Location: Winter Haven
Do Not Show Listings
305 ARBUTHNOT ST, WINTER HAVEN, FL 33881
$299,9991 Day on yellowkey MLS ID: P4938517
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1758 Built: 2022Monthly Fee: $83 Tax: $4,009 (2025)Community: Sanctuary By The Lake Ph 2Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,009
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Assumable low interest rate
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Susan Brown (863-640-5722)
2747 SAN MARCO WAY, WINTER HAVEN, FL 33884
$299,9901 Day on yellowkey MLS ID: O6401087
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 2025Monthly Fee: $13 Tax: $3,035 (2025)Community: Villamar Ph 5Single Family
Taxes:$3,035
Remarks: Ready for immediate move-in, the three bedroom, two bathroom home welcomes you with a perfect blend of style, comfort, and modern living. Thoughtfully designed with an open-concept layout filled with natural light, creating an inviting space for both relaxing and entertaining. At the heart of the home, the spacious great room flows seamlessly into the dining area and kitchen. The gourmet kitchen is sure to impress, showcasing stainless steel appliances, breakfast bar for a casual meal, pantry and plenty of prep space—ideal for everyday living and hosting alike. Beautiful ceramic tile flooring extends through the main living areas, while the bedrooms offer plush carpeting for added comfort. The primary bedroom serves as a peaceful retreat, complete with a generous walk-in closet and en-suite bath featuring dual vanities and a shower with a bench. Two additional bedrooms provide flexibility for guests, or a home office, each offering ample closet space and convenient access to a full bath. A dedicated laundry room with washer and dryer, along with a two-car garage, adds everyday convenience. Step outside to the covered patio to enjoy your backyard. Enjoy the amenities offered in the community with a resort style pool, playground and dog park. Experience the perfect blend of style, convenience, and community living at VillaMar. Come experience a home where comfort, functionality, and beauty come together effortlessly.
Listing is courtesy of: RE/MAX ASSURED (800-393-8600)
Listing Agent: Vilmari Caraballo (407-583-9870)
3056 CAPTAIN JAX WAY, WINTER HAVEN, FL 33884
$232,4901 Day on yellowkey MLS ID: O6401065
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1386 Built: 2026Monthly Fee: $193 Tax: $32 (2025)Community: Serenity At Peace Creek ThTownhouse
Taxes:$32
High School: Bartow High
Middle School: Bartow Middle
Remarks: One or more photo(s) has been virtually staged. Under Construction. Open flow sets the tone for this elegant new Crestone II two-story townhome. There are a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.
Listing is courtesy of: LENNAR REALTY (800-229-0611)
Listing Agent: Ben Goldstein (407-310-7677)
3052 CAPTAIN JAX WAY, WINTER HAVEN, FL 33884
$232,4901 Day on yellowkey MLS ID: O6401061
3048 CAPTAIN JAX WAY, WINTER HAVEN, FL 33884
$232,4901 Day on yellowkey MLS ID: O6401056
3044 CAPTAIN JAX WAY, WINTER HAVEN, FL 33884
$232,4901 Day on yellowkey MLS ID: O6401015
3060 CAPTAIN JAX WAY, WINTER HAVEN, FL 33884
$252,4901 Day on yellowkey MLS ID: O6400964
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1423 Built: 2026Monthly Fee: $193 Tax: $32 (2025)Community: Serenity At Peace Creek ThTownhouse
Remarks: One or more photo(s) has been virtually staged. Under Construction. This upscale new Summit two-story townhome provides ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.
3040 CAPTAIN JAX WAY, WINTER HAVEN, FL 33884
$252,4901 Day on yellowkey MLS ID: O6400954
323 ORANGE BLOSSOM DR #323, WINTER HAVEN, FL 33880
$209,9001 Day on yellowkey MLS ID: P4938498
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1280 Built: 2001Monthly Fee: $408 Tax: $530 (2025)Community: Waters Edge Unit 1 ReplatCondo
Taxes:$530
Remarks: WATERFRONT! ON THE CANAL TO THE CHAIN OF LAKES!! This townhouse is low-maintenance and offers a tranquil setting right in the middle of town, great location!. Primary bedroom with ensuite and screened-in balcony, one car garage and open concrete patio. The screened patio is perfect for enjoying views of boaters and paddle boarders passing between the lakes. Focusing on recreation, this home is in the perfect spot for a multitude of outdoor activities. Community features include a sparkling pool . Fish from your backyard at the bank of Lake Lulu! This residence is convenient to Great restaurants, medical, shopping, entertainment, and LEGOLAND! Check us out today to see what Florida waterfront living is all about!
Listing is courtesy of: CROSBY & ASSOCIATES, INC. (863-293-5600)
Listing Agent: Rick Hemenway (863-289-5657)
3420 AVENUE R NW, WINTER HAVEN, FL 33881
$215,000Listed 04/21/2026 10:14PM MLS ID: S5148239
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 672 Built: 1947 Tax: $1,927 (2025)Community: InwoodSingle Family
Taxes:$1,927
Elementary School: Inwood Elem
High School: Auburndale High School
Middle School: Westwood Middle
Remarks: Fully remodeled 2-bedroom, 1-bath home in the heart of Winter Haven. This move-in-ready property features a new roof, updated electrical and plumbing, and modern finishes throughout. Situated on a spacious lot with no HOA, it offers both comfort and flexibility. Conveniently located near major roads, shopping, dining, schools, and just minutes from downtown Winter Haven and LEGOLAND Florida Resort, making it an excellent option for homeowners or investors.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Maria Loayza Jimenez (570-856-6822)
6002 GRAND OAKS DR SE, WINTER HAVEN, FL 33884
$135,0001 Day on yellowkey MLS ID: P4938477
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1990Monthly Fee: $65 Tax: $1,028 (2025)Community: Garden Grove OaksManufactured Home
Taxes:$1,028
Remarks: S.E. WINTER HAVEN, FLORIDA**HERE YOU OWN YOUR OWN LAND, SO NO LOT RENT**THIS LOVELY 2 BEDROOM 2BATH HOME IS LOCATED IN THE WELL-MAINTAINED GARDEN GROVE OAKS COMMUNITY WITH A LOW $65 MONTHLY ASSOCIATION FEE- **NEW ROOF IN 2022**, **NEW AC IN 2022**, **REPLUMBED IN 2019**, NEW WASHING MACHINE IN 2019, DOUBLE WIDE CARPORT/DRIVEWAY & STORAGE/TOOL ROOM & LARGE LOT. The light and bright kitchen with a breakfast bar & plenty of counter space is open to the living room & dining room. French doors exit from the living room to a side screened patio with vinyl windows. The primary bedroom includes a walk-in closet and an en-suit bathroom. Bedroom #2 has a walk in closet and is convenient to the hall bathroom. Garden Groves Oaks amenities include use of clubhouse, pool, spa, shuffleboard, library, cookout room, & optional RV/boat parking when available. If you wish to participate, the Clubhouse activities can include birthday and anniversary celebrations, dances, water aerobics, billiards & cards. With the low monthly association fee, 2022 roof, 2022 AC and 2019 plumbing pipes, this home is sure to sell soon, so make your appointment to view TODAY!
Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)
Listing Agent: Chris Goode (863-287-5454)
906 LAKE JESSIE DR, WINTER HAVEN, FL 33881
$792,000137 Days on yellowkey MLS ID: L4957757
REDUCED by $88,000 (10.0%) on 04/21/2026
Bed: 9 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5700 Built: 1954 Tax: $5,237 (2024)Community: East View PkwySingle Family
Taxes:$5,237
Elementary School: Auburndale Central Elem
Tax Year: 2024
Remarks: Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces—ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis—complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown’s Sea Plane Base right from your own waterfront sanctuary. Whether you’re seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don’t miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.
Listing Agent: Brandy Duncan (863-585-6849)
210 NASSAU RD, WINTER HAVEN, FL 33884
$518,00041 Days on yellowkey MLS ID: L4960067
1 Days Off yellowkey (back on 3/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1987 Built: 1975 Tax: $1,663 (2025)Community: Eloise Woods Lake Mariam UnitSingle Family
Taxes:$1,663
Remarks: Under contract-accepting backup offers. This beautifully updated split floor plan home in the desirable Eloise Woods subdivision offers the perfect blend of comfort, quality upgrades, and incredible outdoor living. Nearly every part of this home has been improved, making it truly move-in ready. Inside, the home features updated flooring throughout, renovated bathrooms, redone ceilings, updated electrical and plumbing, new interior doors and trim, and an updated kitchen with new counters, custom backsplash, stainless appliances, and a large wrap-around bar that makes the kitchen the true heart of the home. The layout flows nicely with a spacious living area and flexible dining space that could also be used as an additional den or sitting room. The primary bedroom includes an en-suite bathroom, walk-in closet, and sliding glass doors that lead directly to the pool area. The secondary bedrooms are generously sized with great closet space, and the guest bathroom offers convenient access to the pool patio—perfect for when family and friends come over to enjoy the backyard. Step outside and you’ll immediately see what makes this home special. The pool area has been extensively upgraded with an extended deck finished with beautiful travertine tile, creating an incredible space for entertaining. Multiple pergolas, a built-in bar area, paver walkways, and private fencing create a backyard that truly feels like your own personal retreat. Additional improvements include updated windows and sliding glass doors with built-in custom blinds, custom closet systems, updated garage with epoxy flooring and storage, new soffit and fascia, gutters with screens, irrigation system, and a new drain field. Major mechanical updates give peace of mind with a full home re-pipe completed in 2014, new A/C and ductwork in 2019, and a brand new roof installed in April 2024. From the interior upgrades to the incredible outdoor entertaining space, this home offers a rare opportunity to own a fully updated property in Eloise Woods where the list of improvements is truly extensive.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: Sam Daniels (863-412-8218)
6121 FOREST RIDGE WAY, WINTER HAVEN, FL 33881
$315,00016 Days on yellowkey MLS ID: TB8491651
REDUCED by $10,000 (3.1%) on 04/22/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2526 Built: 2017Monthly Fee: $90 Tax: $3,073 (2025)Community: Forest RidgeSingle Family
Taxes:$3,073
Remarks: One or more photo(s) has been virtually staged. Price adjustment on 4/23 .........2500 + sq feet for $315,000 ! Step into comfort, space, and opportunity in this move-in ready 4-bedroom, 2.5-bath home located in the established Forest Ridge community of Winter Haven—with no CDD. From the moment you arrive, the inviting covered front porch and mature landscaping set the tone for what’s inside. The thoughtfully designed layout offers the perfect balance of everyday comfort and flexible living. The main level features an open kitchen and living area, a versatile bonus room near the entry—ideal for a home office, playroom, or creative space—and a convenient half bath for guests. At the center of the home, the open-concept kitchen is built for connection, featuring a center island, black and stainless steel appliances, and seamless flow into the dining and living areas—perfect for entertaining or simply enjoying day-to-day life. Recently upgraded dishwasher and garbage disposal. Durable tile flooring and recently upgraded carpet throughout all the main living spaces and upstairs bedrooms adds a clean, modern feel and abundant natural light creates a bright, welcoming atmosphere. Upstairs, you’ll find all four bedrooms, including a spacious primary suite designed for relaxation, along with two full bathrooms and a conveniently located laundry area equipped with a smart washer and dryer. Each space is designed with comfort and functionality in mind. Step outside to a generously sized backyard ready for your vision—whether it’s a future pool, outdoor kitchen, garden, or play space, the possibilities are endless. Set within the peaceful surroundings of Forest Ridge, you’ll enjoy quiet streets while being just minutes from Highway 27 and a short drive to I-4, giving you easy access to shopping, dining, schools, and everything Central Florida has to offer. This home checks all the boxes—space, flexibility, location, and value. Schedule your private showing today and see the potential for yourself!
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Daniel Henzler (813-293-3603)
3142 WHISPERING TRAILS ST, WINTER HAVEN, FL 33884
$370,00054 Days on yellowkey MLS ID: O6386254
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2203 Built: 2006Monthly Fee: $95 Tax: $3,991 (2025)Community: Whispering Trails Ph 01Single Family
Taxes:$3,991
Remarks: Minutes from Walmart, Winn Dixie, Restaurants, Shopping and Legoland, this charming home offers comfort and convenience in a prime location. Featuring a spacious layout perfect for everyday living and entertaining, its nestled in a well-maintained GATED COMMUNITY with Clubhouse, Pool and Scenic Walking Trails. Recent upgrades inlcude: Kitchen Cabinets, Tile Floors, New Stair Rails and Stair Flooring, updated Bathroom Tile Wall, Refrigerator and Oven, Back Porch, Fenced Yard and enhanced Front Landscaping and Decorative Stones. Enjoy nearby Chain of Lakes recreation, Downtown Winter Haven boutique shopping, farmers market, The Ritz Theatre and lakeside restaurants. Move-In Ready and waiting for you!
Listing is courtesy of: NEWBERRY REALTY & DEV GRP INC. (321-607-2354)
Listing Agent: Gylwerd Sevilla Oviedo (305-989-7853)
2566 PARTRIDGE DR, WINTER HAVEN, FL 33884
$675,00023 Days on yellowkey MLS ID: B4902217
0 Days Off yellowkey (back on 4/21/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3005 Built: 1998Monthly Fee: $100 Tax: $6,283 (2025)Community: Eloise Pointe Ests Phase Two Pb 91 Pg 2Spa: NoSingle Family
Taxes:$6,283
Remarks: One or more photo(s) has been virtually staged. Welcome to your gorgeous new home! This executive style home is located in the highly sought after gated community, Eloise Pointe Estates, and is conveniently located 1/4 mile behind Legoland. Community was originally developed by then Boston Red Sox owner, Buddy Larue when they spring trained in Winter Haven. Upon entering this desirable 4 bedroom 3.5 bathroom home one finds many updates, completely remodeled kitchen and primary bathroom. New cabinetry, granite counter-tops, beautiful tongue and groove wood ceiling in the kitchen, paint (including the pool deck) & LVP flooring throughout. The laundry room is also plumbed for a sink. Upstairs over the garage is the 4th bedroom and full bath or use as a Bonus/Theatre room. Also included is an oversized three car garage, a large lot with some beautiful scrub oak trees on just over a 1/2 an acre & privacy fenced. Screened in 15x30 pool. Another great feature of this home is the low HOA fee of only $1200 for the year and no CDD.
Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)
Listing Agent: Scott Kline (863-287-0204)
373 LAKE DAISY CIR, WINTER HAVEN, FL 33884
$215,000138 Days on yellowkey MLS ID: L4957732
REDUCED by $10,000 (4.4%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1391 Built: 1990 Tax: $3,356 (2025)Community: Lake Daisy EstatesSpa: NoSingle Family
Taxes:$3,356
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: MOTIVATED SELLERS...OPPORTUNITY KNOCKS ON THIS SPACIOUS & AFFORDABLE 3 Bedroom/2 Bath Home in the heart of SE Winter Haven located in Lake Daisy Estates is ready for you & your family!!! NO HOA or CDD in this established neighborhood that is within 3 miles of LEGOLAND and close to multiple restaurants, shopping, & parks. The natural light fills each room of the home. Open floor plan with split bedrooms. You'll love the large open backyard that is fully fenced. Newer roof (2023). Schedule a tour today!!!
Listing Agent: Cheryl Brewer (863-224-0045)
6394 LOLLY BAY LOOP NE, WINTER HAVEN, FL 33881
$179,900120 Days on yellowkey MLS ID: L4958069
REDUCED by $10,000 (5.3%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1620 Built: 1990Monthly Fee: $34 Tax: $2,568 (2024)Community: Brookhaven Village Second AddManufactured Home
Taxes:$2,568
Remarks: Located in the 55+ community of Brookhaven Village, this fee-simple manufactured home offers 1,620 square feet of living space with a functional layout and recent updates. Built in 1990, the home features 2 bedrooms and 2 bathrooms, with vinyl and carpet flooring throughout. The interior includes a spacious living and dining area, an interior laundry closet, and ample storage. An attached storage room provides additional space and may be suitable for use as a workshop, hobby area, or general storage. The home also features a covered and screened porch, offering a comfortable space to enjoy the outdoors. Recent improvements include a roof replaced in 2023 and an HVAC system replaced in 2022. The home may be conveyed fully furnished, providing a convenient option for buyers. Brookhaven Village offers community amenities including a clubhouse, pool, shuffleboard courts, and organized social activities. The HOA fee is $34 per month, and the community enforces age restrictions in accordance with its 55+ designation. Conveniently located in Winter Haven with access to shopping, dining, and local amenities, this property offers an opportunity for low-maintenance living in an established adult community.
Listing is courtesy of: COLDWELL BANKER REALTY (863-687-2233)
Listing Agent: Daniel Mcfee (863-273-6324)
851 VIENNA DR, WINTER HAVEN, FL 33884
$279,9009 Days on yellowkey MLS ID: L4961034
REDUCED by $5,100 (1.8%) on 04/21/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1569 Built: 2022Monthly Fee: $15 Tax: $6,253 (2025)Community: Villamar Ph 2Spa: NoSingle Family
Taxes:$6,253
Elementary School: Chain O Lakes Elem
Remarks: Better Than New 2022 Home – Move-In Ready! VA Assumable Mortgage!!! Welcome to this beautifully maintained 3-bedroom, 2-bath home with a 2-car garage, located on a desirable corner lot in the sought-after Villamar community of Winter Haven. Built in 2022, this home offers modern living without the wait for new construction. Step inside to an open and inviting floor plan featuring tile flooring throughout the main living areas, with comfortable bedrooms and a spacious primary suite. The kitchen comes equipped with appliances and flows seamlessly into the living and dining areas, making it perfect for everyday living and entertaining. Enjoy outdoor living in the screened lanai, ideal for relaxing or hosting guests. The home also includes an irrigation system and established landscaping, features often not included in new builds. Located in a community with resort-style amenities including a pool, playground, and sidewalks, and just minutes from shopping, dining, and local schools, this home offers both convenience and lifestyle. Skip the construction wait, this home is vacant and ready for immediate move-in! Don’t miss your opportunity to own a newer home in a growing area at an incredible value. Schedule your private showing today!
Listing is courtesy of: LA ROSA REALTY PRESTIGE (863-940-4850)
Listing Agent: Regina Moran Pa (863-698-0748)
1601 ROSELAWN ST SW, WINTER HAVEN, FL 33880
$257,000173 Days on yellowkey MLS ID: O6356028
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1099 Built: 1960 Tax: $3,654 (2024)Community: Tranquility Park 02 RepSingle Family
Taxes:$3,654
Elementary School: Lake Shipp Elem
Remarks: Welcome to this beautifully updated home in Winter Haven! This move-in ready property combines classic charm with modern upgrades, featuring stunning high-gloss marble-style porcelain flooring throughout that creates a bright and elegant living space. Enjoy a spacious layout filled with natural light, a well-maintained kitchen with stainless steel appliances, wood cabinetry, and a stylish backsplash — perfect for everyday living. The home also offers a renovated bathroom with modern finishes and a convenient interior laundry area. Step outside to a large, fully fenced backyard, ideal for entertaining, pets, or simply enjoying your own private outdoor space. The covered carport and extended driveway provide ample parking. Located in a quiet, well-established neighborhood, this home is perfect for first-time buyers or investors. Property is being sold AS-IS, presenting a great opportunity for buyers looking for value and flexibility. Schedule your private showing today!
Listing Agent: Gabriel Rivera Gonzalez (407-724-4717)
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