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718 Canberra Road, Winter Haven
$363,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Elevated Living on the Fairway – Fully Renovated & Ready Welcome to 718 Canberra Road—where luxury living meets peace of mind. This completely renovated 3-bedroom, 2-bathroom home spans 2,159 sq ft and overlooks the 17th fairway of the prestigious Cypresswood Golf Course, offering stunning views from your sun-drenched enclosed Florida room. No detail was overlooked in this 2021-to-2025 top-to-bottom remodel, featuring new impact-resistant windows, a Rinnai tankless gas water heater, new HVAC system, updated plumbing, electrical, doors, lighting, and refinished roof with transferable warranty. The split floor plan creates optimal privacy, and custom window treatments—including plantation shutters and automated sunroom shades—add stylish functionality. The chef’s kitchen boasts granite countertops, under-cabinet lighting, a center island, and high-end appliances including a gas range and Wi-Fi-enabled refrigerator. Elegant touches like crown molding, pocket doors, recessed lighting, and luxury vinyl flooring add warmth and sophistication throughout. Enjoy the hurricane-ready upgrades: all impact windows and a generator transfer switch wired directly to the panel. Plus, a new irrigation system, automatic garage screen door, security camera wiring, and smart garage opener ensure comfort and convenience. Nestled in a 24-hour guard-gated community, Cypresswood offers resort-style amenities: clubhouse, pool, fitness center, tennis courts, and championship golf course. With no CDD, county-only taxes, and located just under a mile from Hwy 27, you're minutes from dining, shopping, and an easy drive to Orlando attractions. This home isn’t just move-in ready—it’s future-proofed. Come see why this meticulously crafted home stands out from the rest.

718 Canberra Road, Winter Haven
731 Canberra Road, Winter Haven
$310,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Just REDUCED!! 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 exceptional opportunity to own in one of Winter Haven’s premier neighborhoods. The home does come with appliances and washer and dryer. Some photos have been virtually staged.

731 Canberra Road, Winter Haven
560 Saint Andrews Rd, Winter Haven
$310,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Fresh new price — your opportunity to own in Cypresswood just got better! Welcome to 560 St Andrews Rd in Cypresswood Golf & Country Club!This beautiful patio home is truly move-in ready, offering 2 bedrooms, 2 bathrooms, and plenty of stylish updates.From the moment you arrive, you’ll be impressed by the brick-paver driveway, lush landscaping, and inviting curb appeal. Inside, the spacious living, dining, and kitchen areas feature wood-look ceramic tile floors, adding both elegance and durability.The fully updated kitchen is a chef’s dream with: Wi-Fi–enabled Samsung appliances (all brand new!) Gas range, Granite counters, Rich wood cabinetry, Convenient eat-in area.The master suite includes a walk-in closet and a private toilet and shower area for added comfort. Enjoy year-round living in the enclosed lanai, which is heated and cooled by central HVAC. From there, three sliding glass doors open to the brick-paver patio and a sparkling pool with screen enclosure (2023)—perfect for relaxing or entertaining. Additional highlights include: 2-car garage with laundry area and rolling screen door, New roof (2023) New AC system (2018) This home blends modern updates with low-maintenance living in a desirable golf community. Don’t miss this gem!

560 Saint Andrews Rd, Winter Haven
680 Augusta Road, Winter Haven
$290,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
$5,000 CASH BACK TO BUYER AT CLOSING!!! Come see this beautiful home in Cypresswood gated community. Twenty four hour manned gate. Home has newly installed ADT system. This is a golf community with club house, restaurant, bar, pool and tennis/pickle ball courts. Upgrades include remodeled kitchen and appliances, remodeled bathroom, remote blinds and plantation shutters, ceramic tile roof, Generac whole house generator, natural gas and more. Flood zone area is deemed to be correct but must be verified by buyer/buyer broker.

680 Augusta Road, Winter Haven
606 Turnberry Court, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Looking for a gated community, 3 bedroom home with a bonus room? No need to look any further! Welcome to the highly sought-after Cypresswood Golf Community, where comfort, security, and convenience come together in this spacious 3-bedroom, 2-bath home with an added air conditioned Florida Room that offers a flexible bonus space perfect for anything your lifestyle calls for. Enjoy beautiful golf course views right from your backyard...a peaceful and scenic setting you won’t want to miss! From the moment you arrive, you’ll appreciate the private front patio, offering a peaceful outdoor space to relax or entertain. Step inside to a home that is completely carpet-free, featuring durable laminate and tile flooring throughout, including the garage which is designed for both easy maintenance and a clean, modern feel. The interior layout provides a generous and open living space, with natural flow between the living, dining, and kitchen areas, making it ideal for everyday living and gatherings. One of the standout features is the Florida Room (with A/C), offering incredible flexibility. Whether used as a playroom, home office, guest space, or private suite, this area can easily be adapted to fit your needs complete with the option for a separate private entrance. The garage has been thoughtfully enhanced with a full kitchen setup, creating a unique and functional space perfect for outdoor entertaining, hosting, or extended cooking needs..an efficient and valuable addition. Community features you’ll love living in Cypresswood Golf & Country Club means access to: 24-hour guarded and gated entry,Community pool,Tennis courts,18-hole championship golf course, Clubhouse and on-site restaurant.Prime location conveniently located near U.S. Highway 27, I-4, and the Polk Parkway. This home offers easy access to everything Central Florida has to offer, including:LEGOLAND, Pega Pig Theme Park, Walt Disney World, Orlando International Airport and Tampa International Airport,Gulf Coast beaches near St. Petersburg and Tampa! Surrounded by a growing area filled with shopping, dining, and everyday conveniences, this location supports both lifestyle and accessibility. This home offers versatility, unique features, and access to a lifestyle-rich community—a true opportunity to enjoy the best of Florida living. Don't miss this opportunity! Come see it today!

606 Turnberry Court, Winter Haven
676 Augusta Road, Winter Haven
$272,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Welcome to 676 Augusta, a charming and well-maintained home nestled on a beautifully landscaped 0.18-acre lot with majestic oak trees and a serene backyard setting. The tiled entry foyer leads into a spacious living and dining area with updated carpeting, which opens seamlessly to an enclosed Florida room—perfect for relaxing or entertaining. The kitchen features stainless steel appliances, a custom closet pantry, and tiled flooring for easy maintenance. The primary bedroom offers direct access to the Florida room and includes a stylish bowl sink in the en-suite bathroom, along with a generous custom walk-in closet. Throughout the home, you'll find ample storage, including a partially floored attic for added convenience. Recent updates include a new furnace in 2025, and a roof replacement in 2016. The attached two-car garage is equipped with washer/dryer hookups and extensive built-in storage. It feels expansive and private thanks to the mature oak trees and thoughtful landscaping. This home combines comfort, functionality, and charm in a peaceful setting—ready for its next owner to enjoy. Situated in Cypresswood Golf & Country Club, a guard gated community with; 18 Hole championship golf course with clubhouse, restaurant, pool and tennis courts. Easy access to hwy 27 and I-4.

676 Augusta Road, Winter Haven
533 Saint Andrews Road, Winter Haven
$270,000
3 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
One or more photo(s) has been virtually staged. Below Market Value—Golf Course Property, Seller Wants Offers Now Below-market golf course opportunity with motivated sellers—bring all offers for this value-add property on the 11th fairway. This 3-bedroom, 2-bath home features cathedral ceilings, a gas fireplace, and an open layout with excellent potential. The property is priced to reflect needed personal updates and is ideal for an investor, fix-and-flip, or buyer looking to build instant equity in a desirable golf course setting. Sellers are extremely motivated and will consider all offers. Opportunities like this at this price point do not last.

533 Saint Andrews Road, Winter Haven
428 Gleneagles Court, Winter Haven
$269,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated home. Enjoy the peaceful screened courtyard with your cup of coffee, or watch the gorgeous Florida sunsets. The inside of the home has been lovingly kept up and updated. You won't want for space in this well thought out layout. Plenty of room for entertaining, or a quiet read alone. The garage has been set up for your perfect workspace or storage, whatever suits your needs. You have unlimited options with the screen garage door and a mini split that keeps everything cool when you need it! This golf course community is gated with a guard 24/7. Even if you don't golf, there will be something for you to do. Jr Olympic size pool, tennis courts, soon to be pickleball courts and a full service clubhouse with live music every weekend. Enjoy peace of mind knowing that the AC is less than a year old and the roof was replaced in 2022! Schedule your viewing today and welcome home!

428 Gleneagles Court, Winter Haven
460 Pinehurst Court, Winter Haven
$253,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Relaxed golf community living inside the gated and guarded Cypresswood Golf & Country Club. Welcome to 460 Pinehurst Ct in Winter Haven, Florida — an updated and spacious 2 bedroom, 2 bath patio home tucked away on a quiet cul-de-sac street with no through traffic. A private walled walkway leads to a charming front porch with sitting area, creating a warm and welcoming approach. Step inside the foyer to discover a clean, updated interior offering more than 1,600 square feet of comfortable living space, highlighted by beautiful new flooring, a freshly painted interior, and a long list of thoughtful improvements. All carpeting has been removed, the outdated popcorn ceilings have been scraped and refinished for a more modern look, and the overgrown landscaping has been cleared away to create a clean, attractive, and easy-to-maintain property. The roof was replaced in 2020 for added peace of mind, and gutters have also been installed for convenience and functionality. The great room design creates a spacious and open feel, accentuated by built-in shelving and large glass sliders that bring in natural light while offering the perfect space to showcase personal décor and seasonal accents. Sliding glass doors open to the enclosed, air-conditioned Florida room, seamlessly expanding the living area and creating an easy indoor-outdoor lifestyle that can be enjoyed year-round. The great room also offers space for formal dining in addition to the casual eat-in area found within the kitchen. The generously sized kitchen features abundant real wood cabinetry, a large breakfast bar, closet pantry, and an inviting dining area ideal for casual meals and everyday living. The primary suite offers comfortable dimensions, a walk-in closet, and an en-suite bath complete with a tiled walk-in shower. The guest bedroom is also nicely sized and features its own walk-in closet along with convenient access to the full guest bathroom with tub and shower. Storage is abundant throughout the home with multiple interior closets, garage storage closets, and a spacious 2-car garage with laundry connections, helping keep everything neatly organized and out of sight. Additional features include an irrigation system and low-maintenance exterior living. Beyond the home, Cypresswood delivers one of Winter Haven’s most enjoyable golf community lifestyles. Residents enjoy access to the 18-hole championship golf course, originally opened in 1969 and designed by award-winning architect Ron Garl. Known for its rolling fairways and mature landscaping, the course also features a pro shop, driving range, putting green, and dedicated short-game practice areas. Just a short stroll from the home, residents can enjoy the recently refurbished junior Olympic-sized swimming pool, tennis courts, pickleball courts, and Wellness Center. The Cypresswood Pub & Restaurant serves as the social heart of the community, offering planned events, a full bar, great food, and live weekend music in a relaxed setting overlooking the golf course. Whether you are searching for a full-time residence, winter retreat, or low-maintenance golf community home, 460 Pinehurst Ct offers an exceptional opportunity to enjoy the Florida lifestyle in one of Winter Haven’s most established gated golf communities.

460 Pinehurst Court, Winter Haven
426 Gleneagles Court, Winter Haven
$252,500
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Located on a cul-de-sac, this 2 bedroom home overlooks a greenspace and the golf course beyond. NEW INTERIOR AND EXTERIOR PAINT, NEW STAINLESS APPLIANCES, NEW FLOORING AND LIGHTING. Many quality upgrades performed over the past few years include windows, House re-piped 2021, New water heater 2021, New Electric breakers 2023, New AC/Heat Pump 2023, New roof 2024, New dishwasher 2024. This well maintained home is located in Cypresswood Golf and Country Club in Southeast Winter Haven and the front yard sits directly across from an undeveloped island so it affords the feeling of a much larger yard without all of the extra lawn maintenance to worry about. Enjoy morning sunrises from the family room and relaxing or alfresco dining in the courtyard. Patio furniture and large planters in the courtyard are included. Included with your HOA dues are access to the community pool, clubhouse and tennis courts. Listing agent has an ownership interest.

426 Gleneagles Court, Winter Haven
511 Pebble Springs Court, Winter Haven
$249,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Experience refined living in this beautifully updated 2-bedroom residence, perfectly situated within the coveted gated community of Cypresswood Golf & Country Club. The home has been thoughtfully maintained and enhanced with a long list of valuable updates, including a Roof (2019), A/C (2023), Tankless Water Heater (2024), Dishwasher (2024), Range (2024), and Microwave (2024). Additional upgrades add to the home’s appeal: plantation shutters, vinyl flooring in the living, dining, and guest bedroom, two new water-saving toilets, updated electrical switches and outlets, and modern light fixtures. The interior layout blends comfort with elegance, featuring a light-filled living area that flows seamlessly into the Florida Room. This versatile space offers an ideal retreat for morning coffee or quiet evenings, surrounded by tranquil views of the community. Beyond the home, Cypresswood delivers a true resort-style lifestyle. Residents enjoy the peace of 24-hour manned gate access, a championship 18-hole golf course, six tennis courts, a state-of-the-art fitness center, and a sparkling pool. Social and dining options are just steps away at the popular Cypresswood Pub, creating the perfect balance of leisure and connection. Whether as a seasonal escape or a full-time residence, this home offers the perfect combination of modern convenience, timeless upgrades, and luxury living in one of the area’s most sought-after communities.

511 Pebble Springs Court, Winter Haven
381 Troon Court, Winter Haven
$249,900
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
PRICE SLASHED AND READY TO SELL!! Updated and beautifully maintained 2bd/2bath plus Bonus Room. Definitely one of the loveliest houses in Cypresswood. Golf and Country Club located on the 11th tee. The home offers exceptional views of the Fairway. Mature Landscaping and circular paved driveway. Welcome your buyer to this beautiful, maintained home. Large Living Room and adjacent dining room offers ample room for furnishings. The Bonus Room could be used as an office or an additional space for company and/or family. Disclaimer-measurements are approximate.

381 Troon Court, Winter Haven
374 Troon Court, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
BRAND NEW ROOF INSTALLED NOVEMBER, 2025. New flooring May 2026. Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room. Additional amenities include an expansive master bedroom, 2 car garage with door opener and front courtyard wall. The home is in move-in condition but does have some original features and it's priced accordingly. This is an ideal opportunity to make this home your own with some contemporary updates.

374 Troon Court, Winter Haven
522 Pebble Springs Court, Winter Haven
$225,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Enjoy the Florida country club lifestyle in this affordable and freshly updated home. Located at the end of a cul-de sac, this home features 2 bedrooms, 2 bathrooms, eat in kitchen, spacious living/dining room combo, screened porch and an attached 2 car garage. Recent updates within the past year include a new roof, fresh interior and exterior paint, New AC system, luxury vinyl flooring, water heater and a new dishwasher. Other updates within the past couple years include appliances, blinds and remodeled master bathroom shower. MOVE IN CONDITION! Additional amenities include a rear screened porch overlooking a larger-than-most yard, Architectural Shingles, Pull-down Attic Stairs in the garage, Gas Water Heater and a 2-Car Garage. Cypresswood Golf & Country Club offers a variety of amenities, including an 18-hole golf course, clubhouse with pro shop and lounge, tennis courts, and a swimming pool. Located in close proximity to HWY 27 affording easy access to I-4 and within 1.5 hours of either coast. This ideal location is just a mile down the road from a brand new Publix set to open shortly as well as being conveniently close to shopping, restaurants, and Legoland. Listing Agent has an ownership interest.

522 Pebble Springs Court, Winter Haven
466 Muirfield Court, Winter Haven
$222,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Sited in the desirable golfing community of Cypresswood Golf & Country Club is this charming Patio Home featuring a desirable split-bedroom floor plan with two generously sized bedrooms. As you enter the home, you'll be greeted by a charming side entry porch enhanced with a leaded glass door. The bright and cheerful living room boasts large windows and hardwood flooring, creating an inviting space. The formal dining room is perfect for entertaining, with an easy flow from both the living and kitchen areas. Solid surface flooring and crown molding are featured throughout the home, adding a touch of elegance. The eat-in kitchen offers wood cabinetry, a closet pantry, a gas range, and an upgraded stainless steel appliance package. A glass sliding door from the kitchen brings the outdoors in, providing access to the Florida Room. The primary bedroom suite includes a walk-in closet and an ensuite bath, complete with two linen closets, a single vanity, and a water closet with a walk-in shower. The Florida Room is a perfect retreat to enjoy scenic views year-round, with five glass sliding doors providing seamless access to the patio, an ideal space to relax and unwind. Additional amenities include: Irrigation System, Gutters, Architectural Shingles, Pull-down Attic Stairs, Washer & Gas Dryer, Gas Water Heater and a 2-Car Garage. Cypresswood Golf & Country Club offers an array of amenities, including an 18-hole golf course, clubhouse, pro shop, lounge, wellness center, tennis courts, and a swimming pool. This ideal location is conveniently close to shopping, restaurants, and Legoland, making it the perfect choice for those seeking both luxury and convenience.

466 Muirfield Court, Winter Haven
634 Wexford Court, Winter Haven
$220,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
MOVE-IN CONDITION! Charming 2-bedroom, 2-bath patio home on a shaded, landscaped corner lot in Cypresswood Golf & Country Club. This well-maintained single-level residence features a split-bedroom floorplan, expansive great room for living and dining, breakfast nook, carpet and tile floors, skylight, ceiling fans, ample closets including a walk-in in the primary, and a convenient attached 2-car garage with attic access. Enjoy an oversized screened rear porch overlooking picturesque greenspace and mature oaks. Systems and amenities include architectural shingle roof, gas water heater, and full kitchen appliances (dishwasher, range, microwave, refrigerator, washer/dryer). HOA includes community pool and private road; community amenities include an 18-hole golf course, clubhouse with pro shop and lounge, Jr. Olympic pool, tennis/pickleball/recreation area. Convenient to HWY 27, I-4, shopping, restaurants and near Publix.

634 Wexford Court, Winter Haven
730 Canberra Road, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
The property you are inquiring about is located in Winter Haven, FL, in the Cypresswood area of Polk County. This is a price induced-to-sell home, located in a gated, guarded, golfing community. This is on the fairway so no backyard neighbors, and in a private, peaceful setting. This is a 2-bedrrom, 2-bath, 1,571 sq.ft. home with an open area concept. This house is looking for new owners to make it their own. Divided bedrooms, country-dine in kitchen, plus a gathering room for desired use. Additional enclosed lanai for added space, plus an oversized 2-car garage. Easy to view - call, text, email, and see it today! *Agents, please read MLS remarks.*

730 Canberra Road, Winter Haven
459 Pinehurst Court, Winter Haven
$195,000
2 Beds ⋅ 2 Baths ⋅ Cypresswood Patio Homes SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained patio home located in a desirable gated golf community, offering comfort, convenience, and exceptional value. Nestled on a quiet dead-end street, this charming residence features 2 bedrooms, 2 bathrooms, and a spacious 2-car garage. Property Highlights 2 Bedrooms | 2 Bathrooms 2-Car Garage New Roof (2024) New Gutters (2025) New Hot Water Heater (2025) 10' x 14' Air-Conditioned Patio Dead-End Street Location Beautiful Landscaping with Mature Oak Trees This inviting home offers a functional layout designed for easy living. The 10' x 14' air-conditioned patio provides additional year-round living space—perfect for relaxing, entertaining, or enjoying your morning coffee in comfort. Recent updates provide peace of mind, including a new roof installed in 2024, new gutters in 2025, and a new hot water heater in 2025. Community Features Gated entrance for added security 18-hole golf course Clubhouse Community swimming pool Enjoy resort-style amenities just steps from your door. The beautifully maintained community offers an active lifestyle with golf, swimming, and social opportunities. Prime Location Conveniently located close to shopping, medical facilities, and everyday essentials, this home combines privacy with accessibility. With stunning landscaping, majestic oak trees, and thoughtful updates throughout, this property is truly priced to sell. Don’t miss the opportunity to own a home in this sought-after golf community.

459 Pinehurst Court, Winter Haven