Under contract-accepting backup offers. 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.
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.
Property Details
Price:
$470,000
MLS #:
O6379428
Status:
Pending
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
HIGHLAND VILLAGE 2
Neighborhood:
32708casselberrrywinterspringstuscawilla
Listed Date:
Feb 4, 2026
Finished Sq Ft:
1,962
Total Sq Ft:
2,565
Lot Size:
4,752 sqft / 0.11 acres (approx)
Year Built:
1989
See this Listing
Schools
Elementary School:
Highlands Elementary
Middle School:
South Seminole Middle
High School:
Winter Springs High
Interior
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Luxury Vinyl, Tile
Heating
Central, Electric
Laundry Features
In Garage
Exterior
Architectural Style
Contemporary
Association Amenities
Park, Playground, Pool
Community Features
Deed Restrictions, Park, Playground, Pool, Sidewalks
Construction Materials
Block, Brick, Wood Frame
Exterior Features
Sidewalk, Sliding Doors
Parking Features
Driveway, Garage Door Opener
Roof
Shingle
Financial
HOA Fee
$475
HOA Fee 2
$404
HOA Frequency
Annually
HOA Name
The Highlands Homeowners Association
Tax Year
2025
Taxes
$5,743
Map
Community
- Address416 MACGREGOR ROAD WINTER SPRINGS FL
- SubdivisionHIGHLAND VILLAGE 2
- CityWINTER SPRINGS
- CountySeminole
- Zip Code32708
Subdivisions in WINTER SPRINGS
- AMHERST
- ARROWHEAD AT TUSCAWILLA UNIT 1
- ARROWHEAD AT TUSCAWILLA UNIT 2
- AVERY PARK
- BARCLAY RESERVE TWNHMS
- BARRINGTON ESTATES
- BAY TREE SEC 08
- BAY TREE SEC 09
- BAY TREE SEC 10
- BAYTREE VILLAGE
- BENTLEY CLUB AT BENTLEY GREEN
- CASA PARK VILLAS PH 1
- CASA PARK VILLAS PH 2
- CHELSEA PARC AT TUSCAWILLA PH 2
- COUNTRY CLUB VILLAGE
- COUNTRY CLUB VILLAGE UNIT 1
- COUNTRY CLUB VILLAGE UNIT 3
- COUNTRY CLUB VLG UNIT 1
- CYPRESS CLUB
- CYPRESS VILLAGE 3RD REP TR C PH 1
- D R MITCHELLS SURVEY OF THE LEVY GRANT
- DEER RUN UNIT 19A
- DEER RUN UNIT 23C
- DEERSONG 2
- DUNMAR ESTATES 5 ACRE DEV 28 PARCELS
- EAGLES POINT PH 5
- EAGLES WATCH PH 2
- ENCLAVE AT DUNMAR
- ENTZMINGER FARMS ADD 2
- FOX GLEN AT CHELSEA PARC TUSCAWILLA
- FOX GLEN AT CHELSEA PARC TUSCAWILLA PH 2
- FOXMOOR EAST
- FOXMOOR UNIT 1
- FOXMOOR UNIT 3
- GARDEN CLUB APTS
- GEORGETOWNE UNIT 3
- GLEN EAGLE
- GLEN EAGLE UNIT 1
- GREENBRIAR SUB PH 1
- GREENBRIAR SUB PH 2
- GREENBRIAR/ TUSCAWILLA
- GREENS AT TUSCAWILLA
- GREENS AT TUSCAWILLA BUILDING 3 A REPLAT
- GREENSPOINTE
- HARBOR WINDS
- HERITAGE COMMONS
- HERITAGE PARK TWNHMS
- HICKORY GROVE
- HIGHLAND PATIO HOMES
- HIGHLAND VILLAGE 1
- HIGHLAND VILLAGE 2
- HIGHLANDS SEC 1
- HIGHLANDS SEC 4
- HIGHLANDS SEC 6
- HOLLOWBROOK
- HOWELL CREEK RESERVE PH 3
- INDIAN RIDGE
- INDIAN RIDGE PH 2
- JESUPS LANDING
- JESUPS RESERVE TWNHMS REP
- LAKE JESSUP
- LEW-JIM SUB
- MOUNT GREENWOOD
- MOUNT GREENWOOD UNIT 1
- MOUNT GREENWOOD UNIT 2 OF
- MOUNT GREENWOOD UNIT 4 OF
- MOUNT GREENWOOD UNIT 5 OF
- NORTH ORLANDO
- NORTH ORLANDO 1ST ADD
- NORTH ORLANDO 2ND ADD
- NORTH ORLANDO RANCHES SEC 01B
- NORTH ORLANDO RANCHES SEC 02
- NORTH ORLANDO RANCHES SEC 02A
- NORTH ORLANDO RANCHES SEC 05
- NORTH ORLANDO RANCHES SEC 09
- NORTH ORLANDO RANCHES SEC 10
- NORTH ORLANDO TERRACE UNIT 1 SEC 1
- NORTH ORLANDO TERRACE UNIT 1 SEC 2
- NORTH ORLANDO TERRACE UNIT 1 SEC 3
- NORTH ORLANDO TERRACE UNIT 1 SEC 6
- NORTH ORLANDO TERRACE UNIT 2 SEC 9
- NORTH ORLANDO TOWNSITE 4TH ADD REP
- NORTHERN OAKS
- OAK FOREST
- OAK FOREST UNIT 2
- OAK FOREST UNIT 3
- OAK FOREST UNIT 6
- OAK FOREST UNIT 7
- PARKSTONE
- PARKSTONE UNIT 2
- PARKSTONE UNIT 4
- RESERVE AT TUSCAWILLA PH 2
- SEASONS THE
- SEMINOLE CROSSING TWNHMS
- SEVEN OAKS
- SEVILLE CHASE
- SHEOAH A CONDO SEC 2
- SHEOAH SEC 1
- SUNRISE UNIT 2C
- SUNRISE VILLAGE
- SUNRISE VILLAGE UNIT 2
- SUNRISE VILLAGE UNIT 4
- SUNRISE VILLAGE UNIT 5
- TALMO SUB
- THE LANDINGS AT PARKSTONE
- TUSCANY PLACE PH 1
- TUSCAWILLA
- TUSCAWILLA BRAEWICK AT PH 1
- TUSCAWILLA PARCEL 90
- TUSCAWILLA RIDGE
- TUSCAWILLA UNIT 06
- TUSCAWILLA UNIT 09-B
- TUSCAWILLA UNIT 11B
- TUSCAWILLA UNIT 12
- TUSCAWILLA UNIT 14A
- TUSKAWILLA CROSSINGS PH 1
- TUSKAWILLA CROSSINGS PH 2
- TUSKAWILLA OFFICE PARK
- TUSKAWILLA POINT
- WEDGEWOOD TENNIS VILLAS
- WICKLOW GREENS AT TUSCAWILLA
- WILDWOOD
- WILLIAMSON HEIGHTS
- WINDING HOLLOW
- WINDING HOLLOW UNIT 3
- WINDING HOLLOW UNIT 4
- WINTER SPGS
- WINTER SPGS CENTRE A CONDO
- WINTER SPGS TOWN CENTER A REP
- WINTER SPGS UNIT 3
- WINTER SPGS UNIT 4
- WINTER SPGS VILLAGE PH 2
- WINTER SPRINGS
Market Summary
Current real estate data for Single Family in WINTER SPRINGS as of Mar 19, 2026
130
Single Family Listed
78
Avg DOM
261
Avg $ / SqFt
$569,392
Avg List Price
Property Summary
- Located in the HIGHLAND VILLAGE 2 subdivision, 416 MACGREGOR ROAD WINTER SPRINGS FL is a Single Family for sale in WINTER SPRINGS, FL, 32708. It is listed for $470,000 and features 3 beds, 3 baths, and has approximately 1,962 square feet of living space, and was originally constructed in 1989. The current price per square foot is $240. The average price per square foot for Single Family listings in WINTER SPRINGS is $261. The average listing price for Single Family in WINTER SPRINGS is $569,392. To schedule a showing of MLS#o6379428 at 416 MACGREGOR ROAD in WINTER SPRINGS, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of COMPASS FLORIDA LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 416 MACGREGOR ROAD
WINTER SPRINGS, FL





































