4442 Hollybrook Way, FL
Stellar MLS

$663,000

4442 Hollybrook Way

Sarasota, FL 34233

Listing updated: June 8, 2026 at 2:27 PM ET

Active
4
Beds
2
Baths
2,310
Sq Ft
0.24
Acres
1994
Built
Private poolFireplace$287/sqft360° tour
Single Family Residence

Property type

1994

Year built

10,400 sqft

Lot size

$287

Price / sq ft

$80/mo

HOA dues

21

Days on market

2

Garage spaces

X

Flood zone

About this home

Beautifully updated and move-in ready 4-bedroom, 2-bath home in the highly desirable community of Greenfield, centrally located within top-rated school districts including Ashton Elementary School, Sarasota Middle School, and Sarasota High School. Greenfield offers low HOA fees and a peaceful setting with plenty of convenient shopping and dining amenities nearby and within short proximity to the white sand beaches of Sarasota. This meticulously maintained home is tucked along a quiet section of the neighborhood on an oversized quarter-acre lot. From the moment you arrive, you’ll appreciate the freshly painted exterior accented by timeless brick details and inviting curb appeal. Inside, the easy-living split floor plan offers 2,310 square feet under air with generous living spaces designed for both comfort and entertaining. This home is loaded with quality upgrades and recent improvements, including impact windows and sliders throughout (2025), luxury vinyl plank flooring, newer HVAC (2022), a fully updated kitchen (2022), recessed LED lighting, new ceiling fans (2026), and an impact-rated garage door (2020). The stunning gourmet kitchen features quartz countertops, stylish white shaker soft-close all-wood cabinetry with rollout drawers, stainless steel appliances, a large single-basin stainless sink, pantry storage, and both countertop seating and a dining area overlooking the pool. Just off the kitchen, the cozy living room centers around a charming wood-burning brick fireplace, creating the perfect gathering space for family and friends. The three guest bedrooms share a bathroom with convenient pool access, while the spacious primary suite offers privacy and comfort. Step outside to the generously sized screened lanai, an ideal outdoor retreat with ample shaded space for dining, relaxing, and grilling. The sparkling pool was resurfaced with a pebble finish in 2022 and features a newer Pentair pool pump, plus an outdoor shower for added convenience.The beautifully landscaped backyard is truly special, showcasing native Florida plants and flowering gardens designed for low-maintenance living. Enjoy Sunshine Mimosa ground cover, Mulberry trees, Elderberry, and a magnificent mature oak tree that provides natural shade and character. Additional exterior features include full irrigation and a new side fence installed in 2026. Every detail of this home reflects thoughtful design, exceptional upkeep, and high-quality craftsmanship, creating a stylish and worry-free property ready to be enjoyed for years to come.

Estimated monthly payment

Principal & interest$3,352
Property taxes$379
Home insurance (est.)$304
HOA dues$80

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history21 days on market

  1. Status: Active
    May 18, 2026
  2. Listed$685,000
    May 18, 2026
  3. Price reduced$663,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
21
Subdivision
Greenfield
County
Sarasota
Year built
1994
Living area
2,310 sq ft
Price/sq ft
$287
Building area
3,090 sq ft (Public Records)
Lot size
10,400 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12115C0162G)
Garage
2 spaces
Pool
Private pool
Annual taxes
$4,542 (2025)
Parcel #
0069080055
Zoning
RSF2
MLS #
A4694025

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Interior Details

Bedrooms
4
Full bathrooms
2
Flooring
Luxury Vinyl
Appliances
Dishwasher, Dryer, Electric Water Heater, Freezer, Ice Maker, Microwave, Range, Refrigerator, Washer
Interior features
Ceiling Fans(s), Eat-in Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Thermostat, Window Treatments
Laundry
Laundry Room
Stories / Levels
One
Direction faces
Southeast
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes

HOA & Financial

HOA fee
$960 / Annually
Monthly HOA
$80/mo
Total monthly fees
$80/mo
Total annual fees
$960
HOA name
Lorna Fleenor
CDD
No
Homestead exemption
Yes
Min lease term
1-2 Years
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Buyer to confirm all leasing restrictions with HOA.
Approval process
See HOA documents attached to the MLS.

Exterior & Construction

Exterior features
Lighting, Outdoor Shower, Private Mailbox, Private Yard
Construction materials
Block
Roof
Shingle
Foundation
Slab
Pool
Private pool
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Cable Connected, Electricity Connected, Public, Sewer Connected, Water Connected

Community

Pets allowed
Yes

Schools

ElementaryAshton ElementaryGreatSchools ↗
MiddleSarasota MiddleGreatSchools ↗
High SchoolSarasota HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
KitchenFirst
Primary BedroomFirst
Living RoomFirst

Listing Details

Listing date
2026-05-14
On market date
2026-05-18
Original list price
$685,000
Occupant type
Owner
MLS area
34233 - Sarasota
Listing AOR
Sarasota - Manatee
Status changed
2026-05-18
Tax legal description
LOT 73 GREENFIELD

Flood risk

Minimal riskFEMA Zone XPanel 12115C0162G

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From I-75 exit at Bend Ridge Rd. Make a left on Honore Ave. Make a left on Wilkinson Rd. Make a left on Greenfield Ave. Make a left on Sunnyvale Cir N, make a right on Hollybrook Way and home is one right.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

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.

Based on information submitted to the MLS GRID as of June 8, 2026 at 2:27 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA