Location: Winter Haven
Do Not Show Listings
1290 N LAKE SHIPP DR N, WINTER HAVEN, FL 33880
$795,00013 Days on yellowkey MLS ID: L4961193
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2001 Built: 2021 Tax: $7,094 (2025)Community: N/ASingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,094
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Welcome to true lakefront living on the renowned Chain of Lakes in Winter Haven, perfectly positioned on Lake Shipp with approximately 500 feet of waterfrontage, an extremely rare offering that creates the feel of your own private park right in your backyard. Built in 2021 with block-on-slab construction and a durable metal roof, this 3-bedroom, 3-bathroom home was designed to maximize water views and effortless indoor-outdoor living. Inside, you’ll find soaring ceilings and an open layout that flows seamlessly into the kitchen, featuring 42-inch cabinetry, quartz countertops, a large island, pantry, and a dine-in area—ideal for entertaining or everyday living. Large 8-foot sliding glass doors open out to a fully screened lanai that spans the entire width of the living area, creating a true extension of the home and the perfect place to relax while overlooking the water. The split floor plan offers privacy, with a spacious primary suite positioned to capture lake views, complete with a large walk-in closet and a spa-style en-suite bathroom featuring double vanities and a walk-in shower. One of the additional bedrooms also features its own en-suite bathroom, creating a secondary primary suite—ideal for guests or multi-generational living. The remaining bedroom is well-sized and positioned for convenience. Step outside and embrace the lifestyle this property was built for. With your own private dock, you can moor your boat and enjoy direct access to the Chain of Lakes. Cruise across to local favorites like Harborside Restaurant and take in some of the best sunsets Central Florida has to offer. Additional features include plantation shutters on the front of the home, a spacious indoor laundry room, a detached storage shed, and a rare drive-through 3-car garage with access from the front all the way to the backyard—perfect for boats, trailers, or additional vehicles. With no HOA and close proximity to downtown Winter Haven, this property delivers a unique combination of space, convenience, and true waterfront living. This is more than just a home—it’s a rare opportunity to own a standout piece of lakefront property on the Chain.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
780 OVERLOOK GROVE DR, WINTER HAVEN, FL 33884
$302,5001 Day 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
$475,000304 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
Tax Year: 2024
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)
6103 GREY HERON DR, WINTER HAVEN, FL 33881
$305,000Listed 04/30/2026 8:59AM MLS ID: O6403532
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1828 Built: 2018Monthly Fee: $9 Tax: $5,214 (2025)Community: Lakeside Landings Ph 01Single Family
Taxes:$5,214
Remarks: Welcome to this beautifully maintained 4-bedroom, 2-bathroom home located at 6103 Grey Heron Dr in the desirable Winter Haven community, offering 1,828 square feet of living space with a spacious and comfortable layout, bright open interiors filled with natural light, a 2-car garage with an extended driveway, a well-kept lawn, and excellent curb appeal, perfectly suited for both homeowners and investors, ideally situated just minutes from shopping, dining, and schools with easy access to major roads and nearby attractions, all within a quiet and welcoming neighborhood, with more pictures to follow.
Listing is courtesy of: BROKER HUB REALTY GROUP LLC (219-730-8364)
Listing Agent: Katherine Suero (407-346-4601)
2 CASARENA CT, WINTER HAVEN, FL 33881
$320,00093 Days on yellowkey MLS ID: L4958770
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2377 Built: 1983Monthly Fee: $310 Tax: $5,755 (2025)Community: Casarena On LakesSingle Family
Taxes:$5,755
Remarks: **RECENTLY REDUCED AND PRICED TO SELL** Welcome to this spacious 3 bedroom, 3 bath townhouse located in the private, gated, lakefront community of Casarena on the Lakes. Situated on the Winter Haven Chain of Lakes with a desirable south-facing view of Lake Cannon, this home offers the rare opportunity to enjoy both sunrise and sunset views right from your own space. Three-bedroom properties in this community are seldom available. This would make a PERFECT winter retreat! Boasting over 2,300 square feet of living space, the home provides plenty of room to live comfortably. The second level features two primary suites. One includes a private balcony with beautiful lake views, perfect for morning coffee or winding down in the evening. That same suite also offers an oversized walk-in shower with a built-in steam sauna, creating a relaxing, spa-like retreat at home. The third bedroom is located on the main level and works perfectly for guests or a home office. The kitchen has been thoughtfully updated with high-end stainless steel appliances, granite countertops, and solid wood cabinetry. It opens to the dining area and main living space, which are separated by a striking stone fireplace, making the layout ideal for both everyday living and entertaining. Parking is a standout feature with a two-car garage PLUS an additional parking space, providing room for three vehicles. Community amenities include a pool, tennis court, and a newly rebuilt composite dock with boat slips available on a first-come basis. Leave your boat in the water so you’re always ready for early-morning fishing, evening cruises, or a spur-of-the-moment dinner at one of the Chain’s waterfront restaurants. Additional updates to this home include two new A/C units, a WHOLE-HOUSE GENERATOR, and a tankless water heater, offering comfort and peace of mind year-round. This home delivers space, thoughtful upgrades, and true lakefront living in a secure, well-kept community.
Listing is courtesy of: BERRY REALTY & APPRAISAL SERVICES PA (863-224-6857)
Listing Agent: Kylie Berry (863-224-6857)
120 MIRROR LN NW, WINTER HAVEN, FL 33881
$995,0001 Day on yellowkey MLS ID: L4961404
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3973 Built: 1984 Tax: $7,496 (2025)Community: The ShoresSpa: YesSingle Family
Taxes:$7,496
Remarks: Experience refined lakefront living on the iconic Winter Haven Chain of Lakes, perfectly situated on the coveted shores of Lake Mirror—one of the most picturesque and desirable lakes in the chain. Known for its tranquility, stunning estate homes, and seamless access to the full chain, Lake Mirror offers a rare combination of privacy, beauty, and true waterfront lifestyle. This impeccably maintained 4-bedroom, 3.5-bath residence is a showcase of timeless architecture and elevated design, where every space has been thoughtfully curated to maximize comfort, light, and connection to the outdoors. From the moment you enter, you’re met with expansive living areas, soaring ceilings, and walls of French doors that line the back of the home, flooding the interior with natural light and creating a seamless transition to the outdoor living spaces. These multiple sets of French doors not only enhance the home’s elegance, but also provide direct access from several rooms to the patio, pool, and lakefront setting, blurring the line between indoor and outdoor living in the most effortless way. The outdoor experience is nothing short of exceptional. A resort-style screened pool and spa overlook the water, framed by peaceful lake views and designed for both quiet relaxation and unforgettable entertaining. Whether hosting guests, enjoying a sunset swim, or simply unwinding after a long day, this space delivers a level of serenity that is hard to replicate. Step beyond to your private dock and embrace everything the Chain of Lakes lifestyle has—boating to dinner, skiing across open water, fishing at sunrise, and cruising through one of Central Florida’s most connected and sought-after lake systems. Additional highlights include a brand-new seamless metal roof in 2025, an expansive 3-car garage, and meticulous pride of ownership throughout, ensuring both beauty and peace of mind. This is a rare opportunity to own a home where luxury, lifestyle, and location come together effortlessly—a true lakefront retreat in the heart of Winter Haven.
Listing is courtesy of: THE MARKET REALTY COMPANY (863-999-4643)
Listing Agent: Brock Jennings (863-990-5846)
961 DREXEL AVE NE, WINTER HAVEN, FL 33881
$315,00066 Days on yellowkey MLS ID: L4959592
REDUCED by $5,000 (1.6%) on 04/19/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1856 Built: 1948 Tax: $3,409 (2025)Community: Anna MarSingle Family
Taxes:$3,409
Elementary School: Inwood Elem
High School: Winter Haven Senior
Middle School: Westwood Middle
Remarks: ***PRICE DECREASE +++ SELLER IS OFFERING $5000 in seller concessions!!! This unique 2-story home in Winter Haven is full of character and charm, located just three houses down from scenic Lake Elbert. Thoughtfully updated while preserving its warm, rustic appeal, this property offers a welcoming atmosphere from the moment you arrive. Outdoor enthusiasts will love the 2.4-mile paved loop trail surrounding Lake Elbert, complete with boardwalks and beautiful landscaping—perfect for morning walks, bike rides, or peaceful evening strolls. The home is in walking distance to Downtown Winter Haven, the public boat ramp and park, and Polk State College’s Winter Haven Fine Arts Building, offering exceptional convenience and lifestyle amenities. Inside, you’ll find live-edge wood countertops, natural wood trim, and an open kitchen overlooking the family and dining rooms. The kitchen features stainless steel appliances, newer cabinets, and a rustic flair originally crafted by an Amish family. The spacious family room includes a large picture windows that frame the beautiful front yard and mature oak tree. The primary bedroom and bathroom are conveniently located downstairs, while the second floor offers two additional bedrooms, a bonus room, a full bathroom, and a loft area with generous storage closets. Both bathrooms have been updated with newer cabinets, newer countertops, and newer tile. Additional interior upgrades include newer luxury vinyl plank flooring, newer windows, newer light fixtures and ceiling fans, and fresh interior paint. The home also features a newer A/C system. Outside, the home offers a covered front porch perfect for evening relaxation, mature landscaping, and a fenced yard on nearly a quarter-acre, with most of the outdoor space located in the front of the home. Ideally situated near Lake Elbert, Downtown Winter Haven, Polk State College, shopping, dining, parks, and medical facilities, this home offers both convenience and character. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY SMART (863-577-1234)
Listing Agent: Lisa Ford (863-510-3890)
116 MANDOLIN DR, WINTER HAVEN, FL 33884
$370,0001 Day 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
Middle School: Denison Middle
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)
316 LAKE SMART CIR, WINTER HAVEN, FL 33881
$289,9001 Day on yellowkey MLS ID: L4961472
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1500 Built: 2022Monthly Fee: $50 Tax: $4,224 (2025)Community: Lake Smart PointeSingle Family
Taxes:$4,224
Elementary School: Lake Alfred Elem
Remarks: This property is eligible under the 30 Day Freddie Mac First Look Initiative through 05/28/2026. OWNER OCCUPIED BUYERS and NSP offers will only be considered the first 30 days from initial MLS input date. Investors are encouraged to make an offer and will be considered after the First Look Initiative period has expired. Buyer pays Doc Stamps on deed.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Barry Macchione (863-604-7455)
811 22ND ST NW, WINTER HAVEN, FL 33881
$269,9901 Day on yellowkey MLS ID: S5148769
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1408 Built: 1953 Tax: $4,020 (2025)Community: Hutton RepSingle Family
Taxes:$4,020
Remarks: Welcome to this charming 3-bedroom, 3-full-bath home nestled in the heart of Winter Haven! One of the bedrooms features a private entrance, making it perfect as an IN-LAW SUITE, home office/studio, or an income-producing rental opportunity. The spacious Florida room with screen enclosure is ideal for relaxing and entertaining, while the front screened porch adds extra curb appeal and a cozy outdoor living space. The generous backyard offers endless possibilities — plenty of room to add a pool, create your dream outdoor oasis, or simply enjoy the open space. A storage shed in the back provides additional convenience. No HOA, No CDD, low taxes, public water and sewer. Located just minutes from Downtown Winter Haven, shopping, restaurants, and the beautiful Winter Haven Chain of Lakes. This home has so much to offer, don't miss this opportunity!Equal opportunity housing.
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Romina Peragine, Pllc (407-288-4595)
554 EAGLE LANDING BLVD, WINTER HAVEN, FL 33880
$312,0001 Day on yellowkey MLS ID: O6402516
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1628 Built: 2021Monthly Fee: $38 Tax: $3,739 (2025)Community: Eagle Lndg Ph ISingle Family
Taxes:$3,739
Remarks: Welcome to modern comfort in the heart of Winter Haven! This meticulously maintained 4-bedroom, 2-bathroom home offers 1,628 sq. ft. of move-in-ready living space. The residence features a bright, open-concept floor plan with a seamless flow between the kitchen and living areas, complemented by durable tile and carpet flooring. Enjoy outside living in your private fenced in backyard or sit on the enclosed patio and enjoy the outdoors.
Listing is courtesy of: SPANN & ASSOCIATES REAL ESTATE (407-468-7512)
Listing Agent: Kal Scarvers (863-617-5236)
3904 WARBLER DR, WINTER HAVEN, FL 33880
$259,99934 Days on yellowkey MLS ID: O6394168
REDUCED by $5,001 (1.9%) on 04/30/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1396 Built: 2006Monthly Fee: $12 Tax: $1,241 (2025)Community: Queens Cove Ph 04Single Family
Taxes:$1,241
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully fully remodeled home, where modern design meets everyday comfort. Featuring a brand-new roof, this property offers peace of mind and long-term value from the moment you arrive. Step inside to discover stunning modern bathrooms thoughtfully updated with sleek finishes and contemporary style. The heart of the home is the open-concept kitchen, designed to impress with elegant wood cabinetry, convenient soft-close features, luxurious quartz countertops, and a full suite of stainless steel appliances—perfect for both daily living and entertaining. With its seamless layout and high-quality upgrades throughout, this move-in-ready home is ideal for buyers seeking style, functionality, and worry-free living.
Listing is courtesy of: FUTURE HOME REALTY INC (800-921-1330)
Listing Agent: Constantin Florean (407-953-7810)
542 EAGLE LANDING BOULEVARD, WINTER HAVEN, FL 33880
$290,00024 Days on yellowkey MLS ID: L4960889
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1292 Built: 2021Monthly Fee: $38 Tax: $3,061 (2025)Community: Eagle Landing Phase ISingle Family
Taxes:$3,061
Remarks: Welcome to the Eagle Landing community in Winter Haven, FL. This well-maintained single-family home is move-in ready and waiting for its new owner(s). The open-floor concept creates a comfortable flow throughout the main living areas, while the split floor plan provides added privacy for the primary bedroom and bath with spacious walk-in closet. The kitchen features stainless steel appliances and granite countertops, offering both style and functionality. Additional conveniences include a laundry room, two car garage and low HOA dues, making this home an affordable and practical choice. Experience the charm of small-town living while enjoying the growth and expansion happening throughout Winter Haven. Conveniently located just minutes from Legoland, shopping, dining, and entertainment, and centrally positioned between Tampa and Orlando for easy travel in either direction. Solar panels will be paid off at closing, providing the new owner with the benefit of low electricity bills. The spacious backyard offers room to relax or entertain.
Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)
Listing Agent: Carla Miro (786-897-4081)
874 BUCCANEER BLVD, WINTER HAVEN, FL 33880
$289,900146 Days on yellowkey MLS ID: P4937137
1 Days Off yellowkey (back on 4/29/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1429 Built: 2014Monthly Fee: $68 Tax: $1,888 (2024)Community: Shores At Lake SearsSingle Family
Taxes:$1,888
Remarks: Under contract-accepting backup offers. List Price: $289,999 Property Address: 874 Buccaneer Blvd, Winter Haven, FL 33880 Property Type: Single-Family Residence Bedrooms: 3 Bathrooms: 2 Square Feet (Heated): 1,482 (verify per county records) Lot Size: 5,488 sq ft (approx. 0.13 acres) Year Built: 2014 Subdivision / Community: Buccaneer / Winter Haven Garage: 2-Car Garage (verify) Exterior Construction: Block / Stucco Roof: Shingle Cooling / Heating: Central Air / Electric Water / Sewer: Public County: Polk ? ?? Public Remarks (MLS Ready — ~950 characters) Move-in ready 3-bedroom, 2-bath home in a desirable Winter Haven neighborhood! Built in 2014, this charming single-story residence offers an open floor plan with bright natural light, spacious living and dining areas, and a well-appointed kitchen with ample cabinet space. The primary suite features a private bath and generous closet storage. Enjoy relaxing evenings in the fenced backyard, perfect for pets, gardening, or entertaining. Conveniently located near schools, shopping, and major highways for easy commuting. Well-maintained and ready for its next owner! Sellers are highly motivated—come see this beautiful home and make an offer today!
Listing Agent: Alisa Cotton (863-205-2820)
716 AVENUE I NE, WINTER HAVEN, FL 33881
$235,00057 Days on yellowkey MLS ID: L4958483
REDUCED by $24,000 (9.3%) on 04/16/2026
Bed: 3 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1559 Built: 1951 Tax: $3,043 (2025)Community: Hutchinson AddSingle Family
Taxes:$3,043
Remarks: Lake Elbert Trail neighborhood, classic mid-century 1950s house with over a 1/4 acre property! Roof: 2023, HVAC: 2023, Water Heater: New, Electric: Panel replaced in 2020 and needs significant electrical updating and is priced accordingly. Plumbing: Re-piped in 2025. The potential for this house is real and it is ready for the right person to personalize it and make this house a home. 3/1.5 home in Winter Haven close to downtown (Target is coming!), the hospital and Polk State College. Huge yard big enough for a pool. Storage shed. New carpet in every bedroom. Pretty bathrooms. Walk the new Lake Elbert Trail right from the house! Schedule a showing today! This property has approximately 1,559 square feet of living space on a lot of approximately 0.28 acres, with three bedrooms, one full bathroom and an en-suite half bathroom. Hardwood-style vinyl flooring and stone fireplace creates a warm and inviting tone. Large windows allow for an tons of soft, natural light to fill the rooms, enhancing the open layout and creating a peaceful setting. The separate dining room area provides space for hosting a dinner or game night. The retro vibe flows throughout the house and fits-in with the established neighborhood. An efficient kitchen features a window overlooking the backyard and makes it convenient to have BBQs and fun playtime out back. The backyard has it's own storage shed and is large enough to have a pet, playground or maybe even a pool. The primary bedroom and two additional bedrooms are on opposite sides for privacy and quiet. The vintage-styled bathrooms add a unique charm to the home. The pink tile sequence makes it fun to get ready for the day. Just steps from the college, the property is conveniently located near the college ballfields, offering easy access to recreational activities. A walking trail nearby provides opportunities for exercise, and the home is situated close to the town, allowing for quick and easy access to local shopping. The garage features a work bench and shelves, providing storage and workspace. The property's proximity to the lake allows for enjoyable walks or leisure activities on the water.
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Maria Deary (863-241-8361)
3865 OSPREY POINTE CIR, WINTER HAVEN, FL 33884
$255,000115 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)
1331 34TH ST NW, WINTER HAVEN, FL 33881
$199,99984 Days on yellowkey MLS ID: L4959219
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $10,001 (4.8%) on 04/23/2026
Bed: 2 Bath: 1.0 Gar: 10 Liv Area Sq Ft: 1220 Built: 1954 Tax: $3,823 (2025)Community: InwoodSingle Family
Taxes:$3,823
Remarks: Welcome to 1331 34th St NW in Winter Haven, a property offering exceptional potential and versatility This home is ideal for buyers ready to bring their vision and personal updates, offering the opportunity to build instant equity through thoughtful improvements. In addition to the existing layout, the home features a dedicated office space that, with the addition of a closet, could easily function as a third bedroom, providing added flexibility for growing households, guests, or work-from-home needs. The true show-stopping feature is the MASSIVE EXTENDED GARAGE SPACE, OVER 2000SQFT! capable of accommodating up to 12 vehicles. Whether you are a car collector, small business owner, hobbyist, or someone in need of large-scale storage or workshop space, this structure provides flexibility that is rarely found in residential properties. With the right touch, this property can become a highly functional residence paired with unmatched utility space. Beyond the property itself, Winter Haven offers a strong blend of lifestyle, education, and recreation. The area is home to Polk State College’s Winter Haven campus, providing accessible higher education within the city, while larger universities such as Florida Polytechnic University, Southeastern University, Florida Southern College, and Warner University are all located within roughly a 15-mile radius, supporting a strong educational and workforce presence in the region. This proximity to multiple colleges and universities helps support steady housing demand, local employment opportunities, and long-term community growth. Winter Haven is widely known as the “Chain of Lakes City,” featuring dozens of connected lakes that support boating, fishing, kayaking, and waterfront recreation. The city also offers major attractions including LEGOLAND Florida Resort and the Peppa Pig Theme Park, making it a destination for both tourism and family entertainment. Downtown Winter Haven adds to the lifestyle appeal with locally owned boutiques, antique shops, a year-round farmers market, and historic cultural venues that help maintain the city’s small-town charm while still offering modern conveniences. For buyers looking for a property with unique functionality, strong surrounding amenities, and long-term upside potential, 1331 34th St NW represents a rare opportunity. With renovation potential inside and extraordinary garage and workspace capacity outside, this property is ready to be transformed into something truly special while being positioned in one of Polk County’s most lifestyle-rich communities.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Andrew Fearn (863-812-1755)
643 GROVE ST, WINTER HAVEN, FL 33881
$340,00087 Days on yellowkey MLS ID: O6379127
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1853 Built: 2022Monthly Fee: $50 Tax: $5,200 (2024)Community: Inman GrovesSingle Family
Taxes:$5,200
Elementary School: Elbert Elem
Remarks: Rare opportunity! Exceptional home with 4 bedrooms, 2 baths, and 2-car attached garage. Open-concept living with quarz kitchen, center island, and ceramic tile floors. Primary suite with walk-in closet and en-suite bath. Features include covered screened lanai, fully fenced yard, gutters, irrigation, and inside laundry. Desirable location, this home won’t last!
Listing is courtesy of: MIHOUSE REALTY LLC (407-286-2690)
Listing Agent: Martha Leighton, Pa (407-223-7767)
5351 MICKEY AVE, WINTER HAVEN, FL 33884
$299,999161 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
$314,999337 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!
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