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Cypresswood Homes for Sale with Pool

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  • /36

    $379,999 Open Sat 11AM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,159 Sq Ft

    718 Canberra Rd, Winter Haven, FL 33884

    Elevated Living on the Fairway – Fully Renovated & ReadyWelcome 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

    Veronica Bard LA ROSA REALTY PRESTIGE

    718 Canberra Rd, Winter Haven, FL 33884
  • /31

    $327,000

    • 2 Beds
    • 2 Baths
    • 1,922 Sq Ft

    560 Saint Andrews Rd, Winter Haven, FL 33884

    Immaculate POOL HOME in CYPRESSWOOD – Fully Renovated & Located in a gated golf community!!! Welcome to your dream home in the highly desirable Cypresswood community! This beautifully updated residence features a new roof, stylish wood-look tile flooring throughout, and a completely remodeled kitchen equipped with Wi-Fi-enabled Samsung appliances—perfect for modern living and effortless

    Brooklyn Paul BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

    560 Saint Andrews Rd, Winter Haven, FL 33884
  • /43

    $349,000

    • 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 greeted by

    David Small KELLER WILLIAMS REALTY SMART 1

    708 Canberra Rd, Winter Haven, FL 33884
  • /43

    $320,000 Open Sun 11AM - 1:30PM

    • 3 Beds
    • 2 Baths
    • 1,932 Sq Ft

    680 Augusta Rd, Winter Haven, FL 33884

    NEW PRICE REDUCTION. 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. THIS HOME COMES FULLY FURNISHED!!! Home could be sold unfurnished. Upgrades include remodeled kitchen and appliances, remodeled bathroom, remote blinds

    Darlene Bice BHHS FLORIDA PROPERTIES GROUP

    680 Augusta Rd, Winter Haven, FL 33884
  • /30

    $349,900

    • 3 Beds
    • 2 Baths
    • 1,744 Sq Ft

    416 Sandestin Dr, Winter Haven, FL 33884

    UPSCALE HOME IN CYPRESSWOOD GOLF COMMUNITY. Beautifully remodeled and ready for the discerning buyer. Large 3 BR/2BA patio home located in beautiful Cypresswood Golf Community. This home features updated gourmet kitchen, remodeled baths, newer roof, whole house Generac generator, natural gas instant hot water heater, new refrigerator 2022, new gas range, Bosch dishwasher, real wood/bamboo

    Sharon Watson CENTURY 21 WATSON & MYERS REALTY

    416 Sandestin Dr, Winter Haven, FL 33884
  • /59

    $112,000

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    203 Monterey Cypress Blvd Unit 174, Winter Haven, FL 33881

    **Charming Waterfront Retreat in Florida!** NEW ROOF 2025! Discover your dream home with this stunning 2008 Fleetwood model that boasts breathtaking views of a serene lake. Imagine sipping your morning coffee while watching Florida's vibrant birds from your cozy dining area or spacious living room. This meticulously maintained residence features an inviting vinyl-windowed Florida room, perfectly

    Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

    203 Monterey Cypress Blvd Unit 174, Winter Haven, FL 33881
  • /44

    $159,900

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    312 Siberian Cypress Cir Unit 326, Winter Haven, FL 33881

    LUXURY Finishes - IMMACULATE Condition - NO Rear NEIGHBORS - 1,568 Sq. Ft. of Beautiful Living Space 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, Florida this land-LEASE community allows you to own your home while paying an approximate MONTHLY LOT RENT of $685, which includes

    Tammy Barnhart Renee's Resales

    312 Siberian Cypress Cir Unit 326, Winter Haven, FL 33881
  • /24

    $205,000

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    2282 Firestone Place, Winter Haven, FL 33884

    Welcome to Cypresswood Golf & Country Club Living!Discover this charming 2-bed, 2-bath, single-story Golf Villa at 2282 Firestone Pl in the exclusive gated community of Cypresswood in Winter Haven, FL. Boasting 1,164 sq ft of thoughtfully designed living space, this villa offers the perfect blend of comfort, style, and sweeping golf course views.Key Features & Upgrades:Two inviting

    Juan Yglesias KELLER WILLIAMS REALTY SMART 1

    2282 Firestone Place, Winter Haven, FL 33884
  • /73

    $770,000

    • 4 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    10 Webb Rd, Winter Haven, FL 33881

    Secluded 4-Bedroom Ranch on 5 Acres with Pool, Barns & Country Charm! Discover the perfect blend of privacy, convenience, and space with this 4 bedroom, 2.5 bath ranch-style home nestled on 5 acres in East Winter Haven. Tucked away at the end of a quiet road, this former citrus grove offers a peaceful, no-HOA lifestyle with plenty of room for your family, animals, and hobbies. Built in 1979, the

    Martin E Higgenbotham HIGGENBOTHAM AUCTIONEERS INTERNATIONAL LTD INC

    10 Webb Rd, Winter Haven, FL 33881
  • /43

    $139,900

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft

    336 Monterey Cypress Blvd Unit 169, Winter Haven, FL 33884

    TRANQUIL Living Awaits in This Beautifully Appointed Three-Bedroom Home in the Heart of Central Florida! Welcome to CYPRESS CREEK VILLAGE, one of the newest 55+ Active Adult communities...and PETS are welcome! Homes in CYPRESS CREEK VILLAGE, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot LEASED LAND. Owning the home, but not the land, you pay a monthly LOT RENT of $675

    Tammy Barnhart Renee's Resales

    336 Monterey Cypress Blvd Unit 169, Winter Haven, FL 33884
  • /46

    $234,900

    • 2 Beds
    • 2 Baths
    • 1,563 Sq Ft

    1077 Medinah Way, Winter Haven, FL 33884

    HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA. IT IS A SPACIOUS END UNIT IN THE BEAUTIFUL CYPRESSWOOD GOLF AND TENNIS COMMUNITY WITH LOTS OF AMENITIES INCLUDING GATE SECURITY. CALL TO PREVIEW THIS WELL-MAINTAINED 2 BED 2 BATH CB VILLA, WITH FORMAL LIVING AND DINING AREA, SPACIOUS FLORIDA ROOM OVERLOOKING THE TENNIS COURTS AND POOL AREA, NICE

    Heidi Gravel WESTLAKE REAL ESTATE CO., INC.

    1077 Medinah Way, Winter Haven, FL 33884
  • /46

    $264,900

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft

    13 Enclave Dr, Winter Haven, FL 33884

    Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf community of Cypresswood Golf & Country Club. This spacious end-unit features a functional split-bedroom floor plan, generous living and dining areas, and an inviting Florida room that adds to the overall living space. The kitchen offers ample cabinet

    Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

    13 Enclave Dr, Winter Haven, FL 33884
  • /28

    $57,500

    • 1 Bed
    • 1 Bath
    • 648 Sq Ft

    4320 Dundee Rd Unit 61, Winter Haven, FL 33884

    Live Your Florida Dream You Deserve! Welcome to SOUTHERN DUCKS RV RESORT, an ACTIVE ADULT, PET-FRIENDLY community where you own your home and LEASE THE LAND in Winter Haven, Florida. MONTHLY LOT RENT is approximately $595, which includes WATER, SEWER, TRASH PICKUP, LAWN CARE, along with a wide range of amenities for you and your guests to enjoy. This 648 sq. ft, fully FURNISHED 1993

    Tammy Barnhart Renee's Resales

    4320 Dundee Rd Unit 61, Winter Haven, FL 33884
  • /38

    $74,500

    • 1 Bed
    • 1 Bath
    • 456 Sq Ft

    4320 Dundee Rd Unit 47, Winter Haven, FL 33884

    Experience the PERFECT blend of comfort, STYLE, and convenience Welcome to SOUTHERN DUCKS RV RESORT - an ACTIVE ADULT and PET-FRIENDLY community where you own your home and LEASE THE LAND in Winter Haven, Florida. The MONTHLY LOT RENT is approximately $595, which includes WATER, SEWER, TRASH PICKUP, LAWN CARE, along with a wide range of amenities for you and your guests to enjoy. This

    Tammy Barnhart Renee's Resales

    4320 Dundee Rd Unit 47, Winter Haven, FL 33884
  • /39

    $272,000

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    3173 Whispering Trails Ave, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. WELCOME to this charming 3-bedroom, 3-bathroom home located in the beautiful gated community of Whispering Trails in Winter Haven, Florida. With 1,508 square feet of comfortable living space, this home features an open layout that seamlessly connects the kitchen, dining area, and living room, making it perfect for everyday living and

    Ashley Lopez KELLER WILLIAMS REALTY SMART 1

    3173 Whispering Trails Ave, Winter Haven, FL 33884
  • /51

    $152,500

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft

    268 Monterey Cypress Blvd, Winter Haven, FL 33884

    **Experience Florida Living at Its Finest!** Prepare to be captivated by this immaculate and elegant 2012 Nobility Maria, nestled in the highly sought-after Cypress Creek Village. This mostly furnished and freshly painted home boasts 1196 sq ft of beautifully designed living space, featuring 3 bedrooms, 2 bathrooms, and a delightful rear lanai leading to a bonus patio - all at an unbeatable

    Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

    268 Monterey Cypress Blvd, Winter Haven, FL 33884
  • /36

    $200,000

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

    1102 Eagle Pond Dr, Winter Haven, FL 33884

    Welcome to the Eagle Pond condominium in the Cypress Woods Golf and Country Club community. This coveted community is gated with 24-hour security guard. This bottom floor condo boasts 10-foot ceilings, open floor plan and two bedrooms with walk-in closets. The primary bedroom has an ensuite bathroom. The condo is newly painted with tile flooring in the Livingroom and kitchen. The bedrooms

    Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

    1102 Eagle Pond Dr, Winter Haven, FL 33884
  • /43

    $194,500

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

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

    Welcome to the Eagle Pond condominium in the Cypress Woods Golf and Country Club community. This coveted community is gated with 24-hour security guard. The condo boasts 10-foot ceilings, open floor plan and two bedrooms with walk-in closets. The primary bedroom has an ensuite bathroom. The condo is newly painted with updated flooring. There is a spacious storage closet on the exterior to

    Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

    1507 Eagle Pond Dr Unit 1507, Winter Haven, FL 33884
  • /13

    $269,000

    • 2 Beds
    • 2 Baths
    • 1,440 Sq Ft

    381 Troon Ct, Winter Haven, FL 33884

    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

    Barbara Downs CENTURY 21 WATSON & MYERS REALTY

    381 Troon Ct, Winter Haven, FL 33884
  • /42

    $167,500

    • 3 Beds
    • 2 Baths
    • 1,568 Sq Ft

    244 Siberian Cypress Cir Unit 345, Winter Haven, FL 33881

    STUNNING DESIGN • High-End Finishes • BUILT IN 2019 • NEW ROOF in 2024 Welcome to CYPRESS CREEK VILLAGE, one of the newest 55+ Active Adult communities...and PETS are welcome! Homes in CYPRESS CREEK VILLAGE, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot LEASED LAND. Owning the home, but not the land, you pay a monthly LOT RENT of $684 which gives you and your guest

    Tammy Barnhart Renee's Resales

    244 Siberian Cypress Cir Unit 345, Winter Haven, FL 33881
  • /26

    $255,000

    • 2 Beds
    • 2 Baths
    • 1,731 Sq Ft

    426 Gleneagles Ct, Winter Haven, FL 33884

    Located on a cul-de-sac, this 2 bedroom home overlooks a greenspace and the golf course beyond and in the front yard, it 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.Many quality upgrades performed over the past few years including windows.The hot tub in the screened courtyard works

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    426 Gleneagles Ct, Winter Haven, FL 33884
  • /46

    $269,999

    • 2 Beds
    • 2 Baths
    • 1,725 Sq Ft

    375 Troon Ct, Winter Haven, FL 33884

    Attention Investors & Home Buyers! Located in the desirable Cypresswood Golf & Country Club in Winter Haven, with a LOW HOA FEE of $128.00 MONTHLY, this spacious 2 bedroom, 2 bathroom home offers 1,725 Sq. Ft. of living space with a split-bedroom floor plan and oversized rooms. Enjoy serene golf course views from the sunroom overlooking the 11th green. Features include a screened front entry,

    Joan Diaz REMAX EXPERTS

    375 Troon Ct, Winter Haven, FL 33884
  • /33

    $164,900

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

    1602 Eagle Pond Dr Unit 1602, Winter Haven, FL 33884

    Don't miss this rare opportunity to own this lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club that is PRICED TO SELL! Be greeted by 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas and kitchen breakfast bar. Walk-in closets in both bedrooms offer an abundance

    Kayly Malinas JOHN WOOD REALTY, INC.

    1602 Eagle Pond Dr Unit 1602, Winter Haven, FL 33884
  • /22

    $174,500 Open Fri 3PM - 6PM

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

    1503 Eagle Pond Dr Unit 1503, Winter Haven, FL 33884

    Introducing a must-see condo in the esteemed gated community of Cypress Wood, this charming two-bedroom, two-bath home on the first floor is designed for both comfort and convenience. With beautiful wood laminate flooring, ceramic tile, and cozy carpet in the bedrooms, the open layout enhances the spacious feel, while both bedrooms offer generous walk-in closets. Enjoy your own private patio and

    David Small KELLER WILLIAMS REALTY SMART 1

    1503 Eagle Pond Dr Unit 1503, Winter Haven, FL 33884
  • /33

    $260,000

    • 2 Beds
    • 2 Baths
    • 1,682 Sq Ft

    2809 Wingfoot Ct, Winter Haven, FL 33884

    GOLF COURSE HOME! WELCOME TO THIS AWESOME GOLF VILLA WITH A FAIRWAY VIEW OF THE 8TH HOLE. WELL MAINTAINED HOME. ALL APPLIANCES REMAIN. TANKLESS WATER HEATER. FRESH PAINT. GENEROUS SIZED ROOMS, BEAUTIFUL SUNROOM/FAMILY ROOM WITH OUTDOOR PATIO OVERLOOKS GOLF. FRONT COURTYARD IS PRIVATE AND INVITING. YOUR OWN COVERED PARKING, CARPORT KEEPS CAR PROTECTED. PRIVATE ENTRANCE. GUARD GATED COMMUNITY, LOW

    Patricia France HAPPY DAYS REALTY LLC

    2809 Wingfoot Ct, Winter Haven, FL 33884
  • /31

    $78,900

    • 2 Beds
    • 2 Baths
    • 960 Sq Ft

    1002 Heartwood Cypress Dr Unit 223, Winter Haven, FL 33881

    "Coastal Farmhouse Charm" perfectly describes this stunning home Welcome to CYPRESS CREEK VILLAGE, one of the newest 55+ Active Adult communities...and PETS are welcome! Homes in Cypress Creek Village, a 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot leased land. Owning the home, but not the land, you pay a monthly lot rent of $611 which gives you and your guest

    Tammy Barnhart Renee's Resales

    1002 Heartwood Cypress Dr Unit 223, Winter Haven, FL 33881
  • /91

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 2,900 Sq Ft

    121 Greenfield Rd, Winter Haven, FL 33884

    Truly one of a kind home in the sought after neighborhood of Cypresswood Golf and Country Club. This is the only home with a fenced in yard that is on the award winning golf course! Enjoy your morning coffee out by the pristine pool that overlooks the course. This beautifully maintained home has something for everyone. The spacious kitchen with multiple upgrades and new appliances in the last

    Stacy Tuttle REMAX EXPERTS

    121 Greenfield Rd, Winter Haven, FL 33884
  • /16

    $139,900

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    397 Siberian Cypress Cir Unit 368, Winter Haven, FL 33881

    Cypress Creek Village - Winter Haven - 3 Bedroom / 2 Bathroom / 1,344 SF. / $149,900 *** OWNER OFFERING (6) MONTHS FREE LOT RENT! *** Cypress Creek Village Lot #368 is a "like new" 2020 model home with bright open floor plan! Enjoy the 9 foot ceiling with tray insert which highlights the high-end finishes throughout. Custom backsplash enhances the large kitchen with lots of

    Jennifer Meyers CRF Communities

    397 Siberian Cypress Cir Unit 368, Winter Haven, FL 33881
  • /68

    $175,000

    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    353 Siberian Cypress Cir, Winter Haven, FL 33881

    Move right in and start living the dream! This fully turnkey, two-bedroom home is ready for you, right down to the brand new golf cart! Boasting a desirable split floor plan, the open-concept living area flows seamlessly into the dining and kitchen, each bedroom offering the luxury of a private ensuite. Escape the ordinary and step into paradise! Imagine unpacking your personal belongings and

    Tanya Johnston American Mobile Home Sales of Tampa Bay, Inc.

    353 Siberian Cypress Cir, Winter Haven, FL 33881
  • /70

    $234,000

    • 3 Beds
    • 3 Baths
    • 1,716 Sq Ft

    352 Siberian Cypress Cir, Winter Haven, FL 33881

    STOP and TAKE A LOOK INSIDE! LOW LOT FEE $604/month, 55 Plus Active Lifestyle Community in Cypress Creek Village. 3 bedroom/3 bath home. The beautiful double wide home is not only spacious but comes fully furnished, has a Water Filtration System, is sold with all appliances, MOVE IN READY, Central Air, Storage Shed, Sunroom, Ceiling Fans, Walk In Closet, Ensuite Bathroom, Tray Ceiling, Removable

    Daniel Butler Sun Realty of Florida

    352 Siberian Cypress Cir, Winter Haven, FL 33881
  • /48

    $186,000

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft

    507 Eagle Pond Dr Unit G5, Winter Haven, FL 33884

    FOR SALE - 2 Bedroom/2 Bath Condo in lovely Cypresswood Gulf and Country Club. This condo overlooks a pond and beautiful cypress trees. It is very peaceful and serene. Then, the grounds are gorgeous as they are meticulously maintained for the golf courses. Everywhere one looks is a beautiful sight. The condo itself is very comfortable with generously sized bedrooms and walk-in closets. All

    Linda Andre COLDWELL BANKER REALTY

    507 Eagle Pond Dr Unit G5, Winter Haven, FL 33884
  • /15

    $230,000

    • 2 Beds
    • 2 Baths
    • 1,164 Sq Ft

    2284 Firestone Place, Winter Haven, FL 33884

    **"Embrace comfort and elegance in this beautiful 2-bedroom, 2-bathroom villa, offering nearly 1,400 sq. ft. of well-designed living space. Enjoy a spacious living and dining combo, a bright Florida room, and a master suite with a walk-in closet that opens to the Florida room—showcasing breathtaking golf course views and a peaceful ambiance. Situated in an exclusive, gated community with manned

    Sherifa Campbell MERVIN MORGAN REALTY & PROPERTY MANAGEMENT LLC

    2284 Firestone Place, Winter Haven, FL 33884
  • /31

    $219,900

    • 2 Beds
    • 2 Baths
    • 1,430 Sq Ft

    2254 Firestone Place, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Welcome home to this spacious 2-bedroom/2-bathroom Golf Villa located in the highly-sought-after Cypresswood community of Winter Haven and enjoy nearly maintenance-free living. Renovations completed in recent years include newer luxury vinyl flooring, kitchen appliances, and a freshly painted interior. This single-story villa offers TWO outdoor

    Kayly Malinas JOHN WOOD REALTY, INC.

    2254 Firestone Place, Winter Haven, FL 33884
  • /29

    $229,000

    • 2 Beds
    • 2 Baths
    • 1,139 Sq Ft

    683 Broadmoor Cir, Winter Haven, FL 33884

    NEW, NEW, NEW...this villa has recently been renovated. 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

    Darlene Bice BHHS FLORIDA PROPERTIES GROUP

    683 Broadmoor Cir, Winter Haven, FL 33884
  • /13

    $239,000

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft

    201 Cleveland Ave, Winter Haven, FL 33881

    Here's a chance to purchase a home with 7 lots + 15' of another lot to the north of the 7 lots. Home has had some birthdays & needs renovation/repairs in several areas. All lots are included and part of the land is partially chain-link fenced. Property is located near Dundee Road which provides access to Winter Haven to the west or US 27 to the east. While some may call this home a

    Tim Irby TOWN & COUNTRY REAL ESTATE

    201 Cleveland Ave, Winter Haven, FL 33881
  • /19

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,426 Sq Ft

    620 Wexford Ct, Winter Haven, FL 33884

    Welcome to your dream home-Step inside to discover this spacious and stunning MOVE-IN READY 2 bed/ 2 bath with an oversize 2 car garage located in the desirable 24hr Gated Cypress Club Neighborhood. Which offers the perfect blend of comfort and convenience with an array of neighborhood amenities including an amazing golf community, a park, pool, tennis courts, fitness center, dine-in-club house

    Pamela Brady LPT REALTY, LLC

    620 Wexford Ct, Winter Haven, FL 33884
  • /55

    $549,900

    • 4 Beds
    • 3 Baths
    • 3,257 Sq Ft

    19 Meadowlake Ct, Winter Haven, FL 33884

    New Price Reduction - Priced to Sell! Step into luxury with this stunning ranch-style home in the gated Cypresswood golf community! Nestled on a peaceful cul-de-sac, this spacious 4-bedroom home blends modern elegance with timeless charm, making it the perfect retreat.Inside, wood-look tile flooring flows throughout the main living areas, offering both durability and style. The gourmet kitchen is

    Rebecca Redman Hamaoui REAL BROKER, LLC

    19 Meadowlake Ct, Winter Haven, FL 33884
  • /53

    $212,500

    • 2 Beds
    • 2 Baths
    • 1,590 Sq Ft

    2214 Palma Ceia Rd, Winter Haven, FL 33884

    ***USDA Loan Eligibile and Special Finance Incentives Available*** Welcome to 2214 Sawgrass Ct, a meticulously maintained 2-bedroom, 2-bathroom golf villa nestled within the beautiful Cypresswood Golf and Country Club in Winter Haven, Florida. Built in 1987, this 1,590 square-foot residence offers a harmonious blend of comfort, style, and convenience, making it an ideal choice for those seeking a

    Jared Dunn LPT REALTY, LLC

    2214 Palma Ceia Rd, Winter Haven, FL 33884
  • /65

    $154,900

    • 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
  • /33

    $108,000

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881

    Don't miss out on this Beautiful Upgraded Home on a CORNER LOT in the Perfect Location. Homes in Cypress Creek Village, one of the newest 55+ PET-FRIENDLY community in Winter Haven, Florida, are on lot leased land. Owning the home, but not the land, you pay a monthly lot rent of $637.00 which gives you and your guest access to the amenities of the community. CORNER LOT WITH DOUBLE CARPORT

    Tammy Barnhart Renee's Resales

    502 Leyland Cypress Way Unit 61, Winter Haven, FL 33881

Showing Results 1 - 40, Page 1 of 2

Home Trends in Cypresswood, FL

Housing Trends

Median Sale Price
$275,000
Median Single Family Sale Price
$309,995
Median 2 Bedroom Sale Price
$185,000
Average Price Per Sq Ft
$179
Number of Homes for Sale
52
Last 12 months Home Sales
85
Months of Supply
7.30
Median List Price
$310,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
-12%
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