Winter Haven, FL Homes for Sale under $300,000

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  /68

  $295,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,602 Sq Ft

  3021 Buckeye Pointe Dr, Winter Haven, FL 33881

  Beautiful 3 Bed, 2 Bath home with Stunning Lake View in Winter Haven, FL! Welcome to your dream home, nestled in the heart of Winter Haven, with sunset view from the back porch that will take your breath away. With granite countertops in the kitchen, modern appliances, and a spacious open layout, this home is perfect for families or those seeking comfort and style. The master bedroom features an

  Lidia Queiroz LA ROSA REALTY CW PROPERTIES L

  3021 Buckeye Pointe Dr, Winter Haven, FL 33881
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  /35

  $249,000

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  389 San Jose Dr, Winter Haven, FL 33884

  Welcome to the Patio Homes section of Orchid Springs — ideally positioned in the heart of Winter Haven, right in the center of the state.This well-maintained 3-bedroom home features a desirable split floor plan, offering privacy between the primary suite and guest bedrooms — ideal for visitors, hobbies, or a dedicated home office. Situated on a cul-de-sac street with no rear neighbors, this

  Don Jerue KELLER WILLIAMS REALTY SMART 1

  389 San Jose Dr, Winter Haven, FL 33884
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  /35

  $280,000

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  214 Grove Ridge Dr, Winter Haven, FL 33880

  Stunning ranch modern transformation that will take your breath away!Welcome to this 2019 impeccably redesigned modern rustic 4 bed/2 bath retreat on fenced one-third acre lot on cul-de-sac with seamless indoor-outdoor entertaining.Homeownership pride from the front curb to the back fence!As you approach, you are greeted by a New sprawling 13’x46’ covered front porch with ample space

  Sheryl Manche KELLER WILLIAMS HERITAGE REALTY

  214 Grove Ridge Dr, Winter Haven, FL 33880
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  $229,900

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  1729 Teagan Ln, Winter Haven, FL 33884

  Welcome to this inviting 3-bedroom, 2-bathroom home located in a quiet, well-kept Winter Haven community. The interior showcases a bright, open-concept layout with neutral finishes and clean lines that create a warm, modern feel throughout the main living areas.The kitchen is thoughtfully designed with stainless steel appliances, contemporary cabinetry, sleek countertops, and a functional

  Casandra Vann KELLER WILLIAMS REALTY SMART

  1729 Teagan Ln, Winter Haven, FL 33884
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  /27

  $240,000 Open Sun 11AM - 2AM

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  516 Lake Dexter Blvd, Winter Haven, FL 33884

  This beautifully updated move-in-ready 2/2 home sits in a quiet, established community on Lake Dexter, one of Winter Haven’s pristine spring-fed lakes. The neighborhood offers an exceptional lifestyle with private access to a residents-only boat ramp, a sparkling saltwater community pool, and a serene waterfront park complete with a fishing dock, gazebo, playground, and shady green space to enjoy

  Emily Ward EXP REALTY LLC

  516 Lake Dexter Blvd, Winter Haven, FL 33884
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  /26

  $242,500

  • 3 Beds
  • 3 Baths
  • 2,070 Sq Ft

  35 Enclave Dr, Winter Haven, FL 33884

  NEW PRICE ON THIS SPACIOUS 3 BEDROOM ENCLAVE UNIT IN CYPRESSWOOD!!! VILLA WITH OVER 2,000 PLUS SQ. FT. LIVING 3 BEDROOM 3 BATH PLAN! YOU WILL ENJOY A TRUE FLORIDA LIFESTYLE WITH THE AMENITIES AT CYPRESSWOOD GOLF & COUNTRY CLUB!! This maintenance-free villa is pristine, the largest villa floor plan in the Cypresswood Enclave with over 2,000 sq. ft. of living area designed with an open floor plan,

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  35 Enclave Dr, Winter Haven, FL 33884
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  /51

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft

  715 Magnolia Place, Winter Haven, FL 33884

  Waterfront condo on the Winter Haven Chain of Lakes! Experience beautiful waterfront views, nightly sunsets, and direct access to the world-famous Winter Haven Chain of Lakes in this updated lakefront condo located in the gated community of Winterset. Offering 2 bedrooms, 2 bathrooms, and a private one-car garage, this second-floor residence blends comfort, style, and the relaxed Florida

  Michael Stone THE STONES REAL ESTATE FIRM

  715 Magnolia Place, Winter Haven, FL 33884
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  /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
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  /27

  $235,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  606 Holt Cir, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Welcome home to this well-maintained Winter Haven property offering comfort, functionality, and value all in one! Located in an established neighborhood with convenient access to shopping, dining, and major roadways, this home is perfect for first-time buyers, downsizers, or investors alike. Inside, you’ll find a practical layout with spacious

  Gabriel Tanksley KELLER WILLIAMS REALTY SMART 1

  606 Holt Cir, Winter Haven, FL 33880
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  /7

  $245,000

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

  1540 Avenue C NE, Winter Haven, FL 33881

  Short Sale. Quaint 3/2 home perfect for 1st time homebuyers or could be a great rental property. Contract is contingent upon third party bank approval. Centrally located to major highways and shopping.

  Robert Miller MILLSHIRE REALTY

  1540 Avenue C NE, Winter Haven, FL 33881
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  /13

  $272,670 New Construction

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft

  3889 Giorgio Dr, Winter Haven, FL 33884

  Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet.

  Meritage Homes Builder

  3889 Giorgio Dr, Winter Haven, FL 33884
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  /16

  $289,950 New Construction

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft

  5351 Mickey Ave, Lake Wales, FL 33859

  This Azure floor plan offers a welcoming formal entry and hallway. A spacious great room with kitchen is open to dining and family entertainment area that leads to a covered patio. Also included is a great sized primary bedroom with a primary bath and walk-in closet. Included features: 9"4' ceilings and 8' doors, 42' cabinets and white quartz counter tops in kitchen, ceramic tile throughout the

  Stephanie Morales AXEN REALTY, LLC

  5351 Mickey Ave, Lake Wales, FL 33859
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  /19

  $255,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  878 Killearn Blvd, Winter Haven, FL 33880

  PRICE CHANGE – NO HOA & PRICED TO SELL! Opportunity meets value in this 3-bedroom, 2-bath home located in a well-established Winter Haven neighborhood. Positioned on a spacious, fully fenced corner lot, this property offers exceptional outdoor space and includes an above-ground pool, perfect for cooling off on hot Florida days, entertaining guests, or enjoying your own private backyard retreat.

  Barbi Rodriguez SIGNATURE INTERNATIONAL REAL E

  878 Killearn Blvd, Winter Haven, FL 33880
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  /17

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,369 Sq Ft

  3410 Fox Ridge St, Winter Haven, FL 33884

  Welcome to 3410 Fox Ridge Street in Winter Haven, FL. This 3-bedroom 2 bath home features tiled flooring throughout, new appliances, new interior and exterior paint. Granite countertops in kitchen and bathrooms. Open floor plan with a wood burning fireplace. Inside laundry room. Master bedroom features his and her walk-in closets. The home is within walking distance of Garden Grove elementary

  Sue Ann Williamon THE HOME COMPANY

  3410 Fox Ridge St, Winter Haven, FL 33884
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  /13

  $269,900

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

  1911 Brown St NE, Winter Haven, FL 33881

  Location Location!! NO HOA, NO CDD, Built in 2020. QUIET, YET CONVENIENT LOCATION! Whether you're shopping for a first home, Investment or last home, this beauty is just what you’ve been looking for! Beautiful 3BR/2BA home open floor plan, living room/dinning groom /family room kitchen combo. located in NE Winter Haven. Large walk in closet in the Master Bedroom/Bath. Master bath contains a

  Manuel Duran Jr VYLLA HOME

  1911 Brown St NE, Winter Haven, FL 33881
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  $270,000

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  3365 Raleigh Dr, Winter Haven, FL 33884

  Welcome to Traditions at Lake Ruby — a vibrant 55+ lakeside community where every day feels like a Florida resort getaway. Welcome to this lovely 2-bedroom, 2-bathroom home in the highly sought-after Traditions at Lake Ruby community!Walk through the front door into an open-concept living and dining area that flows seamlessly into the kitchen. With bright windows and quality finishes, the

  James Barris EXP REALTY LLC

  3365 Raleigh Dr, Winter Haven, FL 33884
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  /54

  $299,990

  • 4 Beds
  • 3 Baths
  • 2,101 Sq Ft

  3952 Warbler Dr, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Welcome to this spacious 4-bedroom, 3-bathroom home located in the desirable Winter Haven area. This residence offers an open floor plan with plenty of natural light, a modern kitchen with ample storage, and a comfortable layout ideal for everyday living or entertaining. The owner’s suite includes a private bath and walk-in closet, while the

  Rosalina Esquilin ZARIA REALTY GROUP LLC

  3952 Warbler Dr, Winter Haven, FL 33880
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  $274,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft

  2362 Brassie Ct, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Nestled in the growing Villamar community, this beautifully maintained 3-bedroom, 2-bath Meritage Home offers modern comfort and an ideal location near Chain of Lakes Elementary. Built with energy efficiency in mind, this newer home features an inviting open-concept floor plan where the kitchen flows seamlessly into the spacious great room—perfect

  Millie Brockmeyer RE/MAX INNOVATION

  2362 Brassie Ct, Winter Haven, FL 33884
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  /43

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,118 Sq Ft

  3343 Livingston Way, Winter Haven, FL 33884

  Located in the highly desirable 55+ maintenance-free gated community of Traditions on Lake Ruby, this wonderful 2-bedroom, 2-bathroom home offers charm, functionality, and an exceptional lifestyle. Upon arrival, you’re greeted by a welcoming Screened-in front porch decked out with tile flooring. Inside, the open-concept floor plan features a spacious living room with vaulted ceilings, Laminate

  Eileen Belanger CENTURY 21 MYERS REALTY LAKE WALES

  3343 Livingston Way, Winter Haven, FL 33884
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  /25

  $224,900

  • 3 Beds
  • 2.5 Baths
  • 1,407 Sq Ft

  301 Orange Blossom Dr, Winter Haven, FL 33880

  WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! Renovated, updated & remodeled. This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location! Features include a neutral color scheme, renovated kitchen with plenty of cabinet space and a convenient pass-through bar leading to an open living room and dining area, primary bedroom with ensuite and

  Catherine Kluytenaar THE K TEAM REAL ESTATE SERVICES LLC

  301 Orange Blossom Dr, Winter Haven, FL 33880
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  /27

  $284,990 New Construction

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft

  4952 Kaia Ave, Winter Haven, FL 33884

  The property is located at 4952 Kaia Avenue WINTER HAVEN FL 33884 priced at 284990, the square foot and stories are 1665, 1.The number of bath is 2, halfbath is 0 there are 4 bedrooms and 2 garages. For more details please, call or email.

  D.R. Horton Builder

  4952 Kaia Ave, Winter Haven, FL 33884
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  /21

  $255,000

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

  3930 Country Place, Winter Haven, FL 33880

  Rare rent-to-own opportunity available. Rent-to-own consider though lease option. Property also available for sale. Terms subject to owner approval. Single-family residence situated on owned land, featuring a wood-frame manufactured home permanently affixed and elevated. Property is titled as real property and registered as a single-family home and offers an affordable path to ownership. The home

  Juan Vargas Red Rock Realty

  3930 Country Place, Winter Haven, FL 33880
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  /39

  $289,900

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

  364 Cloverdale Rd, Winter Haven, FL 33884

  Beautiful property with convenient location! Open floor plan with high ceilings invites you into this 3 bedroom 2 bath home in Winter Haven, conveniently located minutes to shops, easy access to 27 and other highways. Flex space currently used as an office but can be converted to accommodate multiple types of room ideas! This split floor plan home offers a nice sized primary bedroom with TWO

  Leslee Davis DALTON WADE INC

  364 Cloverdale Rd, Winter Haven, FL 33884
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  /14

  $264,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  3880 Giorgio Dr, Winter Haven, FL 33884

  Prepare dinner while catching up on the day’s events from this home's chef-inspired kitchen which overlooks a great room.

  Meritage Homes Builder

  3880 Giorgio Dr, Winter Haven, FL 33884
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  /13

  $300,000

  • 4 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  1985 Sarah St, Winter Haven, FL 33884

  Check out this upgraded Columbus on a corner lot! This expansive two-story Columbus has a well-designed layout, featuring a first floordedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, which has upgraded contertops,dining room and family room, with a patio extending the interior space outdoors, patio has also been upgraded with a 12x8

  Garrett Collins MARK SPAIN REAL ESTATE

  1985 Sarah St, Winter Haven, FL 33884
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  /39

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  2817 Wingfoot Ct, Winter Haven, FL 33884

  Welcome to 2817 Wingfoot Ct, located in the desirable Cypresswood Golf Villas. This beautifully maintained villa sits along the 8th fairway of the prestigious Cypresswood Golf & Country Club, a guard-gated community offering both privacy and tranquility. Inside, you'll find three spacious bedrooms and two full bathrooms. The living and dining areas feature vaulted ceilings that enhance the open

  Dee Norris NEXTHOME NORRIS & COMPANY REAL

  2817 Wingfoot Ct, Winter Haven, FL 33884
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  /17

  $284,499 New Construction

  • 3 Beds
  • 2 Baths
  • 1,615 Sq Ft

  6056 Navona Way, Winter Haven, FL 33884

  Feel at home with the Magenta, a single-story home with 3 bedrooms, 2 bathrooms, and a 2-car garage. This layout is a true gem, seamlessly blending modern comfort with Florida charm. Open concept living dazzles with luxury vinyl plank flooring throughout the main living areas. The kitchen, featuring quartz countertops, new stainless-steel appliances and ample storage overlooks the dining and

  Casa Fresca Homes Builder

  6056 Navona Way, Winter Haven, FL 33884
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  /8

  $288,500

  • 3 Beds
  • 2 Baths

  3829 Giorgio Dr, Winter Haven, FL 33884

  PROPERTY IS ALMOST BRAND NEW, SO NOTHING NEEDS TO BE DONE, NO REPAIRS!TAKE ADVANTAGE OF THIS GREAT PROPERTY, IN EXCELLENT LOCATION.

  Ivette Loaiza First Pro International Rlty

  3829 Giorgio Dr, Winter Haven, FL 33884
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  /40

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,417 Sq Ft

  232 Kings Pond Ave, Winter Haven, FL 33880

  Welcome to 232 Kings Pond Ave – A Rare Find in the Heart of Winter Haven! This beautifully maintained 3-bedroom, 2-bathroom home sits on an oversized lot in the desirable Kings Pond community, offering the perfect blend of comfort, space, and convenience. With a split floor plan and high vaulted ceilings in the living room, the home feels open, airy, and inviting the moment you walk through the

  AJ Alessi COLDWELL BANKER REALTY

  232 Kings Pond Ave, Winter Haven, FL 33880
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  /9

  $264,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  Denali Plan at VillaMar - Classic Series, Winter Haven, FL 33884

  Prepare dinner while catching up on the days events from this homes chef-inspired kitchen which overlooks a great room and dining area. Well appointed primary suite provides a restful retreat at the end of the day and has a spacious walk-in closet.

  Meritage Homes Builder

  3745 Giorgio Dr Unit 37076780, Winter Haven, FL 33884
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  /18

  $260,000

  • Land
  • 0.73 Acre
  • $356,164 per Acre

  757 Lake Jessie Dr, Winter Haven, FL 33881

  COME BUILD YOUR DREAM HOME RIGHT ACROSS THE STREET FROM LAKE JESSIE ! LIVE THE BEST LIFE OF WHAT FLORIDA HAS TO OFFER NEAR BEAUTIFUL LAKE JESSIE ! THIS VACANT LAND HAS 3 SEPARATE PARCELS THAT HAVE BEEN DEEDED TOGETHER TO MAKE ONE BUILDABLE LOT THAT IS “JUST SHY” OF ONE ACRE ! THE TOTAL SIZE OF THIS LAND IS .73 OF AN ACRE APPROXIMATELY ! YOU CAN ACCESS LAKE JESSIE WHERE YOU CAN ENJOY THE BEST LAKE

  Brian Allen FLORIDA EXECUTIVE REALTY

  757 Lake Jessie Dr, Winter Haven, FL 33881
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  /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
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  /42

  $292,000

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

  4202 San Rocco Way, Winter Haven, FL 33884

  NEW PRICE! Move-in Ready. This one-story, 4-bedroom, 2-bath home offers 1,851 square feet of well-designed living space and is situated on an oversized corner lot in the VillaMar community. Recent upgrades include a fully vinyl-fenced backyard and a whole-home water filtration system with water softener, providing added comfort and peace of mind.Built in 2023, this Cali floorplan features

  Jennifer NG CANVAS REAL ESTATE

  4202 San Rocco Way, Winter Haven, FL 33884
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  /32

  $280,000

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

  3843 Eloise Estates Ct, Winter Haven, FL 33881

  HUGE PRICE REDUCTION! POND-VIEW MOVE-IN READY HOME! Enjoy a serene setting and modern updates including tile flooring & kitchen backsplash (2022) and a NEW ROOF (2023). Kitchen features granite countertops and stainless steel refrigerator. Spacious master suite with pond view, walk-in closet, and large bathroom. Split bedroom layout offers privacy and comfort. Located near Lake Smart with Chain

  Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

  3843 Eloise Estates Ct, Winter Haven, FL 33881
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  /28

  $224,999

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft

  1904 3rd St NE, Winter Haven, FL 33881

  CONCESSIONS AVAILABLE! Welcome home to this beautifully updated 4 bed, 2 bath in the heart of Winter Haven! Inside you’ll find stylish upgrades like vinyl flooring, granite countertops, and stainless steel appliances. A brand new roof offers peace of mind, and the inviting side yard is perfect for gatherings, gardening, or simply relaxing in the Florida sun. With ~1,400 sq ft, this move-in ready

  Henry Linder XPERT REALTY GROUP

  1904 3rd St NE, Winter Haven, FL 33881
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  /31

  $249,900

  • 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
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  /25

  $279,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft

  Amaryllis Plan at Harbor at Lake Henry - Single-Family Homes, Winter Haven, FL 33881

  Adore life in the Amaryllis by Highland Homes, an affordable, open-layout home designed for modern living! The Amaryllis features: A flowing, open living area including a gathering room, dining room, and kitchen with a pantry and counter-height breakfast bar, all under an airy volume ceiling. An owner's suite with a walk-in wardrobe and private en-suite bath including seated vanity space (or

  Highland Homes Builder

  612 Ituna Cir Unit 37319227, Winter Haven, FL 33881
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  /26

  $209,900

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  Unlisted Address

  Huge fenced yard. A sweet 1st time home or retirement home and everyone else. Newer kitchen, bath, and flooring. Well-kept Property. A must-see.

  Tina Marie TINA MARIE LLC

  Unlisted Address
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  /18

  $299,990 New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,874 Sq Ft

  Columbus Plan at VillaMar, Winter Haven, FL 33884

  This expansive two-story home boasts a well-designed layout, featuring a first floor dedicated to shared living and entertaining. The open concept design seamlessly connects the kitchen, dining room and family room, with a patio extending the interior space outdoors. Upstairs, a spacious loft separates the three secondary bedrooms from the serene owner's suite. Completing the home is a convenient

  Lennar Builder

  6614 Crescent Loop Unit 38667745, Winter Haven, FL 33884
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  /12

  $269,000

  • 3 Beds
  • 2 Baths
  • 1,507 Sq Ft

  4108 Island Lakes Dr, Winter Haven, FL 33881

  EXCELLENT HOME!!! GREAT INVESTMENT OPPORTUNITY!! MUST SEE THIS HOME!

  Roque Acevedo ONE TEAM REALTY

  4108 Island Lakes Dr, Winter Haven, FL 33881

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