Cypresswood Homes for Sale

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  $184,900

  $15K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,988 Sq Ft

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881

  Lot #97 / 3 B / 3 BA / 1,988 Sq. Ft. / $199,500.00 Spectacular Home! Completely Remodeled 2009 Erica Model in popular Cypress Creek Village! This large home is located on a spacious corner lot. It has a double carport with extra covered golf cart parking. Professionally remodeled upgrades include: - New Architectural Shingle Roof - New Air Conditioner and New Mr. Cool a/c for the tiled Florida

  Jennifer Meyers CRF Communities

  440 Midnight Cypress Dr Unit 97, Winter Haven, FL 33881
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  /52

  $175,000

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

  1004 Medinah Dr, Winter Haven, FL 33884

  Don’t miss this incredible opportunity to own a villa in one of Winter Haven’s most sought-after gated golf communities — at an unbeatable price! This 2-bedroom, 2-bathroom villa offers 1,278 sq ft of comfortable Florida living with a peaceful pond view backdrop. The open floor plan flows effortlessly, and the private enclosed Florida room is perfect for year-round entertaining. The generous

  Susan Human HUMAN TOUCH REAL ESTATE FIRM

  1004 Medinah Dr, Winter Haven, FL 33884
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  /22

  $55,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  280 Monterey Cypress Blvd Unit 158, Winter Haven, FL 33881

  Lot #158 - 2 Bed / 2 Bath / 864 Sq. Ft. / $55,000 -- 2008 Cottage Style Home. This cozy - 2 bedroom, 2 bathroom home features 2 large bedroom ensuites at either end (for privacy) - with open living in the center. This one-owner home features a NEW ARCHITECTURAL SHINGLE ROOF! The owner specifically chose this special lot for its peaceful location and views of the oak trees and neighboring farm.

  Jennifer Meyers CRF Communities

  280 Monterey Cypress Blvd Unit 158, Winter Haven, FL 33881
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  /15

  $250,000

  $50K PRICE DROP

  • Land
  • 34,412 Sq Ft
  • $316,456 per Acre

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881

  Just Reduced! Stop by and check on this vacant lot in an area that is growing with new expanded roads. More than 3/4-acre zone C3 lot on Dundee Rd Hwy 542 with approx. 143 feet of road frontage. Ideally positioned in front of the 16th St intersection. The Department of Transportation finished up the Dundee Rd expansion improvements further to the East. This project has given this lot multiple

  Michael Brenner CENTURY 21 MYERS REALTY

  0 Dundee Rd Unit P4924283, Winter Haven, FL 33881
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  $210,000

  • 2 Beds
  • 2 Baths
  • 1,422 Sq Ft

  1052 Medinah Dr, Winter Haven, FL 33884

  Welcome to the affordable lifestyle of living in a Villa within a golf course community. Upon entering the front of the home you will notice a courtyard area on the left and right side of the entrance, which opens up additional outside entertaining space. Once inside the home you will notice it has recently been refreshed with new interior painting throughout, all new flooring, and new stove and

  Della Landfear XCELLENCE

  1052 Medinah Dr, Winter Haven, FL 33884
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  /27

  $340,000

  • 5 Beds
  • 3 Baths
  • 2,460 Sq Ft

  508 Cody Caleb Dr, Winter Haven, FL 33884

  Experience comfort, style, and thoughtful updates in this spacious 5-bedroom, 3-bath home featuring inviting architectural details and functional living spaces throughout. The welcoming entry showcases six stained-glass side windows surrounding the front door, complemented by a large display window above that fills the foyer with natural light. The open-concept kitchen offers abundant space for

  Robert Bermes EPIQUE REALTY, INC.

  508 Cody Caleb Dr, Winter Haven, FL 33884
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  /43

  $98,500

  $7K PRICE DROP

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

  203 Monterey Cypress Blvd, 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, Winter Haven, FL 33881
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  /98

  $779,000

  $21K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,397 Sq Ft

  3050 Crump Rd, Winter Haven, FL 33881

  Welcome to this exceptional lakefront property at 3050 Crump Rd in Winter Haven, offering space, versatility, and direct access to the lifestyle Central Florida is known for. Situated on approximately 1.08 acres along Lake Hamilton, this residence combines a thoughtfully updated main home with a private guest studio, outdoor living, and boating amenities. The main home features three bedrooms and

  Lisa Matheny ENGEL & VOELKERS LAKELAND

  3050 Crump Rd, Winter Haven, FL 33881
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  $370,000

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft

  652 Grove St, Winter Haven, FL 33884

  Welcome to 652 Grove St. TWO living spaces for ONE price. This exceptional property in the heart of Winter Haven offers a spacious main home plus a fully independent Mother-in-Law Suite all under the same roof. The primary residence features 3 bedrooms, 2 bathrooms, a dedicated office/flex space, an open-concept layout filled with natural light, and a 2-car garage designed for comfortable

  Lizandra Troisi Passos MY REALTY GROUP, LLC.

  652 Grove St, Winter Haven, FL 33884
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  /53

  $400,000

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  126 Lake Region Cir, Winter Haven, FL 33881

  ALMOST PARADISE! Enjoy the peaceful surroundings and relaxing environment from this 2142 SF executive style home located in The Gates of Lake Region, a well maintained and GATED community close to the Winter Haven Country Club! NEED SPACE? This customized 4BR/2BA home was designed with an open floor plan with split bedrooms, formal dining room and living room ( which could be easily used as a

  Carol Sheil JUDY B CLEAVES PROPERTIES INC

  126 Lake Region Cir, Winter Haven, FL 33881
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  /38

  $190,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  213 Cleveland Ave, Winter Haven, FL 33881

  Welcome to this charming 2-bedroom, 1-bath home in the growing city of Winter Haven. Situated on a .16-acre oversized lot, this property offers both comfort and opportunity. The home features a functional layout and a new AC installed in 2024, providing added efficiency and peace of mind. The spacious backyard includes a detached shed with great potential, perfect for a workshop, studio, storage,

  Pedro Perez, Jr DALTON WADE INC

  213 Cleveland Ave, Winter Haven, FL 33881
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  /46

  $198,000

  $40K PRICE DROP

  • 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
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  /32

  $340,000

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft

  507 Short Ln, Winter Haven, FL 33881

  ""SELLER MOTIVATED – PRICE IMPROVEMENT! BRING YOUR OFFER!""Beautiful and well-maintained home featuring 4 spacious bedrooms and 2 bathrooms, offering plenty of space for comfortable family living and entertaining guests. Sliding glass doors lead to a covered patio and a private grassy backyard, perfect for relaxing and enjoying Florida’s outdoor lifestyle. The kitchen comes fully equipped

  Anderson Siqueira, Sr WRA BUSINESS & REAL ESTATE

  507 Short Ln, Winter Haven, FL 33881
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  /43

  $359,950

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 2,523 Sq Ft

  241 Greenfield Rd, Winter Haven, FL 33884

  Welcome to this beautifully renovated home in Greenfield Village at Cypresswood Golf & Country Club, perfectly situated on a spacious .37-acre lot on the 13th green. This charming 2-bedroom, 2-bathroom residence features a bright and open layout with a large living area plus an additional family room accented by a cozy brick fireplace and floor-to-ceiling wood built-ins. The brand-new kitchen has

  Angie Reynolds PORCHLIGHT HOMES LLC

  241 Greenfield Rd, Winter Haven, FL 33884
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  /39

  $259,900

  $60K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft

  610 Grove St, Winter Haven, FL 33881

  This 3 YEAR YOUNG, 4 bedroom, 2 bath single-family home built by DR Horton offers 1,867 square feet of thoughtfully designed living space and a 2-car ATTACHED GARAGE with OPENER and NO SOLAR PANELS!! The open floorplan features a seamless kitchen, dining area, and family room combination, ideal for both everyday living and entertaining. The kitchen includes a CENTER ISLAND, GRANITE countertops,

  Pat Pearson VIEWPOINT VALUE REALTY

  610 Grove St, Winter Haven, FL 33881
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  /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
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  /52

  $425,000

  $24K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  108 Lake Region Blvd N, Winter Haven, FL 33881

  Gated custom home in the Gates of Lake Region! This quiet and highly-desirable neighborhood has the look, feel and privacy of an age-restricted community, but it is open to all ages. This property was constructed as a builder’s model home so it offers numerous upgrades and architectural details that can be found throughout. Located within the quaint, gated community of The Gates of Lake Region

  Michael Stone THE STONES REAL ESTATE FIRM

  108 Lake Region Blvd N, Winter Haven, FL 33881
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  /2

  $150,000

  • Land
  • 13,939 Sq Ft
  • $468,750 per Acre

  1776 Lake Hill Dr, Winter Haven, FL 33884

  Large residential lot that will accommodate a variety of floor plans. Builder and building plans must be approved by Owner.

  John Wood, JR JOHN WOOD REALTY, INC.

  1776 Lake Hill Dr, Winter Haven, FL 33884
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  /24

  $337,000

  $17K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,586 Sq Ft

  688 Augusta Rd, Winter Haven, FL 33884

  Welcome to this meticulously maintained 3-bedroom, 2-bath pool home located in the highly sought-after 24-hour guard-gated Cypresswood Golf and Country Club community of Winter Haven. Thoughtfully designed with a desirable split-bedroom floorplan, this residence offers both privacy and functionality for everyday living and entertaining. Plus, seller is currently in the process of installing a NEW

  Kayly Malinas JOHN WOOD REALTY, INC.

  688 Augusta Rd, Winter Haven, FL 33884
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  /16

  $340,000

  New Construction $8K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft

  643 Grove St, Winter Haven, FL 33881

  Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!

  Martha Leighton MIHOUSE REALTY LLC

  643 Grove St, Winter Haven, FL 33881
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  /11

  $215,500

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,158 Sq Ft

  2796 Whispering Trails Dr, Winter Haven, FL 33884

  Discover this charming home ideally located near Legoland, hospitals, businesses, and schools.With easy access to major roads, this property is situated within a community that offers privateaccess, providing both convenience and security.The home requires new flooring, but with a little help and your personal touch, it has great potential to become a cozy haven. Perfect for

  Lucy Martinez CENTURY 21 WOLF'S CROSSING REALTY

  2796 Whispering Trails Dr, Winter Haven, FL 33884
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  /49

  $1,100,000

  • Land
  • 52.52 Acres
  • $20,944 per Acre

  3705 High St, Winter Haven, FL 33881

  Prime investment opportunity in the expanding Winter Haven area! This 52.52± acre parcel of vacant land offers exceptional potential for future development. The property is currently being used for agricultural purposes, with beautiful grazing pasture and cattle on site, providing wide open space and scenic surroundings.Winter Haven and the surrounding Central Florida region continue to

  Stacey Towns STACEY TOWNS REALTY LLC

  3705 High St, Winter Haven, FL 33881
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  $199,000

  $71K PRICE DROP

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

  3025 Silverado Terrace, Winter Haven, FL 33884

  Short Sale. SHORT SALE!! 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 perfect

  Malak Benbachir KELLER WILLIAMS REALTY SMART 1

  3025 Silverado Terrace, Winter Haven, FL 33884
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  /27

  $80,000

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

  1228 Cypress Vine Rd Unit 288, Winter Haven, FL 33884

  CYPRESS CREEK VILLAGE #288 / 2 BED / 2 BATH / 1,000 SF / $80,000 Open Floor Plan with two bed/bath suites! This well maintained 2017 Nobility Home features an open floor plan and two large bedroom suites! The large living room and ample dining room adjoin a light filled kitchen with white cabinets. Vaulted ceilings add volume to the open space. The master bedroom has walk in closet. The guest

  Jennifer Meyers CRF Communities

  1228 Cypress Vine Rd Unit 288, Winter Haven, FL 33884
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  $245,000

  $15K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,444 Sq Ft

  47 Enclave Dr, Winter Haven, FL 33884

  PRICE REDUCED $15,000! Welcome to the Enclave at Cypresswood Golf & Country Club. Cypresswood is a Gated community featuring a 24-Hour Guard, 18 Hole Golf Course, Community Pool, Lighted Tennis Courts, Restaurant, and a Pub. This 2 Bedroom Villa is For Sale and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, and the

  David Shippey XCELLENCE

  47 Enclave Dr, Winter Haven, FL 33884
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  /45

  $100,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  284 Siberian Cypress Creek Cir, Winter Haven, FL 33881

  This 2022 home offers 1344 sq ft of living space, Immaculate and well-maintained. It has three bedrooms and two bathrooms with an open floor plan, perfect for entertaining family/friends or just relaxing. Additional living space can be found in the raised Florida room, along with the covered patio outdoors. Have a cookout and invite neighbors and friends! Key features of this home include a large

  Cynthia Cole Sunset Home Sales

  284 Siberian Cypress Creek Cir, Winter Haven, FL 33881
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  /22

  $180,000

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

  665 Broadmoor Cir, Winter Haven, FL 33884

  Discover how easy life can feel in this beautifully maintained 2-bedroom, 2-bath villa offering over 1,100 square feet of comfortable, thoughtfully designed living space. With a mostly furnished interior and quick occupancy available, you can step right in and start enjoying it from day one. Located inside the gated CypressWood golf community, this home delivers true resort-style living. Spend

  Darin Dobson COMPASS FLORIDA LLC

  665 Broadmoor Cir, Winter Haven, FL 33884
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  /70

  $199,000

  $51K PRICE DROP

  • 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 spacious, 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 Electric Fireplace, Gutters, Newer

  Daniel Butler Sun Realty of Florida

  352 Siberian Cypress Cir, Winter Haven, FL 33881
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  /23

  $129,900

  $7K PRICE DROP

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

  1201 Cypress Vine Rd, Winter Haven, FL 33881

  CYPRESS CREEK VILLAGE #297 - 2BED / 2 BATH / 1,200 SF. / $129,900 POND VIEW HOME with Double Driveway! 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 split floor plan

  Jennifer Meyers CRF Communities

  1201 Cypress Vine Rd, Winter Haven, FL 33881
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  /58

  $187,900

  $21K PRICE DROP

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

  1012 Medinah Dr, Winter Haven, FL 33884

  Fresh new price — NOW OFFERING A HOME WARRANTY! Your opportunity to own in Cypresswood just got better! 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

  Corinna Weaver CROSBY & ASSOCIATES, INC.

  1012 Medinah Dr, Winter Haven, FL 33884
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  /49

  $179,000

  • 3 Beds
  • 3 Baths
  • 1,848 Sq Ft

  332 Siberian Cypress Cir, Winter Haven, FL 33881

  $595 LOT RENT! Welcome home to Cypress Creek Village in Winter Haven, Florida! This beautifully designed 2022 ScotBilt home offers the perfect blend of comfort, space, and resort-style living in one of Winter Haven's sought-after 55+ gated communities. Featuring 3 bedrooms, 3 bathrooms, and nearly 1,850 square feet of living space, this home was built for easy living and entertaining. Step inside

  Daniel Butler Sun Realty of Florida

  332 Siberian Cypress Cir, Winter Haven, FL 33881
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  /32

  $369,900

  $9K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,696 Sq Ft

  204 Inman Blvd, Winter Haven, FL 33881

  New Price and $2500 Seller Credit!!Relocating to Florida? This pristine 5-bedroom, 3-bath home offers nearly 2,700 square feet of thoughtfully designed living space in the heart of Central Florida, providing the space, flexibility, and value many buyers from northern states and high-cost markets are seeking.Priced at $374,900—approximately $140 per square foot—this home delivers

  Veronica Bard LA ROSA REALTY PRESTIGE

  204 Inman Blvd, Winter Haven, FL 33881

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