Location: Winter Haven , 33884
Do Not Show Listings
2968 PLANTATION RD, WINTER HAVEN, FL 33884
$442,00042 Days on yellowkey MLS ID: P4938120
REDUCED by $23,000 (4.9%) on 04/23/2026
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2433 Built: 1997Monthly Fee: $149 Tax: $3,191 (2025)Community: Cypresswood PlantationsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,191
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 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 guard-gated golf-course community with a restaurant, pool, and tennis courts, this home combines comfort, space, and lifestyle. The open, spacious floor plan is ideal for everyday living and entertaining, with an expansive screened porch overlooking the golf course and peaceful pastureland, offering exceptional privacy and views. The primary suite is a true retreat, complete with a screened sitting porch overlooking the water, a spa-like bath with a jetted tub, a walk-in shower, a double vanity, and a bright solarium. The kitchen is well-appointed with a walk-in pantry and built-in shelving, while the large laundry room includes a utility sink and ample cabinetry. An oversized 3-car garage with additional storage cabinets completes the package. First time on the market, a rare opportunity to enjoy relaxed, resort-style living with plenty of flexible space!
Listing is courtesy of: VILLAGE REALTY OF WINTER HAVEN (863-299-6767)
Listing Agent: Joshua Taylor (863-651-5471)
2964 PLANTATION RD, WINTER HAVEN, FL 33884
$579,900197 Days on yellowkey MLS ID: O6352519
REDUCED by $20,000 (3.3%) on 04/30/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3614 Built: 1989Monthly Fee: $137 Tax: $618 (2024)Community: Cypresswood PlantationsSpa: YesSingle Family
Taxes:$618
Tax Year: 2024
Remarks: 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, with stunning views of golf course fairways and water views. Enter inside to discover over 3,600 square feet of thoughtfully designed space. Formal living and dining rooms flow with grace and purpose, while a custom wet bar offers effortless entertaining. The split floor plan is crafted for privacy and connection. The primary suite is complete with dual vanities, walk-in closets, a garden tub, separate shower and private pool access. On opposite wing rests an en-suite bedroom, complete with full bath and independent access. Ideal for multigenerational living, guest privacy or an upscale in-law suite. Two additional bedrooms share a dual bath, while a half bath serves daily living or poolside use. Gourmet gathering begins in the kitchen, including a center island with gas range, generous counter space and views out toward the lanai. The breakfast nook offers a comfortable space for everyday dining, complemented by a nearby utility room and a flexible bonus room. Going outside, this home’s soul lives in its outdoor realm. A pool and spa, and a summer kitchen complete with built-in grill, sink and prep station, invite all-day alfresco living. A covered lanai frames those golf and pond vistas beautifully, offering shade and breeze for lounging or entertaining. Cypresswood is a full-amenity, guard-gated community with an 18-hole golf course, clubhouse with restaurant and lounge, tennis and pickleball, fitness/wellness center, and social programming. A $10,000 seller concession and one-year home warranty.
Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)
Listing Agent: Audrey Christman (516-547-5343)
4009 CYPRESS LNDG S, WINTER HAVEN, FL 33884
$239,00045 Days on yellowkey MLS ID: TB8487328
REDUCED by $8,000 (3.2%) on 04/30/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1291 Built: 1987Monthly Fee: $83 Tax: $3,230 (2025)Community: Cypress Landing Ph 02Single Family
Taxes:$3,230
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. Newly renovated 2 bedroom, 2 bathroom home with all the major updates already done for you — new roof, new floors ,new AC, and new water heater. This is a boater and fisher’s dream property located on beautiful Lake Dexter, Enjoy boating, water skiing, and freshwater fishing right from your backyard playground. The community offers a dock with boat slips available on a first-come, first-served basis, perfect for boats up to 24 feet. Residents also enjoy a clubhouse, pickleball courts, and tennis courts, making it easy to enjoy the Florida lifestyle. Whether you're looking for a full-time residence or a weekend lake retreat, this home offers the perfect mix of updates, amenities, and waterfront living.
Listing is courtesy of: ELEVE REAL ESTATE LLC (813-562-5002)
Listing Agent: Danielle Davis (813-526-5002)
780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$302,5002 Days on yellowkey MLS ID: L4960255
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1583 Built: 2013Monthly Fee: $38 Tax: $4,294 (2025)Community: Overlook RdgSingle Family
Taxes:$4,294
Remarks: Need 4 bedrooms, but don't need to break the budget? This is what you've been searching for here in the heart of Winter Haven! Situated perfectly W of Hwy 27 and out of the hustle and bustle of the city, this 4/2/2 home is ready for you! Close to houses of worship, schools, shopping, golf, and SO much more! Upon arrival, you note the quaint neighborhood, which quickly says "community." The home is situated on a corner lot, as well as on a cul de sac. Upon entry, the new homeowners will be delighted to see easy to maintain flooring throughout the home. No detail was missed in this home's update! New flooring, paint, ceiling fans, kitchen & baths, so she's MOVE-IN READY! The kitchen boasts new countertops, stainless appliances, a cook's workstation, generous sized pantry, and lots of storage. The open floor plan with combined living and dining space is ideal for gatherings and entertaining. The owners suite is spacious, and has a walk in closet and updated bathroom. Three MORE bedrooms, each situated around the living space. This floor plan is superb for daily function of a busy household. Fenced with a durable vinyl fence, the outdoor space is secure for pets. The shed is sturdy for your lawn & garden tools, as well as storage. Leased solar panels increase energy efficiency, with lease to be assumed by the buyer. Water Heater 2021. Roof 2022. Seller is offering a one year American Home Shield warranty!
Listing is courtesy of: FLORIDA REAL ESTATE COMPANY (863-701-3487)
Listing Agent: Cyleste Goodson (863-701-3487)
5200 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$475,000305 Days on yellowkey MLS ID: P4935325
2 Days Off yellowkey (back on 4/25/2026)
REDUCED by $35,000 (6.9%) on 04/16/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2443 Built: 2008Monthly Fee: $5 Tax: $6,051 (2024)Community: Lake Ashton West Ph 01Spa: YesSingle Family
Taxes:$6,051
Remarks: Under contract-accepting backup offers. PRICE REDUCTION! MOTIVATED SELLER! With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites year-round outdoor enjoyment, framed by the beauty of Lake Ashton's natural surroundings. Ideally situated near Lake Wales and Winter Haven this home offers exceptional access to shopping and entertainment; medical facilities and restaurants. The spacious three-bedroom, two-bath layout includes a large den, ideal for a home office or flexible living space. The chef's kitchen features upgraded 42" cabinets, tiled backsplash, granite counter top and breakfast bar all designed for both form and function. The primary suite offers a spa-like escape with double vanities, a walk-in shower, a large soaking tub, separate water closet, and His and Her walk-in closets. Direct access from the PRIMARY SUITE to the outdoor living space is a BONUS. The outdoor living space is covered and screened to enhance the home's entertaining capabilities, creating a seamless flow between indoor and outdoor living. This ST. JOHN floor plan is a split plan home, which is desirable and spacious. Golf enthusiasts will appreciate the separate golf cart entry garage. Additional home features include: Travertine Flooring in the Living Areas (Bedrooms have carpet), Custom Shelving in the Den/Office with Glass Doors, Tray Ceiling in the Primary and Living Room areas, Sliding Glass Doors that Disappear into a Pocket in the Living Room and Beautiful Window Treatments, Floor outlets in the LR and MORE.... IT'S AS MUST SEE!!! Located in Lake Ashton, a 55+ community, residents enjoy access to a resort-style pool, fitness center, pickleball and tennis courts, and planned activities. Lake Ashton offers 2- 18 hole golf courses (Memberships Optional), Restaurant, Pro Shop and Eagles Nest. If you are seeking luxury, security and an active lifestyle, Lake Ashton could be your next home.
Listing is courtesy of: LAKE ASHTON REALTY INC. (863-221-5970)
Listing Agent: Lori Raath (863-409-6899)
6502 OAK HAMMOCK LN, WINTER HAVEN, FL 33884
$169,000178 Days on yellowkey MLS ID: P4936840
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1512 Built: 1998Monthly Fee: $65 Tax: $1,088 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$1,088
Remarks: One or more photo(s) has been virtually staged. Best deal in Garden Grove Oaks! 55 plus manufactured home in Garden Grove Oaks! One of the best values in the community given the size, price and condition. Quietly tucked away in the peaceful 55+ community of Garden Grove Oaks, this home in excellent condition with lots of valuable updating and a spacious interior easy living. This move-in-ready 2-bedroom, 2-bath home offers thoughtful updates designed for easy, low-maintenance living, including double-pane energy-efficient windows, luxury vinyl plank flooring, a brand-new water heater, extra wide driveway, covered carport, screened patio, and a workshop/storage space. Inside, the bright and open layout provides multiple comfortable living areas, including a welcoming family room, a sunny Florida room, and a dedicated dining area—perfect for everyday living or hosting visiting friends and family. The spacious kitchen features ample cabinetry, generous counter space, and all appliances included. The primary suite offers a peaceful retreat with a walk-in closet and private bath with walk-in shower, while the guest bedroom and second full bath are ideal for visitors. At the front of the home, a light-filled Florida room with bay windows creates the perfect space for morning coffee, a home office, or hobbies. Step out to the screened porch and enclosed workshop to enjoy Florida’s mild weather year-round. Residents of Garden Grove Oaks enjoy an active, well-maintained community with a swimming pool, spa, clubhouse, shuffleboard courts, community pond, RV and boat parking, and a full calendar of social activities—making it easy to stay as engaged or as relaxed as you choose. Located in the heart of Winter Haven, you’re surrounded by over 50 lakes, including the renowned Winter Haven Chain of Lakes, along with golf courses, parks, local restaurants, and nearby attractions such as LEGOLAND Florida Resort. Everyday conveniences—Publix, Aldi, Walmart, TJ Maxx, and medical facilities—are all just minutes away. A comfortable home, a friendly 55+ community, and a convenient Central Florida location—all at an exceptional value. Don’t miss this opportunity to enjoy the Florida lifestyle at Garden Grove Oaks.
Listing is courtesy of: THE STONES REAL ESTATE FIRM (863-412-2080)
Listing Agent: Michael Stone (863-412-9733)
116 MANDOLIN DR, WINTER HAVEN, FL 33884
$370,0002 Days on yellowkey MLS ID: O6403313
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2248 Built: 2009Monthly Fee: $56 Tax: $5,678 (2025)Community: MandolinSingle Family
Taxes:$5,678
Elementary School: Chain O Lakes Elem
High School: Lake Region High
Remarks: Welcome to 116 Mandolin Dr in the desirable GATED COMMUNITY of WINTER HAVEN, FL! This spacious 4-bedroom, 2-bathroom home offers 2,248 square feet of COMFORTABLE LIVING on a generous 0.26-acre lot WITH A LOW HOA AND NO CDD! Step inside to soaring VAULTED CEILINGS in the living and dining areas—these ELEVATED CEILINGS create an open, airy feel that makes the home even larger than its footprint. The entire home features durable VINYL FLOORING, and all bedrooms are generously sized, offering FLEXIBILITY FOR FAMILIES, guests, or a home office. NATURAL LIGHT pours in throughout the home, creating a bright and welcoming atmosphere that’s perfect for new homeowners. Major updates include a NEW A/C SYSTEM (2025) and GUTTERS INSTALLED (2024), while the WATER HEATER was replaced in 2017. The roof and plumbing are original, but the seller is willing to NEGOTIATE A BRAND NEW ROOF — making this property an UN-BEATABLE VALUE for the price. Situated in a quiet gated community, this property offers both privacy and security. The location is a standout—just a short walk from a newly constructed Publix set to open in the coming months, as well as nearby Dollar General and 7-Eleven for everyday convenience. You’re also just minutes away by car from Eagle Ridge Mall, LEGOLAND Florida Resort, and all the shopping, dining, and entertainment that downtown Winter Haven has! —making this home not only comfortable, but perfectly located.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Nomar Rosa (646-673-3900)
1100 MARTINIQUE DR #208, WINTER HAVEN, FL 33884
$94,750602 Days on yellowkey MLS ID: P4931920
1 Days Off yellowkey (back on 4/30/2026)
REDUCED by $249 (0.3%) on 04/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1024 Built: 1974Monthly Fee: $313 Tax: $1,085 (2025)Community: Orchid Spgs Vill 300 BarcelonaSpa: NoCondo
Taxes:$1,085
Remarks: Under contract-accepting backup offers. This spacious 2-bedroom condo features 2 full baths and sits nestled in the back upper corner of the Barcelona building of Orchid Springs! It is NOT a 55+ community, so families and young folks are welcome! This gorgeous condo could be your very own Florida home or investment property. Enjoy stunning views from three sides, with plenty of natural light and air flow only available on end units. Recent upgrades including non-popcorn ceilings, an acoustic ceiling in the kitchen, neutral vinyl plank flooring throughout, and neutral monochromatic ZERO VOC paint. No mismatched floorings or walls, no plastic kitchen ceilings, no carpeting, no outdated popcorn ceilings, and no bedrooms carved out of living room space commonly found in condos. There is an updated full-sized kitchen, not just a galley, that boasts 17 cabinets, 10 drawers & a pantry. It has a spacious great room/dining area, and large primary bedroom easily can handle a king size bed with a full en suite bath & a spacious walk-in closet with hardwood shelves and rods, ready for customization for your personal wardrobe needs! The second bedroom is ample and ready to use for your family member, roommate, or a home office . The stairway is just outside the door, with assigned parking below. And importantly, there is almost zero foot traffic from delivery people or other residents passing in front of this unit since it is the only one on the back side of the stairs in its own little corner! This additional privacy is rare and priceless! You will enjoy walking the ample, lush grounds of Orchid Springs while not having to do outdoor chores in the Florida heat. One small monthly HOA/Management fee (unchanged from 2025) of $312.69 is one of the lowest in this area, and makes this an affordable housing opportunity. The fee covers the building exterior, grounds maintenance, parking lot, laundry & mailroom, common gas water heaters, tree care, water, sewer, trash disposal, gas for heating/cooking if desired, exterior pest control, capital accounts, etc. Of special note is that the electricity SMART meter bank is located in a different building on the first floor, not in this unit, so there is lesser than normal radiation found on a tri-field meter. Also, 5 HOA commercial hot water heaters are in a lower floor common room to serve all of Barcelona, so one less appliance for the homeowner to buy and maintain! Same with the common area HOA laundry facility- no personal washers or dryers to buy or maintain. This unit is around the corner from Legoland, conveniently situated between Orlando & Tampa. Southeast Winter Haven is surrounded by its famous Chain-O-Lakes known for boating, fishing and waterski shows available for you to enjoy! IMPORTANT NOTE: the Barcelona Building and this condominium unit are NOT subject to the statutory engineering inspections and repairs that many high rise condos 3+ stories tall are, thus eliminating the potential associated astronomical, unanticipated assessments that may occur as a result.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Karel Cain (863-287-0196)
2735 RUTLEDGE CT, WINTER HAVEN, FL 33884
$220,000107 Days on yellowkey MLS ID: TB8462826
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1419 Built: 2006Monthly Fee: $250 Tax: $1,639 (2025)Community: Traditions Ph 01Townhouse
Taxes:$1,639
Remarks: Under contract-accepting backup offers. Move-in-ready, one-story townhome is now available in the highly sought-after Verandahs at Lake Reeves community. This well-maintained home offers 2 spacious bedrooms and 2 full bathrooms, plus a large bonus room that can be used as an office, den, or potential third bedroom. The kitchen features solid wood cabinetry, solid surface countertops, and ample space for cooking and entertaining. High ceilings and an open floor plan create a bright, airy atmosphere throughout the home. Enjoy relaxing on the screened lanai overlooking peaceful community greenspace. Residents of The Verandahs enjoy access to a community pool and fishing pier on scenic Lake Reeves. The low monthly HOA covers internet, cable, and lawn maintenance—so you can stay cool and carefree in the Florida sunshine. Furnture can be included with purchase if buyer has interest in it. Major updates include a new roof in 2018, along with a recently replaced water heater and dryer. Simply move in and start enjoying the Florida lifestyle.
Listing is courtesy of: KELLER WILLIAMS TAMPA PROP. (813-264-7754)
Listing Agent: Cynthia Kladakis (813-415-7277)
3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$255,000116 Days on yellowkey MLS ID: S5141071
REDUCED by $10,000 (3.8%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1603 Built: 2006Monthly Fee: $210 Tax: $3,716 (2025)Community: Osprey PointeSingle Family
Taxes:$3,716
Remarks: "OWNER WILL CREDIT UP TO $15,000 FOR THE COST OF ROOF REPLACEMENT AT CLOSING" FOR SALE: Attractive 3-Bedroom, 2-Bathroom Single-Family Home in Winter Haven! Discover your dream home in Osprey Pointe, where comfort meets style. This home is designed for modern living and entertaining. An open floor plan connects the eat-in kitchen and breakfast bar seamlessly to the living and dining areas, perfect for gatherings. Equipped kitchen with an eat-in area and a breakfast bar, ready for family meals and casual dining. Luxurious Master Suite: Retreat to your sanctuary featuring an elegant tray ceiling, a generous walk-in closet, double vanities in the primary bathroom, and a large glass shower stall. Enjoy the Florida lifestyle on your covered and screened rear porch. A paver driveway and an attached 2-car garage add to the curb appeal. The home includes inside laundry with washer and dryer hook-ups. Tiled common areas and bathrooms offer easy maintenance, while plush carpet in the bedrooms provides comfort. Exceptional Community Amenities: Live like you're on vacation every day! Enjoy access to a community clubhouse and a sparkling pool. Plus, take advantage of the private waterfront dock on beautiful Lake Ned for fishing and recreational activities. Lawncare included in HOA. Don't miss this opportunity to own a piece of paradise in Winter Haven. Schedule your showing today!
Listing is courtesy of: FLORIDA REALTY RESULTS LLC (407-498-3838)
Listing Agent: Debbie Browning (407-908-9060)
5351 MICKEY AVE, WINTER HAVEN, FL 33884
$299,999162 Days on yellowkey MLS ID: S5138935
INCREASED by $10,049 (3.5%) on 04/13/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1700 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Taxes:$0
Remarks: 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 wet and main living areas of the home. All bedrooms, family room, and covered lanai are prewired for ceiling fans. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
Listing is courtesy of: AXEN REALTY, LLC (480-399-1218)
Listing Agent: Stephanie Morales, Llc (407-399-2055)
5147 KINSLEY DR, WINTER HAVEN, FL 33884
$314,999338 Days on yellowkey MLS ID: S5127810
REDUCED by $3,636 (1.1%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1919 Built: 2025Monthly Fee: $38Community: Seasons At Annabelle EstatesSingle Family
Remarks: Discover this stunning Ruby home, ready for quick move-in! Included features: a welcoming covered entry; a smartly planned kitchen boasting white 42" cabinets, a center island, a large walk-in pantry, and an open dining area; an immense great room; a secluded primary suite showcasing a generous walk-in closet and a private bath; three secondary bedrooms; a shared hall bath; a central laundry; and a comfortable covered patio. *Take advantage of special financing on quick move-in homes OR buy a to-be-built home and enjoy up to $20,000 in Flex Funds toward homes that can close in a timely manner! Options may vary by community, and offers are available on select homes on a first-come, first-served basis. Contact builder for more information!
215 SANTA ROSA DR, WINTER HAVEN, FL 33884
$329,90025 Days on yellowkey MLS ID: TB8494313
REDUCED by $20,000 (5.7%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2355 Built: 1988Monthly Fee: $46 Tax: $3,255 (2025)Community: Overlook EstatesSingle Family
Taxes:$3,255
Elementary School: Elbert Elem
Remarks: One or more photo(s) has been virtually staged. This is a 4 bedroom, 2 bathroom single family home with approximately 2,355 square feet on about 0.34 acres, a 2 car garage, a wood burning fireplace, and a screen enclosed pool and jacuzzi inside a gated community just minutes from Legoland. This home stands out for buyers who want strong square footage, a functional layout, and outdoor features that are already in place. The floor plan gives plenty of room for daily living, guests, or flexible use, and the 2 car garage adds practical storage and parking that matters for long term ownership. The gated setting brings added privacy and neighborhood appeal while keeping the property close to shopping, dining, schools, and the main conveniences that make this part of Winter Haven attractive. Inside, the home gives a buyer a solid starting point with the chance to update key finish areas over time. The kitchen and bathrooms are the main spaces where a future owner may choose to remodel, making this a value add opportunity for someone who wants to improve the home around an already desirable footprint. The wood burning fireplace adds character to the living area and helps give the interior more presence than a basic builder layout. This is the kind of house that works well for a buyer who wants size, location, and lifestyle features first, then the freedom to make design changes at their own pace. The outdoor setup is a major part of the appeal. The screen enclosed pool and jacuzzi create a more complete Florida living experience and give the backyard a true entertaining and relaxation element. The screened enclosure adds usability and helps the pool area feel like an extension of the home rather than just an extra feature. The pool is reported to be working, with the main noted item being a light, and seller will have the pool fully cleaned and ready to go. For buyers searching online for a Winter Haven pool home, a gated community home near Legoland, a house with jacuzzi and screened pool, or a Polk County property with indoor and outdoor living space, this home checks multiple search points that matter. Major system notes also help frame the opportunity clearly. The AC is reported at about 10 years old, the water heater about 2 years old, and the roof about 10 years old, with a prior note that inspection suggested roof replacement due to age and mentioned one small leak in a closet. The septic system was replaced, which is an important update for future maintenance planning. HOA is reported at approximately $550 a year, and rental restrictions are reported as no. For buyers looking for a 4 bedroom 2 bathroom home in Winter Haven, a gated neighborhood property near Legoland, or a Florida home with pool, fireplace, garage, and room to personalize, 215 Santa Rosa Dr presents a strong opportunity. SOME PHOTOS HAVE BEEN VIRTUALLY EDITED.
Listing is courtesy of: SILVER DOOR REALTY LLC (954-993-0696)
Listing Agent: Michelle Paez (954-589-0144)
240 SANTA ROSA DR, WINTER HAVEN, FL 33884
$434,900128 Days on yellowkey MLS ID: L4958092
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2850 Built: 1988Monthly Fee: $46 Tax: $2,790 (2023)Community: Overlook Ests Ph 3Spa: YesSingle Family
Taxes:$2,790
Tax Year: 2023
Remarks: Beautiful 4/2.5 pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
Listing is courtesy of: LIVE FLORIDA REALTY (863-868-8905)
Listing Agent: Brian Surrency (863-204-4298)
4019 CARTERET DR, WINTER HAVEN, FL 33884
$269,99949 Days on yellowkey MLS ID: S5145776
REDUCED by $4,901 (1.8%) on 04/29/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1719 Built: 2006Monthly Fee: $484 Tax: $1,704 (2025)Community: Traditions Ph 01Spa: NoSingle Family
Taxes:$1,704
Remarks: Welcome to this beautifully maintained residence located in the lakefront community of Traditions, one of Winter Haven’s premier 55+ gated communities known for its vibrant lifestyle and exceptional amenities. Fully upgraded with a brand new HVAC system and water heater installed (both in March 2026), an updated roof (November 2023), updated kitchen appliances (2024), refreshed landscaping (2026), newer irrigation controller and bidet (2025), fresh interior paint (December 2025) and exterior paint (2024). This thoughtfully designed 2 bedroom, 2 bathroom home also includes a versatile office that can easily serve as a third bedroom, along with a spacious family room that provides additional living space for relaxing or entertaining. As you arrive, you’re welcomed by a covered and screened front entry. Inside, the open concept floor plan is enhanced by vaulted ceilings and a stylish blend of luxury vinyl flooring in the main living areas and ceramic tile in the kitchen, bathrooms and laundry room, creating both elegance and easy maintenance. The eat in kitchen is bright and inviting, featuring a closet pantry, stainless steel appliances that are just two years old and a comfortable dining space ideal for everyday meals. An interior laundry room is conveniently located just off the kitchen and provides direct access to the two car garage. Sliding glass doors from the living room lead to a screen enclosed patio, offering the perfect spot to unwind, entertain guests, or simply enjoy Florida’s beautiful year round weather. The primary suite serves as a relaxing retreat, highlighted by a tray ceiling, walk in closet and an ensuite bathroom with a double sink vanity and step-in shower. Outside, the property is beautifully framed by mature landscaping, with an attached two car garage, brick paved driveway and walkway that enhance the home’s inviting curb appeal. Residents of Traditions enjoy a true resort style lifestyle, featuring a lakefront clubhouse with a library, fitness center, card room, and billiards, as well as a resort style pool, hot tub and sauna. Additional amenities include tennis and shuffleboard courts, a dog park, a boat ramp and a dock overlooking Ruby Lake, providing endless opportunities for relaxation and recreation. The $484 monthly HOA fee covers lawn care (including bush/tree trimming and mulch replacement), exterior painting, cable, and internet. Ideally located near shopping, dining, and medical facilities with Publix opening soon just down the street, this home offers the perfect combination of comfort, convenience, and an active community lifestyle.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Patricia De Graaff, Llc (863-307-0061)
720 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$300,00063 Days on yellowkey MLS ID: O6386447
3 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1892 Built: 2014Monthly Fee: $38 Tax: $5,040 (2025)Community: Overlook RidgeSpa: NoSingle Family
Taxes:$5,040
Remarks: Under contract-accepting backup offers. Welcome to 720 Overlook Grove Dr in beautiful Winter Haven! This move-in ready home has just received a fresh interior and exterior paint update, giving it a clean, modern feel throughout. Enjoy peace of mind with a new roof (2023) and numerous upgrades that make this property truly stand out. The updated kitchen features modern finishes, refreshed cabinetry, and upgraded countertops—perfect for everyday living and entertaining alike. Natural light fills the living spaces, creating a warm and inviting atmosphere. Situated on a large lot within the subdivision, the property offers plenty of outdoor space and is completely fenced in for added privacy—ideal for pets, gatherings, or simply relaxing outdoors. Step outside to your patio lanai, the perfect spot for morning coffee or evening unwinding. Located in a rapidly growing area, this community is seeing exciting expansion with new construction homes and grocery stores being built nearby, adding convenience and future value. With easy access to shopping, dining, and major roadways, this home offers the perfect blend of comfort, updates, and prime location. Don’t miss your opportunity to own this beautifully updated property!
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Jenny Nguyen (407-202-2640)
5352 NICKLAUS DR, WINTER HAVEN, FL 33884
$349,90030 Days on yellowkey MLS ID: L4960750
REDUCED by $10,000 (2.8%) on 04/29/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2354 Built: 2007Monthly Fee: $5 Tax: $5,617 (2025)Community: Lake Ashton West Ph 01Single Family
Taxes:$5,617
Remarks: RESORT-STYLE FLORIDA LIVING IN HIGHLY DESIRED LAKE ASHTON! Welcome to your own slice of paradise, where comfort meets connection in one of Central Florida’s most sought-after 55+ communities. This beautifully maintained home offers an easygoing, laid-back lifestyle with soaring ceilings that create an open, breezy feel the moment you walk in—perfect for relaxing or entertaining. At the heart of the home is a fully enclosed and expanded Florida Room, complete with dedicated AC vents, giving you year-round comfort whether you’re enjoying a quiet morning coffee or hosting friends after a day on the course. Thoughtful design continues throughout, including extra-tall closets that provide impressive storage space—keeping everything organized without sacrificing style. BIG-TICKET UPDATE: Enjoy peace of mind with a brand new roof installed on 4/6/2026—a major upgrade already taken care of, with the rest of the home in excellent condition. LIVE THE RESORT LIFE EVERY DAY: Step outside and experience everything that makes Lake Ashton so special: • Health & Wellness: State-of-the-art fitness center, indoor walking track, sauna, plus multiple heated indoor & outdoor pools and spas. • Endless Recreation: Private movie theater, bowling alley, billiards room, and a grand ballroom with live entertainment. • Championship Sports: Two 18-hole golf courses, along with pickleball, tennis, and bocce ball courts. • Dining & Social Scene: Golf cart to the Eagles Nest restaurant, explore 100+ social clubs, or enjoy direct access to Lake Ashton via the community boat ramp. • Peace of Mind: 24-hour manned security and a golf-cart-friendly community. Whether you’re looking for a full-time residence or the perfect seasonal escape, this home delivers the best of Florida living—relaxed, social, and full of opportunity. Homes in this highly desired community don’t last long. Contact your realtor today to schedule your private showing!
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Wes Fleming (863-666-4136)
6040 NAVONA WAY, WINTER HAVEN, FL 33884
$357,999218 Days on yellowkey MLS ID: TB8431485
0 Days Off yellowkey (back on 3/26/2026)
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2470 Built: 2025Monthly Fee: $18 Tax: $8,495 (2025)Community: Villa MarSingle Family
Taxes:$8,495
Elementary School: Pinewood Elem
Remarks: Under Construction. BELOW MARKET INTEREST RATES with use of Sellers Preferred Lender. Stylish spaces, flexible floor plans, and all the modern amenities—this home is built for your vibe. With quartz countertops throughout, stainless-steel appliances and a smart thermostat for energy efficient climate control, this home is sure to check all your boxes. The front door opens to luxury vinyl plank flooring and soaring ceilings that flows seamlessly to the main living areas. Off the foyer is a secluded in-law suite, providing privacy and comfort for family or visitors. The sliding glass doors off the kitchen offer an easy escape to the Florida sunshine. The second floor features the additional bedrooms, a laundry room equipped with new washer and dryer, and a large bonus room for efficient family living. The owner's suite is a true retreat, featuring a walk-in shower, a spacious walk-in closet and a double vanity. With 5-bedrooms, 3-bathrooms, and a 2-car garage, the Indigo is the perfect home for growing families or those who enjoy entertaining. Contact or make an appointment for more details on interest rates. Just off US-27 with quick access to I-17, Villa Mar puts you close to local hotspots, and everything that makes Central Florida shine. Discover Winter Haven’s Chain of Lakes, explore the historic downtown district, or enjoy a fun-filled day with the family at LEGOLAND® Florida Resort. At Villa Mar, you’ll enjoy a fresh approach to relaxed living, with everyday essentials and local favorites right around the corner. Images shown are for illustrative purposes only and may differ from actual home. Completion date subject to change. Contact or make an appointment for more details on interest rates.
Listing is courtesy of: CASA FRESCA REALTY (813-343-4383)
Listing Agent: Michael Human (813-343-4383)
1059 MICHELANGELO LN, WINTER HAVEN, FL 33884
$365,00093 Days on yellowkey MLS ID: S5142551
REDUCED by $4,000 (1.1%) on 04/29/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1844 Built: 2024Monthly Fee: $55 Tax: $3,878 (2025)Community: Estates/Lk FlorenceSpa: NoSingle Family
Taxes:$3,878
Remarks: YOU'RE INVITED! DONUTS & DEALS! This is the house you donut want to miss! Motivated Sellers! Welcome home to this immaculate 4 bedroom / 2 bathroom / 2 car garage home in Winter Haven! Shows like a model! GREAT OPEN FLOORPLAN with lots of living space, this home was BUILT IN 2024 and has plenty of features throughout. The home has tiled flooring throughout the main living areas and a huge great room, perfect for entertaining! The kitchen features a spacious center island, granite countertops, stainless steel appliances, tiled backsplash, and plenty of cabinetry space. There are 4 spacious bedrooms. The owner's suite boasts an en suite bathroom with dual sinks. The backyard is generously sized and is FULLY FENCED! Other features back here include a screened patio and a shed. Lots of upgrades!
Listing is courtesy of: RIGHT TRACK REALTY (953-437-4747)
Listing Agent: Phyllis Haigler (804-641-9763)
20 BREVARD DR SE, WINTER HAVEN, FL 33884
$515,0008 Days on yellowkey MLS ID: L4961284
0 Days Off yellowkey (back on 4/29/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2340 Built: 1976 Tax: $2,154 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$2,154
Remarks: Under contract-accepting backup offers. Private tri-level pool home on a quiet dead-end street—just minutes from the Winter Haven Chain of Lakes and LEGOLAND® Florida Resort. This 4-bedroom, 3.5-bath home is designed for flexibility, privacy, and real Florida living. Situated at the end of a street with no drive-by traffic, this property offers a peaceful setting that’s hard to come by—perfect for those who value space and quiet. One of the biggest advantages here is the tri-level layout, featuring a separate downstairs bedroom and full bathroom—ideal for guests, multi-generational living, or even a private office setup with its own space away from the main living areas. Out back, you’ll find a screen-enclosed pool and expansive patio, built for year-round enjoyment and entertaining. The large, fully fenced yard adds another layer of privacy and gives you room to spread out without feeling boxed in. And here’s where this one separates itself—there’s plenty of room for RV or boat parking with coverage, making it a rare find for buyers needing space for larger vehicles or recreational toys. Inside, the home offers a comfortable flow with multiple living areas, a spacious primary suite, and well-sized secondary bedrooms—giving everyone their own space while still feeling connected. Highlights: 4 Bedrooms | 3.5 Bathrooms Tri-level layout with private downstairs bedroom & full bath Dead-end street – no through traffic Screen-enclosed pool with large outdoor living area Fully fenced yard with strong privacy Covered parking for RV, boat, or extra vehicles Close to Chain of Lakes, boat ramps, and LEGOLAND® If you’re looking for a home that offers privacy, flexibility, and outdoor living—while still being close to everything—this one delivers. Call for your very own private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Don Jerue (863-259-9550)
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