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.
Est. $2,772 per month, based on comparable rentals
Sale and tax history for 416 Macgregor Rd
Sale History
Tax History
Date
Event
Price
Stellar MLS as Distributed by MLS Grid #O6379428
Apr 1, 2026
Sold
$462,000
$235/sq ft
Feb 27, 2026
Pending
—
Feb 12, 2026
Relisted
—
Feb 9, 2026
Pending
—
Feb 4, 2026
Listed
$470,000
$240/sq ft
Stellar MLS as Distributed by MLS Grid #O6347470
Nov 20, 2025
Sold
$330,000
$168/sq ft
Oct 27, 2025
Pending
—
Oct 20, 2025
Price Changed
$375,000
$191/sq ft
Oct 7, 2025
Price Changed
$399,000
$203/sq ft
Sep 27, 2025
Listed
$414,000
$211/sq ft
Feast your eyes on this 3-bedroom, 2.5 bath, 2-story home in the sought after Highlands community in Winter Springs. Enjoy the convenience of a formal living room, dining room and family room. The kitchen is open and has a perfect view into the family room. The master suite has a private location on the first floor. Beautiful high vaulted ceilings add the perfect touch. The other bedrooms are located upstairs as well as the open loft that looks down over the family room and kitchen. The loft has a closet and can easily be converted into a 4th bedroom. The interior has been freshly painted. A brand-new roof was just installed for a peace of mind for years to come. Glass sliders lead out to the screened patio and the spacious yard. Enjoy the privacy of No rear neighbors. This one does need all new flooring and your personal touches. The community offers a swimming pool, tennis and playground. It's conveniently located to great shopping, restaurants, and expressways. Don't forget the top-rated schools.
Public Records
Dec 1, 1988
Sold
$1,308,000
$667/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$5,783 (+267.7%)
$85,000 + $272,251
$357,251
2021
$1,573 (+1.1%)
2020
$1,555 (+1.7%)
2019
$1,529 (+1.1%)
2018
$1,513 (+1.1%)
2017
$1,496 (−2.6%)
2015
$1,537 (+0.8%)
2014
$1,525 (−0.9%)
2013
$1,539 (+0.7%)
2012
$1,528
Public record
Public record
Zoning
Permits
Beds
3
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
4,757 Sq. Ft.
Year renovated
1989
Sq. Ft.
1,962
Year built
1989
Style
Single Family Residential
County
Seminole County
APN
34203053200000700
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 3, 2026.
PUD
Planned Unit Development District
The intent and purpose of the planned unit development PUD district are to accomplish, through a master plan with an appropriate mix of uses, a more desirable environment and efficient land use pattern than would be possible through a strict application of Euclidian zoning, while adhering to the provisions of the comprehensive plan and applicable federal and state regulations. The purpose of the PUD is further defined to: Allow a more flexible management structure for the efficient, orderly, and sustainable integration of uses, consistent with and complementary to their context within the community; Create a greater sense of place, community, and neighborhood identity, through superlative urban design and innovation; Provide a development plan that is compatible with and complements the surrounding community, creating a safe inviting environment, a sense of place, and neighborhood cohesiveness; Maintain, enhance, and preserve salient or otherwise significant existing natural features, by identifying these features and designing the project to incorporate them as view-sheds, terminating vistas, focal points, and/or other scenic amenities; Provide the greatest choice of realistic, safe, functional, interconnected, and convenient multi-modal transportation options within the PUD and with the surrounding areas; Limit urban sprawl, greenhouse gas emissions, stormwater runoff, and vehicle miles traveled; Provide economically efficient means for delivery of government services and infrastructure; Provide a mix of housing designed in pedestrian scale neighborhood unit increments; Incorporate energy and water efficient land use patterns and technologies beyond the minimums required by state law or the Florida Building Code; Promote positive interaction among and between uses and, where residential is included, the use of residential housing types that could not readily be accomplished through Euclidean zoning; Incorporate crime prevention through environmental design CPTED principles compatible with the pedestrian-oriented design; and Further the goals, objectives and policies of the comprehensive plan.
Sep 8, 2025 • Final
Roof - residential
Remove and replace asphalt shingles for a residential re-roofing project.
Roofing
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Lot Features: City Limits, In County, Sidewalk, Paved
Lot Size Acres: 0.11
Road Surface Type: Asphalt
Lot Size Square Meters: 441
Building Information
MFR_BuildingAreaTotalSrchSqM: 238.30
Financial
Tax Information
Tax Annual Amount: $5,743
Tax Year: 2025
Lease / Rent Details
Lease Restrictions YN: 0
Utilities
Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: BB/HS Internet Available, Electricity Connected, Public, Sewer Connected, Water Connected
Location
Multi-Family Financial Information
Total Annual Fees: $879
Total Monthly Fees: $73.25
Multi-Unit Information
Unit Number YN: 0
Furnished: Unfurnished
HOA Information
Association Name: The Highlands Homeowners Association
Association 2 Name: The Highlands
Has HOA
MFR_Association2YN: 1
Association Fee Requirement: Required
Association Approval Required Y/N: 0
Monthly HOA Amount: 39.58
Association Amenities: Park, Playground, Pool
Association Fee: $475
Association Fee Frequency: Annually
Association Fee 2: $404
Association Fee 2 Frequency: Annually
School Information
Elementary School: Highlands Elementary
Middle Or Junior High School: South Seminole Middle
High School: Winter Springs High
Location Information
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.
Community Information
Community Features: Deed Restrictions, Park, Playground, Pool, Sidewalks, Street Lights
Pets Allowed: Cats OK, Dogs OK
Public facts
Beds: 3
Baths: 3.0
Sq. Ft.: 1,962
Stories: 2.0
Lot Size: 4,757 square feet
Style: Single Family Residential
Year Built: 1989
Year Renovated: 1989
County: Seminole County
APN: 34203053200000700
Home facts updated by county records on Aug 3, 2026
Other
Miscellaneous Information
Third Party YN: 1
Listing Information
Attribution Contact: 407-203-9441
Previous Status: Pending
Backups Requested YN: 1
Listing Date Information
Days to Contract: 22
BOM Date: 2026-02-12T00:00:00.000
Status Contractual Search Date: 2026-04-01
Listing Price Information
Calculated List Price By Calculated Sq Ft: 239.55
Green Information
Green Verification Count: 0
Direction Faces: South
Home Information
Living Area: 1962
Living Area Units: Square Feet
Living Area Source: Public Records
Living Area Meters: 182.28
Building Area Total: 2565
Building Area Units: Square Feet
Building Area Source: Public Records
Foundation Details: Slab
Stories Total: 2
Levels: Two
Around this home
Schools
Highlands Elementary School
Public PreK-5 • Assigned • 0.8mi
7/10
A Seminole County Virtual School
Public K-12 • Assigned • 3.7mi
Winter Springs High School
Public 9-12 • Assigned • 2.7mi
6/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
8/10 Heat Factor
7 days above 108° expected this year, 22 days in 30 years
9/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Winter Springs, FL • 32708
Average low and high temperatures (°F)
68
47
74
53
80
59
83
64
90
71
91
74
93
75
91
76
89
74
82
67
78
58
73
54
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
In this area, properties receive around 8.7 hours in
June and 6.7 hours in December, placing it above the
U.S. average for solar exposure.
8.7 hrs
6.7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$472,000 – $571,000
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