1557 N LAKE SHIPP DRIVE SW, WINTER HAVEN, FL, 33880
Pending14 days on marketListed Aug 1, 2026MLS #L4963966
About this home
1557 N LAKE SHIPP DRIVE SW
Welcome to your own private Florida retreat! This beautifully maintained 3-bedroom, 2-bath home is nestled beneath majestic oak trees in an established Winter Haven neighborhood, offering timeless curb appeal and a warm, inviting atmosphere. Inside, you'll find a functional floor plan filled with natural light, creating comfortable living spaces for both everyday life and entertaining. The thoughtful layout offers the perfect blend of openness and privacy. Step outside and discover the true centerpiece of the home—a sparkling saltwater pool surrounded by a screened lanai, allowing you to enjoy Florida's outdoor lifestyle year-round with added comfort and protection. Whether you're sipping your morning coffee, hosting family and friends, or unwinding after a long day, this backyard oasis is designed for relaxation. Conveniently located near Winter Haven's Chain of Lakes, downtown shopping and dining, parks, schools, medical facilities, and LEGOLAND Florida Resort, this home offers the perfect combination of tranquility and convenience. Don't miss your opportunity to own this move-in-ready pool home in one of Winter Haven's most desirable locations. Schedule your private showing today!
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,172
Sqft
0.27 ac
Lot size
1961
Year built
One
Levels
$230
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.
$1,916 /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
$1,916/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
+7.7%
$/sqft vs Winter Haven actives
$230 vs $170
Days on market
14 vs 49 typical
Where $230/sqft sits among the 400 Winter Haven actives
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 Tranquility Park
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Haven. See the full Winter Haven guide →
Tranquility Park — neighborhood snapshot
Population
320
Median age
40
Median income
$62,870
Median home value
$162,000
Avg household
2
Households w/ children
71%
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 → $280K
Winter Haven median sold, yr/yr
97.2%
Sale-to-list ratio (12 mo)
194 of 400
Winter Haven actives have cut their price
Median sold price, Winter Haven, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 23% above the WINTER HAVEN 33880 median. See the full Winter Haven market guide →
Paper trail
This home's history
Reality check
What actually sold near 1557 N LAKE SHIPP DRIVE SW
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Aug ’25$540,000
656 LAKE CHARM DRIVE · same community
4 bd · 3 ba · 2,526 sqft · $214/sqft · 29 DOM
Sold · Jul ’26$71,150
1935 FRUITLAND PARK CIRCLE
3 bd · 2 ba · 1,150 sqft · $62/sqft · 54 DOM
Sold · Nov ’25$135,000
102 ORANGE AVENUE
3 bd · 1 ba · 1,080 sqft · $125/sqft · 24 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
John Carpenter
CFO/Broker · CENTURY 21 Edge
Tours, negotiation, and every question about 1557 N LAKE SHIPP DRIVE SW — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1557 N LAKE SHIPP DRIVE SW — before you fall in love.
See it in person
Schedule a tour
Live availability from John's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1557 N LAKE SHIPP DRIVE SW FAQs
What would the monthly payment be for 1557 N LAKE SHIPP DRIVE SW?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $1,916/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 1557 N LAKE SHIPP DRIVE SW?+
The most recent tax bill on record (2025) was $565. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Haven?+
At $270,000, this home is listed about 5% below the Winter Haven median of $284,995. The market section on this page shows how the area is trending.
Which schools are assigned to 1557 N LAKE SHIPP DRIVE SW?+
Lake Shipp Elementary School (elementary), Denison Middle School (middle), Winter Haven Senior High School (high) — Polk County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of HOUSE OF GLASS REAL ESTATE PM · Tiffani Kline. MLS #L4963966.
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.
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