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4442 HOLLYBROOK WAY

House Active With Contract
$663,000

BTC: 10.97682119

ETH: 415.75478620

-$22K (2026/06/08)
27 days
4 bds
2 ba
2,310 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
No Data
Year Built:
1994
Lot:
0.24 Acres
Heating:
Central / Electric
Price/sqft:
$287
Cooling:
Central Air
HOA:
$960

Valuation

Our model vs. what's actually selling nearby.
Estimate
$570,000
$517K – $682K
Confidence Low
List vs. estimate
$93K above estimate
List $663,000 · +16.3%
Our model says this listing is priced above recent comparable activity. Room to negotiate.
Price per sq ft
$287
-6.8% vs. city median $307
Based on
7 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$4,542
2025
HOA
$960/yr
Pool
In Ground
Garage
2 car garage
Pets
Allowed
All facts and features
  • Flooring

    • Luxury Vinyl

    Heating

    • Central

    • Electric

    Cooling

    • Central Air

    Appliances

    • Dishwasher

    • Dryer

    • Electric Water Heater

    • Freezer

    • Ice Maker

    • Microwave

    • Range

    • Refrigerator

    • Washer

    Other interior features

    • Ceiling Fan(s)

    • Eating Space In Kitchen

    • Open Floorplan

    • Primary Bedroom Main Floor

    • Solid Surface Counters

    • Solid Wood Cabinets

    • Thermostat

    • Window Treatments

    Bedrooms and bathrooms

    • Bedrooms: 4

    • Full bathrooms: 2

  • Property

    • Levels: One

    • Pool Private: Yes

    • Exterior Features: Lighting / Outdoor Shower / Private Mailbox / Private Yard

    Lot

    • Lot: 0.24 Acres

    Other Property Information

    • Parcel Number: 0069080055

    • Zoning: RSF2

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Single Family Residence

  • Utility

    • Cable Connected

    • Electricity Connected

    • Public

    • Sewer Connected

    • Water Connected

  • Other financial information

    • HOA: $960

    • HOA Frequency: Annually

    • Annual tax amount: $4,542

  • Source details

    • MLS ID: A4694025

    Other facts

    • Construction Materials: Block

    • Foundation Details: Slab

    • Fireplace Features: Wood Burning

    • Laundry Features: Laundry Room

    • Pool Features: In Ground

    • Direction Faces: Southeast

    • Fireplace: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 2310

    • Water Source: Public

    • Subdivision Name: GREENFIELD

Private inquiry
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: COLDWELL BANKER REALTY