Below you can view all the homes for sale in the Cypress Wood Tennis Villas subdivision located in Winter Haven Florida. Listings in Cypress Wood Tennis Villas are updated daily from data we receive from the Orlando multiple listing service.

To learn more about any of these homes or to receive custom notifications when a new property is listed for sale in Cypress Wood Tennis Villas, give us a call at 386 801 5417.

31 Results

Cypress Wood Tennis Villas Winter Haven Florida Homes For Sale

Cypress Wood Tennis Villas For Sale $260,000

Inviting entryway featuring a glass storm door, tasteful decor, and colorful plants at 2809 Wingfoot Ct, Winter Haven, FL 33884
Picturesque golf course view with mature trees, manicured lawns and golfers at 2809 Wingfoot Ct, Winter Haven, FL 33884
Foyer with tile flooring, coat closet, and neutral tones create a welcoming atmosphere at 2809 Wingfoot Ct, Winter Haven, FL 33884
On Market Today
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1682

  • Year Built

    1990

  • $/SqFt

    $155

Best Location In Cypresswood, Not A Thru Street. HAPPY DAYS REALTY LLC.

Cypress Wood Tennis Villas For Sale $247,500

Cozy condo patio with two chairs, a small table, and a window at 2246 Firestone Pl, Winter Haven, FL 33884
Inviting condo front door and welcoming decoration at 2246 Firestone Pl, Winter Haven, FL 33884
Carport view of the condo's entrance at 2246 Firestone Pl, Winter Haven, FL 33884
On Market Today
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1164

  • Year Built

    1986

  • $/SqFt

    $213

Polk County Fla #1 Place To Live, Central Location Between East And West Coasts. Furnishings Negotiable. HAPPY DAYS REALTY LLC.

Cypress Wood Tennis Villas For Sale $260,000

Charming home with well-kept lawn, mature tree providing shade and a quaint entrance at 460 Pinehurst Ct, Winter Haven, FL 33884
A spacious front yard with a mature tree creates a park-like feel to the home at 460 Pinehurst Ct, Winter Haven, FL 33884
Bright living room with large built-in shelving, ceiling fan, and sliding glass doors at 460 Pinehurst Ct, Winter Haven, FL 33884
On Market For 2 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1660

  • Year Built

    1980

  • $/SqFt

    $157

Must see affordable home. Make your appointment to see. CENTURY 21 WATSON & MYERS REALTY.

Cypress Wood Tennis Villas For Sale $263,000

Charming single-story brick home with a well-manicured lawn and mature landscaping at 398 Troon Ct, Winter Haven, FL 33884
Bright sunroom with brick wall, tile floors, multiple windows, and comfortable seating at 398 Troon Ct, Winter Haven, FL 33884
Charming outdoor patio area with brick pavers, seating, and access to the sunroom at 398 Troon Ct, Winter Haven, FL 33884
On Market For 5 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1758

  • Year Built

    1977

  • $/SqFt

    $150

Conveniently located near shopping, dining, and entertainment, this gem won’t last long—schedule your showing today! RE/MAX HERITAGE PROFESSIONALS.

Cypress Wood Tennis Villas For Sale $499,900

Backyard featuring a refreshing pool, patio with lounge chairs, palm trees, and serene landscaping at 121 Greenfield Rd, Winter Haven, FL 33884
Close-up shot of a pool with an umbrella and two lounge chairs next to it at 121 Greenfield Rd, Winter Haven, FL 33884
Aerial view of the property featuring a solar panel roof, backyard pool, and lush landscaping at 121 Greenfield Rd, Winter Haven, FL 33884
On Market For 9 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2900

  • Year Built

    1979

  • $/SqFt

    $172

Come and tour it today and you will know you are home! REMAX EXPERTS.

Cypress Wood Tennis Villas For Sale $449,000

Relaxing screened-in pool area with lush landscaping, and an inviting space for outdoor enjoyment at 141 Greenfield Rd, Winter Haven, FL 33884
Well-maintained single-story home featuring a spacious front yard, mature trees and an inviting landscape at 141 Greenfield Rd, Winter Haven, FL 33884
Charming single-story home with spacious front yard featuring mature trees and lush green lawn at 141 Greenfield Rd, Winter Haven, FL 33884
On Market For 14 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2328

  • Year Built

    1977

  • $/SqFt

    $193

Don’t miss your chance to own this exceptional property – schedule your private tour today! COVENANT REALTY.

Cypress Wood Tennis Villas For Sale $334,800

Bright, open-concept living room flows into modern kitchen with white cabinets and stainless steel appliances at 692 Augusta Rd, Winter Haven, FL 33884
Bright living room featuring vaulted ceilings, a stylish blue rug, modern furniture, and sliding glass doors at 692 Augusta Rd, Winter Haven, FL 33884
Spacious open concept layout featuring a living room, dining area, and kitchen with lots of natural light at 692 Augusta Rd, Winter Haven, FL 33884
On Market For 16 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1605

  • Year Built

    1984

  • $/SqFt

    $209

Secluded neighborhood with well known golfing, gated community with manned gate, multiple tennis courts, mini Olympic size pool, clubhouse, restaurant and pro shop, fitness center, library, driving range and lots of planned social events. S & D REAL ESTATE SERVICE LLC.

Cypress Wood Tennis Villas For Sale $229,900

Exterior view of the condo community highlighting the well-maintained lawns and stucco privacy walls at 2254 Firestone Pl # 2254, Winter Haven, FL 33884
The property features a secure courtyard entry with lush landscaping and well-maintained lawn at 2254 Firestone Pl # 2254, Winter Haven, FL 33884
Carport of property 2254 provides covered parking for two vehicles and convenient access at 2254 Firestone Pl # 2254, Winter Haven, FL 33884
On Market For 25 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1430

  • Year Built

    1986

  • $/SqFt

    $161

Schedule your private showing today, this property is truly a must-see! JOHN WOOD REALTY, INC..

Cypress Wood Tennis Villas For Sale $300,000

Reduced By $10,000

Villa boasts a two-car garage, neat landscaping, and well-kept driveway at 42 Enclave Dr, Winter Haven, FL 33884
Open-concept living room with hardwood floors, high ceilings, and staircase at 42 Enclave Dr, Winter Haven, FL 33884
Charming kitchen with stainless steel appliances and tile floors next to dining area at 42 Enclave Dr, Winter Haven, FL 33884
*POTENTIAL GREAT VALUE
On Market For 28 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2370

  • Year Built

    1999

  • $/SqFt

    $127

All information is believed to be accurate but buyer and or buyers agent should verify. S & D REAL ESTATE SERVICE LLC.

Cypress Wood Tennis Villas For Sale $238,000

Inviting home exterior with a red fence, secured gate, and well-kept walkway at 683 Broadmoor Cir # 683, Winter Haven, FL 33884
Brick-paved patio area enclosed by a red fence and a green leafy tree at 683 Broadmoor Cir # 683, Winter Haven, FL 33884
The patio is paved with red bricks, fenced in, and has some shrubbery at 683 Broadmoor Cir # 683, Winter Haven, FL 33884
On Market For 28 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1139

  • Year Built

    1981

  • $/SqFt

    $209

Don't miss out on this one, call to view today. TOWN & COUNTRY REAL ESTATE.

Cypress Wood Tennis Villas For Sale $280,000

Reduced By $15,000

Cozy home exterior featuring well-kept lawn and a walkway leading to the entrance at 620 Wexford Ct, Winter Haven, FL 33884
Inviting entrance with a well-lit walkway and neatly trimmed landscaping at 620 Wexford Ct, Winter Haven, FL 33884
Bright entryway featuring wood-look flooring and a view into the dining area at 620 Wexford Ct, Winter Haven, FL 33884
On Market For 30 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1426

  • Year Built

    1979

  • $/SqFt

    $196

This Is Truly A Gem And A Must See To Appreciate! ! LPT REALTY, LLC.

Cypress Wood Tennis Villas For Sale $599,999

Close up of charming front porch with brick detail, gray shutters, and welcoming front door at 19 Meadowlake Ct, Winter Haven, FL 33884
Beautiful screened-in pool with lounge chairs, lush landscaping and view of the golf course at 19 Meadowlake Ct, Winter Haven, FL 33884
Bright foyer featuring wood floors, a decorative mirror and a stylish accent bench at 19 Meadowlake Ct, Winter Haven, FL 33884
On Market For 33 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3257

  • Year Built

    1977

  • $/SqFt

    $184

This is the dream home you’ve been waiting for—schedule your private tour today before it’s gone! REAL BROKER, LLC.

Cypress Wood Tennis Villas For Sale $375,000

Spacious living room featuring tile floors, a ceiling fan, and a comfortable seating area, with an open view to the dining area at 762 Canberra Rd, Winter Haven, FL 33884
Well-equipped kitchen boasts granite countertops, wooden cabinets, and modern appliances, including a black oven and dishwasher at 762 Canberra Rd, Winter Haven, FL 33884
Serene bedroom features a blue wall, a white bed frame with neutral bedding, and ample natural light from a large window at 762 Canberra Rd, Winter Haven, FL 33884
On Market For 33 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2002

  • Year Built

    1990

  • $/SqFt

    $187

All information is believed to be accurate but not guaranteed. JUDY B CLEAVES PROPERTIES INC.

Cypress Wood Tennis Villas For Sale $369,900

Inviting foyer with neutral walls, marble floors, and decorative nautical accents at 734 Canberra Rd, Winter Haven, FL 33884
Comfortable living area with a plush gray sofa and stylish marble-patterned rug at 734 Canberra Rd, Winter Haven, FL 33884
Inviting living room featuring a comfortable gray sofa, TV, and cozy lighting at 734 Canberra Rd, Winter Haven, FL 33884
On Market For 40 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2136

  • Year Built

    1993

  • $/SqFt

    $173

Schedule your private showing today and experience everything this exceptional property has to offer. RE/MAX HERITAGE PROFESSIONALS.

Cypress Wood Tennis Villas Pended $284,900

Charming home featuring a two-car garage, well-manicured lawn, tropical landscaping, and an American flag at 37 Enclave Dr, Winter Haven, FL 33884
Beautiful home with lush landscaping, a two-car garage, and an American flag waving gently at 37 Enclave Dr, Winter Haven, FL 33884
Bright entryway features tile flooring, a decorative screen, and a glass-paneled front door for natural light at 37 Enclave Dr, Winter Haven, FL 33884
On Market For 41 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1682

  • Year Built

    1997

  • $/SqFt

    $169

Additional amenities include an automatic garage screen door and a whole-house generator. LOCKHART & ASSOCIATES INC.

Cypress Wood Tennis Villas For Sale $217,500

Reduced By $2,500

Community carport providing covered parking spaces for residents and visitors, enhancing convenience at 2214 Se Sawgrass Ct, Winter Haven, FL 33884
Inviting hallway featuring neutral paint, tile flooring and a view to the home's living spaces at 2214 Se Sawgrass Ct, Winter Haven, FL 33884
Open-concept living area showcasing neutral tones, tile floors, and a dining space at 2214 Se Sawgrass Ct, Winter Haven, FL 33884
*POTENTIAL GREAT VALUE
On Market For 41 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1590

  • Year Built

    1987

  • $/SqFt

    $137

Schedule a private showing today and discover all that this charming golf villa has just for you. LPT REALTY, LLC.

Cypress Wood Tennis Villas For Sale $338,500

Reduced By $500

Enclosed lanai featuring a small pool, seating and umbrella for relaxing outdoors at 768 Canberra Rd, Winter Haven, FL 33884
Aerial view of home with mature trees, landscaping and near a golf course at 768 Canberra Rd, Winter Haven, FL 33884
Cypresswood Golf & Country Club entrance with lush landscaping and well-maintained signage at 768 Canberra Rd, Winter Haven, FL 33884
On Market For 47 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1888

  • Year Built

    1986

  • $/SqFt

    $179

Come experience the lifestyle of Cypresswood and discover everything Central Florida has to offer! THE STONES REAL ESTATE FIRM.

Cypress Wood Tennis Villas For Sale $339,000

Reduced By $10,000

Charming single-story home with a red door, landscaped yard, and brick driveway at 3226 Oak Tree Ln, Winter Haven, FL 33884
Aerial view of the home's roof, backyard, and neighboring properties at 3226 Oak Tree Ln, Winter Haven, FL 33884
An aerial view of the home showcasing its landscaped front yard and brick driveway at 3226 Oak Tree Ln, Winter Haven, FL 33884
On Market For 98 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2086

  • Year Built

    2006

  • $/SqFt

    $163

You will not want to miss out on this one so schedule your private tour today!!! ! CHARLES RUTENBERG REALTY ORLANDO.

Cypress Wood Tennis Villas Pended $339,900

Reduced By $20,000

Front view of a house with a two-car garage and landscaping at 723 Canberra Rd, Winter Haven, FL 33884
Aerial view showing a house with a pool and surrounding neighborhood at 723 Canberra Rd, Winter Haven, FL 33884
Bright living room with tile floors and a ceiling fan at 723 Canberra Rd, Winter Haven, FL 33884
On Market For 102 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2006

  • Year Built

    1986

  • $/SqFt

    $169

Improvements to this home include: a whole home generator, the enclosed porch constructed in 2006, a new roof in 2016, new ceramic tile in 2016, and all new pool equipment installed in 2024. KELLER WILLIAMS REALTY SMART 1.

Cypress Wood Tennis Villas For Sale $799,000

Gray house with a metal roof, landscaping, and a paved driveway at 4040 Palma Ceia Cir, Winter Haven, FL 33884
Gray house with a metal roof, landscaping, and a paved driveway at 4040 Palma Ceia Cir, Winter Haven, FL 33884
Gray house with a metal roof and nicely landscaped yard at 4040 Palma Ceia Cir, Winter Haven, FL 33884
On Market For 125 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2493

  • Year Built

    2005

  • $/SqFt

    $320

Come experience the best of Florida living that is waiting for you! PREMIER SOTHEBY'S INTL. REALTY.

Cypress Wood Tennis Villas For Sale $217,000

Reduced By $28,000

Carport offers covered parking for residents and guests at 2256 Firestone Pl, Winter Haven, FL 33884
Aerial view of the community showing well maintained lawns, mature trees, and covered parking at 2256 Firestone Pl, Winter Haven, FL 33884
Aerial view showcasing villas and lush green landscaping at 2256 Firestone Pl, Winter Haven, FL 33884
On Market For 147 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1422

  • Year Built

    1986

  • $/SqFt

    $153

Great opportunity here at an attractive price. LIVE FLORIDA REALTY.

Cypress Wood Tennis Villas For Sale $309,000

Reduced By $40,000

Inviting entryway with a paved walkway leading to the front door, surrounded by lush landscaping at 645 Augusta Rd, Winter Haven, FL 33884
View through the front door, showing a brick walkway leading to the backyard at 645 Augusta Rd, Winter Haven, FL 33884
Living room featuring a display cabinet, stained-glass windows, and a violin at 645 Augusta Rd, Winter Haven, FL 33884
On Market For 149 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2140

  • Year Built

    1993

  • $/SqFt

    $144

This is a true gem on Cypresswood’s stunning fairway—don’t miss out! CENTURY 21 WATSON & MYERS REALTY.

Cypress Wood Tennis Villas For Sale $234,900

Condo exterior with red fence and landscaping at 1039 Medinah Dr, Winter Haven, FL 33884
Condo exterior with red fence and landscaping at 1039 Medinah Dr, Winter Haven, FL 33884
Address marker for unit 1039 at 1039 Medinah Dr, Winter Haven, FL 33884
On Market For 149 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1278

  • Year Built

    1980

  • $/SqFt

    $184

The home has all new flooring, paint, and granite counter tops. Make your appointment TODAY! ! JOHN WEBB INC.

Cypress Wood Tennis Villas For Sale $251,000

Reduced By $17,900

Charming single story home with a welcoming front porch at 466 Muirfield Ct, Winter Haven, FL 33884
Single story home with attached garage and lush landscaping at 466 Muirfield Ct, Winter Haven, FL 33884
Spacious living room featuring hardwood floors and comfortable seating at 466 Muirfield Ct, Winter Haven, FL 33884
On Market For 152 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1232

  • Year Built

    1984

  • $/SqFt

    $204

This ideal location is conveniently close to shopping, restaurants, and Legoland, making it the perfect choice for those seeking both luxury and convenience. CENTURY 21 MYERS REALTY LAKE WALES.

Cypress Wood Tennis Villas For Sale $320,000

Reduced By $10,000

Bright kitchen with granite countertops and stainless steel appliances at 571 Saint Andrews Rd, Winter Haven, FL 33884
Updated kitchen featuring wood cabinets and granite island at 571 Saint Andrews Rd, Winter Haven, FL 33884
Spacious living room with tiled floors and comfortable seating at 571 Saint Andrews Rd, Winter Haven, FL 33884
On Market For 174 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1872

  • Year Built

    1984

  • $/SqFt

    $171

Recent updates include a new AC system (2023), hot water heater, and bathroom renovations. Don’t miss this gem! COLDWELL BANKER RESIDENTIAL RE.

Cypress Wood Tennis Villas For Sale $295,000

Reduced By $44,000

Spacious backyard with a patio and lush green grass at 35 Enclave Dr, Winter Haven, FL 33884
Inviting front porch with a bench and charming decor at 35 Enclave Dr, Winter Haven, FL 33884
Bright and airy entryway with views into the living room at 35 Enclave Dr, Winter Haven, FL 33884
*POTENTIAL GREAT VALUE
On Market For 172 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2070

  • Year Built

    1997

  • $/SqFt

    $143

This property is within close proximity to shopping, restaurants, LEGOLAND, and so much more, so call today to set up a private showing!! ! THE K TEAM REAL ESTATE SERVICES LLC.

Cypress Wood Tennis Villas For Sale $350,000

Single-story home with landscaped yard and attached garage at 708 Canberra Rd, Winter Haven, FL 33884
Spacious living room with red sectional sofa and hardwood floors at 708 Canberra Rd, Winter Haven, FL 33884
Bright living room featuring a red sectional sofa and hardwood floors at 708 Canberra Rd, Winter Haven, FL 33884
On Market For 173 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2004

  • Year Built

    1997

  • $/SqFt

    $175

Don't miss out on this opportunity—schedule your private tour today! KELLER WILLIAMS REALTY SMART 1.

Cypress Wood Tennis Villas For Sale $234,900

Reduced By $14,100

Condo with red fence and walkway, near green space at 1077 Medinah Way, Winter Haven, FL 33884
Condo with red fence and walkway, large oak tree nearby at 1077 Medinah Way, Winter Haven, FL 33884
Tan condo with a walkway and landscaping at 1077 Medinah Way, Winter Haven, FL 33884
On Market For 222 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1563

  • Year Built

    1980

  • $/SqFt

    $150

Don'T Delay In Making Your Appointment To See This Home WESTLAKE REAL ESTATE CO., INC..

Cypress Wood Tennis Villas For Sale $364,900

Single-story house with attached garage and palm trees at 706 Canberra Rd, Winter Haven, FL 33884
Single-story house with attached garage and palm trees at 706 Canberra Rd, Winter Haven, FL 33884
Single-story house with attached garage and palm trees at 706 Canberra Rd, Winter Haven, FL 33884
On Market For 231 Days
  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2114

  • Year Built

    1994

  • $/SqFt

    $173

Whether you are looking for a relaxing serene retreat or a place to entertain, this home combines luxury with a vibrant community atmosphere. CENTURY 21 WATSON & MYERS REALTY.

Cypress Wood Tennis Villas For Sale $339,900

Reduced By $25,100

Tan single story house with brown roof and landscaping at 680 Augusta Rd, Winter Haven, FL 33884
Landscaped side yard with lush greenery and a stone border at 680 Augusta Rd, Winter Haven, FL 33884
Small, grassy backyard with hedges and a paved pathway at 680 Augusta Rd, Winter Haven, FL 33884
On Market For 265 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1932

  • Year Built

    1986

  • $/SqFt

    $176

Upgrades include remodeled kitchen and appliances, remodeled bathroom, wood shutters and remote blinds, ceramic tile roof, Generac whole house generator, natural gas and more. TOWN & COUNTRY REAL ESTATE.

Cypress Wood Tennis Villas Pended $350,000

House nestled in a residential neighborhood, close to other homes and a golf course at 300 Greenfield Rd, Winter Haven, FL 33884
The foyer features tile flooring, double doors, and a coat rack at 300 Greenfield Rd, Winter Haven, FL 33884
A carpeted staircase leads upstairs with hardwood flooring on the bottom at 300 Greenfield Rd, Winter Haven, FL 33884
On Market For 128 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2350

  • Year Built

    1975

  • $/SqFt

    $149

Call today for a private tour. HOMAN REALTY GROUP INC.

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(386) 801-5417