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

$349,400

Trulia Estimate
as of Sep 12, 2026
  • 3 Beds
  • 2 Baths
  • 1,453 sqft

320 Mac Gregor Rd, Winter Springs, FL 32708

Home Highlights

Single-Family Home
1,453 sqft
$240/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 320 Mac Gregor Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.

This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices.

Want to tour on your own? Click the "Self Tour" button on this home's RentProgress.

Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and connected. Homes like this don't stay on the market for longdon't miss your chance to make it yours. Apply today!

The Homeowners Association (HOA) for this home has a separate application process that applicants will need to complete in addition to Progress Residential's application. This includes self-registering with the HOA, completing the HOA's approval process, and paying any fees required by the HOA.

Some images have been virtually staged to help showcase the potential of spaces in the home. The furnishings shown are for illustrative purposes only and are not included in the home.
320 Mac Gregor Rd, Winter Springs, FL 32708 is a 3 bedroom, 2 bathroom, 1,453 sqft single-family home. It last sold for $255,000 on Jan 27, 2021 (10,547% above the $2,395 asking price). More recently, it was listed as a rental in February 2026 with an asking price of $2,545 per month. That rental listing was removed on March 31, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $349,400, with a rent estimate of $2,266/month.
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Home Details for 320 Mac Gregor Rd

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For DetailsAvailable: now

Interior Features

Heating & Cooling
Cooling System: Ceiling Fan
Levels, Entrance, & Accessibility
Floors: Tile

Exterior Features

Parking & Garage
GarageParking: Attached Garage, On Site

Comparable Sales for 320 Mac Gregor Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
224 HIGHLANDS GLEN CIRCLE, Winter Springs, FL
0.24
Single-Family Home
$290,000
07/10/26
3
2
1,185 sqft
324 DORNOCH COURT, Winter Springs, FL
0.20
Single-Family Home
$399,000
07/01/26
3
2
1,579 sqft
140 Bombay Ave, Winter Springs, FL
0.19
Single-Family Home
$200,000
08/10/26
3
2
1,373 sqft
60 Moree 45 Loop, Winter Springs, FL
0.26
Single-Family Home
$185,000
10/01/25
3
2
1,187 sqft
240 N DEVON AVENUE, Winter Springs, FL
0.30
Single-Family Home
$332,000
08/18/26
3
2
1,238 sqft
662 NIGHTHAWK CIRCLE, Winter Springs, FL
0.30
Single-Family Home
$270,000
11/26/25
3
3
1,583 sqft
448 MACGREGOR ROAD, Winter Springs, FL
0.26
Single-Family Home
$350,000
08/04/26
2
2
1,477 sqft
466 Club Dr, Winter Springs, FL
0.42
Single-Family Home
$282,000
10/22/25
3
2
1,218 sqft
121 N FAIRFAX AVENUE, Winter Springs, FL
0.40
Single-Family Home
$330,000
03/10/26
3
2
1,336 sqft
625 NIGHTHAWK CIRCLE, Winter Springs, FL
0.37
Single-Family Home
$385,000
03/09/26
3
2
1,522 sqft

Nearby homes

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Rental Market Trends in Winter Springs

Last updated Sep 2026
Trulia Rent Estimate$2,266/mo
Average rent
$2.2K
$99MoM
Available listings
84
View rental market trends in Winter Springs, FL

Around this home

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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Angeltillis
    "The neighborhood is very family friendly and the public areas are beautiful. It is a very safe and nice neighborhood."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Marie B.
    "Heavy traffic at peak hours but not outrageous. Not too bad. Traffic is thick around schools. Toll roads help. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Mar 31, 2026
Source: Zillow Rentals
ListingRemoved
$2,395
Mar 31, 2026
Source: Zillow Rentals
PriceChange
$2,395
Price decreased by 1%
Mar 17, 2026
Source: Zillow Rentals
PriceChange
$2,420
Price decreased by 2%
Mar 10, 2026
Source: Zillow Rentals
PriceChange
$2,470
Price decreased by 3%
Mar 1, 2026
Source: Zillow Rentals
PriceChange
$2,545
Price increased by 7%

Frequently asked questions about 320 Mac Gregor Rd

  • What is 320 Mac Gregor Rd estimated to be worth?
    Trulia's estimated value for 320 Mac Gregor Rd in Winter Springs, FL is $349,400.
  • What is the price history for 320 Mac Gregor Rd?
    320 Mac Gregor Rd in Winter Springs, FL last sold for $255,000 in January 2021.
  • Is Winter Springs a buyer's or seller's market?
    Winter Springs is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Springs?
    The median sale price in Winter Springs is $414K. That is up $8K from the prior month.
  • Does 320 Mac Gregor Rd have air conditioning?
    Yes, 320 Mac Gregor Rd in Winter Springs, FL has air conditioning.
  • Does 320 Mac Gregor Rd have a garage?
    Yes, 320 Mac Gregor Rd in Winter Springs, FL has an attached garage.

Homes for rent near 320 Mac Gregor Rd

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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