Cypresswood Country Club, FL homes for sale & real estate

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ABOUT THIS HOME
Cypresswood Country Club, FL Homes for Sale
Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath complete with a double vanity and a generous walk-in closet. Additional updates include a roof replaced in July 2022, windows in May 2023, appliances in November 2016, an updated water heater and A/C, a garage screen added in September 2019, and a motorized awning installed in July 2022. This is an except

$335,000

3 beds2 baths2,140 sq ft

731 Canberra Rd, Winter Haven, FL 33884

Clubhouse • Community pool • Renovated kitchen

ABOUT THIS HOME
Cypresswood Country Club, FL Homes for Sale
Welcome to this well-kept home in the highly sought-after Cypresswood Golf and Country Club, a gated community known for its beautiful grounds and exceptional amenities. Inside, you’ll find bright, open living spaces that flow seamlessly from the living room to the dining area and kitchen, creating a warm and functional layout for everyday comfort. The kitchen offers ample cabinetry and a practical design, while the bedrooms provide generous space and a relaxing atmosphere. The bathrooms are clean, comfortable, and thoughtfully maintained. At the front of the home, a charming courtyard gives you a private spot to unwind or personalize with your own touches. Residents of Cypresswood en

$215,000

2 beds2 baths1,439 sq ft

2270 Firestone Pl, Winter Haven, FL 33884

Gated community • Access to golf • Ample cabinetry

ABOUT THIS HOME
Cypresswood Country Club, FL Homes for Sale
PROBATE DEAL!!! Property is priced to sell and ready for a quick closing. Now is you chance to purchase the deal. Welcome home to this beautiful 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Home also features a stunning Florida room, ready for relaxation. dry bar with sink in living room perfect for entertaining your guests. Step out to your outside patio for even more enjoyment. The clubhouse is just steps away from your front door, imagine walking to the golf course from your new home!!! With access to golf, clubhouse, Restaurant, pool and recreational facilities, this home offers a low-maintenance lifestyle in a

$157,500

2 beds2 baths1,278 sq ft

649 Broadmoor Cir, Winter Haven, FL 33884

Outside patio • Access to golf • Clubhouse

ABOUT THIS HOME
Cypresswood Country Club, FL Homes for Sale
Florida living at its best! The spacious golf course home has three bedrooms two baths and is located in the gated, guarded, golf course community of Cypresswood. Situated on an oversized, landscaped lot on the 11th tee, this home boast soaring ceilings, open floor plan and a bright airy eat in kitchen. The luxurious master garden bath features dual sink vanity with solid surface top and large walk-in closet. Enjoy the screened back porch as you overlook the tee box. Call today for your private showing!

$324,000

3 beds2 baths2,076 sq ft

533 Saint Andrews Rd, Winter Haven, FL 33884

Master garden bath • Screened back porch • Large walk-in closet

ABOUT THIS HOME
Cypresswood Country Club, FL Homes for Sale
Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for priva

$629,000

4 beds3.5 baths3,614 sq ft

2964 Plantation Rd, Winter Haven, FL 33884

Golf course fairways • Water views • Circular drive

Property at 10 Meadowlake Ct, Winter Haven, FL 33884, 4 beds, 2.5 baths

$425,000

4 beds2.5 baths2,465 sq ft

10 Meadowlake Ct, Winter Haven, FL 33884

Property at 423 Greenfield Rd, Winter Haven, FL 33884, 2 beds, 2 baths

$220,000

2 beds2 baths1,432 sq ft

423 Greenfield Rd, Winter Haven, FL 33884

Property at 560 Saint Andrews Rd, Winter Haven, FL 33884, 2 beds, 2 baths

$319,500

2 beds2 baths1,922 sq ft

560 Saint Andrews Rd, Winter Haven, FL 33884

Property at 374 Troon Ct, Winter Haven, FL 33884, 2 beds, 2 baths

$238,500

2 beds2 baths1,634 sq ft

374 Troon Ct, Winter Haven, FL 33884

Property at 511 Pebble Springs Ct, Winter Haven, FL 33884, 2 beds, 2 baths

$264,000

2 beds2 baths1,361 sq ft

511 Pebble Springs Ct, Winter Haven, FL 33884

Property at 1062 Medinah Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$229,990

2 beds2 baths1,398 sq ft

1062 Medinah Dr, Winter Haven, FL 33884

Property at 3025 Silverado Ter, Winter Haven, FL 33884, 2 beds, 2 baths

$255,000

2 beds2 baths1,281 sq ft

3025 Silverado Ter, Winter Haven, FL 33884

Property at 381 Troon Ct, Winter Haven, FL 33884, 2 beds, 2 baths

$259,900

2 beds2 baths1,600 sq ft

381 Troon Ct, Winter Haven, FL 33884

Property at 708 Canberra Rd, Winter Haven, FL 33884, 3 beds, 2 baths

$325,000

3 beds2 baths2,004 sq ft

708 Canberra Rd, Winter Haven, FL 33884

Property at 718 Canberra Rd, Winter Haven, FL 33884, 3 beds, 2 baths

$369,000

3 beds2 baths2,159 sq ft

718 Canberra Rd, Winter Haven, FL 33884

Property at 1507 Eagle Pond Dr #1507, Winter Haven, FL 33884, 2 beds, 2 baths

$185,000

2 beds2 baths1,017 sq ft

1507 Eagle Pond Dr #1507, Winter Haven, FL 33884

Property at 307 Eagle Pond Dr #307, Winter Haven, FL 33884, 2 beds, 2 baths

$189,977

2 beds2 baths1,017 sq ft

307 Eagle Pond Dr #307, Winter Haven, FL 33884

Property at 4030 Palma Ceia Cir, Winter Haven, FL 33884, 3 beds, 3 baths

$785,000

3 beds3 baths2,541 sq ft

4030 Palma Ceia Cir, Winter Haven, FL 33884

Property at 680 Augusta Rd, Winter Haven, FL 33884, 3 beds, 2 baths

$290,000

3 beds2 baths1,932 sq ft

680 Augusta Rd, Winter Haven, FL 33884

Property at 1606 Eagle Pond Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$200,000

2 beds2 baths1,017 sq ft

1606 Eagle Pond Dr, Winter Haven, FL 33884

Property at 35 Enclave Dr, Winter Haven, FL 33884, 3 beds, 3 baths

$247,500

3 beds3 baths2,070 sq ft

35 Enclave Dr, Winter Haven, FL 33884

Property at 1102 Eagle Pond Dr #1102, Winter Haven, FL 33884, 2 beds, 2 baths

$170,000

2 beds2 baths1,017 sq ft

1102 Eagle Pond Dr #1102, Winter Haven, FL 33884

Property at 2282 Firestone Pl, Winter Haven, FL 33884, 2 beds, 2 baths

$180,000

2 beds2 baths1,164 sq ft

2282 Firestone Pl, Winter Haven, FL 33884

Property at 1012 Medinah Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$203,000

2 beds2 baths1,458 sq ft

1012 Medinah Dr, Winter Haven, FL 33884

Property at 14 Enclave Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$259,900

2 beds2 baths1,368 sq ft

14 Enclave Dr, Winter Haven, FL 33884

Property at 416 Sandestin Dr, Winter Haven, FL 33884, 3 beds, 2 baths

$334,900

3 beds2 baths1,744 sq ft

416 Sandestin Dr, Winter Haven, FL 33884

Property at 2817 Wingfoot Ct, Winter Haven, FL 33884, 3 beds, 2 baths

$280,000

3 beds2 baths1,666 sq ft

2817 Wingfoot Ct, Winter Haven, FL 33884

Property at 1077 Medinah Way, Winter Haven, FL 33884, 2 beds, 2 baths

$234,900

2 beds2 baths1,563 sq ft

1077 Medinah Way, Winter Haven, FL 33884

Property at 1039 Medinah Dr, Winter Haven, FL 33884, 2 beds, 2 baths

$219,900

2 beds2 baths1,278 sq ft

1039 Medinah Dr, Winter Haven, FL 33884

Property at 2284 Firestone Pl, Winter Haven, FL 33884, 2 beds, 2 baths

$230,000

2 beds2 baths1,164 sq ft

2284 Firestone Pl, Winter Haven, FL 33884

Property at 683 Broadmoor Cir #683, Winter Haven, FL 33884, 2 beds, 2 baths

$215,000

2 beds2 baths1,139 sq ft

683 Broadmoor Cir #683, Winter Haven, FL 33884

Property at 2809 Wingfoot Ct, Winter Haven, FL 33884, 2 beds, 2 baths

$260,000

2 beds2 baths1,682 sq ft

2809 Wingfoot Ct, Winter Haven, FL 33884

Property at 450 Palma Ceia Rd, Winter Haven, FL 33884

$150,000

— beds— baths— sq ft

450 Palma Ceia Rd, Winter Haven, FL 33884

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Based on information submitted to the MLS GRID as of Fri Nov 28 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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$279,500

+15.3% YoY | Oct 2025

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Cypresswood Country Club, FL

$279,500

+15.3%

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