440 MACGREGOR RD, Winter Springs, FL 32708
OFF MARKET

$381,800

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,834 sqft

440 MACGREGOR RD, Winter Springs, FL 32708

Est. Refi. Payment $2,525/mo*
Refinance Your Home
Currently Off Market - Sold Jun 3, 2025 for $390,000

Home Value

Trulia Estimate
$382K
Since last month
Decreased$2K (-0.5%)
Since last year
Decreased$7K (-1.9%)
Since last sale
Decreased$9K (-2.3%)
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 +75% in the last 10 years
MonthEstimated value
2026
August 2026$381K
August 2026$381K
July 2026$383K
June 2026$379K
May 2026$382K
April 2026$383K
March 2026$388K
February 2026$386K
January 2026$386K
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
0.05
Single-Family Home
$399,000
07/01/26
3
2
1,579
448 MACGREGOR ROAD, Winter Springs, FL
0.03
Single-Family Home
$350,000
08/04/26
2
2
1,477
416 MACGREGOR ROAD, Winter Springs, FL
0.10
Single-Family Home
$462,000
04/01/26
3
2.5
1,962
625 NIGHTHAWK CIRCLE, Winter Springs, FL
0.37
Single-Family Home
$385,000
03/09/26
3
2
1,522
662 NIGHTHAWK CIRCLE, Winter Springs, FL
0.32
Single-Family Home
$270,000
11/26/25
3
3
1,583
746 N GRETNA COURT, Winter Springs, FL
0.49
Single-Family Home
$410,000
01/09/26
3
2
1,652
240 N DEVON AVENUE, Winter Springs, FL
0.37
Single-Family Home
$332,000
08/18/26
3
2
1,238
721 GALLOWAY COURT, Winter Springs, FL
0.36
Single-Family Home
$359,999
06/30/26
3
2.5
1,840
224 HIGHLANDS GLEN CIRCLE, Winter Springs, FL
0.47
Single-Family Home
$290,000
07/10/26
3
2
1,185

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
446 MACGREGOR ROAD, Winter Springs, FL 32708
0.03
$356,900
3
2.5
1,741
Off Market
448 MACGREGOR ROAD, Winter Springs, FL 32708
0.03
$350,000
2
2
1,477
Recently Sold
324 DORNOCH COURT, Winter Springs, FL 32708
0.05
$399,000
3
2
1,579
Recently Sold
450 DEWARS COURT, Winter Springs, FL 32708
0.08
$365,500
3
2
2,036
Off Market
428 MAC GREGOR ROAD, Winter Springs, FL 32708
0.05
$365,000
3
2
1,617
Off Market
316 DORNOCH CT, Winter Springs, FL 32708
0.08
$417,200
3
2
1,617
Off Market
314 BRIDIE COURT, Winter Springs, FL 32708
0.07
$379,600
3
2
1,579
Off Market
60 MOREE LOOP #45, Winter Springs, FL 32708
0.08
$182,200
3
2
1,187
Off Market
70 MOREE LOOP #61, Winter Springs, FL 32708
0.11
$179,900
2
1.5
1,080
For Sale
70 MOREE LOOP #65, Winter Springs, FL 32708
0.11
$169,300
2
1.5
1,080
Off Market
304 BRIDIE COURT, Winter Springs, FL 32708
0.11
$380,400
3
2
1,613
Off Market

Local Information

  • Map ViewExplore the area around 440 MACGREGOR RD.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1989
1,834 sqft
$208/sqft
2 Car Garage
HOA $35/mo

About this House

Welcome home to this stunning 3 bedroom, 2 bath home in The Highlands Village Community. Nestled in this serene and highly sought-after neighborhood, this charming property offers the perfect blend of comfort, style, and functionality to fit any lifestyle. Step into this 3-bedroom 2 bath home with a spacious open floor plan, perfect for entertaining, with a beautifully appointed kitchen showcasing granite countertops and oversized cabinets. The master bedroom is a tranquil retreat with a large walk-in closet and spa-inspired en-suite, complete with a garden tub and dual sinks. Additionally, the home features a cozy Florida room great for enjoying the greenery of your own private oasis. Natural light floods the living spaces, creating a warm and inviting atmosphere. The property is conveniently located near great restaurants, shopping and parks making it ideal for families, professionals, or anyone seeking convenience and tranquility. Don't miss this incredible opportunity to make 440 MacGregor Road your forever home. Schedule your showing today and experience all this property has to give.
440 MACGREGOR RD, Winter Springs, FL 32708 is a 3 bedroom, 2 bathroom, 1,834 sqft single-family home built in 1989. It last sold for $390,000 on Jun 3, 2025 (2% below the $399,990 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $381,800, with a rent estimate of $2,463/month.
Last check for updates: about 22 hours ago
Listed by Tiffany Polite, (321) 276-2178
LA ROSA REALTY LLC, (321) 939-3748
Bought with: Kathy Richmond, (407) 463-5975, KDR REAL ESTATE, (407) 463-5975
Originating MLS: Osceola
Source: Stellar MLS, MLS#O6269960
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 440 MACGREGOR RD

Interior Features

Interior Details
Number of Rooms: 7Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Dinette, Florida Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1834 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Cooktop, Dishwasher, Disposal, Electric Water Heater, Freezer, Microwave, RefrigeratorDishwasherDisposalLaundry: In GarageMicrowaveRefrigerator
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: French DoorsFlooring: Carpet, Ceramic Tile, Vinyl
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Ceramic Tile, Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: SidewalkFoundation: Block, SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 108

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Brick, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 34203053200000820

Price & Status

Price
List Price: $399,990
Status Change & Dates
Off Market Date: Mon Apr 28 2025

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: 2489 Square Feet

Community

Not Senior Community

HOA

HOA Name: 407-260-1011HOA Name (second): The HighlandsAssociation for this Listing: OsceolaHas an HOAHOA Fee: $35/Monthly

Lot Information

Lot Area: 4853 sqft

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6269960Showing Considerations: No Sign, See RemarksShowing Requirements: Go Direct, Lockbox, See Remarks, ShowingTimeUniversal Property Id: US-12117-N-34203053200000820-R-N

Price and Tax history

DateEventPrice
Jun 3, 2025
Source: Stellar MLS #O6269960
Sold
$390,000
Apr 29, 2025
Source: My State MLS #11406299
Contingent
$399,990
Apr 28, 2025
Source: Stellar MLS #O6269960
Pending
$399,990
Apr 25, 2025
Source: Stellar MLS #O6269960
PriceChange
$399,990
Price decreased by 3%
Mar 28, 2025
Source: Stellar MLS #O6269960
PriceChange
$413,900
Price decreased by 1%

Market trends in Winter Springs

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$406K
$10.67KMoM
Sale-to-List Price
98.5%
0.2%MoM
Price per sq ft
$230
$6MoM
Available listings
191
9MoM

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
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  • 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
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  • 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
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  • 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
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  • 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 !"
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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. "
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  • 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
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  • Pam
    "Annual Family Picnic. Very neighborly neighborhood. Lots of children and activities for them through out the year. "
    0
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  • 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
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  • 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
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  • 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
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  • Marie B.
    "Heavy traffic at peak hours but not outrageous. Not too bad. Traffic is thick around schools. Toll roads help. "
    0
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  • 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
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  • 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 440 MACGREGOR RD

  • What is 440 MACGREGOR RD estimated to be worth?
    Trulia's estimated value for 440 MACGREGOR RD in Winter Springs, FL is $381,800.
  • What is the price history for 440 MACGREGOR RD?
    440 MACGREGOR RD in Winter Springs, FL last sold for $390,000 in June 2025.
  • 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 $406K. That is down $10.67K from the prior month.
  • Does 440 MACGREGOR RD have air conditioning?
    Yes, 440 MACGREGOR RD in Winter Springs, FL has air conditioning.
  • Does 440 MACGREGOR RD have laundry facilities?
    Yes, 440 MACGREGOR RD in Winter Springs, FL has laundry facilities.

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Off Market Homes Near 440 MACGREGOR RD

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