Polk, FL Homes

• 

  

  

  /47

  $275,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,836 Sq Ft

  1844 Emily Dr, Winter Haven, FL 33884

  Under contract-accepting backup offers. With ALL the space you need, this 2,836 sq ft home is a blank canvas waiting for your personal vision! Bring your ideas and transform this house into your dream home – being sold AS-IS, but brimming with potential! Downstairs you’ll find a formal dining room, formal living room, and a family room just off the kitchen, providing plenty of room for family

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 474-8406

  1844 Emily Dr, Winter Haven, FL 33884
• 

  Explore Cypresswood

• 

  

  

  /22

  $1,699 per month

  • 3 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • House for Rent

  2110 Whispering Trails Blvd, Winter Haven, FL 33884

  GATED COMMUNITY WITH AWESOME POOL waiting for a good tenant. Updated Home Minutes from Legoland! This charming 3/ 2 home / garage blends comfort and convenience. Newer roof and fresh paint inside and out, this is a move-in ready home! Spacious living room perfect for gatherings, a well-equipped kitchen, 3 comfortable bedrooms, including a master suite with a private bathroom. Additional features

  

  Silvana Friedel

  The Keyes Company

  (863) 593-8022

  2110 Whispering Trails Blvd, 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
• 

  

  

  /23

  Est $320,754 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,770 Sq Ft

  2972 Whispering Trails Dr, Winter Haven, FL 33884

  2972 Whispering Trails Dr, Winter Haven, FL 33884
• 

  

  

  /10

  Call for Price

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  10 Webb Rd, Winter Haven, FL 33881

  Live On-Site Auction | Secluded 4-BD Ranch on 5 AC with Pool, Barns & Country Charm10 Webb Rd. Winter Haven, FL 33881Bidding Ends: September 13th at 11 AMPrivate 4BR/2.5BA ranch on 5 acres in East Winter Haven! Enjoy 2,000 sq ft, pool, screened porch, fireplace, and 2 barns. Former citrus grove with no HOA or flood zone. Peaceful setting at roads end, yet close to Hwy 27, I-4, and

  Marty Higgenbotham

  10 Webb Rd, Winter Haven, FL 33881
• 

  

  /19

  $1,999 per month

  • 4 Beds
  • 2 Baths
  • 2,237 Sq Ft
  • House for Rent

  3013 Whispering Trails Dr, Winter Haven, FL 33884

  Featuring sparkling pool!Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,237 square feet, this well-maintained

  3013 Whispering Trails Dr, Winter Haven, FL 33884
• 

  /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
• 

  

  /80

  Est $511,461 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft

  1877 Woodpointe Dr, Winter Haven, FL 33884

  1877 Woodpointe Dr, Winter Haven, FL 33884
• 

  

  /62

  $339,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,136 Sq Ft

  740 Canberra Rd, Winter Haven, FL 33884

  Well maintained 3 bedroom, 2 bath, 2,136 SF heated space, 2 car garage home in the Cypresswood Golf Community in Winter Haven for sale. Move In Ready! Wow, the floor plan is awesome - nice spacious rooms - lots of storage closets in this home. Split floor plan, pocket doors between dining rm & family rm, sliding doors to the back porch. Updates in Kitchen & Bathrooms, Windows, Flooring and

  Cheryl Skinner-Marble XCELLENCE REALTY, INC

  740 Canberra Rd, Winter Haven, FL 33884
• 

  

  /40

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  2956 Whispering Trails Dr, Winter Haven, FL 33884

  Charming 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 bar with plenty of

  Kim Connahey HOUSE OF GLASS REAL ESTATE PM

  2956 Whispering Trails Dr, 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
• 

  

  /28

  Est $249,701 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  4815 Summerfield Cir, Winter Haven, FL 33881

  4815 Summerfield Cir, Winter Haven, FL 33881
• 

  

  /54

  $474,900

  • 4 Beds
  • 3 Baths
  • 2,781 Sq Ft

  1908 Crossroads Blvd, Winter Haven, FL 33881

  Immaculate 4-Bedroom, 3-Bathroom Plus Office Home in the Coveted Crossroads at Lake Region Welcome to this beautifully maintained residence located in the highly desirable gated community of Crossroads at Lake Region. This spacious four-bedroom, three-bathroom home with a dedicated office offers the perfect blend of comfort and functionality. As you arrive, you’re welcomed by a

  Jill Lingenfelter CENTURY 21 MYERS REALTY

  1908 Crossroads Blvd, Winter Haven, FL 33881
• 

  

  /18

  $1,759 per month

  • 4 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • House for Rent

  2936 Whispering Trails Dr, Winter Haven, FL 33884

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2 bathrooms, and approximately 1,728 square feet, this well-maintained home offers a high standard of

  2936 Whispering Trails Dr, 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
• 

  

  /53

  Est $255,733 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,253 Sq Ft

  3268 Whispering Trails Ave, Winter Haven, FL 33884

  3268 Whispering Trails Ave, Winter Haven, FL 33884
• 

  

  /37

  $460,000

  • 4 Beds
  • 3 Baths
  • 2,667 Sq Ft

  351 Greenfield Rd, Winter Haven, FL 33884

  SPACE FOR EVERYONE! COUNTRY CLUB LIFESTYLE!! Huge four bedroom, three full bath POOL home on .52 acres! Lot overlooks the 13th tee in the private, guard-gated 24/7 golf community of Cypresswood Golf & Country Club. Beautiful brick wood-burning fireplace in family room plus a large bonus room that was being used as a game and theater room - a great spot!! The kitchen features quartz countertops

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  351 Greenfield Rd, Winter Haven, FL 33884
• 

  

  /45

  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • House for Rent

  2900 Whispering Trails Dr, Winter Haven, FL 33884

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable gated community of Whispering Trails. Built in 2017 and ideally situated just minutes from Hwy 27, this home offers both comfort and convenience.Step inside to a spacious open floorplan featuring sleek, low-maintenance contemporary concrete flooring and a large kitchen with stainless steel appliances

  Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

  2900 Whispering Trails Dr, 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
• 

  

  /10

  Est $295,396 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  1417 Austin Terrace, Winter Haven, FL 33884

  1417 Austin Terrace, Winter Haven, FL 33884
• 

  

  /36

  $379,999

  • 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
• 

  

  /16

  $1,765 per month

  • 3 Beds
  • 2 Baths
  • 1,384 Sq Ft
  • House for Rent

  2968 Whispering Trails Dr, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  2968 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
• 

  

  /10

  Est $303,384 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  1466 Austin Terrace, Winter Haven, FL 33884

  1466 Austin Terrace, Winter Haven, FL 33884
• 

  

  /14

  $334,900

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft

  3132 Country Club Cir, Winter Haven, FL 33881

  This home is located in the awesome Lake Region of Winter Haven. In a very desired area of right off Dundee road onto Country Club. Central to everything! Minutes away from Legoland & 45 min to Tampa or all of the Orlando attractions and close to downtown Winter Haven area, shopping, several lakes and travel.! This meticulously 4 Bedroom,2 bath, over 1828 sf., split floor plan have ceramic tiled

  Irma Cruz FLORIDA REALTY MARKETPLACE

  3132 Country Club Cir, Winter Haven, FL 33881
• 

  

  /15

  $2,200 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
• 

  

  /10

  Est $293,567 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft

  1458 Austin Terrace, Winter Haven, FL 33884

  1458 Austin Terrace, 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
• 

  

  /16

  $2,295 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 $2439.90. That covers your base rent, $2295.00 + 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

  $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
• 

  

  /10

  Est $301,219 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
• 

  

  /65

  $395,000

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

  623 Grove St, Winter Haven, FL 33881

  Welcome to Inman Grove a prime location just minutes from Legoland, Hwy 27, top-rated schools, shopping, medical facilities, and popular dining options! This spacious 5-bedroom, 3-bathroom Hayden model offers both comfort and functionality, including a first-floor bedroom and full bath perfect for guests or multigenerational living. The home features a formal dining room, large family room, and

  Victoria Escobar KELLER WILLIAMS SUBURBAN TAMPA

  623 Grove St, Winter Haven, FL 33881
• 

  

  /8

  $1,475 per month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  1105 Eagle Pond Dr Unit 11E, Winter Haven, FL 33884

  Second floor two bedroom, two bathroom condo located in the gated golf community of Cypresswoods. Enjoy the numerous HOA amenities, including private gated community entrance with 24/7 guard, pool, gym, tennis courts, and golf. Condo features inside laundry, brand new carpet, storage room and spacious living room. Home available immediately. 12-month lease. No smoking. One small pet under 25

  Sharon Billups SKYELINE REALTY LLC

  1105 Eagle Pond Dr Unit 11E, Winter Haven, FL 33884
• 

  /2

  $1,325,000 Sold Jun 30, 2025

  • 3,309 Sq Ft
  • $400/SF
  • 71 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1987

  3640 Crump Rd, Winter Haven, FL 33881

  LAKEFRONT PARADISE WITH RESORT-STYLE AMENITIES! Nestled on Lake Hamilton with NO HOA, this 4-bed, 3-bath home on 1.23 acres offers the ultimate lakeside lifestyle. Bring your boat and jet skis and enjoy the convenience of a dock with an electric, covered BOAT LIFT, and built-in bench—perfect for fishing!Step through the French doors to the sparkling SALTWATER PebbleTec pool, featuring

  Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

  3640 Crump Rd, Winter Haven, FL 33881
• 

  

  /32

  Est $255,024 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
• 

  

  /53

  $350,000

  • 4 Beds
  • 3.5 Baths
  • 3,050 Sq Ft

  1905 Emily Blvd, Winter Haven, FL 33884

  Welcome to your new dream home! This spacious 4-bedroom, 3.1-bathroom gem spans over 3,000 square feet, offering ample room for comfort and creativity. Nestled in a vibrant, family-friendly community, this two-story haven boasts a BRAND-NEW ROOF, ensuring worry-free living for years to come. ADDITIONAL UPDATES: TOILETS WERE UPGRADED, KITCHEN CABINETS PAINTED, SECOND FLOOR FLOORING, GARAGE

  Roselin Diaz ELITE REALTY, LLC

  1905 Emily Blvd, Winter Haven, FL 33884
• 

  

  /14

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 2,087 Sq Ft
  • House for Rent

  500 Cody Caleb Dr, Winter Haven, FL 33884

  BEAUTIFULLY RENOVATED HOME IN THE SAVANNAH ESTATES SUBDIVISIONCLOSE TO DUNDEE ROAD AND MANY SHOPS AND SCHOOLS

  Nell Nelson FLORIDA LAND OFFICE LLC

  500 Cody Caleb Dr, Winter Haven, FL 33884
• 

  /2

  $242,500 Sold Jun 27, 2025

  • 1,176 Sq Ft
  • $206/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2013

  713 Overlook Grove Dr, Winter Haven, FL 33884

  Motivated Seller – Priced to Sell! Bring All Offers!Welcome to 713 Overlook Grove Dr in Winter Haven – a beautifully maintained open-concept home that offers both comfort and value. The seller is extremely motivated, and this home is priced to move quickly, so don’t wait—schedule today!This spacious residence features a brand-new roof and comes with paid-off solar panels at

  Austin Waters KELLER WILLIAMS REALTY SMART 1

  713 Overlook Grove Dr, Winter Haven, FL 33884
• 

  

  /85

  Est $716,518 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

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