Cypress Point Homes for Sale

Cypress Point Homes for Sale

Welcome to Cypress Point, an enchanting subdivision nestled in the heart of Winter Haven, Florida. This picturesque community in Polk County boasts a serene atmosphere, making it the ideal setting for families, retirees, and anyone seeking a tranquil lifestyle amidst stunning natural beauty. Cypress Point is characterized by its lush landscapes, charming streets, and a warm, welcoming community spirit that invites you to call it home.

Cypress Point features a variety of homes for sale, each thoughtfully designed to cater to diverse tastes and lifestyles. From spacious single-family homes to cozy residences, there’s something for everyone in this delightful neighborhood. Many of these homes come equipped with modern amenities, open floor plans, and beautiful outdoor spaces perfect for entertaining or enjoying a quiet evening under the stars.

The location of Cypress Point is a true gem, offering residents easy access to the pristine lakes and parks that Winter Haven is known for. With nearby recreational opportunities such as boating, fishing, and hiking, you’ll never run out of ways to enjoy the great outdoors. Plus, the subdivision is conveniently located near shopping centers, dining options, and top-rated schools, ensuring that all your daily needs are just a stone’s throw away.

If you’re ready to discover the charm and beauty of Cypress Point, explore our current listings of homes for sale. Your dream home awaits in this idyllic Winter Haven community, where comfort meets convenience in a vibrant Florida setting!

Newest Cypress Point Homes for Sale

2248 Cypress Point Drive W, Clearwater
$569,000
3 Beds ⋅ 2 Baths ⋅ Cypress Point SubDv. ⋅ 33763 Zip Code
Gorgeous 3/2 POOL HOME with a 2-car garage on an oversized lot! Your own private resort is waiting! Lovingly enjoyed as a second home, this property has been meticulously maintained, remodeled, and updated throughout. The sellers’ plans have changed, giving a lucky new owner the chance to enjoy everything they created! The star of this reimagined Mid-Century modern gem is the sparkling SCREENED POOL with a freshly painted patio — swim, lounge, and entertain bug-free year-round. And the setting makes it magic: lush, mature vegetation wraps the backyard into a private oasis, and with natural green space bordering one side — no side neighbor! — this oversized 0.31-acre fenced lot is remarkably quiet and serene. Inside, lofted ceilings and abundant natural light show off designer finishes, all-new custom blinds and window treatments, luxury vinyl plank flooring, and a showstopper kitchen anchored by an 11-foot quartz island, stainless-steel appliances, and two-toned shaker cabinets with soft-close hinges. The spacious primary suite offers a stunning ensuite with designer tile, walk-in shower, double vanity, and gold accents; two more bedrooms and an updated guest bath complete the private wing, plus laundry with a NEW stylish matte black washer and dryer (2025). The big-ticket items are DONE: Roof 2024, HVAC 2021, New Pool Pump (2026), all-new fully insulated Air Ducts for outstanding energey efficiency (2026), whole-house Water Filtration System, EV/Tesla charger, new front door, fresh landscaping, and freshly painted doors and garage floors. High and dry — no flood zone! And you’re just steps from neighborhood favorite Cypress Point Park — paved trails, picnic areas, and a beloved spot for morning strolls and dog walks. Centrally located to Clearwater’s beaches, Safety Harbor, and Downtown Dunedin. Pool days, beach days, and quiet evenings in your private oasis — schedule your showing today!

2248 Cypress Point Drive W, Clearwater
2109 Cypress Point Drive N, Clearwater
$520,000
3 Beds ⋅ 2 Baths ⋅ Cypress Point SubDv. ⋅ 33763 Zip Code
Move-in Ready! This beautifully updated corner-lot home offers 3 bedrooms, 2 bathrooms, and 1,520 square feet of relaxed living. The split-bedroom floor plan provides a natural flow between the living areas, with a generous primary suite and an oversized screened lanai for relaxing or entertaining. Thoughtful seller updates include waterproof LVP flooring, all appliances, smoothed ceilings, new lighting and fans, closet systems, gutters & leaf guards, a reconditioned HVAC system, whole-house water softener and filtration system, and much more! With no HOA, no flood zone, and no hurricane evacuation zone, plus convenient access to shopping, entertainment, highways, and only 20 minutes to Clearwater Beach, this home offers an optimal blend of updates, flexibility, and peace of mind.

2109 Cypress Point Drive N, Clearwater
2185 Little Brook Lane, Clearwater
$519,999
3 Beds ⋅ 2 Baths ⋅ Cypress Point SubDv. ⋅ 33763 Zip Code
Virtually Staged. Sophisticated. Refined. Completely Reimagined. Welcome to a truly exceptional residence where luxury design, modern comfort, and meticulous craftsmanship come together. Completely renovated from top to bottom, this designer-inspired home offers a level of finish and attention to detail rarely found at this price point. Step inside to an impressive open-concept living space anchored by a spectacular chef’s kitchen. Custom white oak cabinetry pairs beautifully with exquisite Taj Mahal quartzite countertops, while a cabinet-ready Sub-Zero refrigerator, upgraded cooktop with pot filler, and brand-new double oven with microwave create a kitchen that is as functional as it is stunning. Throughout the home, designer lighting, custom feature walls, sophisticated finishes, and carefully selected materials create a cohesive, elevated aesthetic. The spa-inspired bathrooms offer a luxurious retreat, while the beautifully renovated bedrooms provide comfort, style, and versatility. Offering approximately 1,510 sq. ft. of living space, the home also features an approximately 240 sq. ft. covered patio, extending the living experience outdoors and creating an ideal setting for entertaining, dining, or simply enjoying the Florida lifestyle. Additional upgrades include a brand-new washer and dryer and a brand-new air conditioning system, providing modern convenience and peace of mind. Perfectly positioned just 15–20 minutes from award-winning Clearwater Beach, with convenient access to restaurants, shopping, parks, golf, and everyday amenities, this home delivers the perfect combination of luxury and location. Seller is requesting the highest and best offers from interested buyers. Offers will be reviewed after the first weekend on the market. Seller reserves the right to accept an offer prior to the review period. This is more than a renovation—it’s a complete lifestyle upgrade. IMPORTANT DISCLOSURES: All information, including but not limited to square footage, room dimensions, lot size, measurements, distances, features, improvements, and other property details, is believed to be accurate but is approximate and subject to verification. Buyer and buyer’s agent are responsible for independently verifying all information that is important to their purchase decision, including measurements, dimensions, zoning, permitting, property condition, and any other material facts, through appropriate inspections, public records, and other sources. Some photographs have been virtually staged or digitally enhanced for marketing purposes. Virtually staged images are intended to illustrate potential furniture placement, décor, or use of space and may not represent the property’s actual furnishings, condition, finishes, or appearance. Buyers should rely on the actual property and not solely on digitally enhanced or virtually staged photographs.

2185 Little Brook Lane, Clearwater
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