Cypresswood Homes for Sale with Pool

Lot #360 / 3 B / 3 BA / 1,992 Sq. Ft. / $209,800.00 Beautiful Like New 2023 Home! Builder's Model Showpiece - 2023 Erica Model in popular Cypress Creek Village! This large, one-owner home is located on a pond lot! It has a glass window enclosed screen room overlooking a patio and pond beyond. Enter into the large open concept home and look across the large Living Room, Dining Room, and Kitchen.

Jennifer Meyers CRF Communities

Located in the highly sought-after gated golf community of Cypresswood in Winter Haven, this beautiful 4-bedroom, 3-bathroom home offers over 2,800 square feet of spacious living when pool room footage is added. The offering includes a private pool, and a 9x9 pool house complete with a half bath, perfect for guests, poolside entertaining, or an additional flex space. Inside, the home boasts a

Lovett Johnson LBJ REALTY AND ASSOCIATES LLC

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

**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.

Enjoy serene golf-front living in this beautifully designed 2BR/2BA home, featuring two versatile bonus rooms perfect for a media room, home office, or guest space. This home features an irrigation well for watering the beautiful landscaping, and inside, there is an emergency whole-home Generac generator system! There is also a nice gas fireplace in the living area. Located in a desirable

Josh Taylor VILLAGE REALTY OF WINTER HAVEN

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

Lot #372 - 2 Bed / 2 Bath / 1,120 Sq. Ft. / $139,800.00 -- 2023 Builder's Model - Turnkey Home! Your retirement or seasonal home is all furnished, decorated, and ready for you! Just bring your clothes and enjoy. This STUNNING - 2 bedroom, 2 bathroom home features 2 large bedroom ensuites at either end (for privacy) - with open living in the center. Walk in closets are one of many luxury features.

Jennifer Meyers CRF Communities

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

One or more photo(s) has been virtually staged. Welcome to 1936 Crossroads Blvd in the highly sought-after gated community of Crossroads at Lake Region. This exquisite entertainer’s paradise comes partially furnished, features a private screened pool and spa, upgraded finishes throughout, and a fully fenced backyard designed for relaxation and entertaining. This meticulously upgraded Rockingham

Craig Murrell REMAX EXPERTS

New to the market is this "one owner" villa located in the sought-after Enclave neighborhood located in Cypresswood Golf and Country Club in SE Winter Haven. This 3 bedroom 2 bathroom end unit has just undergone a professional interior paint job. Enjoy Easterly pasture and sunrise views from the lanai. The country club amenities include access to the clubhouse with bar and grill, jr. olympic

Steven Smith, PA LOCKHART & ASSOCIATES INC

Welcome to 2813 Wingfoot Court in the sought-after Cypresswood Golf Villas! Perfectly positioned along the 8th fairway of Cypresswood Golf & Country Club, this guard-gated community offers peaceful golf course views and a relaxed Florida lifestyle.This beautifully maintained 2-bedroom, 2-bathroom villa is being sold fully furnished and truly turn-key — just bring your suitcase. The professionally

Corinna Weaver CROSBY & ASSOCIATES, INC.

Charming 3-bedroom, 2-bath home located in a desirable HOA community in Winter Haven! This well-maintained residence offers 1,148 square feet of comfortable living space with a functional layout designed for everyday living. Enjoy the convenience of an interior laundry area and a spacious living room that flows into the dining and kitchen areas. The primary suite features a private bathroom,

Marisela Quintero LA ROSA REALTY PRESTIGE

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.

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, FULLY FURNISHED, and Move-In Ready! The owners updated their Home in 2023, just 3 years ago, with Granite Countertops, Stainless Steel Appliances, New Furniture,

David Shippey XCELLENCE

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

Step into this beautifully maintained home in the sought-after 55+ gated community of Cypress Creek Village in Southeast Winter Haven. The open-concept kitchen, dining, and living areas are bright and airy, perfect for everyday living and entertaining. The kitchen features stainless steel appliances, a farmhouse sink overlooking the carport, and a center island with ample storage and seating. The

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

Tucked away on the golf course in the highly sought after Cypresswood Golf and Country Club community of SE Winter Haven with serene pond views and lush natural foliage for privacy, this beautifully maintained single-family pool home offers the perfect blend of comfort, elegance, and resort-style living. A circular drive sets the tone as you arrive, leading into a thoughtfully designed

Kayly Malinas JOHN WOOD REALTY, INC.

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

This well-maintained 2014 Nobility Lindsay, owned and occupied part-time by its original owner, is perfectly priced and move-in ready. Located in beautiful Cypress Creek Village, a premier 55+ community, this 3-bedroom, 2-bath home offers an affordable and comfortable Florida lifestyle - and it comes fully furnished. The spacious living room (16'6" x 18'2") features an open layout with

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

MOVE IN CONDITION! Nestled on a beautifully landscaped and tree shaded lot this well maintained 2 bedroom 2 bathroom patio home features split bedrooms with ample closets, an expansive great room with space for living and dining areas, breakfast nook in the kitchen and an attached 2 car garage. Additional amenities include an oversized rear screened porch overlooking a picturesque greenspace with

Steven Smith, PA LOCKHART & ASSOCIATES INC

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

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.

Welcome to this beautifully maintained 3-bedroom, 2-bath home located in the highly sought-after Cypresswood golf community in Winter Haven. Enjoy resort-style living with an 18-hole golf course, 24-hour gated security, clubhouse, community pool, and more. Inside, the renovated kitchen features granite countertops and custom cabinetry. The spacious primary suite offers a large ensuite bath

Melissa Witter KELLER WILLIAMS REALTY SMART 1

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

This cozy home offers a warm and inviting layout, perfect for anyone who prefers comfort and easy living. It features a functional floor plan with a modern kitchen, bright bedrooms, and low-maintenance spaces that make everyday life simple. Ideally located near US-27, US-17, SR-540, and with quick access to I-4, you’re just a short drive from Orlando, Tampa, Disney, Legoland, lakes, parks,

Jenny Caso LIFESTYLE INTERNATIONAL REALTY

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

Welcome to this refined sanctuary where timeless elegance meets Florida’s tranquil landscape. On a premium golf-adjacent lot within the guarded, gated community, 2964 Plantation Road blends gracious scale, luminous living and multi-generational flexibility in one seamless layout. Upon arrival, you are greeted by mature landscaping, a circular drive and side-entry access to a three-car garage,

Audrey Christman PREMIER SOTHEBYS INT'L REALTY

Welcome to this beautifully updated 3-bedroom, 2-bathroom home offering 1,344 square feet of comfortable living in the sought-after 55+ community of Cypress Creek Village in Winter Haven. Built in 2020, this residence is move-in ready and designed for relaxed Florida living. The home features well-manicured landscaping that enhances its curb appeal, along with low-maintenance vinyl siding, a

Daniel Butler Sun Realty of Florida

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

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

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

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.

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

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

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

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.

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

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