
1097 CAREFREE COVE DR, WINTER HAVEN, FL, 33881
Active11 days on marketListed Oct 7, 2026MLS #S5159095
About this home
1097 CAREFREE COVE DR
There is something different about living where the water is part of your everyday routine. This new-construction Winter Haven home sits along a freshwater canal connecting Lake Conine and Lake Hartridge within the Winter Haven Chain of Lakes, giving you a lifestyle that most new homes simply cannot offer. Inside, the home feels bright, clean and thoughtfully designed for the way people actually live. The kitchen, dining area and living room flow together naturally, keeping everyone connected whether you are preparing dinner, entertaining friends or enjoying a quiet evening at home. The kitchen features white shaker-style cabinetry, stone countertops, stainless-steel appliances and a generous center island that works equally well for meal prep, casual dining and conversation. Warm wood-look flooring adds contrast and warmth throughout the main living areas. Sliding glass doors extend the living space to the screened covered lanai, creating a comfortable place to enjoy morning coffee, evening conversations, summer rainstorms or the canal-side setting just beyond the backyard. The primary suite is positioned apart from the secondary bedrooms for added privacy. Its bathroom includes dual sinks, a long vanity and an oversized glass-enclosed shower with large-format tile and a rainfall-style showerhead. Two additional bedrooms and a second full bath provide flexibility for family, guests or a home office. A dedicated laundry room, pantry storage and two-car garage make everyday routines easier, while the open layout keeps the home functional without wasting space. What really sets this property apart is the setting. Instead of backing up to another row of homes, the backyard opens toward a freshwater canal with access to one of Winter Haven’s most defining features: the Chain of Lakes. Whether you enjoy fishing, boating, spending time outdoors or simply being near the water, this home offers a direct connection to the Florida lifestyle. And there is another combination that is increasingly difficult to find in new construction: no HOA and no CDD. You can enjoy a newer home, modern finishes and canal access without the recurring community fees common in many newer developments. Convenient access to Winter Haven shopping, dining, medical services, downtown destinations and Central Florida attractions adds even more appeal. If you have been looking for a home that offers more than just new construction, one with modern design, screened outdoor living, canal access and the freedom of no HOA or CDD—this is one worth experiencing in person.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,484
Sqft
0.25 ac
Lot size
2026
Year built
One
Levels
$216
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$2,234 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:

Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$2,234/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−0.6%
$/sqft vs CAREFREE COVE
$216 vs $193
Days on market
11 vs 74 typical
Where $216/sqft sits among the 6 homes for sale in CAREFREE COVE
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside Winter Haven
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Haven. See the full Winter Haven guide →
WINTER HAVEN 33881 — neighborhood snapshot
Population
39,189
Median age
43.6
Median income
$53,867
Median home value
$177,400
Avg household
2.61
Households w/ children
3,730
For the school run
Polk County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Haven market
$283K → $279K
Winter Haven median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
3 of 6
CAREFREE COVE have cut their price
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 33% above the WINTER HAVEN 33881 median. See the full Winter Haven market guide →
Paper trail
This home's history
Reality check
What actually sold near 1097 CAREFREE COVE DR
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Sep ’26$170,000
1114 CAREFREE COVE DRIVE · same community
3 bd · 1.5 ba · 1,300 sqft · $131/sqft · 8 DOM
Sold · Apr ’26$261,999
1130 CAREFREE COVE DRIVE · same community
3 bd · 2 ba · 1,204 sqft · $218/sqft · 7 DOM
Sold · Sep ’26$260,000
316 LAKE SMART CIRCLE
3 bd · 2 ba · 1,500 sqft · $173/sqft · 83 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.

Your agent
Tommy Trainer
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1097 CAREFREE COVE DR — start here.

Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1097 CAREFREE COVE DR — before you fall in love.
See it in person
Schedule a tour
Live availability from Tommy's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1097 CAREFREE COVE DR FAQs
What would the monthly payment be for 1097 CAREFREE COVE DR?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $2,234/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 1097 CAREFREE COVE DR?+
The most recent tax bill on record (2026) was $595. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 1097 CAREFREE COVE DR?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Haven?+
At $319,900, this home is listed about 12% above the Winter Haven median of $286,450. The market section on this page shows how the area is trending.
Which schools are assigned to 1097 CAREFREE COVE DR?+
Fred G. Garner Academy (elementary), Winter Haven Senior High School (high), Lake Alfred Polytech Academy (middle) — Polk County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of RE/MAX HERITAGE PROFESSIONALS · Frankie Eizere. MLS #S5159095.
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
Never miss a listing
New Winter Haven homes, in your inbox
Like 1097 CAREFREE COVE DR but not quite? A daily digest of every new listing in Winter Haven — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask Tommy to ping you on any price or status change →


