Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$470,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,962 Sq. Ft.
  • Updated 2 hours ago

Next open house:

Open House: 4:00 PM - 6:00 PM

Friday 2/6 4:00 PM - 6:00 PM

416 Macgregor Road,Winter Springs, FL 32708

416 Macgregor RoadWinter SpringsFL32708

Get directions

View more dates

Join us at 416 Macgregor Road on:

  • Open House: 11:00 AM - 2:00 PM

    Saturday 2/7 11:00 AM - 2:00 PM

    416 Macgregor Road,Winter Springs, FL 32708
    416 Macgregor RoadWinter SpringsFL32708
  • Open House: 1:00 PM - 3:00 PM

    Sunday 2/8 1:00 PM - 3:00 PM

    416 Macgregor Road,Winter Springs, FL 32708
    416 Macgregor RoadWinter SpringsFL32708
See This Home
Save This Home
See This Home
Save This Home
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.

Full Property Details for 416 MacGregor Rd

General

  • Price: $470,000
  • HOA FEE: $40/month
  • HOA FEE FREQ.: Annually
  • Taxes: $5,743 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6379428
  • Updated: 2/5/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 10
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
  • Appliances: Dishwasher, Disposal, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Luxury Vinyl, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: In Garage

Additional Information

  • Shared Amenities: Park, Playground, Pool

Exterior

  • Exterior Features: Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Patio, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Patio, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • County: Seminole
  • Development Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • Subdivision: HIGHLAND VILLAGE 2
  • Driving Directions: From I-4 east, turn right onto State Road 434. Travel approximately 3 miles towards Winter Springs. Turn left on Sheoah. Right on Third St, Left on MacGregor.
  • Direction Faces: South

School Information

  • Elementary School: Highlands Elementary
  • Middle School: South Seminole Middle
  • High School: Winter Springs High

Community

  • Community Name: 32708 - Casselberrry/Winter Springs / Tuscawilla
  • Community Features: Deed Restrictions, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Park, Playground, Pool
  • Association: Yes
  • Assoc. Name: The Highlands Homeowners Association
  • Pet Restrictions: Buyer and Buyer Agent to Verify Any Pet Restrictions with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Electricity Connected, Public, Sewer Connected, Street Lights, Water Connected

Structural Information

  • Architectural Info: Contemporary
  • Architectural Style: Contemporary
  • Exterior Const.: Block, Brick, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 1,962
  • Sq. Ft. Source: Public Records
  • Year Built: 1989

Lot Features

  • Lot Size (Acres): 0.11
  • Lot Size (Sq. Ft.): 4,752
  • Lot Size: 4752
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Association Fee: $475
  • Assoc Fee Freq.: Annually
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,743
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 70 HIGHLAND VILLAGE 2 PB 40 PGS 40 & 41
  • Flood Zone Info: X
  • APN: 34203053200000700
  • Property ID: 34203053200000700

Listed by Compass Florida Llc

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 416 MacGregor Rd —

  • Compass Florida Llc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 416 MacGregor Rd

School District:Seminole County School District
NameGradesDistance
Highlands Elementary School, Winter Springs, FL
1600 Shepard Road, Winter Springs, FL 32708
K-50.8 mi
Seminole Academy Of Digital Learning
450 Technology Park, Lake Mary, FL 32746
6-83.7 mi
Winter Springs High School
130 Tuskawilla Road, Winter Springs, FL 32708
9-122.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 416 MacGregor Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/04/2026
Listed
$470,000
42.42%
MLS
11/20/2025
Sold
$330,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 416 MacGregor Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,744
-3%
$357,251
-5%
2024
$5,930
259%
$377,254
156%
2023
$1,650
-1%
$147,114
3%
2022
$1,662
6%
$142,829
3%
2021
$1,573
1%
$138,669
1%
2020
$1,555
3%
$136,754
4%
2018
$1,513
1%
$131,186
2%
2017
$1,496
-2%
$128,488
2%
2016
$1,520
-1%
$125,845
1%
2015
$1,538
1%
$124,970
-7%
2019
$1,529
—
$133,679
8%
2014
$1,526
-1%
$123,978
1%
2013
$1,539
—
$122,146
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 416 MacGregor Rd

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Compass Florida Llc

Similar Properties near 416 MacGregor Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

557 Karen Ave, Altamonte Springs, FL 32701 - Photo 1
$475,000

557 Karen Ave  Altamonte Springs, FL 32701

  • Single Family
  • Active
  • Updated 13 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,961
    Sq. Ft.
Listed by Adair Realty Inc
7618 Waunatta Ct, Winter Park, FL 32792 - Photo 1
$465,000

7618 Waunatta Ct  Winter Park, FL 32792

  • Single Family
  • Active
  • Updated 13 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,970
    Sq. Ft.
Listed by Phoenix Realty Advisors Llc and Stellar Non-Member Office
562 Pleasant Grove Dr, Winter Springs, FL 32708 - Photo 1
$470,000

562 Pleasant Grove Dr  Winter Springs, FL 32708

  • Single Family
  • Active
  • Updated 7 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,579
    Sq. Ft.
Listed by Regency Real Estate Llc
1352 Ortega St, Winter Springs, FL 32708 - Photo 1 Price Reduced
-$15,000 (-3.09%)
$470,000

1352 Ortega St  Winter Springs, FL 32708

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,407
    Sq. Ft.
Listed by Florida Connexion Properties

Just Listed near 416 MacGregor Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

342 Coble Dr, Longwood, FL 32779 - Photo 1 Just Listed
$560,000
Open House

342 Coble Dr  Longwood, FL 32779

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,596
    Sq. Ft.
Listed by Veronica Parker (407) 718-6983
1404 & 1436 N Ronald Reagan Blvd, Longwood, FL 32750 - Photo 1 Just Listed
$2,800,000

1404 & 1436 N Ronald Reagan Blvd  Longwood, FL 32750

  • Office
  • Active
Listed by Mike Palombi (407) 754-6230
2878 Willow Bay Terrace, Casselberry, FL 32707 - Photo 1 Just Listed
$600,000

2878 Willow Bay Terrace  Casselberry, FL 32707

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,892
    Sq. Ft.
Listed by The Suzanne Muchow Team (407) 696-8000
248 Cambridge Dr, Longwood, FL 32779 - Photo 1 Just Listed
$520,000
Open House

248 Cambridge Dr  Longwood, FL 32779

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,001
    Sq. Ft.
Listed by Adams, Cameron & Co., Realtors

Price Reduced near 416 MacGregor Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

314 E Bonnie Trail, Longwood, FL 32750 - Photo 1 Price Reduced
-$13,000 (-3.25%)
$387,000

314 E Bonnie Trail  Longwood, FL 32750

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,293
    Sq. Ft.
Listed by Karen O'Neil (407) 789-5565
1742 Fifeshire Ct, Longwood, FL 32779 - Photo 1 Price Reduced
-$105,000 (-7%)
$1,395,000

1742 Fifeshire Ct  Longwood, FL 32779

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 7
    Total Baths
  • 4,053
    Sq. Ft.
Listed by Trusthome Properties Inc
4000 Crossroads Pl, Casselberry, FL 32707 - Photo 1 Price Reduced
-$10,000 (-4.02%)
$239,000

4000 Crossroads Pl  Casselberry, FL 32707

  • Townhouse
  • Active
  • Updated 7 days ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,260
    Sq. Ft.
Listed by Set Homes Realty Llc
1260 Seminola Blvd, Casselberry, FL 32707 - Photo 1 Price Reduced
-$100 (-0.03%)
$374,900

1260 Seminola Blvd  Casselberry, FL 32707

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,644
    Sq. Ft.
Listed by Cameron Realty Group Llc

Recent Sales near 416 MacGregor Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

746 N Gretna Ct, Winter Springs, FL 32708 - Photo 1 Sold
$410,000

746 N Gretna Ct  Winter Springs, FL 32708

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,652
    Sq. Ft.
Listed by Re/Max 200 Realty
Sold by Century 21 Integra
821 Sheoah Cir, Winter Springs, FL 32708 - Photo 1 Sold
$430,000

821 Sheoah Cir  Winter Springs, FL 32708

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,185
    Sq. Ft.
Listed by Cfrp Realty Llc
Sold by Young Real Estate
540 Seven Oaks Blvd, Winter Springs, FL 32708 - Photo 1 Sold
$525,000

540 Seven Oaks Blvd  Winter Springs, FL 32708

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 3,108
    Sq. Ft.
Listed by Sand Dollar Realty Group Inc
Sold by Alliance Real Estate Group
881 E Church Ave, Longwood, FL 32750 - Photo 1 Sold
$400,000

881 E Church Ave  Longwood, FL 32750

  • Single Family
  • Closed
  • 4
    Beds
  • 2
    Total Baths
  • 1,620
    Sq. Ft.
Listed by House Hunting in Florida Llc
Sold by House Hunting in Florida Llc and Kardosh Realty

416 Macgregor Road, Winter Springs, FL 32708 (MLS# O6379428) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 416 Macgregor Road is currently listed for $470,000 and was received on February 04, 2026. Want to learn more about 416 Macgregor Road? Do you have questions about finding other Single Family real estate for sale in Winter Springs? You can browse all Winter Springs real estate or contact a Coldwell Banker agent to request more information.

Tour this property