Cypresswood Homes under $400,000

Cypresswood Homes under $400,000

Welcome to Cypresswood, a picturesque subdivision nestled in the heart of Winter Haven, Florida! This charming community is the perfect blend of serene living and vibrant lifestyle, making it an ideal choice for families, retirees, and everyone in between. With its lush landscapes and friendly atmosphere, Cypresswood is more than just a place to live; it’s a place to thrive.

Cypresswood boasts a variety of homes designed to meet diverse needs and tastes, with many properties available for under $400,000. These homes are not only affordable but also offer excellent value, featuring modern amenities, spacious layouts, and beautiful outdoor spaces. Whether you’re looking for a cozy single-family home or a comfortable townhome, Cypresswood has something for everyone.

Living in Cypresswood means enjoying a wealth of community features. Residents have access to a stunning golf course, perfect for leisurely weekends or friendly competitions. The community also offers a clubhouse, where neighbors gather for social events and activities, fostering a strong sense of camaraderie. Plus, with Winter Haven's renowned Chain of Lakes nearby, outdoor enthusiasts will find endless opportunities for boating, fishing, and exploring nature.

Cypresswood is conveniently located near shopping, dining, and recreational facilities, ensuring that everything you need is just a short drive away. With its welcoming community spirit and affordable housing options, Cypresswood is the perfect place to call home in Winter Haven. Discover your dream home today and experience the charm of this delightful subdivision!

Newest Cypresswood Homes under $400,000

251 Greenfield Road, Winter Haven
$224,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
VACANT AND PRICED TO SELL! NEW ROOF 2025! 2 BED 2 BATH CONCRETE BLOCK STUCCO (CBS) HOME IN GUARD GATED CYPRESSWOOD GOLF AND COUNTRY CLUB, WINTER HAVEN FL 33884. Vacant single story home on a 0.44 acre lot with an attached garage, central air, and no CDD. Roof replaced 2025 and water heater 2017. The home needs some work and is priced for its condition. Seller is open to making repairs needed for FHA or conventional loan approval. Cypresswood is a golf cart friendly golf course community with a 24 hour guard gate, 18 hole championship golf course, clubhouse, community pool, and tennis. Located in Polk County near Legoland Florida, Cypress Gardens, the Chain of Lakes, shopping, dining, US 27, and the I-4 corridor between Orlando and Tampa. FHA, VA, conventional, and cash welcome. Sold as is.

251 Greenfield Road, Winter Haven
300 Greenfield Road, Winter Haven
$399,000
4 Beds ⋅ 3 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
REDUCED PRICE! ON THE GOLF COURSE! THIS RECENTLY REMODELED 4 BEDROOM 2.5 BATH HOME IN THE BEAUTIFUL, GATED COMMUNITY OF CYPRESSWOOD GOLF & COUNTRY CLUB!!! Open, spacious floor plan & ready to move in! Enjoy the Cypresswood Country Club lifestyle, including an active clubhouse, junior Olympic size pool, pickle ball courts, tennis, golf and a great restaurant with bar! When you're not enjoying all of the amenities, take a walk or ride your bike on the quiet, tree-lined streets throughout the community! This is a one-of-a-kind, two-story classic home on an extra-large lot, so plenty of room for a swimming pool!!! No rear neighbors, just Florida nature and golf in your backyard! Great place for socializing, family gathering and just lots of relaxing! You can park a dozen cars in your driveway and room to park your fishing boat or up to 6 cars in your garage! The oversized garages come complete with a "golf cart" garage in the rear of the home. Freshly remodeled by Bill Reed Construction, the updates include a freshly painted & neutral color scheme and luxury vinyl flooring throughout. You'll enjoy the golf-course views in the updated kitchen with granite tops and GE appliances. The open & bright kitchen nook area has sliding glass doors, and the family room is adjacent as well as a spacious dining room with lots of windows to enjoy! There is a separate living room with glass sliding doors to the oversized screened lanai and features a brick wood-burning fireplace creating a cozy area with lots of "flex" space. Room for all with 4 bedrooms and the primary suite boasts a walk-in closet, built-ins, dual sinks and a modern barn door. Three of the bedrooms are on the second floor. Mature landscaping and shade trees make perfect areas for enjoying the outdoor beauty and watching golf. Cypresswood is just minutes to Highway 27, great shopping, medical and the new Publix. Right in the heart of Central Florida with a "Chain of Lakes" for boating, fishing and a great "foodie" scene in the charming downtown district. This property has so much for your family to enjoy!!! Call today to schedule your private tour!

300 Greenfield Road, Winter Haven
683 Broadmoor Circle Unit 683, Winter Haven
$193,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood SubDv. ⋅ 33884 Zip Code
NEW LOWER PRICE!! This villa has recently had upgrades added and the seller is offering $7,000 AT CLOSING TOWARD CLOSING COSTS OR ADDITIONAL UPGRADES. New HVAC system, new kitchen cabinets, new appliances, new flooring, and even new drywall. This beautiful home is located directly on golf course frontage and has newer metal roof. You will be living in a community with a manned guard gate and your villa is only a short walk to the clubhouse, restaurant, and pool. Don't miss out on this one, call to view today. Flood zone area is deemed to be correct but must be verified by buyer/buyer broker.

683 Broadmoor Circle Unit 683, Winter Haven
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