416 MACGREGOR ROAD, Winter Springs, FL 32708
SOLD
APR 1, 2026

$459,600

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 1,962 sqft

416 MACGREGOR ROAD, Winter Springs, FL 32708

Est. Refi. Payment $3,068/mo*
Refinance Your Home
Currently Off Market - Sold Apr 1, 2026 for $462,000 (2% below list price)

Home Value

Trulia Estimate
$460K
Since last month
Decreased$1K (-0.2%)
Since last year
Increased$62K (+15.5%)
Since last sale
Decreased$3K (-0.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +106% in the last 10 years
MonthEstimated value
2026
August 2026$459K
August 2026$459K
July 2026$460K
June 2026$459K
May 2026$460K
April 2026$461K
March 2026$463K
February 2026$463K
January 2026$367K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
324 DORNOCH COURT, Winter Springs, FL
0.09
Single-Family Home
$399,000
07/01/26
3
2
1,579
448 MACGREGOR ROAD, Winter Springs, FL
0.13
Single-Family Home
$350,000
08/04/26
2
2
1,477
662 NIGHTHAWK CIRCLE, Winter Springs, FL
0.26
Single-Family Home
$270,000
11/26/25
3
3
1,583
625 NIGHTHAWK CIRCLE, Winter Springs, FL
0.32
Single-Family Home
$385,000
03/09/26
3
2
1,522
472 DEWARS COURT, Winter Springs, FL
0.21
Single-Family Home
$505,000
08/28/26
4
2.5
2,222
224 HIGHLANDS GLEN CIRCLE, Winter Springs, FL
0.37
Single-Family Home
$290,000
07/10/26
3
2
1,185
721 GALLOWAY COURT, Winter Springs, FL
0.42
Single-Family Home
$359,999
06/30/26
3
2.5
1,840
240 N DEVON AVENUE, Winter Springs, FL
0.35
Single-Family Home
$332,000
08/18/26
3
2
1,238
746 N GRETNA COURT, Winter Springs, FL
0.54
Single-Family Home
$410,000
01/09/26
3
2
1,652

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
410 MACGREGOR ROAD, Winter Springs, FL 32708
0.03
$389,400
3
2
1,757
Off Market
423 SHEOAH BOULEVARD #11, Winter Springs, FL 32708
0.08
$190,900
3
2
1,187
Off Market
428 MAC GREGOR ROAD, Winter Springs, FL 32708
0.05
$365,000
3
2
1,617
Off Market
417 SHEOAH BOULEVARD #17, Winter Springs, FL 32708
0.09
$170,000
2
2
936
For Sale
421 SHEOAH BOULEVARD #5, Winter Springs, FL 32708
0.10
$156,900
2
1.5
1,080
Off Market
314 BRIDIE COURT, Winter Springs, FL 32708
0.05
$379,600
3
2
1,579
Off Market
30 MOREE LOOP #39, Winter Springs, FL 32708
0.10
$201,600
3
2.5
1,400
Off Market
30 MOREE LOOP #37, Winter Springs, FL 32708
0.10
$125,000
3
2.5
1,400
Recently Sold
10 MOREE LOOP #3, Winter Springs, FL 32708
0.11
$125,000
2
1.5
1,080
Recently Sold
40 MOREE LOOP #1, Winter Springs, FL 32708
0.11
$229,000
3
2.5
1,400
Off Market
40 MOREE LOOP #11, Winter Springs, FL 32708
0.11
$166,000
3
2.5
1,400
Recently Sold

Local Information

  • Map ViewExplore the area around 416 MACGREGOR ROAD.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1989
1,962 sqft
$235/sqft
2 Car Garage
HOA $73/mo

About this House

This home is a true MUST SEE!!! This beautifully renovated 3-bedroom, 2.5-bath with a loft, two-story home is located in the highly sought-after Highlands community of Winter Springs. This spacious and open floor plan offers a living room/dining room combo as well as a family room, all enhanced by soaring cathedral ceilings that flood the home with natural light. The stunning kitchen is truly a chef’s delight, featuring brand-new appliances, ample cabinetry, generous countertop space, a breakfast bar, and an island—all perfectly positioned to overlook the family room, making it ideal for entertaining. The first-floor primary suite offers a private retreat, while upstairs you’ll find the additional bedrooms and an open loft that overlooks the main living areas. The loft includes a closet and can easily be converted into a fourth bedroom or home office. This home has been thoughtfully updated from top to bottom with new roof (9/2025), new flooring, new fixtures, fresh interior paint, and a new roof, offering peace of mind for years to come. Sliding glass doors lead to a screened patio and a spacious backyard with no rear neighbors, providing added privacy and outdoor enjoyment. Residents of The Highlands enjoy access to community amenities including a swimming pool, tennis courts, and a playground. Conveniently located near top-rated schools, shopping, dining, and major expressways, this open, bright, and move-in-ready home truly has it all.
416 MACGREGOR ROAD, Winter Springs, FL 32708 is a 3 bedroom, 3 bathroom, 1,962 sqft single-family home built in 1989. It last sold for $462,000 on Apr 1, 2026 (2% below the $470,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $459,600, with a rent estimate of $2,572/month.
Last check for updates: about 14 hours ago
Listed by Mario Zendeli, (407) 325-3893
COMPASS FLORIDA LLC, (407) 203-9441
Bought with: Crystal Adams, (407) 927-9610, RE/MAX INNOVATION, (407) 281-1053
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6379428
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 416 MACGREGOR ROAD

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 2, Dining Room, Family Room, Kitchen, Living Room, Loft
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1962 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Electricity Connected, Public, Sewer Connected, Street Lights, Water ConnectedAppliances: Dishwasher, Disposal, Microwave, Range, RefrigeratorDishwasherDisposalLaundry: In GarageMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: Sliding DoorsFlooring: Carpet, Luxury Vinyl, Tile
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Luxury Vinyl, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Patio, Rear Porch, ScreenedVegetation: Oak Trees, Trees/LandscapedExterior: SidewalkFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 19

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Block, Brick, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 34203053200000700

Price & Status

Price
List Price: $470,000Price Per Sqft: $235/sqft
Status Change & Dates
Off Market Date: Thu Feb 26 2026Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER SPRINGSCommunity: HIGHLAND VILLAGE 2
School Information
Elementary School: Highlands ElementaryJr High / Middle School: South Seminole MiddleHigh School: Winter Springs High

Building

Building Area
Building Area: 2565 Square Feet

Community

Community Features: Deed Restrictions, Park, Playground, Pool, SidewalksNot Senior Community
Other
Playground

HOA

HOA Name: The Highlands Homeowners AssociationHOA Phone: 407-260-1011HOA Name (second): The HighlandsAssociation for this Listing: Orlando RegionalHas an HOAHOA Fee: $73/Monthly

Lot Information

Lot Area: 4752 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6379428Back On Market Date: Thu Feb 12 2026Showing Requirements: ShowingTimeUniversal Property Id: US-12117-N-34203053200000700-R-N

Additional Information

HOA Amenities: Park,Playground,Pool

Price and Tax history

DateEventPrice
Apr 1, 2026
Source: Stellar MLS #O6379428
Sold
$462,000
Feb 27, 2026
Source: Stellar MLS #O6379428
Pending
$470,000
Feb 12, 2026
Source: Stellar MLS #O6379428
PendingToActive
$470,000
Feb 9, 2026
Source: Stellar MLS #O6379428
Pending
$470,000
Feb 4, 2026
Source: Stellar MLS #O6379428
Listed For Sale
$470,000

Market trends in Winter Springs

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$414K
$8KMoM
Sale-to-List Price
99.1%
0.6%MoM
Price per sq ft
$229
$1MoM
Available listings
173
18MoM

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
    Flag
  • 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
    Flag
  • Ismel
    "Great neighborhood, very quiet place to live, is near to a lot of markets very secure, a dog friendly neighborhood "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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

Frequently asked questions about 416 MACGREGOR ROAD

  • What is 416 MACGREGOR ROAD estimated to be worth?
    Trulia's estimated value for 416 MACGREGOR ROAD in Winter Springs, FL is $459,600.
  • What is the price history for 416 MACGREGOR ROAD?
    416 MACGREGOR ROAD in Winter Springs, FL last sold for $462,000 in April 2026.
  • 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 416 MACGREGOR ROAD have air conditioning?
    Yes, 416 MACGREGOR ROAD in Winter Springs, FL has air conditioning.
  • Does 416 MACGREGOR ROAD have a pool?
    Yes, 416 MACGREGOR ROAD in Winter Springs, FL has a pool.

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