299 Case Road
Winthrop, ME 04364
3 Beds
2.5 Baths
2,569 sqft (on 3 acres)
3 Beds
2.5 Baths
2,569 sqft
(on 3 acres)
Local Information
© Google
-- mins to
Last check for updates: about 14 hours ago
Listed by Portside Real Estate Group
Bought with: LAER
Source: Maine Listings, MLS#1605491
Description
Welcome to this spacious Colonial! This home is oozing fall vibes, campfires, and fun! Sitting back from the road, this turnkey home features a BRAND NEW DECK, NEW ROOF, a master suite, a sunroom and a full bonus room above the garage where the skies the limit on opportunities! Offering so much yet still retaining it's classic colonial charm with its wood floors, spacious layout, and quintessential setting. Minutes to downtown Winthrop, less than a half mile from the Kennebec Land Trust's Western Woods Preserve (hiking trails!), and still just 15 minutes from Augusta / I95 and an hour to Portland. -- Quick closing possible
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from April 01, 2025
Home Highlights
Parking
2 Car Garage
Outdoor
Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 299 Case Road
|
|---|
MLS Status: Closed |
|
|---|
Interior Details Basement: Bulkhead,Interior Entry,Full,UnfinishedNumber of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Bonus Room, Dining Room, Kitchen, Living Room, Sunroom |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2569 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Microwave, Electric Range, Refrigerator, Trash CompactorDishwasherMicrowaveRefrigerator |
Heating & Cooling Heating: Baseboard,Hot WaterNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa No Fireplace |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Carpet, Tile, Vinyl, Wood |
Levels, Entrance, & Accessibility Floors: Carpet, Tile, Vinyl, Wood |
|
|---|
Exterior Home Features Roof: ShinglePatio / Porch: DeckNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Paved,1 - 4 Spaces,On Site |
Frontage Road Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Private Sewer |
Finished Area Finished Area (above surface): 2569 Square Feet |
|
|---|
Year Built Year Built: 1985 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Wood Frame, Clapboard, Wood Siding |
|
|---|
Price List Price: $499,000 |
Status Change & Dates Off Market Date: Mon Dec 02 2024 |
|
|---|
|
|---|
Direction & Address City: Winthrop |
|
|---|
Building Area Building Area: 2569 Square Feet |
|
|---|
Lot Area: 3 Acres |
|
|---|
BasementMls Number: 1605491Above Grade Unfinished Area: 2569 |
Price History for 299 Case Road
| Date | Price | Event | Source |
|---|---|---|---|
| 01/13/2025 | $480,000 | Sold | Maine Listings #1605491 |
| 12/03/2024 | $499,000 | Contingent | Maine Listings #1605491 |
| 10/01/2024 | $499,000 | Listed For Sale | Maine Listings #1605491 |
| 07/13/2021 | $435,000 | Sold | Maine Listings #1491675 |
| 05/17/2021 | $425,000 | Pending | Maine Listings #1491675 |
| 05/17/2021 | $425,000 | Contingent | Maine Listings #1491675 |
| 05/14/2021 | $425,000 | Listed For Sale | Maine Listings #1491675 |
Market trends in Winthrop
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
16
1MoM
- Results are loading
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $5,408 |
| Assessment | $234,100 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$3,274/mo
Comparable Sales for 299 Case Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.78 | Single-Family Home | $480,000 | 05/13/26 | 3 | 2.5 | 2,175 | |
1.17 | Single-Family Home | $525,000 | 05/29/26 | 3 | 2.5 | 1,905 | |
1.03 | Single-Family Home | $745,000 | 03/09/26 | 3 | 2.5 | 2,100 | |
1.03 | Single-Family Home | $479,000 | 05/08/26 | 4 | 3 | 2,625 | |
1.03 | Single-Family Home | $410,000 | 08/08/25 | 4 | 2 | 2,100 | |
1.13 | Single-Family Home | $169,000 | 03/31/26 | 4 | 2.5 | 2,020 | |
1.18 | Single-Family Home | $325,000 | 07/03/25 | 3 | 1.5 | 1,874 | |
1.24 | Single-Family Home | $345,000 | 08/22/25 | 3 | 2.5 | 1,621 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETSprague & Curtis Real Estate, Closed
SOLDMAY 13, 2026Sprague & Curtis Real Estate, Closed
OFF MARKETSprague & Curtis Real Estate, Closed
OFF MARKETRizzo Mattson, Closed
OFF MARKETBrookewood Realty, Closed
SOLDMAY 8, 2026Portside Real Estate Group, Closed
SOLDMAR 9, 2026Brookewood Realty, Closed
OFF MARKETYour Home Sold Guaranteed Realty, Closed
OFF MARKETSprague & Curtis Real Estate, Closed
Assigned Schools
These are the assigned schools for 299 Case Road.
- Winthrop Grade School
- PK-5
- Public
- 387 Students
6/10GreatSchools RatingParent Rating AverageExcellent to say the least. I left because I had better job opportunityParent Review6y ago - Winthrop Middle School
- 6-8
- Public
- 223 Students
6/10GreatSchools RatingParent Rating Average2015 Update. School does a wonderful job. Our bullying incident was handled promptly and firmly.The school has its own principal now. I am a retired 35 year career middle school teacher and regularly sub at the school so I am speaking from a personal first hand experience. Look at this school ratings and be impressed.Other Review10y ago - Winthrop High School
- 9-12
- Public
- 221 Students
6/10GreatSchools RatingParent Rating AverageUnless you are a white male, chances are you will struggle socially and mentally at WHS. I attended Winthrop schools from 6th grade up to my freshman year. From my first year to my last I was constantly being mistreated by the people around me and when I spoke up about it the administration/staff did nothing. Many girls including me were sexually harassed and/or assaulted and when the administrators were alerted of this they brushed it off with no punishments given out. My younger sibling attends the middle school and has seen sexual assault happening with nothing being done about it. Kids do drugs and drink in the bathrooms, and despite the administration’s “efforts” to keep them under control, nothing works. I would say from experience that while the school promotes equality and respect as their core values, the majority of the community is homophobic, racist, and ableist with nothing being done about it. This school system is overall very corrupt and I do not recommend it to anyone.Other Review3y ago 
Check out schools near 299 Case Road.
What Locals Say about Winthrop
At least 21 Trulia users voted on each feature.
93 % Say parking is easy
92 % Say it's dog friendly
88 % Say yards are well-kept
84 % Say people would walk alone at night
77 % Say kids play outside
76 % Say it's walkable to restaurants
75 % Say there's holiday spirit
73 % Say they plan to stay for at least 5 years
72 % Say car is needed
72 % Say it's walkable to grocery stores
69 % Say there's wildlife
67 % Say streets are well-lit
63 % Say neighbors are friendly
58 % Say there are sidewalks
45 % Say it's quiet
28 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
APPLY INSTANTLYPET FRIENDLY
APPLY INSTANTLY
APPLY INSTANTLYFURNISHED
See more homes for rent inWinthrop
Explore by feature - Washer/dryer
FURNISHEDBlueground Furnished Apartments
APPLY INSTANTLYFURNISHED
APPLY INSTANTLY
APPLY INSTANTLY
APPLY INSTANTLY
PET FRIENDLYFURNISHEDHouseStay Inc.
PET FRIENDLYFURNISHEDHouseStay Inc.
Homes for sale near 299 Case Road
NEW - 2 DAYS AGO0.4 ACRESRizzo Mattson, Active
0.75 ACRESElevate Maine Realty, Active
22 ACRESPouliot Real Estate, Active
Coldwell Banker Plourde Real Estate, Active
0.61 ACRESBetter Homes & Gardens Real Estate/The Masiello Group, Active
0.54 ACRESYour Home Sold Guaranteed Realty, Active
NEW20.95 ACRESBrookewood Realty, Active
0.85 ACRESBetter Homes & Gardens Real Estate/The Masiello Group, Active
1.15 ACRESLandmark Realty, Active
See more homes for sale inWinthrop
Off Market Homes Near 299 Case Road
SOLDJUN 10, 2026Homestead Realty, Closed
SOLDMAY 29, 2026NextHome Northern Lights Realty, Closed
SOLDMAY 26, 2026Homestead Realty, Closed
SOLDMAY 19, 2026Androvise Realty, Closed
SOLDMAY 18, 2026Fontaine Family-The Real Estate Leader, Closed- SOLDMAY 18, 2026
- SOLDMAY 13, 2026Sprague & Curtis Real Estate, Closed
- SOLDMAY 8, 2026Portside Real Estate Group, Closed
- See more homes for sale inWinthrop
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified.
© 2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
Zillow Inc. 415 Congress St #202 Portland, ME 04101 206-424-8443
299 Case Road, Winthrop, ME 04364 is a 3 bedroom, 3 bathroom, 2,569 sqft single-family home built in 1985. This property is not currently available for sale. 299 Case Road was last sold on Jan 13, 2025 for $480,000 (4% lower than the asking price of $499,000). The current Trulia Estimate for 299 Case Road is $494,000.