Cypresswood Homes

/43
$332,500
- 3 Beds
- 2 Baths
- 2,004 Sq Ft
708 Canberra Rd, Winter Haven, FL 33884

Welcome to your dream retreat! This stunning 3-bedroom, 2-bathroom home is perfectly nestled in a tranquil cul-de-sac within a highly sought-after gated golfing neighborhood, just minutes from the excitement of Legoland. This property offers an ideal blend of an active lifestyle and serene living, making it perfect for families and those seeking relaxation.As you step inside, you'll be

David Small KELLER WILLIAMS REALTY SMART 1

708 Canberra Rd, Winter Haven, FL 33884
/20
$2,149 per month
- 4 Beds
- 2.5 Baths
- 2,733 Sq Ft
- House for Rent
552 Cody Caleb Dr, Winter Haven, FL 33884

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2293.90. That covers your base rent, $2149.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

552 Cody Caleb Dr, Winter Haven, FL 33884
/2
$310,000 Sold Jul 31, 2025
- 1,872 Sq Ft
- $166/SF
- 90 Days On Market
- 3 Beds
- 2 Baths
- Built 1984
571 Saint Andrews Rd, Winter Haven, FL 33884

Seller Motivated!! Welcome to 571 St Andrews Rd in Winter Haven, a beautifully updated 3-bedroom, 2-bathroom home in the highly sought-after Cypresswood Golf & Country Club, a gated community with 24/7 security. This 1,872 sq. ft. residence features an open-concept, split-bedroom floor plan designed for comfort and functionality. The stunning 2022 kitchen boasts solid wood, soft-close cabinets,

Corinna Weaver CROSBY & ASSOCIATES, INC.

571 Saint Andrews Rd, Winter Haven, FL 33884

/10
Est $307,380 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 1,879 Sq Ft
1446 Austin Terrace, Winter Haven, FL 33884

1446 Austin Terrace, Winter Haven, FL 33884

/46
$319,900 Pending
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
312 Inman Blvd, Winter Haven, FL 33881

Under contract-accepting backup offers. Welcome to the home you've been waiting for! This charming, energy-efficient gem is barely two years old and has been meticulously maintained, making it move-in ready. Inside, you’ll be greeted by beautiful tile flooring that flows seamlessly through the main living areas, with carpet in the bedrooms creating a warm, cozy atmosphere. The open-concept

Kaitlin Sidders HOGAN REALTY GROUP INC

312 Inman Blvd, Winter Haven, FL 33881
/37
$1,995 per month
- 4 Beds
- 2 Baths
- 1,848 Sq Ft
- House for Rent
668 Grove St, Winter Haven, FL 33884

Enjoy living in this beautiful one-story home in the Inman Groves Community. The home features 4 bedrooms, 2 baths, with an open floor plan. The floor is all tile, the kitchen has all brand new, stainless-steel appliances and 42” cabinets, and a 2-car garage. A large master suite with a shower, all carpet in bedrooms, and a laundry room with a washer/dryer. The home is approximately 1853 sq ft of

Amanda Yuan MULTI CHOICE REALTY LLC

668 Grove St, Winter Haven, FL 33884
/2
$340,000 Sold Jul 28, 2025
- 1,749 Sq Ft
- $194/SF
- 6 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
741 Canberra Rd, Winter Haven, FL 33884

"A Step Above the Rest" describes this spacious 3BR/2BA beauty w/ upgrades galore located in the desirable, gated, golfing community of Cypresswood! From the moment you enter, you'll be delighted with the quality of amenities & the pride of ownership that is displayed throughout this immaculate home. It has a fabulous open floor plan w/ soaring ceilings in the great rm that boasts triple

Julie Matthews JULIE MATTHEWS GROUP LLC

741 Canberra Rd, Winter Haven, FL 33884

/32
Est $244,923 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,262 Sq Ft
2949 Whispering Trails Dr, Winter Haven, FL 33884

2949 Whispering Trails Dr, Winter Haven, FL 33884

/10
$310,195 Pending
- 4 Beds
- 2.5 Baths
- 1,879 Sq Ft
1445 Austin Terrace, Winter Haven, FL 33884

Under Construction. The two-story Atlanta Plan has the “WOW-Factor” with four bedrooms, two and a half baths, and a two-car garage. This exquisite home offers an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a covered lanai via sliding glass doors. The

Ben Goldstein LENNAR REALTY

1445 Austin Terrace, Winter Haven, FL 33884
/37
$1,875 per month
- 3 Beds
- 2 Baths
- 1,688 Sq Ft
- House for Rent
4907 Summerfield Cir, Winter Haven, FL 33881

Welcome to your new home at 4907 Summerfield Circle Winter Haven, FL 33881!Walk into this 3 bed 2 bath charming home and the first thing you'll notice is the abundance of natural light shining into the kitchen-to-family room combo. The kitchen offers ease & accessibility with all the major appliances including a dishwasher. The master suite is a dream come true with all the storage space

Marilyn Kuczynski FLORIDA HOMES SALES & MANAGEMENT LLC

4907 Summerfield Cir, Winter Haven, FL 33881
/2
$243,000 Sold Jul 28, 2025
- 1,682 Sq Ft
- $144/SF
- 16 Days On Market
- 2 Beds
- 2 Baths
- Built 1990
2835 Wingfoot Ct, Winter Haven, FL 33884

Welcome to this beautiful 2 bedroom/2 bath home. Enjoy cooking in this spacious kitchen with leather granite countertops, shaker cabinets, and stainless steel appliances. In the evenings enjoy the gorgeous sunsets while relaxing in the sunroom overlooking the golf course views from the 8th hole tee off. Open floor plan with cathedral ceilings, luxury vinyl floors and 5 inch baseboards. This home

Denise Jones CENTURY 21 MYERS REALTY

2835 Wingfoot Ct, Winter Haven, FL 33884

/2
Est $322,113 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,216 Sq Ft
1410 Austin Terrace, Winter Haven, FL 33884

1410 Austin Terrace, Winter Haven, FL 33884

/30
$325,000 Pending
- 4 Beds
- 2.5 Baths
- 2,200 Sq Ft
1815 Emily Dr, Winter Haven, FL 33884

Under contract-accepting backup offers. A FOUR BEDROOM HOME FOR UNDER 330K! On top of that, the ROOF is 2022 & A/C 2023! This lovely 2-story home includes lots of BONUS space – so everyone has room to spread out. The property has great curb appeal, with landscaped planting beds and a palm tree lining the front walkway. Inside, the foyer offers soaring ceilings, archways, built-in niches and tile

Marc Collazo OLYMPUS EXECUTIVE REALTY INC

1815 Emily Dr, Winter Haven, FL 33884
/17
$1,795 per month
- 3 Beds
- 2 Baths
- 1,148 Sq Ft
- House for Rent
2049 Whispering Trails Blvd, Winter Haven, FL 33884

Nice single-family home with 3 beds and 2 baths for rent in Winter Haven, open floor plan ready to move in, Washer and Dryer included.Don't miss out on the opportunity to make this beautiful unit your new home. Contact us today to schedule a showing!FCG REALTY residents are enrolled in the Resident Benefits Package (RBP) which includes a convenient option for renters insurance, HVAC

Amber Madera FCG REALTY

2049 Whispering Trails Blvd, Winter Haven, FL 33884
/2
$292,500 Sold Jul 25, 2025
- 1,875 Sq Ft
- $156/SF
- 47 Days On Market
- 3 Beds
- 2 Baths
- Built 1989
432 Sandestin Dr, Winter Haven, FL 33884

Price Just Reduced!!!! Welcome to 432 Sandestin Drive in Cypresswood Golf & Country Club!This beautifully updated 3-bedroom, 2-bathroom home offers 2,048 sq ft in one of Winter Haven’s most sought-after gated communities. Recent updates include a brand-new roof and an updated Electrical Panel to allow you to connect a standby generator... Your insurance agent will thank you!Step

Steve Donahue LIVE FLORIDA REALTY

432 Sandestin Dr, Winter Haven, FL 33884

/85
Est $614,935 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,549 Sq Ft
440 Palma Ceia Rd, Winter Haven, FL 33884

440 Palma Ceia Rd, Winter Haven, FL 33884

/34
$249,900
- 3 Beds
- 2 Baths
- 1,242 Sq Ft
749 Overlook Grove Dr, Winter Haven, FL 33884

Welcome to 749 Overlook Grove Dr in Winter Haven! This charming home offers a desirable split floor plan with 3 bedrooms and 2 bathrooms, providing both comfort and functionality. The open layout makes it easy to entertain, while the spacious kitchen flows seamlessly into the living and dining areas. The primary suite includes its own private bathroom. Outside, you’ll find a fenced backyard—ideal

Derek McGehee ALL COUNTY POLK PROPERTY MANAG

749 Overlook Grove Dr, Winter Haven, FL 33884
/30
$2,450 per month
- 5 Beds
- 2.5 Baths
- 2,254 Sq Ft
- House for Rent
1454 Austin Terrace, Winter Haven, FL 33884

Make Winter Haven your new home. In Peace Creek Reserve, a master-planned community along a beautiful creek, this Edison home offers an open layout that integrates the kitchen, living room, and dining area and extends to the patio for outdoor enjoyment. Upstairs, five bedrooms surround a versatile loft (home office, study, or game room). The master suite offers a walk-in closet and en suite

Carla Moreno Pineda EXP REALTY LLC

1454 Austin Terrace, Winter Haven, FL 33884
/2
$425,000 Sold Jul 25, 2025
- 2,328 Sq Ft
- $183/SF
- 107 Days On Market
- 4 Beds
- 3 Baths
- Built 1977
141 Greenfield Rd, Winter Haven, FL 33884

Highly motivated! Price reduction! Plus offering $5,000 in seller concessions! Let's make a deal! Welcome to your dream home! Nestled on a picturesque golf course, this beautiful 4-bedroom, 3-bathroom home offers the perfect combination of space, comfort, and tranquility. Step inside to discover a spacious open floor plan featuring lots of natural light and breathtaking views of the lush greens

Aaron Clark COVENANT REALTY

141 Greenfield Rd, Winter Haven, FL 33884

/8
Est $273,104 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,444 Sq Ft
1462 Austin Terrace, Winter Haven, FL 33884

1462 Austin Terrace, Winter Haven, FL 33884

/35
$64,900
- 1 Bed
- 1 Bath
4320 Dundee Rd Unit 36, Winter Haven, FL 33884

This IMMACULATE Beach Bungalow is the Perfect Dream Home come true! Located in the Pristine ALL-AGE community of Southern Duck RV Resort in central Florida! With Exquisite curb appeal, first notice the pristine landscaping, clean-coated driveway under carport, and outdoor back patio with raised pavers for an evening under the warm Florida stars! This adorable cottage offers every modern

Linda Wilson Sunset Home Sales

4320 Dundee Rd Unit 36, Winter Haven, FL 33884
/9
$1,475 per month
- 2 Beds
- 2 Baths
- 1,017 Sq Ft
- Condo for Rent
1406 Eagle Pond Dr Unit 14F, Winter Haven, FL 33884

Second-floor two-bedroom, two-bathroom condo located in the gated golf community of Cypresswoods. Condo features inside laundry, upgraded kitchen, storage room and spacious living room. Enjoy the numerous HOA amenities including a private gated entrance with 24/7 guard, pool, gym, tennis courts, and golf. Home available immediately.

Sharon Billups SKYELINE REALTY LLC

1406 Eagle Pond Dr Unit 14F, Winter Haven, FL 33884
/2
$253,000 Sold Jul 24, 2025
- 2,370 Sq Ft
- $107/SF
- 133 Days On Market
- 3 Beds
- 3 Baths
- Built 1999
42 Enclave Dr, Winter Haven, FL 33884

Luxury, Leisure & Little Maintenance—Welcome to Cypresswood Living!2 primary suites! Excellent floorplan! Primary suite on bottom level and then a separate suite upstairs as a bonus! Private screened porch/patio! Low maintenance home!Nestled in the highly coveted Cypresswood Golf and Country Club community, this charming 3-bedroom, 3-bathroom home is where elegance meets ease. Step inside

Andrea Anderson S & D REAL ESTATE SERVICE LLC

42 Enclave Dr, Winter Haven, FL 33884

/12
Est $340,007 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,853 Sq Ft
110 Inman Blvd, Winter Haven, FL 33881

110 Inman Blvd, Winter Haven, FL 33881

/44
$159,900
- 3 Beds
- 2 Baths
- 1,568 Sq Ft
220 Monterey Cypress Blvd Unit 145, Winter Haven, FL 33884

SPACIOUS, STYLISH & SERENE ... Your PEACE CREEK RETREAT Welcome to CYPRESS CREEK VILLAGE, one of Central Florida's NEWEST 55+ active ADULT, PET-FRIENDLY communities, where lifestyle comes first. Located in WINTER HAVEN, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $781.00, which includes full access to RESORT-STYLE amenities for you and

Tammy Barnhart Renee's Resales

220 Monterey Cypress Blvd Unit 145, Winter Haven, FL 33884
/40
$1,700 per month
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- House for Rent
2956 Whispering Trails Dr, Winter Haven, FL 33884

NEW IMPROVED PRICE for this 3 Bedroom, 2 Bathroom Home for rent in a Gated Community, just minutes from Legoland! This 1,500 sq. ft. rental home is ready for its new tenant(s)! Nestled in the highly desirable Whispering Trails community, this property offers a spacious open layout with a split floorplan, spacious living room, and a large kitchen featuring an oversized island and breakfast

Kim Connahey HOUSE OF GLASS REAL ESTATE PM

2956 Whispering Trails Dr, Winter Haven, FL 33884
/2
$337,000 Sold Jul 22, 2025
- 1,888 Sq Ft
- $178/SF
- 101 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
768 Canberra Rd, Winter Haven, FL 33884

***SELLER IS OFFERING $2,000 TOWARDS AN INTEREST RATE BUYDOWN or TOWARDS BUYER'S CLOSING COSTS and a 1-YEAR HOME WARRANTY (with an acceptable offer)!*** Welcome to 768 Canberra Rd, located in the highly sought-after, gated/guarded community of Cypresswood, where country club living meets comfort and convenience. This beautifully updated 3-bedroom, 2-bathroom home sits on a generous 1/3-acre lot,

Deanna Stone THE STONES REAL ESTATE FIRM

768 Canberra Rd, Winter Haven, FL 33884

/26
Est $320,761 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,828 Sq Ft
405 Chance Ave, Winter Haven, FL 33881

405 Chance Ave, Winter Haven, FL 33881

/43
$123,400
- 2 Beds
- 2 Baths
- 1,184 Sq Ft
1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881

WELCOME to Your Stunning DREAM HOME... Welcome to CYPRESS CREEK VILLAGE, one of Central Florida's NEWEST 55+ active ADULT, PET-FRIENDLY communities, where lifestyle comes first. Located in WINTER HAVEN, this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $684, which includes full access to RESORT-STYLE amenities for you and your guests to

Tammy Barnhart Renee's Resales

1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881
/15
$1,995 per month
- 3 Beds
- 2 Baths
- 1,998 Sq Ft
- House for Rent
553 Saint Andrews Rd, Winter Haven, FL 33884

This three bedroom, two bathroom home is located in the gated Cypresswood golf subdivision. Enjoy the numerous HOA amenities, including a private gated community entrance with 24/7 guard, pool, fitness center, tennis courts, and golf. Home features a split floor plan, updated kitchen with stainless steel appliances and a gas range, brand new carpet in bedrooms, an enclosed sunroom that overlooks

Sharon Billups SKYELINE REALTY LLC

553 Saint Andrews Rd, Winter Haven, FL 33884
/2
$447,000 Sold Jul 16, 2025
- 2,188 Sq Ft
- $204/SF
- 3 Days On Market
- 3 Beds
- 2 Baths
- Built 2003
128 Lake Region Cir, Winter Haven, FL 33881

One or more photo(s) has been virtually staged. Welcome to your impeccably upgraded retreat within the sought-after, gated community of Gates of Lake Region in Winter Haven. This home offers a seamless blend of modern luxury and tranquil living, where everydetail has been thoughtfully enhanced for your comfort and enjoyment. Imagine stepping outside to your private pool, inviting you to

Lauren Deem RE/MAX TITANIUM GROUP

128 Lake Region Cir, Winter Haven, FL 33881

/12
Est $315,333 Not Listed For Sale
- 4 Beds
- 2 Baths
- 1,851 Sq Ft
3156 Country Club Cir, Winter Haven, FL 33881

3156 Country Club Cir, Winter Haven, FL 33881

/65
$139,900
- 3 Beds
- 2 Baths
- 1,566 Sq Ft
1182 Heartwood Cypress Dr, Winter Haven, FL 33884

MUSTANG RED GOLF CART INCLUDED. FRESHLY PAINTED INSIDE, 55 Plus Active Lifestyle Community. Seller is motivated. Only 6 years old which mean there is still plenty of life on the roof. LOW LOT FEE $521/month. This home has furniture that you can keep or can be removed if you have no need for it. You'll have all matching appliances, spacious shed, Golf CART INCLUDED, all season sunroom, laundry

Daniel Butler Sun Realty of Florida

1182 Heartwood Cypress Dr, Winter Haven, FL 33884
/16
$2,200 per month
- 3 Beds
- 2 Baths
- 1,511 Sq Ft
- House for Rent
2700 Crump Rd, Winter Haven, FL 33881

Lakefront Living at Its Finest!Discover the perfect blend of comfort, convenience, and stunning natural beauty with this 3-bedroom, 2-bath home located on the highly sought-after Lake Hamilton. This property offers unbeatable location — just minutes from shopping, dining, and entertainment, yet far enough to enjoy peace and privacy away from the city bustle.Recently updated, this home delivers

Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

2700 Crump Rd, Winter Haven, FL 33881
/2
$165,000 Sold Jul 03, 2025
- 1,139 Sq Ft
- $145/SF
- 47 Days On Market
- 2 Beds
- 2 Baths
- Built 1981
697 Broadmoor Cir Unit O71, Winter Haven, FL 33884

SELLER NOW OFFERING $5,000 TOWARDS BUYER CLOSING COSTS! Welcome to 697 Broadmoor Circle—an immaculately kept 2-bedroom, 2-bathroom villa offering maintenance-free living right on the 10th tee of Cypresswood’s beautiful golf course. This home blends comfort, style, and leisure in one of Winter Haven’s most desirable gated golf communities. Step inside to a bright, inviting interior where the

Andrew Fearn BHHS FLORIDA PROPERTIES GROUP

697 Broadmoor Cir Unit O71, Winter Haven, FL 33884

/25
Est $175,906 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,017 Sq Ft
203 Eagle Pond Dr, Winter Haven, FL 33884

203 Eagle Pond Dr, Winter Haven, FL 33884

/58
$209,000
- 2 Beds
- 2 Baths
- 1,139 Sq Ft
1012 Medinah Dr, Winter Haven, FL 33884

Welcome to The Tennis Villas!?Nestled in the highly desired Cypresswood Golf & Country Club, this gated community with 24/7 security offers the perfect blend of comfort, convenience, and resort-style living.At the entry, a classic wrought iron gate opens to a private front patio, creating a welcoming first impression and a charming space to enjoy.This 2-bedroom, 2-bath villa features expansive

Corinna Weaver CROSBY & ASSOCIATES, INC.

1012 Medinah Dr, Winter Haven, FL 33884
/12
$2,200 per month
- 4 Beds
- 2 Baths
- 1,851 Sq Ft
- House for Rent
3240 Country Walk Club Cir, Winter Haven, FL 33881

Brochure Available, Docs Available, Floor Plan Available

Moises Dominguez, LLC TBO REAL ESTATE PARTNERS INC

3240 Country Walk Club Cir, Winter Haven, FL 33881
/2
$310,000 Sold Jul 02, 2025
- 1,940 Sq Ft
- $160/SF
- 81 Days On Market
- 3 Beds
- 2 Baths
- Built 2001
204 Lake Region Blvd S, Winter Haven, FL 33881

25K Price Drop!!! Welcome to this beautifully updated 3-bedroom, 2-bathroom home with a bonus room in the sought-after Lakes of Gate Region gated community. Nestled among mature landscaping, this home boasts stunning curb appeal, a low HOA, and modern finishes throughout. Step inside to discover a spacious open floor plan filled with natural light and luxury vinyl plank flooring. The gourmet

Tyler Labod COLDWELL BANKER REALTY

204 Lake Region Blvd S, Winter Haven, FL 33881

/3
Est $300,065 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,756 Sq Ft
172 Inman Blvd, Winter Haven, FL 33881

172 Inman Blvd, Winter Haven, FL 33881

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