Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 2 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 3 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 4 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 5 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 6 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 7 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 8 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 9 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 10 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 11 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 12 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 13 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 14 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 15 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 16 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 17 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 18 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 19 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 20 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 21 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 22 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 23 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 24 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 25 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 26 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 27 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 28 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 29 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 30 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 31 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 32 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 33 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 34 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 35 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 36 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 37 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 38 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 39 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 40 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 41 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 42 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 43 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 44 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 45 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 46 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 47 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 48 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 49 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 50 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 51 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 52 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 53 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 54 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 55 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 56 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 57 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 58 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 59 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 60 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 61 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 62 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 63 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 64 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 65 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 66 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 67 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 68 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 69 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 70 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 71 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 72 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 73 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 74 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 75 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 76 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 77 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 78 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 79 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 80 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 81 of 82
Single Family Residence at 27 WINDING CREEK WAY, ORMOND BEACH, photo 82 of 82
82 photos

$612,000

27 WINDING CREEK WAY
ORMOND BEACH, FL 32174
Listed by James Sheehan · BETTER HMS & GARDENS RE SYNERG
Bedrooms
3
Bathrooms
2.5
Living area
2,370 sqft
Year built
1992

About this home

Experience the best of Florida living in this move-in ready, beautifully updated pool home, nestled within the prestigious Estate Homes section of Breakaway Trails—one of Ormond Beach’s most sought-after 24-hour guard-gated private communities. Drive up to this stunning brick home featuring a circular driveway and an easy-to-maintain, fully fenced yard with thoughtful plantings, creating a peaceful and serene setting. Inside, you’ll find 3 bedrooms, 2.5 bathrooms, and 2,370 square feet of thoughtfully designed living space filled with comfort, style, and elegant upgrades throughout. In the heart of the home is the bright, inviting kitchen, offering abundant cabinetry with convenient pull-out storage, a functional peninsula perfect for casual dining or entertaining, and sun tunnels that fill the space with natural light. Plantation shutters add timeless charm and sophistication across the home. The living areas flow seamlessly, highlighted by a refaced wood-burning fireplace that creates a warm and welcoming focal point. French doors lead you outside to your private outdoor oasis—an oversized screened lanai complete with custom sun shades, ideal for relaxing or hosting guests year-round. Step into the sparkling solar-heated pool with gas heated spa, perfect for enjoying Florida’s sunshine in total privacy. The spa-like primary suite offers a true retreat, featuring a luxurious soaking tub and a walk-in shower designed for relaxation. With a newer roof, thoughtful updates throughout, and rare bonus storage with an attached shed, this home truly checks every box. Breakaway Trails is known for its exceptional amenities, family-friendly atmosphere, and unbeatable location—just minutes from the Atlantic Ocean beaches, top-rated schools, shopping, dining, and medical facilities. Whether you’re looking for an upscale family home or a peaceful retreat, this property delivers the perfect blend of privacy, convenience, and resort-style living.

Highlights

Private poolFireplace

Property details

MLS
Stellar MLS
MLS #
MFRFC315957
Property type
Single Family Residence
Subdivision
BREAKAWAY TRAILS PH 01 UNIT 01
Status
Active
Days on market
187
On market date
February 6, 2026
Stories
N/A
Total bathrooms
2.5
Garage spaces
2
Parking spaces
N/A
Lot size
0.36 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
PATHWAYS ELEMENTARY SCHOOL
1.08 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
698
Student:teacher ratio
14.5:1
District
VOLUSIA
Middle
DAVID C. HINSON SR. MIDDLE SCHOOL
2.81 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
952
Student:teacher ratio
18.7:1
District
VOLUSIA
High
PACE CENTER FOR GIRLS
4.94 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
38
Student:teacher ratio
9.5:1
District
VOLUSIA

Walkability

Blended score for ORMOND BEACH's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

19
Very car-dependent
out of 100
EPA National Walkability Index
6.3 / 20 -- Below average walkable
Google Places amenity density
0 / 100
Restaurants & cafes0
Grocery stores0
Parks0
Schools0
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in ORMOND BEACH, from live MLS data.

On the market 187 days -- 96 more days than ORMOND BEACH's current average of 91 days.
For reference, the median list price across 626 active listings in ORMOND BEACH right now is $384,950.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$3,836/mo
$122,400 down
$489,600 loan
Principal & interest$3,176
Property tax (est.)$510
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated August 12, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.