27 Winchester Rd, Ormond Beach, FL 32174
OFF MARKET

27 Winchester Rd
Ormond Beach, FL 32174

  • 3 Beds
  • 2 Baths
  • 3,252 sqft

$504,500

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $3,276/mo*
Refinance Your Home

$504,500

Trulia Estimate
as of May 13, 2026
Est. Refi. Payment $3,276/mo*
Refinance Your Home
3 Beds
2 Baths
3,252 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

NOT A SHORT SALE OR FORCLOSURE! FYI-the price reflects payoff plus closing costs and 249,900 is a firm figure.Unique combination of acreage and water. This home was built around a large pond that borders two sides of the house with decks, docks and fountains. 3BR, 2BA with a large living room that overlooks the grounds and wildlife. A generous family room open to a large deck that sits pond side with a bridge to a gazebo. 5.6 acres that is ideal for outdoor entertaining or living in seclusion (can't see the home from road). Covered boat or R.V. parking. A small guest quarters or in-law unit is detached and could use some T.L.C. This home is being offered for the first time in 15 years
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
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View
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HOA
None
Price/Sqft
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Listed
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Home Details for 27 Winchester Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood

Property Information

Year Built
Year Built: 1987Year Updated: 1992
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 2

Price History for 27 Winchester Rd

DatePriceEventSource
11/03/2011$249,900Sold
N/A
09/29/2011$249,900PriceChange
Agent Provided
09/18/2010$299,000PriceChange
Agent Provided
07/10/2010$349,000PriceChange
Agent Provided
03/25/2010$394,900Listed For SaleAgent Provided
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Property Tax and Assessment

Year2024
Tax$3,651
Assessment$498,828
Home facts updated by county records

Comparable Sales for 27 Winchester Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
115 Bay Lake Dr, Ormond Beach, FL
0.44
Single-Family Home
$420,000
08/26/25
3
2
2,111
10 Remington Rd, Ormond Beach, FL
0.41
Single-Family Home
$625,000
05/07/26
3
2
2,340
1068 Hampstead Ln, Ormond Beach, FL
0.34
Single-Family Home
$833,500
05/29/25
3
3
3,131
40 Winchester Rd, Ormond Beach, FL
0.25
Single-Family Home
$575,000
06/26/25
4
3
2,386
63 Bay Lake Dr, Ormond Beach, FL
0.57
Single-Family Home
$589,000
12/05/25
3
2
2,121
1066 Hampstead Ln, Ormond Beach, FL
0.32
Single-Family Home
$959,000
07/09/25
4
2.5
2,692
15 Winchester Rd, Ormond Beach, FL
0.36
Single-Family Home
$700,000
02/13/26
5
2.5
3,956
46 Winchester Rd, Ormond Beach, FL
0.46
Single-Family Home
$750,000
05/20/25
3
3
2,274
1324 Dovercourt Ln, Ormond Beach, FL
0.56
Single-Family Home
$830,000
09/19/25
3
2.5
2,605
1329 Sunningdale Ln, Ormond Beach, FL
0.79
Single-Family Home
$460,000
07/24/25
3
2
2,172

Assigned Schools

These are the assigned schools for 27 Winchester Rd.

What Locals Say about Ormond Beach

At least 484 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 87 % Say parking is easy

  • 87 % Say car is needed

  • 79 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 76 % Say people would walk alone at night

  • 72 % Say it's quiet

  • 64 % Say there are sidewalks

  • 63 % Say they plan to stay for at least 5 years

  • 61 % Say streets are well-lit

  • 60 % Say there's wildlife

  • 58 % Say neighbors are friendly

  • 54 % Say kids play outside

  • 51 % Say it's walkable to restaurants

  • 46 % Say it's walkable to grocery stores

  • 32 % Say there are community events

Learn more about our methodology.
  • Marcella Hill
    "Public transportation via bus stops directly in front of condo. But traffic is really starting to get congested due to influx of people. "
    0
    Flag
  • 7ph4kwwbnh
    "Great safe place to live and the community is quiet and pleasant. Great place to raise kids and have a family "
    0
    Flag
  • Metaldiz2000
    "I lived here for more then 10 years and love it. Doing all the hobbies and the entertainment is a large part for me. I love the beach and festivities are great"
    0
    Flag
  • Janmgrfla
    "Family oriented neighborhood. Park with playgrounds and walking paths across the street. Friendly, Safe neighborhood. "
    0
    Flag
  • Aliciaccaputo
    "Travel on Granada is difficult. Give yourself extra time. There is a lot of traffic and narrow roadways. "
    0
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  • James J.
    "I live and work here. My commute is 20 minutes. On a busy day it is 25 minutes. Beach Street runs along the intracoastal waterway and it is common to see sail boats and dolphins while driving to and from work. "
    0
    Flag
  • Greg Smith
    "Nice dog friendly area , take my dogs out daily very nice area to take them out in your neighborhood "
    0
    Flag
  • Stan Trojak
    "Great little city, lots of community events for the family year round. You’re only a few minutes away from the outlet mall and International Speedway. "
    0
    Flag
  • Ezwiser50
    "It’s a quiet neighborhood. From families with littles, to an older crowd. Very peaceful neighborhood. Great food, entertainment, and artsy influence nearby. Highly recommended! "
    0
    Flag
  • Dallas Lovelace
    "It’s apartments It’s easy and well lit . Friends and neighbors very close by , walking circle for measured distances "
    0
    Flag
  • Jpwenterprises
    "We have the coolest Thanksgiving a party every year down the street at Ormond beach brewery and there is also a Big party that goes on on the ocean side of the Granada bridge with bands and shops where every can enjoy our amazing river and bridge. These are really fun events that everyone should go to and check out for some good times and get the vibe for the community "
    0
    Flag
  • Heather
    "I work from home. Traffic doesn’t seem too bad, except around the times schools let out. Everything is within easy driving distance. "
    0
    Flag
  • Chance A
    "Ormond is a great area, I grew up here and live here as an adult, great place to bring up a family. "
    0
    Flag
  • Greg Smith
    "I lived in Ormond beach for over a year and I love it here shops and medical facilities are close the ocean is a 10 min drive , people are really friendly "
    0
    Flag
  • Metaldiz2000
    "25 mins at 60. There is no assistance at all out here. Not for the Weak. But there is little outside problems here"
    0
    Flag
  • Artisanabodes
    "I would like to see more protected crosswalks to the beach walkovers. Also, there needs to be lights flashing for the crosswalks especially at night."
    1
    Flag
  • Cynthia
    "Barry I live in is good for people 55 and older is all the doctors food stores drugstores are all in one room"
    0
    Flag
  • Mamariano518
    "Wildlife, landscaping and surrounded by natural Preserve . Low crime area. Lots of pets especially dogs of all kinds."
    1
    Flag
  • Becky Darnell
    "This is mostly a neighborhood of retirees and older citizens with no young children. Kids can play and ride bikes on side streets but A1A is busy with traffic."
    4
    Flag
  • Pnlweaver412
    "I’ve lived here now for 3 years and it’s quiet calm and relaxing it’s a 55 plus community and all the residents are polite and look after each other no problems with dogs in the area or cats "
    0
    Flag
  • Cynthia
    "No dog park in my development. And we have lots of dogs in the area there’s dog parks outside my neighborhood."
    0
    Flag
  • Janmgrfla
    "There is a park nearby with a lake and playground along with basketball court and a pavilion. Ormond Beach has great beaches and good schools. "
    1
    Flag
  • Sgiacomo1125
    "This area is beautiful. Mixed population. Very laid back. Would love to see more professional families move here. "
    6
    Flag
  • Heidi T.
    "This area seems very friendly and people watch out for one another. I love the location and all the activity “s"
    1
    Flag
  • Tom R.
    "Little traffic makes for a better dog walk. I have not heard any barking dogs anywhere near me. No stray cats have been seen"
    1
    Flag
  • Heather
    "Dogs are welcome, just check the breed and weight restrictions that some communities have. Lots of outdoor dining that is dog friendly, and the dog beach in Flagler is only 20 minutes away! Volusia county is NOT dog friendly on the beaches, no dogs are even allowed in your car. "
    1
    Flag
  • Jared O.
    "Plenty of sidewalks and lots of dogs so everyone is very welcoming to dog owners. Not many dog parks close by. "
    0
    Flag
  • Marcia
    "No events that I’ve seen this is a community with an hoa so there are meetings for that but other than a garage sale no events"
    0
    Flag
  • Marcia
    "Lots of dog owners and sidewalks and trails to walk. Everyone out walks dogs in this area very common. "
    0
    Flag
  • Salli010308
    "There are many dog owners in town. Most are respectful of each other’s property. There is no specific dog park but people bring their dogs to different parks in town."
    24
    Flag
  • Cheryl.kohen
    "Events at the community pool. Events in the trails shopping center. Granada events and shoppes and parade. Beach up the road. "
    0
    Flag
  • Heather V.
    "I love this neighborhood! My kids love their friends and we love our neighbors. We live close to shopping and grocery stores."
    10
    Flag
  • Danielle M.
    "They would dislike the lack of sidewalks where I live, there also needs to be a puppy park available. "
    6
    Flag
  • Jennifer M.
    "I feel safe, I think it’s a nice neighborhood, my family lives here It’s close to many stores . It’s close to the date we have a nine public park called Rockefeller Gardens, and the Granada Bridge is close and great for exercise"
    0
    Flag
  • Melissa C.
    "beautiful nice amazing friendly people............................. i love it its perfect for families and children"
    0
    Flag
  • Johnc781
    "Ormond Beach is awesome but the Over building has started, traffic is getting bad. 10 years from now you will Not Want To Live Here."
    0
    Flag
  • Lisa M.
    "There is an event at the casement park almost every other weekend. The fishing is great. The area is a little older but there’s 2 breweries, there is no traffic and you can ride your bike everywhere . I love living here! "
    0
    Flag
  • Betsy
    "We are in a gated community and love it. We have events all throughout our neighborhood. We live in Plantation Bay and love it."
    0
    Flag
  • Tim C
    "good people and great beach lots of things to see and do very pet friendly if you like quiet and a peaceful style of living I highly recommend Ormond-By-The-Sea "
    3
    Flag
  • Grneyespetite@yahoo.com
    "There are different activities however you must belong to the country club which is too expensive so we don’t have opportunity seeing we don’t belong "
    0
    Flag

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27 Winchester Rd, Ormond Beach, FL 32174 is a 3 bedroom, 2 bathroom, 3,252 sqft single-family home built in 1987. This property is not currently available for sale. 27 Winchester Rd was last sold on Nov 3, 2011 for $249,900. The current Trulia Estimate for 27 Winchester Rd is $504,500.