Winter Haven Homes with Buyer Approval Required Community Features

Winter Haven Homes with Buyer Approval Required Community Features

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, where sunshine and serenity meet! Known for its picturesque lakes and vibrant community, Winter Haven offers a unique blend of small-town charm and modern amenities. With over 50 lakes in the area, residents can enjoy a variety of water activities, from fishing and boating to simply soaking up the sun on the shores of beautiful Lake Eloise or Lake Howard.

The city is also home to a rich history and a thriving arts scene, featuring the renowned Cypress Gardens, which was once a world-famous botanical garden and theme park. Today, Winter Haven boasts a lively downtown area filled with delightful shops, restaurants, and cultural events that bring the community together. Plus, with its convenient location between Orlando and Tampa, residents can easily access the excitement of larger cities while enjoying the peaceful atmosphere of their own neighborhood.

For those looking to settle down in this idyllic environment, Winter Haven offers homes in communities that require buyer approval. These exclusive neighborhoods provide a sense of security and camaraderie among residents, ensuring that your investment is protected while fostering lasting relationships with your neighbors. With community features that prioritize safety and quality living, you’ll find a welcoming atmosphere that encourages a fulfilling lifestyle.

Whether you're a first-time homebuyer or seeking a tranquil retreat, Winter Haven's diverse real estate options cater to every need. Discover your dream home in this enchanting city today, and embrace the vibrant lifestyle that Winter Haven has to offer!

Newest Winter Haven Homes with Buyer Approval Required Community Features

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

A Home That's Ready When You Are — Oakwood Estates, Winter Haven Some of life's best decisions are also the simplest ones. This lovingly maintained, fully furnished manufactured home in Oakwood Estates invites you to skip the hassle and step straight into the lifestyle you've been looking forward to — because everything has already been taken care of, and everything stays. Fresh interiors, thoughtful updates, and a warm, welcoming layout make this one of the most effortless purchases you'll make. Step inside and you're immediately greeted by natural light pouring through double-pane windows, setting a bright, airy tone throughout. The kitchen shines with stainless steel appliances, wood-look countertops, a newer sink, and crisp white cabinetry — and yes, everything stays, right down to the air fryer. The dining area features beautiful built-in cabinetry and shelving, flowing seamlessly into a spacious living room complete with an electric reclining sofa, flat screen TV, and comfortable seating. Luxury vinyl plank flooring runs throughout, tying it all together with style and ease of maintenance. Both bedrooms are generously sized and fully furnished. The primary suite features a walk-in closet, electric reclining bed, and a quality foam mattress. The Florida room offers updated ceiling fans, a brand-new AC unit, and convenient access to the in-home washer and dryer hookups — a true bonus in this community. Slide open the door to the enclosed lanai and enjoy your morning coffee overlooking lush, manicured landscaping — your own quiet corner of Florida. Additional highlights include hurricane shutters, vinyl siding, a 2017 roof, an irrigation system, and an updated electrical panel for peace of mind. Then there's the community. Oakwood Estates is a gated, beautifully maintained 55+ resident-owned community in the heart of Winter Haven — one of Polk County's most desirable areas. Residents enjoy two heated pools, two clubhouses, tennis and pickleball courts, shuffleboard, bocce ball, a miniature golf course, horseshoes, a fishing lake with pier, RV and boat storage, a library and activities center, pool tables, and a vibrant, active activities committee that keeps the social calendar full year-round. Lighted streets, underground utilities, and security cameras throughout the common areas reflect a community that takes pride in where it lives. This is Florida living, fully loaded and ready to go.

4332 Cherrywood Street, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

New Carpet throughout most of the home. Plus many of the windows have been updated to thermal pane insulated windows. If that is not enough the TPO roof was installed in December 2023. The home has a nice layout with a huge primary bedroom with huge walk in closet. Location is convenient in Oakwood Estates, a 55+ community, right across from the office and close proximity to one of the pools. Enjoy the many amenities at Oakwood including two pool, two clubhouses, miniature golf, fishing pier, shuffleboard and much, much more. Join in on the many activities including weekly Koffee Klatch, potluck meals, and dances. The two heated pools offer many hours of relaxation. Or just sit out on the screened front porch and watch the world go by. This home is priced to sell. Check it out today!!

4027 Rolling Oaks Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code

Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code

Move right into this furnished home located in Oakwood Estates, a 55+ community. The carpet throughout the home is in excellent condition. The rooms are very spacious and inviting. The home has been very well maintained. The dishwasher was installed in 2018, the washer and dryer 2020, and the refrigerator in 2024. Enjoy the bonus room on the front of the home or sit and watch the world go by on the comfortable lanai. Oakwood Estates offers many activities and amenities. If you are looking for exercise, you can join in with the pool or indoor aerobics. Chair Yoga is offered twice a week, or play some pool volleyball. The tennis court has recently been refinished and there is a pickle ball group that meets three times a week. During the winter months, there are several exciting dances as well as many activities. If food is your thing, Oakwood offers potluck dinners, ice cream socials, and weekly coffee and donuts. If you are looking for full time or just part time, this is your opportunity to move into a wonderful community, conveniently priced.

4807 Plumwood Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Winter Ridge Condo SubDv. ⋅ 33881 Zip Code

This well-maintained unit is a corner lot unit with 3bed/2bath. Features: ceramic tiles flooring throughout, a huge living room and a kitchen with the laundry space area. The kitchen comes fully equipped with appliances, including a washer and dryer. Large Florida room with a separate A/C unit, could serve as a 4th bedroom/guest bedroom or play room. Two assigned parking spaces out front, one with aluminum carport. Additional guest parking is available near the unit with proper permit tags. Community for ALL Ages and conveniently located close to dining and stores. Low maintenance living with an HOA that takes care of it and include the home Insurance: covering roof maintenance and exterior building maintenance, landscaped grounds, road maintenance. Facilities: heated pool, clubhouse, shuffleboard and boat slip. Allows 2 pets under 40 pounds. Located just minutes from HWY 27. New roof installed in March 2025. Call today and schedule your private tour.

344 Winter Ridge Boulevard Unit 344, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Traditions Ph 01 SubDv. ⋅ 33884 Zip Code

Welcome to 2820 Traditions Blvd S, located in the desirable 55+ gated community of Traditions at Lake Ruby in Winter Haven. This well-maintained Augusta model offers 3 bedrooms, 2 bathrooms, a spacious 2-car garage, and a peaceful pond-front setting. This home is perfect for Florida living! The open and comfortable floor plan provides beautiful pond views from the kitchen, dining area, living room, primary suite, and enclosed patio, allowing you to enjoy the tranquil Florida surroundings throughout the home. The kitchen offers ample cabinetry and workspace, while the spacious living areas create an inviting environment for both everyday living and entertaining. The split bedroom layout provides privacy for owners and guests alike. The enclosed patio is a wonderful space to relax, enjoy your morning coffee, or unwind while taking in the water views. Just outside your door, enjoy all that Traditions at Lake Ruby community provides, including a clubhouse, resort-style amenities, pool, fitness facilities, and recreational opportunities designed for an active adult lifestyle. Conveniently located in Winter Haven with easy access to shopping, dining, medical facilities, golf, and Central Florida attractions. Whether you are looking for a full-time residence or a seasonal retreat, this home offers comfort, convenience, and the opportunity to enjoy the relaxed lifestyle of Traditions at Lake Ruby.

2820 Traditions Boulevard S, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Spring Lake Towers SubDv. ⋅ 33881 Zip Code

Enjoy maintenance-free lakefront living in this 2-bedroom, 2-bathroom condominium located in the highly sought-after Spring Lake Towers, a premier 55+ active adult community in the heart of Winter Haven. Updated in 2020, this inviting residence offers BREATHTAKING VIEWS OF SPRING LAKE, part of the scenic Spring Lake Meander, and a bright, open living space that feels like an indoor lanai, where walls of windows create the perfect setting to relax while overlooking the tranquil water. Both the primary bedroom and the second bedroom have direct access to this enclosed lakefront space, creating a seamless connection to the serene waterfront and providing the perfect spot to enjoy your morning coffee, unwind with a book, or simply take in the picturesque views of Spring Lake throughout the day. The updated kitchen is designed for both style and function, featuring soft-close cabinetry, porcelain countertops, recessed lighting, a decorative tile backsplash, a convection oven, and a convenient center island cart. Luxury vinyl flooring flows throughout the main living areas, while the bedrooms offer the comfort of carpet. The spacious primary suite features a walk-in closet and an ensuite bath, while the secondary bathroom has been tastefully updated with a beautifully tiled glass-enclosed shower. The all-inclusive condo fee provides exceptional value, covering cable TV, high-speed internet, water, sewer, trash removal, exterior building maintenance, roof maintenance, building insurance, reserve funds, on-site management, groundskeeping, and assigned covered parking. Residents enjoy an impressive selection of community amenities, including a waterfront in-ground concrete pool, fitness center, recreation room with a full kitchen, library, game area, shuffleboard courts, laundry facilities, private boat docks, and a year-round social calendar. Take advantage of the community's private dock, where boat slips are available on a first-come, first-served basis for a minimal monthly fee, offering convenient access to Spring Lake Meander for boating, fishing, or simply enjoying the peaceful waterfront setting. Ideally located just minutes from historic downtown Winter Haven, the renowned Chain of Lakes, shopping, dining, medical facilities, golf courses, and LEGOLAND® Florida Resort, this waterfront condo offers the perfect blend of low-maintenance living, spectacular views, and an active Florida lifestyle.

700 Mirror Terrace Nw Unit 511, Winter Haven

1 Beds ⋅ 1 Baths ⋅ Orchid Spgs Vill 200 Condo SubDv. ⋅ 33884 Zip Code

Enjoy carefree Florida living in the desirable Seville Building at Orchid Springs! This well-maintained 1-bedroom, 1-bath third-floor corner unit offers 1,078 square feet of comfortable living space with elevator access and peaceful views of the beautifully landscaped lagoon. The spacious open floor plan features a large great room with endless furniture arrangement possibilities and an enclosed sunroom that fills the home with natural light while providing the perfect space to relax, work from home, or enjoy your morning coffee. The generous primary bedroom easily accommodates a king-size bedroom suite and includes a walk-in closet, while multiple additional storage closets throughout the home provide exceptional storage. This corner unit is conveniently located just steps from the elevator, laundry facilities, and stairwell, making everyday living even easier. Improvements include energy-efficient sunroom windows (2016), a newer gas furnace and coil with Honeywell thermostat (2018), repiping/plumbing (2018), building roof replacement for added peace of mind. A reserved parking space is also included. The monthly HOA fee covers water, sewer, natural gas, trash, exterior maintenance, grounds maintenance, and access to the community clubhouse and sparkling pool, allowing you to spend more time enjoying Florida and less time maintaining your home. Nestled in the heart of Southeast Winter Haven, Orchid Springs is known for its mature landscaping, tranquil setting, and convenient location. You'll be just minutes from Downtown Winter Haven, the Chain of Lakes, Cypress Gardens Boulevard shopping and dining, Publix, Winter Haven Hospital, Polk State College, and LEGOLAND® Florida Resort. Easy access to US-27 and the Polk Parkway makes commuting to Lakeland, Orlando, and Tampa a breeze. Whether you're searching for a year-round residence, winter retreat, or low-maintenance home, this move-in-ready condo offers comfort, convenience, and an exceptional Central Florida lifestyle.

200 El Camino Drive Unit 306, Winter Haven

2 Beds ⋅ 1 Baths ⋅ Winter Haven Harbour Apts Condo SubDv. ⋅ 33881 Zip Code

Virtually Staged. Perched on the third floor, Unit A38 at Winter Haven Condominiums offers the perfect combination of privacy, comfort, and peaceful views. As a desirable end unit, you'll enjoy extra windows that fill the home with natural light along with added privacy from neighboring units. Best of all, elevator access means you can enjoy the top-floor location without worrying about the stairs. Inside, the condo has been thoughtfully updated with newer flooring, fresh interior paint, and modern kitchen cabinetry featuring soft-close doors, creating a bright, inviting space that's truly move-in ready. Just outside your front door, the screened breezeway becomes an extension of your living space. Sip your morning coffee as the day begins, relax with a good book in the afternoon, or unwind in the evening while enjoying Florida's warm breeze and peaceful surroundings. Life here is about more than just the condo. Cool off in the community pool, enjoy a friendly game of outdoor shuffleboard, or take advantage of the community clubhouse, a comfortable, air-conditioned gathering space designed for both relaxation and entertainment. Inside, you'll find a pool table, indoor shuffleboard, fitness equipment, television, and a fully equipped kitchen that's perfect for hosting birthdays, holiday gatherings, game nights, or casual get-togethers. Just bring your favorite food, invite your family and friends, and enjoy the space without the hassle of entertaining at home. Covered, assigned parking is conveniently located just steps from the building, making everyday living even easier. Whether you're looking for a year-round residence or a seasonal escape from colder climates, Unit A38 offers low-maintenance living in a welcoming community where comfort, convenience, and relaxation come together. Schedule your private showing today and experience everything this charming condo has to enjoy.

1700 6th Street Nw Unit A38, Winter Haven

2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code

NEW LISTING IN CENTRAL FLORIDA. CONDO IN 55+ Gated Community. This condominium provides 1.347 SF of living area 2 bedrooms, 2 baths, Bonus room with views of Spring Lake & is located in the beautiful City of Winter Haven. Lakeridge Condominiums offers a maintenance free lifestyle with heated pool, tennis, shuffleboard, community room, gated secured entrances and covered assigned parking space. Water, sewer, cable, internet, trash removal and use of recreational facilities are included in the monthly fee. This well appointed move in ready condo has a large bright kitchen with lots of cabinets, great counter space, appliances and pantry closet. The kitchen overlooks the great room that also adjoins the additional bonus area and storage closet. The primary bedroom has a walk in closet & bathroom with a walk in shower. Beautiful views of Spring Lake can be enjoyed from the Primary bedroom & living areas. Washer/Dryer are included. Convenient to shopping, groceries & restaurants. Extra assigned storage bin on same floor. Lakeridge Condominiums is an age restricted, well maintained & well managed community.

1776 6th Street Nw Unit 807, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Imperial Harbours Ph 01 SubDv. ⋅ 33880 Zip Code

Remodeled and updated 2nd floor condo with picturesque views of the pool and lush landscaping. This 3 bedroom unit is ready for immediate occupancy. Recent updates include fresh interior paint, new flooring, new kitchen cabinets and solid surface counters. This established 55 and over community is nestled on the shores of Lake Howard on the famous Chain of Lakes and includes a community boat dock/fishing pier. Additional amenities include a heated pool, gazebo with bathrooms, shuffleboard, activities and secure storage. Located close to the heart of downtown Winter Haven, This condo provides an opportunity to enjoy the Lakefront Florida lifestyle at an affordable price. Monthly fees include water, cable, internet, trash, sewer, exterior maintenance and grounds maintenance making this an attractive opportunity for year round residents or snowbirds. Seller is a licensed Realtor in the State of Illinois.

333 Lake Howard Drive Nw Unit 211B, Winter Haven

3 Beds ⋅ 3 Baths ⋅ Hartridge Landing SubDv. ⋅ 33881 Zip Code

Check out this wonderful opportunity to own a spacious 3-bedroom, 2.5-bath home in the desirable 55+ community of Hartridge Landings! This well-maintained community offers a low HOA fee that includes access to the community pool and a private boat ramp on Lake Hartridge, providing access to Winter Haven's renowned Chain of Lakes. Step inside to an open and versatile floor plan featuring two expansive living areas that have endless possibilities for entertaining, relaxing, or creating a dedicated den, formal living room, or family room. The spacious first-floor primary suite serves as a private retreat, complete with an en-suite bathroom featuring dual sinks and a walk-in shower. The galley-style kitchen is conveniently located just off the dining area and offers the perfect space for a cozy breakfast nook. Also on the first floor are a half bath, a generously sized laundry room with built-in shelving, and a flexible office/bonus room with a built-in desk. Both the kitchen and office provide direct access to the private courtyard, creating a great space for outdoor relaxation or entertaining. Upstairs, you'll find two generously sized guest bedrooms and a full bathroom, providing plenty of space for family and visitors. Conveniently located near shopping, dining, medical facilities, and everyday conveniences, this home offers the perfect combination of comfort, functionality, and low-maintenance living. Schedule your private showing today!

2216 Starboard, Winter Haven

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