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419 Greenfield Rd, Winter Haven, FL, 33884

$174/sqft·Cypresswood Mdws

3 bd2 ba1,924 sqft2 car garageSingle Family
Listed by BOARDWALK REALTY ASSOCIATES, LLC· Last updated · MLS# TB8513442

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

Est. monthly payment
$2,298/mo
Down payment (20%)
$66,998
Property taxes
$226/mo
HOA
$1,892/yr
Rate assumed
6.8% · 30 yr
View full breakdown

At a glance

Single family
Built 1990
Community pool
Shared amenity
2 car garage
6,778 sqft lot
Lot size
1,924 sqft
Living area

About this home

Ceiling Fans(s)Open FloorplanStone CountersRain GuttersClubhouseDeed RestrictionsGated Community - GuardGolf Carts OK

419 Greenfield Rd is a 1990-built home in Cypresswood Mdws, Winter Haven. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,924 square feet of living space. Listed at $334,990 (about $174/sqft), 95 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable. HOA runs $1,892 annually.

From the listing

Cypresswood Golf & Country Club welcomes you to 419 Greenfield Drive. This desirable gated golf community has a host of activities and treasures, but by far the most impressive one is this gem and it shows. As you pull up to the extended driveway, low maintenance landscape ushers you into a well appointed home. Once in the front door, sparkling floor tiles guide you through this beautiful 3 bedroom 2 bath split floor plan home. Quartz counters and wall to wall cabinet space give anyone that loves to cook the space they need to store items and create meals while hosting family or company. Right off of the kitchen there is a climate controlled Florida room, with an additional screened-in patio to the rear. When you are ready to retire for the evening, your primary bedroom has plenty of space to stretch out in and keep your belongings in the large walk-in closet. Move right in and leave your worries behind. Not only has the kitchen and flooring been recently upgraded, all your major components have been replaced within the last 5 years - brand new electric panel w/surge protection installed (May 2026), roof (2022) , water heater (2021), A/C (2021). Schedule your private tour and make this home yours for years to come.

The essentials

Built
1990
Price / sqft
$174
On market
106 days
Annual tax
$2,715
HOA
$1,892/yr
Flood zone
X · Low risk
Lot
6,778 sqft
Type
Single Family Residence

Location

419 Greenfield Rd
Winter Haven, FL, 33884·33884 - Winter Haven / Cypress Gardens
Type
Single Family Residence
Year Built
1990
Lot
6,778 sqft
Cooling
Central Air
Heating
Electric, Natural Gas
Parking
-
Days on Market
106
Ceiling Fans(s)
Open Floorplan
Stone Counters
Rain Gutters
Clubhouse
Deed Restrictions
Gated Community - Guard
Golf Carts OK
Golf
Pool
Sidewalks
Tennis Court(s)
Dishwasher
Disposal
Dryer
Gas Water Heater
Microwave
Range
Refrigerator
Washer
Homestead exemption on fileFlood Zone X

Annual Tax (2025)

$2,715

Parcel #

27-28-29-000000-044320

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision

Cypresswood Mdws

County

Polk

MLS Area

33884 - Winter Haven / Cypress Gardens

Lot Size

6,778 sqft

HOA
$1,892/yr
John Tashin
Date
Event
Price
9/2/2026
Price change
Source: Stellar MLS #TB8513442
$334,990-1.5%
$174/sqft
Price change
Source: Stellar MLS #TB8513442
$339,990-2.9%
$177/sqft
5/30/2026
Listed for sale
Source: Stellar MLS #TB8513442
$349,990
$182/sqft
Est. monthly payment$2,299/mo
Principal & interest$1,747
Property taxes$226
Insurance$167
HOA$158
Down payment20% · $66,998
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. HOA is the fee reported on the listing. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Offer Insights

Choose an offer strength

List price: $334,990
$332,500 – $334,990
99.5% – 100% of listTops out right at the list price
80% of listList price
163 of the last 255 home closings in 33884 landed at this number or higher (64%). The median one sat 39 days before it went under contract, and this one is on day 106 after a $15,000 cut.

Sample: 255 closed home sales in 33884 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

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