415 Mac Gregor Rd, Winter Springs, FL 32708
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Property image
OFF MARKET

415 Mac Gregor Rd
Winter Springs, FL 32708

  • 4 Beds
  • 3 Baths
  • 1,697 sqft

$377,200

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $2,483/mo*
Refinance Your Home

$377,200

Trulia Estimate
as of Jul 25, 2026
Est. Refi. Payment $2,483/mo*
Refinance Your Home
4 Beds
3 Baths
1,697 sqft

Local Information

  • Map ViewExplore the area around 415 Mac Gregor Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1981
Living Area
1,697 sqft
Price/Sqft
$222
Parking
Garage

About this House

Located in the Highland subdivision in Winter Springs highly desirable neighborhood A+ schools two-story corner lot freshly painted new carpet new lighting beautiful.

1 year lease
415 Mac Gregor Rd, Winter Springs, FL 32708 is a 4 bedroom, 3 bathroom, 1,697 sqft single-family home built in 1981. It last sold for $340,000 on Jan 24, 2022. More recently, it was listed as a rental in May 2017 with an asking price of $1,600 per month. That rental listing was removed on February 26, 2021. It is currently off market. The Trulia Estimate is $377,200, with a rent estimate of $2,453/month.

Home Details for 415 Mac Gregor Rd

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: OtherHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Other
Appliances & Utilities
Dishwasher

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stucco, Cement ConcreteFoundation Type: FootingLawn
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1981Year Updated: 1991
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 5009 sqft

Additional Information

On Site Laundry Available

Price History for 415 Mac Gregor Rd

DatePriceEventSource
01/24/2022$340,000Sold
N/A
12/16/2021$325,000PendingStellar MLS #O5991054
12/11/2021$325,000Listed For SaleStellar MLS #O5991054
02/26/2021ListingRemovedN/A
05/21/2017$1,600ListingRemovedN/A
05/16/2017$1,600Listed For RentN/A

Market trends in Winter Springs

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$416K
$6.33KMoM
Sale-to-List Price
98.3%
0.4%MoM
Price per sq ft
$237
$4MoM
Available listings
200
2MoM
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Property Tax and Assessment

Year2025
Tax$4,690
Assessment$332,072
Home facts updated by county records

Comparable Sales for 415 Mac Gregor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
416 Mac Gregor Rd, Winter Springs, FL
0.03
Single-Family Home
$462,000
04/01/26
3
2.5
1,962
324 Dornoch Ct, Winter Springs, FL
0.07
Single-Family Home
$399,000
07/01/26
3
2
1,579
662 Nighthawk Cir, Winter Springs, FL
0.29
Single-Family Home
$270,000
11/26/25
3
3
1,583
309 Kirkcaldy Dr, Winter Springs, FL
0.19
Single-Family Home
$307,000
09/03/25
3
2
1,326
448 Mac Gregor Rd, Winter Springs, FL
0.12
Single-Family Home
$318,400
03/27/26
2
2
1,477
221 N Devon Ave, Winter Springs, FL
0.35
Single-Family Home
$335,000
10/31/25
4
2
1,604
625 Nighthawk Cir, Winter Springs, FL
0.35
Single-Family Home
$385,000
03/09/26
3
2
1,522
721 Galloway Ct, Winter Springs, FL
0.44
Single-Family Home
$359,999
06/30/26
3
2.5
1,840
509 Osprey Ln, Winter Springs, FL
0.36
Single-Family Home
$420,000
07/30/25
3
2.5
1,756
610 Huntly Ln, Winter Springs, FL
0.39
Single-Family Home
$337,000
07/31/25
3
2
1,131

Nearby homes

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Assigned Schools

These are the assigned schools for 415 Mac Gregor Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Springs

At least 325 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say car is needed

  • 87 % Say there are sidewalks

  • 85 % Say parking is easy

  • 76 % Say it's quiet

  • 76 % Say there's holiday spirit

  • 69 % Say kids play outside

  • 69 % Say yards are well-kept

  • 68 % Say people would walk alone at night

  • 66 % Say streets are well-lit

  • 55 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say it's walkable to grocery stores

  • 47 % Say there's wildlife

  • 46 % Say it's walkable to restaurants

  • 31 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Fnybound
    "Great area to raise a Family "
    0
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  • Trulia User
    "Winter Springs is a beautiful and family-friendly community known for its peaceful neighborhoods, great schools, parks, and strong local connections. The city offers a perfect balance of nature and modern living, with walking trails, community events, and local businesses that make residents feel at home. Winter Springs continues to grow while maintaining its welcoming small-town atmosphere and community pride."
    0
    Flag
  • Jacinda.de_jesus
    "People here are usually very friendly. I’ve met a lot of nice neighbors while on walks and they always say hello, sometimes even hold full conversations about my dogs. My neighbors look out for me and I do the same for them. "
    0
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  • heisa pulgarin
    "Is a very safe and clean area to live in, very green and peaceful, if you’re looking for a place close to stores , and with variety this is the place , all the stores are around winter springs , schools,churches and grocery stores are literally minutes :)"
    0
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  • Ismel
    "Great neighborhood, very quiet place to live, is near to a lot of markets very secure, a dog friendly neighborhood "
    0
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  • Jayme Messana
    "Lots of parks; great neighborhood! Very friendly people in the area Some neighborhoods do not have sidewalks. But that is okay for us. Just be careful crossing streets of course. "
    0
    Flag
  • Trulia User
    "Neighborhood is quite well maintained and is safer than most locations. Stores are nearby , supermarkets etc.. "
    0
    Flag
  • Kbarontini
    "The people that complain about dogs being walked and owners not picking up after them. Also dogs urinatiing in the grass. Dogs must be on leash always. No where for them to run."
    1
    Flag
  • Jhxr74
    "There are many areas to walk dogs. We are happy that owners police the area when the dog does it's business."
    3
    Flag
  • Emelinda10
    "The area is very clean, great parks, easy traffic. Close to major stores. The whole are is new a lot of restaurants and green areas. "
    2
    Flag
  • Kimberly_Vach
    "It’s a great place to raise kids and the county is an A+ school district! You are far enough away for privacy, but close enough to be involved in whatever your family chooses."
    0
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  • Christine
    "Dogs are on leash at all times. When meeting other dogs, owners are good about asking for pet introductions."
    0
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  • Erica G.
    "My mother lives in the area and has been for the last 10yrs. We have always felt very safe and it’s always clean."
    2
    Flag
  • Tina B.
    "quarterly neighborhood parties, great schools, safe and good neighbors of all backgrounds get along "
    0
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  • Laxsurfer1117
    "I’ve lived here since I was a kid and I’m 28 now, never had any huge issues wherever I’ve lived. Overall winter springs is very community driven and that’s what makes it unique."
    1
    Flag
  • Bobbie V.
    "Winter springs, in general, is fine. Nothing really going on here, but it is not a bad place to live. My street and the area surrounding me are not great, but to be fair, I only the people living next to us (fairly social guy, myself) and they ARE nice and cool. I have heard so many bad things, the police are ALWAYS in and out of my neighborhood AND held my girlfriend up for questioning as she walked out of our back door because they thought I was somebody else. We’re trying to move out of here. TL;DR: Winter Springs: Nothing going on, Not an awful spot, stay off Lori Anne Ln and maybe the block or two around it."
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  • Darren J. W.
    "Living at the apartments is always going to be tricky but for the most part the leasing offices do an amazing job; when it comes to the people living there, just be aware that some care and some don’t. "
    0
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  • Angeltillis
    "The neighborhood is very family friendly and the public areas are beautiful. It is a very safe and nice neighborhood."
    0
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  • Nellieroth
    "You can walk your dog, seems like most people have a dog in this neighborhood, so don’t think you’ll have a problem feeling welcomed. "
    0
    Flag
  • Shelby S.
    "No dog park or large area for them to run and play. Not many other dogs in the neighborhood.. not many big back yards either"
    0
    Flag
  • Joelchoate5
    "I have lived in the neighborhood for 5 years And it's a nice place to raise your children It's generally a quiet and peaceful place"
    0
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  • Jrutherf32708
    "I have lived in Winter Springs / Tuskawilla area over 25 years. It’s been an excellent place to live and raise 3 children. We have never any problems with crime or neighbors. Great public schools here ; all “A” rated. I highly recommend this area !"
    0
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  • Abdul I.
    "Diversity and everyone is polite. People mind their own business but also friendly. Affordable rent and education in local school is relatively high standards. "
    0
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  • Robin M.
    "There are great spaces and wide sidewalks with lots of green area. Plus a huge dog park right in the middle of the town"
    5
    Flag
  • Kimberly P.
    "Close to 417 and main highways for easy travel. Near Orlando for attractions and fun. Schools are rated A. "
    1
    Flag
  • Miketabo
    "good, safe. the school system is great just have to travel to oviedo for shopping and restaurants. but it is very family friendly in winter springs"
    0
    Flag
  • Pam
    "Annual Family Picnic. Very neighborly neighborhood. Lots of children and activities for them through out the year. "
    0
    Flag
  • Cindysnead28
    "No sidewalks kids ride bikes in streets not safe the kids need to watch out for cars and trucks sidewalks are needed badl"
    0
    Flag
  • Shirley R.
    "I love this neighborhood it’s safe and secluded but still close enough to all the action. Great schools "
    0
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  • Arniearmadillo
    "Plenty of public transportation options and access to multiple highway options. Great restaurants and shopping options."
    0
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  • Signupzachary
    "Great place to raise a family or for new home owners. Close to a lot but also very quiet. The city is growing and has lot to offer but it’s also close to a main highway that can cause working in a different part of ORLANDO much easier "
    0
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  • Marie B.
    "Heavy traffic at peak hours but not outrageous. Not too bad. Traffic is thick around schools. Toll roads help. "
    0
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  • Colleen J.
    "Right off of numerous major roads, but also tucked back away from the chaos. Close to I4 making for a easy commute in multiple directions "
    0
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  • Nancyn425
    "Our neighbors care about each other and go out of their way to help each other. We make meals for each other, talk often, have get togethers for Halloween, 4th of July, Super Bowl, etc."
    0
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Explore by feature - Pet Friendly

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Homes for sale near 415 Mac Gregor Rd

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Off Market Homes Near 415 Mac Gregor Rd

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