Displaying: For Sale
Location: Winter Haven
Property Type(s): Single Family
Beds: 2 to 2
Do Not Show Listings
Winter Haven - 60 properties found
428 GLENEAGLES CT, WINTER HAVEN, FL 33884
$289,000103 Days on yellowkey MLS ID: L4960230
1 Days Off yellowkey (back on 6/4/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1621 Built: 1979Monthly Fee: $129 Tax: $1,717 (2025)Community: Cypresswood Patio HomesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,717
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Now is your chance! Come and be a part of this active, Golf Course community and live in this beautifully maintained, updated home. Enjoy the peaceful screened courtyard with your cup of coffee, or watch the gorgeous Florida sunsets. The inside of the home has been lovingly kept up and updated. You won't want for space in this well thought out layout. Plenty of room for entertaining, or a quiet read alone. The garage has been set up for your perfect workspace or storage, whatever suits your needs. You have unlimited options with the screen garage door and a mini split that keeps everything cool when you need it! This golf course community is gated with a guard 24/7. Even if you don't golf, there will be something for you to do. Jr Olympic size pool, tennis courts, soon to be pickleball courts and a full service clubhouse with live music every weekend. Enjoy peace of mind knowing that the AC is less than a year old and the roof was replaced in 2022! Schedule your viewing today and welcome home!
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Stacy Tuttle (863-602-9554)
940 OLEANDER DR SE, WINTER HAVEN, FL 33880
$250,000159 Days on yellowkey MLS ID: S5141917
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1527 Built: 1958 Tax: $3,326 (2025)Community: Cooper EstatesSingle Family
Taxes:$3,326
Remarks: Auction Property. Ranch-style home offering 2 bedrooms and 1.5 bathrooms with a spacious living room and a good-sized yard. Features include a durable metal roof, RV electrical hookups, and a chicken coop. Some updates in the kitchen. Short Sale subject to lender approval.
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: David Hartigan (407-955-1156)
441 SAN JOSE DR, WINTER HAVEN, FL 33884
$275,000411 Days on yellowkey MLS ID: P4934776
REDUCED by $10,000 (3.5%) on 04/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1843 Built: 1984Monthly Fee: $5 Tax: $1,000 (2024)Community: Orchid Springs Patio HomesSpa: NoSingle Family
Taxes:$1,000
Tax Year: 2024
Remarks: Welcome to this exceptional 2-bedroom, 2-bathroom patio home nestled within the highly sought after Orchid Springs community. Positioned on an expansive double lot, this residence offers a serene & secluded wooded vista visible from the open kitchen and the generously proportioned screened patio. Noteworthy exteri9or features; Paved drive and walkways, attractive canopies and covered front porch invites you inside to discover a charming home. The kitchen boasts custom pantry space, ample counter area & is thoughtfully designed for hosting guests without compromising meal preparation. Beyond the kitchen, the spacious living room, flex apace is adjacent to a second private patio. The large family room offers expansive sliding doors and windows making the perfect space for relaxation. Leading to a beautiful lanai ideal for sharing a glass of wine or enjoying a barbeque, with its scenic outlook. The dining room is designed for casual or formal entertainment. The master bedroom features an ensuite bath and picturesque views while additional bedrooms and guest bathroom complete the layout. Flooring; Tiled foyer, kitchen and bathrooms with plush carpet in the master bedroom as well as the second bedroom, living and dining rooms. Designed with single level living in mind this Orchid Springs Patio Home offers ease of mobility and low maintenance. Stop outside to the spacious outdoor area enveloped by lush trees providing privacy and a natural ambiance. Additional amenities include a spacious 2 car garage with natural gas water heater & washer & dryer. Roof will be replaced before closing. Conveniently located in SE Winter Haven, this central Florida home provides easy access to downtown, Chain of Lakes boat launches, LegoLand, and major highways. The neighborhood also features a community clubhouse and pool, enhancing the overall Florida lifestyle experience.
Listing is courtesy of: NEXTHOME NORRIS & COMPANY REALTY (863-875-5583)
Listing Agent: Michael Norris (863-287-3105)
221 AVENUE F SE, WINTER HAVEN, FL 33880
$185,00076 Days on yellowkey MLS ID: L4960995
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 804 Built: 1948 Tax: $1,272 (2025)Community: Berry J B SubSingle Family
Taxes:$1,272
Remarks: Back on market! Cute as a button, historic charm with some nice updates. From the welcoming front porch to the massive fenced back yard, complete with dog washing station, this is a cozy spot to call home! Love the original hardwood floors, open bright kitchen, and character such as built ins. Roof is less than 10 years old, and the sellers have updated the HVAC including adding a mini split to the main bedroom for those who like it extra cold at night. Plenty of parking and extra storage outside as well...check this one before it gets away!
Listing is courtesy of: HARPER REALTY FL, LLC (863-687-8020)
Listing Agent: Paula Shields (863-581-1498)
5352 NICKLAUS DR, WINTER HAVEN, FL 33884
$319,90084 Days on yellowkey MLS ID: L4960750
1 Days Off yellowkey (back on 6/1/2026)
REDUCED by $10,000 (3.0%) on 05/21/2026
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)
769 AVENUE Q SE, WINTER HAVEN, FL 33880
$199,500116 Days on yellowkey MLS ID: L4959823
0 Days Off yellowkey (back on 6/1/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 960 Built: 1969Monthly Fee: $110 Tax: $1,783 (2025)Community: Parkland VillageSingle Family
Taxes:$1,783
Remarks: Under contract-accepting backup offers. Welcome home to this beautifully renovated 2-bedroom, 1.5-bath condo nestled in a peaceful 55+ community in the heart of Winter Haven. Completely move-in ready, this charming residence has been thoughtfully upgraded from top to bottom with over $50,000 in modern improvements designed for comfort, style, and easy living. Step inside to discover brand-new luxury vinyl plank flooring, a stunning fully remodeled kitchen featuring new appliances and sleek finishes, beautifully refreshed bathrooms, fresh interior and exterior paint, and a brand-new roof completed in 2025. Energy efficiency meets peace of mind with new double-pane windows backed by a lifetime warranty, new gutters, a recently serviced AC unit, and the added convenience of a covered carport. Imagine hosting friends in your stylish kitchen, savoring quiet mornings with coffee in the sun-filled living space, or enjoying relaxing afternoons in your private backyard — perfect for gardening, unwinding, or spending time with your furry companion. Perfectly positioned near everyday conveniences like Walmart and Publix, plus local shops and dining, this location truly puts everything within reach. Spend weekends exploring nearby favorites such as LEGOLAND Florida Resort, the historic Cypress Gardens, or enjoying craft brews at Port 27 Brewery. Outdoor enthusiasts will appreciate close proximity to scenic parks, golf courses, and the beautiful Winter Haven Chain of Lakes — ideal for waterfront dining, boating, and year-round recreation. Plus, exciting day trips and fine dining await within easy driving distance of Orlando and Tampa. Whether you’re searching for a seasonal retreat or a full-time residence, this home delivers the perfect blend of low-maintenance living, modern upgrades, and Central Florida charm. Schedule your private showing today and discover resort-style living at its finest!
Listing is courtesy of: CENTURY 21 MYERS REALTY (863-875-5656)
Listing Agent: Tony Acosta (863-224-5956)
2014 10TH ST NW, WINTER HAVEN, FL 33881
$215,000160 Days on yellowkey MLS ID: O6374317
2 Days Off yellowkey (back on 5/31/2026)
REDUCED by $5,000 (2.3%) on 05/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1229 Built: 1953 Tax: $2,753 (2024)Community: Villa ManorSingle Family
Taxes:$2,753
Elementary School: Frank E. Brigham Academy
High School: Winter Haven Senior
Remarks: One or more photo(s) has been virtually staged. Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara white quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. Roof 2020 - - Repipe 2025 - The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants, this home is perfect for first-time buyers, downsizers, or investors seeking turnkey potential.
Listing is courtesy of: KELLER WILLIAMS LEGACY REALTY (407-855-2222)
Listing Agent: Daniel Araque (321-276-0747)
277 MARIPOSA, WINTER HAVEN, FL 33884
$215,00061 Days on yellowkey MLS ID: L4961311
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1142 Built: 1977Monthly Fee: $5 Tax: $2,118 (2025)Community: Florida Highland CoSingle Family
Taxes:$2,118
Elementary School: Elbert Elem
Middle School: Denison Middle
Remarks: Welcome to this charming 2 bedroom, 2 bathroom home in Orchid Springs, a non–age-restricted community where all ages are welcome, located in SE Winter Haven. Thoughtfully updated, this home features new wood plank tile flooring. The open floor plan is highlighted by a spacious and light-filled great room with vaulted ceilings creating a warm and inviting space ideal for everyday living. Just off the great room is a beautiful atrium to fill with your favorite plants or enjoy the evenings outside in your private sanctuary. The primary suite includes built-in closets, sliding glass door open to the back courtyard and an en-suite bathroom with updated wood plank tile flooring, updated vanity and mirror the secondary bedroom is generously sized and located next to the guest bathroom, which features updated vanity and tile flooring. Additional highlights include a one-car garage with laundry area Outdoors, enjoy a paver patio courtyard ideal for BBQs and entertaining. There are plenty of private outdoor spaces for relaxing there is are front and rear screened porches as well as the outdoor courtyard. Orchid Springs is a well-established community offering a swimming pool and clubhouse, with lawn maintenance and amenities included for a low monthly fee. Conveniently located within minutes of shopping, dining, medical facilities, and LEGOLAND® Florida, and centrally positioned between Tampa and Orlando for easy access to theme parks and international airports. Call today to schedule your private showing.
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Anita Lowe (863-269-6461)
4130 BEDFORD AVE, WINTER HAVEN, FL 33884
$309,90032 Days on yellowkey MLS ID: L4962090
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1819 Built: 2006Monthly Fee: $485 Tax: $1,268 (2025)Community: Traditions Ph 01Single Family
Taxes:$1,268
Remarks: WELCOME TO CAREFREE LIVING WITH THIS WELL-MAINTAINED RESIDENCE WITHIN THE DESIRABLE 55+ GATED, LAKEFRONT COMMUNITY AT "TRADITIONS OF RUBY LAKE". This home is MOVE IN READY and is situated withing very close proximity to the clubhouse and Lake Ruby!!! NEW ROOF and NEW HOT WATER HEATER both installed in 2023. With nearly (1,820 Sqft.) of heated and cooled space, this OPEN-CONCEPT SPLIT PLAN with SOARING CEILINGS will not disappoint. There is plenty of room for the chef in the family with your OVERSIZED KITCHEN that has an ABUNDANCE of cabinetry and GRANITE COUNTERTOPS! The kitchen also has 2 windows, giving you a pleasant view along with plenty of extra natural light. Just off the kitchen sits the great room leading into 2 bedrooms and another room (11 x 10) that would be perfect for an office, craft room, or out of town guests. You'll love the (21 x 9) BONUS ROOM that has its own AC and gives you so much extra cooled living space. As if this wasn't enough, the bonus room also overlooks a (21 x 9) SCREENED, PAVERED PATIO for outside grilling or just relaxing. The large primary en-suite has a WALK-IN-SHOWER WITH BUILT-IN BENCH and GLASS SLIDERS, DUAL SINKS, and OVERSIZED WALK-IN-CLOSET. You have direct access to the bonus room from the primary bedroom. Cleaning is a breeze in this home featuring NO CARPET!!! The clubhouse is beautiful and boasts amazing views beyond the pool of 2 lakes (Ruby and Bess). The clubhouse also features an oversized pool and spa, dock, boat ramp, boat slips, tennis courts, pickle ball, basketball, shuffleboard, ball room, billiards, library, craft room, fitness center, dog park and much more! Golf carts are allowed in the community for ease of navigating. Traditions is centrally located in close proximity to medical, shopping, restaurants, 2 major international airports (Tampa/Orlando) and the up and coming airline Avelo in Lakeland, FL. LEGOLAND, FL is just minutes away!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Bryan Dicks (863-287-7851)
5024 PEBBLE BEACH BLVD, WINTER HAVEN, FL 33884
$299,90039 Days on yellowkey MLS ID: P4938726
0 Days Off yellowkey (back on 5/19/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1784 Built: 2007Monthly Fee: $5 Tax: $3,423 (2025)Community: Lake Ashton West Ph ISingle Family
Taxes:$3,423
Remarks: Welcome to your personal haven in Lake Ashton—Central Florida’s premier 55+ active-adult community. This beautifully maintained 2-bedroom, 2-bath home offers 1,805 square feet of thoughtfully designed living space, and the CDD DEBT IS FULLY PAID. The home feels bright, crisp, and truly move-in ready with all home furnishings, the golf cart and charger conveying with purchase. Most important, the home sits on a private lot that backs up to a large seasonal pond with nature preserve beyond, providing beautiful and relaxing views of nature from the Florida room. The home’s curb appeal shines with quoin accents, lush landscaping, and elegant double entry doors with glass inserts, all complemented by a screened front entry for added comfort. Inside, the kitchen is a delight with a granite countertop, 42” cabinets and updated stainless appliances. The spacious open layout flows across wood laminate flooring in the living area and both bedrooms. A pocket door enhances privacy in the guest suite. The primary bath is a retreat with dual sinks and a large tiled walk-in shower. Perfect for relaxed living and gracious entertaining, the expansive 10’ x 30’ enclosed and air conditioned Florida room features tiled flooring and surrounded by manicured hedges, mature palms, and tasteful plantings. A new roof was installed in 2025, and the included furniture and golf cart make this an effortless move. Life at Lake Ashton is more than a home—it’s a lifestyle. Residents enjoy two 18-hole championship golf courses, a 26,000 sq. ft. clubhouse, a state-of-the-art health and fitness center, indoor and outdoor pools, pickleball courts, a bowling alley, theater, on-site dining, and a vibrant calendar of social events and clubs. Don’t miss this opportunity to make a warm, welcoming, and beautifully appointed home your own. Schedule your private showing today and start living your Florida dream at Lake Ashton.
Listing is courtesy of: GLOBAL LIFESTYLE LLC (727-537-6242)
Listing Agent: Brad Kirwan (863-280-0390)
213 CLEVELAND AVE, WINTER HAVEN, FL 33881
$180,00085 Days on yellowkey MLS ID: P4938281
REDUCED by $10,000 (5.3%) on 05/19/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1949 Tax: $1,588 (2025)Community: Eastwood SubSingle Family
Taxes:$1,588
Remarks: Welcome to this charming 2-bedroom, 1-bath home in the growing city of Winter Haven. Situated on a .16-acre oversized lot, this property offers both comfort and opportunity. The home features a functional layout and a new AC installed in 2024, providing added efficiency and peace of mind. The spacious backyard includes a detached shed with great potential, perfect for a workshop, studio, storage, or a future conversion to fit your needs. Conveniently located just minutes from shopping, dining, and everyday essentials, and close to the new Publix plaza currently under development, this home is perfectly positioned in an area experiencing exciting growth. A great opportunity for homeowners or investors looking to own in one of Winter Haven’s expanding neighborhoods.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Pedro Perez, Jr (863-236-8799)
4040 CARTERET, WINTER HAVEN, FL 33884
$254,00081 Days on yellowkey MLS ID: B4902225
0 Days Off yellowkey (back on 5/18/2026)
REDUCED by $5,000 (1.9%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1599 Built: 2006Monthly Fee: $484 Tax: $1,588 (2024)Community: Traditions Phase 1Single Family
Remarks: Under contract-accepting backup offers. This is a very well maintained home which is priced to sell! The property has many upgrades; a new roof in 21, new AC coil in 25, and newer countertops. It is also located close to the side entrance gate for easy access. No rear neighbors provides for a more serene atmosphere and the north facing rear screened porch is pleasantly shady and backyard has room to be expanded. This is truly Central Florida's retirement living at its best. Located in a master planned community with most exterior maintenance included for easy living and full resort-like amenities. The beautifully maintained on-site managed lakefront community clubhouse offers many opportunities for an active lifestyle. This home is move-in ready.
Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)
Listing Agent: Scott Kline (863-287-0204)
194 S LAKE MARIAM DR, WINTER HAVEN, FL 33884
$400,000127 Days on yellowkey MLS ID: L4959447
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1538 Built: 2000 Tax: $3,770 (2025)Community: Valencia Wood Estates First AddSingle Family
Taxes:$3,770
Remarks: Welcome to this beautifully updated home in desirable Southeast Winter Haven, offering space, privacy, and modern upgrades on a generous half-acre lot. Step inside to vaulted ceilings and rich hardwood flooring that create a warm, open feel. The living room features a gas fireplace with mantle detail, adding character and comfort to the main gathering space. The fully renovated kitchen stands out with stainless steel appliances, granite countertops throughout, updated shaker-style cabinetry, and a sleek glass vent hood for a clean, contemporary finish. The layout flows effortlessly into the dining and living areas, making it ideal for both everyday living and entertaining. The enclosed rear patio is fully incorporated into the heated and cooled square footage, providing additional living space in a controlled climate year-round. From here, you overlook the expansive backyard with mature trees and complete privacy — and with no rear neighbors, that view and buffer will never change. The updated bathroom features a spacious walk-in shower with modern tile accents, granite vanity top, and upgraded lighting for a polished, spa-like feel. Outside, the half-acre homesite offers exceptional flexibility. There is ample room for a future pool, garden, or additional structure, along with space for boat or RV parking. A detached shed provides extra storage. The property backs to natural privacy with no rear neighbors ever, creating a peaceful setting that’s hard to find. Located in a one-way-in, one-way-out area of Southeast Winter Haven, the neighborhood offers limited traffic and added privacy while still being conveniently close to everything. With a little effort, this home could easily be converted into a 3-bedroom layout, adding even more value and flexibility for future owners. If you’re looking for updated interiors, privacy, and room to grow — this one checks boxes that most homes simply don’t.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Don Jerue (863-259-9550)
1108 SAWGRASS DR, WINTER HAVEN, FL 33884
$422,99948 Days on yellowkey MLS ID: S5149437
REDUCED by $2,001 (0.5%) on 05/14/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1533 Built: 2021Monthly Fee: $5 Tax: $9,972 (2025)Community: Lake Ashton West Ph Ii SouthSpa: NoSingle Family
Taxes:$9,972
Remarks: This is a must see charming oasis located behind the secure gates of Lake Ashton, you don’t want to miss this opportunity of becoming an homeowner in this Exclusive 55+ community in Florida, comes with a upgraded custom13’6 x 28’ saltwater pool with propane heater and expanded screened enclosure that measures 44’ x 24’ tankless propane water heater, and gas hookup for an outdoor kitchen in Lake Ashton! If you are seeking a stunning 2-bedroom, 2-bath property this is the one it sits on the Lake Ashton West golf course and this environment for Living certified Green home features several builder upgrades PLUS extensive builder and owner upgrades Inside, you’ll find tile flooring throughout (no carpet), upgraded kitchen cabinetry with roll-out shelving, Calcatta Silestone countertops with beveled edge; custom kitchen pantry cabinet with roll-outs; under-cabinet lighting, custom closets in both bedrooms and laundry room plus a custom pantry storage. Additional features include custom closets, updated bathrooms with a walk-in shower and glass doors, remote-controlled blinds, upgraded lighting and fans, epoxy garage flooring, and enhanced landscaping Located in Lake Ashton, a premier 55+ community offering two 18-hole golf courses, a 26,000 + sq ft Health and Fitness Center, pickleball courts , a bowling alley, a restaurant and much more, activities are abundant in this exceptional community . Don’t miss this very special pool home. Schedule your showing today.
Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)
Listing Agent: Samuel Williams (863-528-0930)
121 BATES AVE SE, WINTER HAVEN, FL 33880
$189,00091 Days on yellowkey MLS ID: OM721475
REDUCED by $10,000 (5.0%) on 05/13/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1080 Built: 1945 Tax: $2,085 (2025)Community: Haven TerraceSingle Family
Taxes:$2,085
Remarks: Located in the heart of downtown Winter Haven, FL, this versatile R-3 zoned property presents an excellent opportunity for homeowners, investors, or those seeking future development potential! This charming residence features 2 bedrooms and 1 full bathroom, offering a functional layout with comfortable living spaces. The home includes a spacious kitchen with ample cabinetry and room for dining, perfect for everyday living or rental use. A dedicated utility room adds convenience and extra storage space. Connected to city water and sewer, this property provides reliable infrastructure and ease of maintenance. The R-3 zoning allows for a variety of potential uses (buyer to verify with city) making this a flexible investment in a growing and desirable downtown location. Enjoy close proximity to local shops, dining, parks, and all that Winter Haven has to offer, including its renowned chain of lakes! Whether you're looking for a primary residence, rental property, or future development opportunity - this property checks all the boxes!
Listing is courtesy of: RE/MAX REALTY PLUS (863-385-0077)
Listing Agent: Emily Jones (863-446-3246)
601 AVENUE U NE, WINTER HAVEN, FL 33881
$200,000320 Days on yellowkey MLS ID: P4935845
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1274 Built: 1959 Tax: $2,161 (2024)Community: Eula Vista SubSingle Family
Taxes:$2,161
Remarks: EXCELLENT INVESTMENT OPPORTUNITY IN THE HEART OF WINTER HAVEN! LOCATED AT 601 AVE U NE, THIS PROPERTY OFFERS INCREDIBLE POTENTIAL FOR RENTAL INCOME OR FUTURE DEVELOPMENT. WITH A SPACIOUS LOT AND SOLID STRUCTURE, IT'S PERFECT FOR INVESTORS LOOKING TO RENOVATE, RENT, OR FLIP. CONVENIENTLY SITUATED NEAR DOWNTOWN WINTER HAVEN, SCHOOLS, SHOPPING, AND MEDICAL FACILITIES, THIS LOCATION IS IDEAL FOR LONG-TERM TENANTS OR RESALE VALUE. BENEATH THE EXISTING CARPETING, YOU WILL FIND WELL-PRESERVED HARDWOOD FLOORING READY TO BE DISCOVERED AND ENJOYED. DO NOT MISS YOUR CHANCE TO OWN A PIECE OF RAPIDLY GROWING WINTER HAVEN-OPPORTUNITIES LIKE THIS DO NOT LAST LONG!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Brian Reeves (877-366-2213)
1678 LINZ CT, WINTER HAVEN, FL 33884
$258,50096 Days on yellowkey MLS ID: L4960316
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1158 Built: 2019Monthly Fee: $455 Tax: $3,009 (2025)Community: Vienna Square Ph 2CSingle Family
Taxes:$3,009
Remarks: BETTER THAN NEW!!! Why wait to build when you can move into this HIGHLY UPGRADED, MAINTENANCE FREE villa in the 55+ GATED COMMUNITY of Vienna Square, centrally located in Winter Haven, FL. Before entering this beautiful residence, you will notice the BRICK PAVERED driveway/walkway leading through the MATURE LANDSCAPE and CUSTOM LIGHTING to the front SCREENED LANAI. Walk right into this very OPEN FLOORPLAN with HIGH CEILINGS and SPLIT BEDROOM CONCEPT. The kitchen is a CHEF'S DREAM, featuring UPGRADED STAINLESS APPLIANCES, IMPRESSIVE WINE FRIG., and BREAKFAST BAR. The CASCADING WATERFALL EDGE QUARTZ COUNTERTOPS add a MODERN, ELEGANT and LUXURIOUS focal point to this AMAZING KITCHEN!!! The adjoining great room is very spacious and overlooks the rear SCREENED LANAI with a view of the pond. The primary en-suite will not disappoint which also features QUARTZ COUNTERTOPS and an UPGRADED WALK-IN SHOWER with GLASS DOOR. CUSTOM PLANTATION SHUTTERS in the kitchen and bedrooms ensure you have the privacy you deserve! Don't forget about the second bathroom that has also been UPGRADED with QUARTZ COUNTERTOPS as well. This residence is truly TURN-KEY and one of the most WELL KEPT, ONE-OWNER homes you'll find anywhere. The reasonable monthly HOA dues include: ROOF REPLACEMENT, EXTERIOR PAINTING, YARD MAINTENANCE, LAWN IRRIGATION, and INTERNET/TV PACKAGE! Enjoy the other amenities including, but not limited to: pool/hot tub, tennis/pickle ball, gym, craft room, billiard room, movie room, and large meeting room with remodeled kitchen area. This wonderful property is in close proximity to medical, restaurants, shopping, worship, and LEGOLAND, FL. Winter Haven is well-known for it's beautifully interconnected lakes and being centrally located between the Tampa International and Orlando International Airports.
1581 OAKVIEW CIR SE, WINTER HAVEN, FL 33880
$214,900124 Days on yellowkey MLS ID: G5108372
REDUCED by $5,000 (2.3%) on 04/02/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1220 Built: 1996Monthly Fee: $180 Tax: $923 (2025)Community: OakviewSingle Family
Taxes:$923
Remarks: Welcome to a move-in ready villa in the desirable 55+ Oakview community of Winter Haven—now strategically repositioned to reflect today’s market and create immediate opportunity. This well-maintained 2-bedroom, 2-bath home offers 1,220 sq ft of comfortable living with a functional open layout, spacious bedrooms with walk-in closets, and a screened lanai designed for relaxed Florida mornings and evenings. Major updates are already done for you, including a NEW ROOF (2024) and HVAC (2019), giving buyers confidence where it matters most. The kitchen has been refreshed with brand-new appliances, making this a truly easy transition with no extra projects needed. A standout feature is the garage screen system, allowing you to enjoy fresh air and added flexibility during the day—an underrated benefit for Florida living. The HOA covers lawn care and exterior maintenance, supporting a low-maintenance, lock-and-leave lifestyle many buyers are actively seeking. Now repositioned to align with current market conditions—creating one of the most compelling opportunities in Oakview today. With recent activity in the community, buyers are moving quickly when the value makes sense—schedule your showing today.
Listing Agent: Vanessa Aybar Badillo (352-557-1682)
21 CASARENA CT, WINTER HAVEN, FL 33881
$285,000233 Days on yellowkey MLS ID: L4956453
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2045 Built: 1984Monthly Fee: $310 Tax: $3,325 (2024)Community: Casarena On LakesSingle Family
Taxes:$3,325
Elementary School: Inwood Elem
Middle School: Westwood Middle
Remarks: Move in ready and located on the Winter Haven Chain of Lakes! Welcome to the gated community of Casarena on the Lakes. This well-designed and meticulously maintained home is set up just right for indoor and outdoor living. The first floor is an open design with the fireplace separating the living and dining area. Enjoy granite countertops and updated appliances in the spacious kitchen that provides the perfect setting to create all of your favorite culinary delights. The living area is a versatile space with a cove for a hosting or exercise area. The main floor is also equipped with a half bath. Head upstairs to the loft that overlooks the living area and separates the two bedrooms. The primary bedroom leads to an open balcony on one side and an updated bathroom on the other. Both bedrooms are oversized with plenty of closet space. The new metal roof was installed in October 2023, The HVAC system has been well maintained, there is a new water heater and the home is also equipped with a whole home generator that is tested regularly. Enjoy the community pool, tennis or pickleball court and access to Lake Cannon, which is on the Winter Haven Chain of Lakes. Downtown Winter Haven is only 10 minutes away and you have quick access to Hwy 92 and 27. Call today for your private showing.
Listing is courtesy of: HOMETRUST REAL ESTATE & PTY MGT (863-450-0602)
Listing Agent: Kami Rickert (954-629-7828)
374 TROON CT, WINTER HAVEN, FL 33884
$225,000259 Days on yellowkey MLS ID: P4936606
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1634 Built: 1978Community: Cypresswood Patio HomesSingle Family
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Remarks: BRAND NEW ROOF INSTALLED NOVEMBER, 2025. Enjoy the Florida Country Club Lifestyle in this 2 bedroom patio home featuring a foyer with wet bar, spacious living room, dining area, kitchen with wood cabinets and converted Florida room, ideal as a den, office or play room. Additional amenities include an expansive master bedroom, 2 car garage with door opener and front courtyard wall. The home is in move-in condition but does have some original features and it's priced accordingly. This is an ideal opportunity to make this home your own with some contemporary updates. The home is currently tenant occupied on a month to month rental but the tenant may be willing to stay on for an investor purchase. Tenant has been there for 3 years.
Listing Agent: Steven Smith, Pa (863-224-2297)
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