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Studio to 2 Bedroom Homes for Sale in Cypresswood

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  • /39

    $188,977

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

    307 Eagle Pond Dr, Winter Haven, FL 33884

    PRICE IMPROVEMENT! Welcome home to this charming condo in the 24/7 guard-gated Cypresswood Golf & Country Club, where you can unwind with beautiful pond views from the living room and both bedrooms. The open layout feels bright and inviting, with 10-foot ceilings, rich wood cabinets, and a breakfast-bar kitchen that’s perfect for morning coffee or hosting friends. You’ll love the spacious walk-in

    Agent Photo

    Mabel Vassallo

    CENTURY 21 MYERS REALTY

    (863) 431-4399

    307 Eagle Pond Dr, Winter Haven, FL 33884
  • /28

    $53,500

    • 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 $630, 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
  • /14

    $210,000

    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft

    423 Greenfield Rd, Winter Haven, FL 33884

    Great house in gated Cyrpresswood neighborhood, close to US 27 and I 4, gplf community with multiple courses in the neighborhood. Fresh paint on the house, roof is right at 10 years old, A/C is about 7 years old estimated. Great place to live with clubhouse and restaurant in neighborhood, community pool, no need to leave the neighborhood. Nice 2 bed/2bath with Florida room that has the

    Chace Vaughn TOWN & COUNTRY REAL ESTATE

    423 Greenfield Rd, Winter Haven, FL 33884
  • /32

    $98,800

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

    502 Leyland Cypress Way, Winter Haven, FL 33881

    CYPRESS CREEK VILLAGE #61 / 2 BED / 2 BATH / 1,344 SF / $98,800 POND VIEW HOME with Double Driveway! This Large WELL MAINTAINED updated home is partially furnished and move-in-ready for you! This 2006 Nobility Home features an open floor plan and large two-level lanai overlooking a pond! Lanai includes tile floors, vinyl windows, roman shades, and a covered patio that is perfect for grilling out!

    Jennifer Meyers CRF Communities

    502 Leyland Cypress Way, Winter Haven, FL 33881
  • /28

    $148,900

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

    1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884

    Lot #256 - 2 Bed /2 Bath + Den /1,568 Sq. Ft./$148,900.00 Spectacular Pond Views from this 2016 Ashley Model in beautiful Cypress Creek Village! This spacious home is located on a waterfront lot with breathtaking views! It offers a double carport with an additional golf cart path! This gorgeous home offers: *Vaulted Ceilings *Kitchen with coffee station and pantry *French doors into large den

    Jennifer Meyers CRF Communities

    1221 Cypress Vine Rd Unit 256, Winter Haven, FL 33884
  • /54

    $315,500

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

    560 Saint Andrews Rd, Winter Haven, FL 33884

    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

    Corinna Weaver CROSBY & ASSOCIATES, INC.

    560 Saint Andrews Rd, Winter Haven, FL 33884
  • /9

    $189,999

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

    2284 Firestone Place, Winter Haven, FL 33884

    Welcome to this spacious 2-bedroom, 2-bath villa located within a gated golf-course community in the heart of Winter Haven, Florida. This home features a well-designed floor plan with comfortable living areas, ample natural light, and a low-maintenance lifestyle. The community offers beautifully maintained grounds and a peaceful setting surrounded by scenic golf-course views. Ideally situated

    Stephanie Class Cordero EXP REALTY LLC

    2284 Firestone Place, Winter Haven, FL 33884
  • /49

    $299,999

    • 2 Beds
    • 2 Baths
    • 1,293 Sq Ft

    469 Muirfield Ct, Winter Haven, FL 33884

    Charming and Affordable 2/2 Block Home in Cypresswood Golf CommunityDiscover comfort and convenience in this beautifully maintained 2 bedroom, 2 bathroom split floor plan block home located in the highly desirable Cypresswood Golf Community. This inviting residence offers a bright, open layout with spacious living areas and large walk-in closets in both bedrooms, providing plenty of storage

    Vikki Thielen THE MARKET REALTY COMPANY

    469 Muirfield Ct, Winter Haven, FL 33884
  • /45

    $110,000

    • 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 $724, which includes full access to RESORT-STYLE amenities for you and your guests to enjoy.

    Tammy Barnhart Renee's Resales

    1209 Cypress Vine Rd Unit 295, Winter Haven, FL 33881
  • /59

    $150,000

    • 2 Beds
    • 2 Baths

    353 Siberian Cypress Cir, Winter Haven, FL 33881

    Welcome home to this impeccable 2-bedroom 2-bath sanctuary awaiting your arrival! This STUNNING 2023-built residence is nestled in one of Winter Haven's most sought-after 55+ communities, Cypress Creek Village. **LOW LOT LEASE $660** and Close to all! With Palm trees lining the streets, this lovely community offers resort-style living at its finest. FULLY FURNISHED with well-appointed features,

    Linda Wilson Sunset Home Sales

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

    $259,900

    • 2 Beds
    • 2 Baths
    • 1,368 Sq Ft

    14 Enclave Dr, Winter Haven, FL 33884

    Fresh on the market is this meticulously maintained and professionally updated 2 bedroom 2 bath villa located in the sought after "Enclave" neighborhood in Cypresswood, a gated golf community in SE Winter Haven.The open floor plan features an expansive kitchen with breakfast nook, spacious living/dining room combo, split bedrooms with ample closets, inside laundry area equipped with a washer

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    14 Enclave Dr, Winter Haven, FL 33884
  • /20

    $89,500

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    1008 Heartwood Cypress Dr, Winter Haven, FL 33881

    CYPRESS CREEK VILLAGE #222 / 2 BED / 2 BATH / 1,000 SF / $89,500 COZY HOME with tranquil views! This 2016 Nobility Home features an open floor plan AND two large bedroom suites! The screen room overlooks a meadow framed by live oak trees. An additional covered area by the shed is a perfect spot for grilling! The open plan combines a breakfast nook, living room, and light filled kitchen. Vaulted

    Jennifer Meyers CRF Communities

    1008 Heartwood Cypress Dr, Winter Haven, FL 33881
  • /24

    $215,000

    • 2 Beds
    • 2 Baths
    • 1,439 Sq Ft

    2270 Firestone Place, Winter Haven, FL 33884

    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

    Darin Dobson COMPASS FLORIDA LLC

    2270 Firestone Place, Winter Haven, FL 33884
  • /17

    $238,500

    • 2 Beds
    • 2 Baths
    • 1,634 Sq Ft

    374 Troon Ct, Winter Haven, FL 33884

    BRAND NEW ROOF INSTALLED NOVEMBER, 2025.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

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    374 Troon Ct, Winter Haven, FL 33884
  • /62

    $149,900

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

    388 Siberian Cypress Cir, Winter Haven, FL 33881

    TREAT YOURSELF TO THIS GORGEOUS 2019, 1 OWNER HOME IN BEAUTIFUL CYPRESS CREEK VILLAGE. FEATURING TWO BEDROOMS, TWO BATHROOMS, A DEN (CAN BE A GUEST ROOM), VINYL FLOORING WITH A WOOD GRAIN LOOK THROUGHOUT. A GOURMET KITCHEN AND HUGE MASTER RETREAT WITH A PRIVATE MASTER BATH. LOCATED IN PHASE 4, WITH NO REAR NEIGHBORS!! FURNISHED, WITH A GOLF CART! FOYER - As you enter this Beautiful Entry Way into

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

    388 Siberian Cypress Cir, Winter Haven, FL 33881
  • /34

    $170,000

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

    2282 Firestone Place, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. 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

    Juan Yglesias KELLER WILLIAMS REALTY SMART 1

    2282 Firestone Place, Winter Haven, FL 33884
  • /35

    $59,900

    • 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
  • /46

    $215,000

    • 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 this one,

    Darlene Bice BHHS FLORIDA PROPERTIES GROUP

    683 Broadmoor Cir, Winter Haven, FL 33884
  • /44

    $219,900

    • 2 Beds
    • 2 Baths
    • 1,278 Sq Ft

    1039 Medinah Dr, Winter Haven, FL 33884

    1 OWNER HOME!! Don't miss out on this 2 bed 2 bath tennis villa in the highly desired neighborhood of Cypresswood. The HOA takes care of the roof, lawn, paint, and exterior maintenance. Enjoy the security of living in a community with a 24 hour guard at the gate. There is plenty to do all within the community. There is a golf course, restaurant, community pool and tennis courts. The home has all

    Robert webb JOHN WEBB INC

    1039 Medinah Dr, Winter Haven, FL 33884
  • /51

    $75,000

    • 2 Beds
    • 2 Baths
    • 1,008 Sq Ft

    707 Red Cypress Ln, Winter Haven, FL 33881

    2006 home in Cypress Creek Village, a premier 55+ community, will allow 40+! Super cute home with split bedroom plan with 2 large bedrooms, 2 baths, and a den! Spacious and open floor plan with an open-concept living area. Fully furnished with laminate flooring in the main areas, all window treatments remain. LIVING ROOM 17' 6 X 15' 9 Welcome to your new home! Spacious, Bright, and Open to the

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

    707 Red Cypress Ln, Winter Haven, FL 33881
  • /13

    $259,900

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    381 Troon Ct, Winter Haven, FL 33884

    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

    Barbara Downs CENTURY 21 WATSON & MYERS REALTY

    381 Troon Ct, Winter Haven, FL 33884
  • /36

    $156,000

    • 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 have

    Robin McClendon CENTURY 21 MYERS REALTY LAKE WALES

    1102 Eagle Pond Dr, Winter Haven, FL 33884
  • /27

    $200,000

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

    1606 Eagle Pond Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. This is Eagle Pond, a beautiful section of the Cypress Woods Golf and Country Club. This secure, gated community offers around-the-clock security for added peace of mind. Situated on the second floor, this condo showcases impressive 10-foot ceilings and a spacious open layout. It features two bedrooms, walk-in closets, ceiling fans and the primary

    Juan Yglesias KELLER WILLIAMS REALTY SMART 1

    1606 Eagle Pond Dr, Winter Haven, FL 33884
  • /28

    $219,500

    • 2 Beds
    • 2 Baths
    • 1,398 Sq Ft

    1062 Medinah Dr, Winter Haven, FL 33884

    Location, Lifestyle & Leisure — All in One!Discover the perfect blend of comfort, convenience, and community in this beautifully maintained villa located in a sought-after gated Cypresswood Community with 24-hour security. Enjoy resort-style living with access to championship golf, tennis courts, a fitness center, community pool, on-site restaurant, and so much more — all just steps from your

    Doug DeWitt NEW HOME ADVANTAGE LLC

    1062 Medinah Dr, Winter Haven, FL 33884
  • /33

    $149,000

    • 2 Beds
    • 2 Baths
    • 1,647 Sq Ft

    1222 Cypress Vine Rd Unit 287, Winter Haven, FL 33884

    CYPRESS CREEK VILLAGE #287 - 2 BED + DEN / 2 BATH / 1,647 SF. / $149,900 CUSTOM BUILT HOME with Double Driveway! This OPEN FLOOR PLAN home is furnished and move-in-ready! This immaculately maintained home is VERY SPACIOUS! It features an open floor plan, integrated Florida Room, and screened front porch. This sought after Model has large rooms throughout. The spacious master bedroom suite has a

    Jennifer Meyers CRF Communities

    1222 Cypress Vine Rd Unit 287, 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
  • /33

    $255,000 Open Sat 3PM - 6PM

    • 2 Beds
    • 2 Baths
    • 1,281 Sq Ft

    3025 Silverado Terrace, Winter Haven, FL 33884

    THIS HOME QUALIFIES FOR 0% DOWN !! Welcome to 3025 Silverado Terrace, a desirable 2-bedroom, 2-bath home in the highly sought-after Cypresswood Golf & Country Club community. This gated neighborhood offers 24-hour security and resort-style amenities, including a sparkling pool with poolside service, tennis courts, a clubhouse with dining and entertainment, fitness center, and pro shop. It’s also

    Malak Benbachir KELLER WILLIAMS REALTY SMART 1

    3025 Silverado Terrace, Winter Haven, FL 33884
  • /38

    $239,500

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft

    466 Muirfield Ct, Winter Haven, FL 33884

    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

    Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

    466 Muirfield Ct, Winter Haven, FL 33884
  • /25

    $256,000

    • 2 Beds
    • 2 Baths
    • 1,361 Sq Ft

    511 Pebble Springs Ct, Winter Haven, FL 33884

    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

    Gina Morgando MORGANDO REALTY SERVICES, LLC

    511 Pebble Springs Ct, Winter Haven, FL 33884
  • /26

    $136,900

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    1201 Cypress Vine Rd Unit 297, Winter Haven, FL 33881

    CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $136,900 POND VIEW HOME with Double Driveway! Golf cart included! This MODERN, TURNKEY HOME is furnished and move-in-ready for you! This immaculately maintained home is only 5 years old! It features an open floor plan, air-conditioned four-season Florida Room and lower screened lanai - all of which have a tranquil pond view. This home has a

    Jennifer Meyers CRF Communities

    1201 Cypress Vine Rd Unit 297, Winter Haven, FL 33881
  • /58

    $199,500

    • 2 Beds
    • 2 Baths
    • 1,458 Sq Ft

    1012 Medinah Dr, Winter Haven, FL 33884

    Fresh new price — your opportunity to own in Cypresswood just got better! Seller will pay the first year’s HOA fees! 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,

    Corinna Weaver CROSBY & ASSOCIATES, INC.

    1012 Medinah Dr, Winter Haven, FL 33884

Home Trends in Cypresswood, FL

Housing Trends

Median Sale Price
$290,000
Median Single Family Sale Price
$299,499
Median 2 Bedroom Sale Price
$165,000
Average Price Per Sq Ft
$167
Number of Homes for Sale
52
Last 12 months Home Sales
85
Months of Supply
7.30
Median List Price
$308,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
0%
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