeted toilet. 2-car garage, architectural shingles. Peace Creek Reserve is a Masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. safe small town feel with convenience, the perfect place to raise a family.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Marian Capriles Garcia (407-738-2301)

Remarks: Spacious 2,336 SF pool home in the gated, tranquil Overlook Estates. This 4BR/2BA floorplan features a split-bedroom layout and generous living space including an eat-in kitchen, 17x18 vaulted family room, 10x16 dining room with bay window, and a large foyer. The master suite includes a dressing alcove and walk-in closet; an adjacent bedroom makes an ideal office or nursery. High-traffic areas feature tile flooring; sliding glass doors in three rooms recess into the wall and open to a 31x50 pool deck — perfect for indoor/outdoor living. Additional highlights: 95x130 lot, terraced front walkway, 7x8 laundry with cabinetry and utility sink, 22x23 garage with built-in storage. Ready for your finishing touches!

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

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: Welcome to Garden Grove Oaks – a friendly, active 55+ community in beautiful Winter Haven and you OWN THE LAND! This well-maintained 2-bedroom, 2-bathroom manufactured home with a bonus office/den and Florida room offers the perfect blend of comfort, functionality, and easy Florida living. Step inside and you’ll immediately appreciate the bright, open layout, featuring a spacious living area ideal for relaxing or entertaining. The kitchen provides ample storage and prep space, while the adjoining dining area creates a natural flow for everyday living. Outside, you’ll enjoy a low-maintenance yard, covered parking, and plenty of room for outdoor seating. Garden Grove Oaks residents love the clubhouse, community pool & hot tub, social activities, and peaceful setting, all while being close to shopping, dining, medical facilities, and the best of Winter Haven. Whether you’re seeking a seasonal retreat or a year-round home, this charming property is move-in ready and waiting for you!

Listing is courtesy of: DREAM REALTY GROUP (863-450-7973)

Listing Agent: Nicole Castro (863-547-5647)

Remarks: One or more photo(s) has been virtually staged. Under Construction. BELOW MARKET INTEREST RATES with use of Seller's Preferred Lender. Never run out of space with the Catalina, a spacious two-story home designed for ultimate comfort and flexibility! This home boasts 5 bedrooms, 3 bathrooms, a versatile den, a generous upstairs recreation space and a private 2-car garage. The open concept floorplan, perfect for entertaining or just hanging out, is complemented by stylish luxury vinyl plank flooring. The kitchen and throughout the home feature elegant quartz countertops, while the stainless-steel appliances and smart thermostat with voice control add a touch of modern technology. The laundry room features a new washer and dryer and is conveniently located upstairs with all the bedrooms. The owner’s suite is situated at the back of the home with a spa-like owner’s bathroom and spacious walk-in closet. Completing this home is beautifully designed landscaping curated for the Florida lifestyle. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.

Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)

Listing Agent: Michael Human (813-343-4383)

Remarks: Beautifully maintained home located in the sought after community of Mandolin. This generous open floor plan is great for entertainment.

Listing is courtesy of: ILLUSTRATED PROPERTIES LLC (CO (561-626-7000)

Listing Agent: Cheryl Rubman (954-254-1844)

Remarks: One or more photo(s) has been virtually staged. Fully refreshed and move-in ready, this Ruby Lake home delivers space, thoughtful upgrades, and a layout that stands out from the rest. Offering high ceilings and a well-designed flow from the L-shaped formal living room that transitions into the formal dining area, creating a defined yet open feel. The kitchen sits at the center with a dinette overlooking the family room. A standout feature is the seamless connection to the outdoor space, with three separate access points to the 33x10 screened-in lanai, from the dinette, formal dining area, and primary suite—creating true indoor-outdoor living. The kitchen has been tastefully updated with brand new granite countertops, new range, and new microwave, along with ample cabinetry, a closet pantry, and breakfast bar. The primary suite is generously sized and opens into an en-suite featuring dual walk-in closets, split vanities, a garden tub, walk-in tile shower, and a private water closet. The split-bedroom floor plan offers privacy, while all bedrooms include walk-in closets. Recent improvements make this one stand out from others in the neighborhood, including brand new carpet throughout, fresh interior paint, and a new water heater, giving buyers peace of mind from day one. Located in the gated Ruby Lake community in Southeast Winter Haven, just minutes from convenient access to shopping, dining, Publix, Walmart, Legoland, and Hwy 27 for an easy commute.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Under contract-accepting backup offers. PRICE ADJUSTMENT ALERT—the opportunity you've been waiting for! Welcome to easy, low-maintenance living in the 24/7 guard-gated Cypresswood Golf & Country Club. This charming condo offers peaceful POND VIEWS from the living room and both bedrooms, creating the perfect backdrop for relaxing mornings and quiet evenings. Inside, you'll love the bright, open layout with 10' ceilings, rich wood cabinetry, and a breakfast-bar kitchen—ideal for casual meals, morning coffee, or entertaining. Both bedrooms feature spacious walk-in closets, plus you'll appreciate the extra outdoor storage for bikes, golf gear, and more. Enjoy the benefits of a low HOA that covers exterior maintenance, landscaping, pest control, and trash, along with access to the community pool and tennis courts. Cypresswood residents also enjoy resort-style amenities, including an 18-hole Ron Garl-designed golf course, clubhouse, restaurant, and junior Olympic pool. Ideal for first-time buyers, families, professionals, golf enthusiasts, seasonal residents, or investors seeking a turnkey rental in a premier gated community. Prime location: Minutes to I-4 and Hwy 27 for easy commuting. Close to LEGOLAND, Bok Tower Gardens, shopping, dining, medical facilities, and entertainment. Centrally located between Tampa and Orlando—the best of Central Florida at your doorstep. Don't miss this opportunity! Pond-view units in Cypresswood are highly desirable and move quickly. Schedule your private showing today and see why Cypresswood is such a wonderful place to call home.

Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)

Listing Agent: Mabel Vassallo (863-604-0499)

Remarks: Discover this thoughtfully designed Moonstone home. Included features: an inviting covered entry; a quiet study; a spacious great room; a well-appointed kitchen offering 42" cabinets, quartz countertops, a walk-in pantry, a center island and an adjacent dining area; a convenient laundry; a lavish primary suite showcasing a generous walk-in closet and a deluxe bath with double sinks; an airy loft; a mudroom and a covered patio. This home also offers ceramic tile flooring and ceiling fan prewiring in select rooms. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!

Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)

Listing Agent: Stephanie Morales, Llc (407-399-2055)

Remarks: Beautifully updated cottage-style villa located in a desirable 55+ gated community. This fully remodeled home features ceramic tile flooring throughout, with the exception of the second bedroom. The spacious two-car garage includes a laundry area that can easily be enclosed for additional privacy or functionality. The appliances are approximately four years old and have been gently used. ***Please note that the chandeliers and corner hanging lamps do not convey with the sale.**** Residents of this active retirement community enjoy a wide range of amenities, including fishing, a pool and spa, card room, billiards room, social events, fitness center, cable, internet, front lawn maintenance, irrigation, boat dock access (for an additional fee), and boat slips. Don’t miss this opportunity to own your own piece of Florida paradise!

Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)

Listing Agent: Beena Kokeram (813-458-6634)

Remarks: This meticulously maintained 3-bedroom, 3-bath home showcases eco-smart features and true pride of ownership, all within the sought-after 55+ gated community of Traditions. Thoughtfully designed and beautifully upgraded, this residence offers comfort, efficiency, and a relaxed Florida lifestyle. Upon arrival, you’re greeted by Florida-friendly landscaping accented with stone curb edging and a decorative paved walkway. The welcoming foyer features a transom window and a convenient coat closet. The spacious living and dining areas offer an open-concept layout enhanced with tile flooring—ideal for entertaining. Oversized sliding glass doors open to an extended screened-in lanai, seamlessly expanding the living space outdoors. The well-equipped kitchen features 42" upper cabinetry trimmed with crown molding, a stainless steel appliance package, and a walk-in pantry to meet all your culinary needs. A center island adorned with quartz countertops perfectly complements the glass tile backsplash, adding both function and style. The generously sized primary bedroom suite is a luxurious retreat, offering wall-to-wall carpeting and dual walk-in closets. The primary bath impresses with a handicap-accessible tiled shower featuring decorative listello tile, a comfort-height double-sink vanity, and a linen closet. A junior bedroom suite includes a private en-suite bath with a comfort-height vanity and quartz countertop—ideal for guests or extended stays. Step outside to your private oasis, where the paved screened lanai provides a peaceful setting for outdoor entertaining. This premium lot with no rear neighbors enhances privacy and tranquility. Additional Features & Upgrades Screened-in front entrance with paved walkway, Smart thermostat and smart home technology, Hybrid water heater, Low-E double-pane windows, Ring doorbell and MyQ garage door opener, Laundry room with washer and dryer, In-wall pest control system and termite bait traps, Exterior carriage lighting, Gutters, Two-car garage with epoxy finished floor. The picturesque Community of Traditions offers Planned Community Activities and an array of amenities such as a Lake Front Clubhouse, Dock & Boat Ramp, Heated Swimming Pool and Spa, Ballroom, Billiards, Meeting Room, Library, Computer Room, Craft Room, Dog Park, Tennis Courts, Basketball Court, Bocce, Shuffleboard, Fitness Center, and Aerobics Studio. Conveniently located near Shopping, Restaurants, Legoland and Major Routes, this home offers the perfect combination of luxury, comfort, and convenience.

Listing is courtesy of: CENTURY 21 MYERS REALTY LAKE WALES (863-676-4448)

Listing Agent: Eileen Belanger (863-221-0229)

Remarks: Brand new, energy-efficient home available NOW! Open floor plan creates a unified living space with a large great room that overlooks the kitchen. Visit Villamar and explore new single-family homes for sale in Winter Haven, FL. Residents will have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park. A brand-new model and new phase are coming soon. Each of our homes is built with innovative, energy-efficient features designed to help you enjoy more savings, better health, real comfort and peace of mind.

Listing is courtesy of: MERITAGE HOMES OF FL REALTY (813-703-8860)

Listing Agent: Bryan Sumner (813-336-5895)

Remarks: Welcome to this beautifully updated mostly furnished end unit condo located on the second floor offering 1,666sf of comfortable living space in the desirable 55+ community of Orchid Springs. Tucked away in a serene setting, this end unit offers exceptional privacy and a peaceful feel while enjoying the security and convenience of community living. Inside you will find updated luxury vinyl flooring, windows, stainless appliances and blinds, creating a move in ready space with modern touches throughout. The kitchen appliances, washer/dryer and AC were all just replaced in 2024! Wonderful split floor plan which offers 3 bedrooms and 2 full bathrooms, plus a guest half bathroom. There is an extended living room/ enclosed Florida room as well which is adding on to the spacious feel of this great unit. The bedrooms have plenty of storage space. All appliances are included also including the washer/dryer. The extended living space/enclosed Florida room provides the perfect place to relax and enjoy the tranquil surroundings and amazing views. Orchid Springs is a private, well maintained community featuring a clubhouse and community pool. Located in Winter Haven, right of Overlook Dr. with easy access to shopping, churches, dining and medical facilities, this home offers the perfect blend of comfort, privacy and active 55+ living. Located in Central Florida, about 1 hour from Orlando and Tampa and 1,5 hour to each coast this is the perfect spot for affordable retirement living in the Sunshine State!

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

Listing Agent: Patricia De Graaff, Llc (863-307-0061)

Remarks: Short Sale. Welcome to your 5 bedroom 3 bathroom home located conveniently in Winter Haven with easy access to dining, shopping, and major roadways. This home features tile flooring throughout the living areas and an open floor plan making it perfect for entertaining. There is a separate living room at the front of the home which could make the perfect office or library. The large kitchen provides a large island, granite countertops, updated lighting, tiled backsplash, stainless steel appliances, and a closet pantry. The large family room is adjacent to the kitchen. You’ll also find sliding doors to your outdoor patio and backyard. One of the 5 bedrooms is located downstairs with its own bathroom, the perfect spot for guests. The primary bedroom is upstairs and features an en-suite with a stand up shower, dual sink vanity and 2 walk in closets! The remaining bedrooms provide plenty of space and share the main hall bathroom with a dual sink vanity and tub/shower combo. This home checks all the boxes! Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)

Listing Agent: Casandra Vann (863-546-5446)