33 Oak Drive
Gray, ME 04039
5 Beds
4.5 Baths
3,580 sqft (on 1.80 acres)
5 Beds
4.5 Baths
3,580 sqft
(on 1.80 acres)
Local Information
© Google
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Last check for updates: about 18 hours ago
Listed by RE/MAX By The Bay
Bought with: The Boulos Company
Source: Maine Listings, MLS#1568982
Description
Located on the upper lake of Little Sebago this stunning cottage sits on 745 feet of water frontage. The eat-in kitchen kitchen with beautiful white cabinetry offers a pantry, new appliances, ample cabinet space and a peninsula with seating for four. The open concept dining and living room with stone fireplace, vaulted ceiling and windows on all three sides creates a fantastic place for everyone to gather. The screen porch on the southeast side of the home provides a perfect spot to enjoy the sun and views out to the water. First floor laundry and bedroom make one level living possible. The second floor primary suite is a private oasis with cathedral ceilings, double vanities, a large soaking tub and access to a second floor deck and a custom exterior fireplace. This lakeside retreat has a family compound feel with two outbuildings. The first carriage house has a two car garage with bonus room, heat pump and full bath above. This space makes the perfect home office, game room or bunkhouse. The second carriage house was built in 2021, it has three garage bays, one currently being used as a gym space, and a studio above. Equipped with a kitchenette, high ceilings, a full bath and heat pumps it offers a comfortable and private space for long and short term guests. Three separate docks, float, boat house, saltwater hot tub and patios make it easy to entertain, access the water or have a quiet moment by the shore. This prime location on a natural point, surrounded by water, makes the property feel secluded and private. Enjoy being 10 minutes to Gray town amenities and under 15 minutes to Raymond favorites, such as the Good Life Market and Fisherman's Catch!
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 January 16, 2025
Home Highlights
Parking
Garage
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
$10/Monthly
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 33 Oak Drive
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MLS Status: Closed |
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Interior Details Basement: Interior Entry,Crawl Space,Full,UnfinishedNumber of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Laundry, Living Room |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 3580 Square Feet |
Appliances & Utilities Appliances: Dishwasher, Microwave, Electric Range, RefrigeratorDishwasherMicrowaveRefrigerator |
Heating & Cooling Heating: Baseboard,Forced Air,Heat Pump,Hot WaterHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa Number of Fireplaces: 3Has a FireplaceHas a Spa |
Gas & Electric Electric: Circuit Breakers |
Windows, Doors, Floors & Walls Flooring: Tile, Vinyl, Wood |
Levels, Entrance, & Accessibility Floors: Tile, Vinyl, Wood |
View Has a ViewView: Scenic |
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Exterior Home Features Roof: ShinglePatio / Porch: Deck, PatioOther Structures: OutbuildingNo Private Pool |
Parking & Garage Number of Garage Spaces: 5Number of Covered Spaces: 5No CarportHas a GarageNo Attached GarageParking Spaces: 5Parking: Paved,5 - 10 Spaces,Detached,Heated Garage |
Frontage WaterfrontRoad Frontage: Private RoadRoad Surface Type: Gravel, DirtOn Waterfront |
Water & Sewer Sewer: Private SewerWater Body: Little Sebago |
Farm & Range Frontage Length: Waterfrontage: 745, Waterfrontage Owned: 745 |
Finished Area Finished Area (above surface): 3580 Square Feet |
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Year Built Year Built: 2008 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cottage |
Building Construction Materials: Wood Frame, Shingle Siding, Wood Siding |
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Price List Price: $2,195,000 |
Status Change & Dates Off Market Date: Tue Aug 22 2023 |
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Direction & Address City: Gray |
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Building Area Building Area: 3580 Square Feet |
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Has an HOAHOA Fee: $125/Annually |
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Lot Area: 1.8 Acres |
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BasementMls Number: 1568982Above Grade Unfinished Area: 3580 |
Price History for 33 Oak Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 09/27/2023 | $2,205,000 | Sold | Maine Listings #1568982 |
| 08/23/2023 | $2,195,000 | Pending | Maine Listings #1568982 |
| 08/16/2023 | $2,195,000 | Listed For Sale | Maine Listings #1568982 |
| 11/08/2016 | $850,000 | Sold | Maine Listings #1288446 |
| 10/02/2012 | $825,000 | ListingRemoved | Agent Provided |
| 09/01/2012 | $825,000 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $19,943 |
| Assessment | $2,056,000 |
Home facts updated by county records
Comparable Sales for 33 Oak Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $683,000 | 12/05/25 | 3 | 2.5 | 2,284 | |
0.88 | Single-Family Home | $1,700,000 | 02/02/26 | 3 | 2.5 | 2,750 | |
0.92 | Single-Family Home | $700,000 | 12/30/25 | 4 | 2.5 | 2,376 | |
1.17 | Single-Family Home | $650,000 | 07/31/25 | 4 | 2.5 | 2,856 | |
1.21 | Single-Family Home | $595,000 | 07/28/25 | 4 | 3 | 2,372 | |
0.92 | Single-Family Home | $1,250,000 | 09/05/25 | 3 | 3 | 2,207 | |
1.30 | Single-Family Home | $1,300,000 | 08/20/25 | 4 | 2 | 2,626 | |
1.20 | Single-Family Home | $519,000 | 12/31/25 | 3 | 2 | 1,568 |
Assigned Schools
These are the assigned schools for 33 Oak Drive.
- Gray-New Gloucester High School
- 9-12
- Public
- 601 Students
5/10GreatSchools RatingParent Rating AverageI would absolutely recommend this school to parents in the area. We have had a wonderful relationship with most teachers and staff here (there are always going to be issues - they don't have to sour you on the entire system). My children are engaged and seem to like every aspect of this school. Both are multi sport athletes who are getting good grades in spite of having no time due to sports. My senior is and has been a 4.0 student her entire High School career while juggling a very hectic schedule. The friends and relationships they are making here are some of the best I've seen. This is a great community to raise your children, and this is a great school district to have them in.5 stars in my opinion!Parent Review6y ago - Russell School
- K-2
- Public
- 211 Students
NAGreatSchools RatingParent Rating AverageWe love Russell. It was so good for our kids.Parent Review3y ago - Burchard A Dunn School
- PK-4
- Public
- 346 Students
9/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Gray-New Gloucester Middle School
- 5-8
- Public
- 495 Students
5/10GreatSchools RatingParent Rating AverageThis school is just downright bad, i’ll give an example why.Firstly, the teachers there are just god awful, some disrespect you for saying the wrong stuff. And don’t even get me started on the bullying that forwards in GNGMS, constant- bullying-.And if you tell any teacher about it all they do is give them lunch and recess detention. And the teachers just sit back and let their tvs and computers do the work, on a rare occasion we do worksheets. My advice, try fiddlehead, not gng.. unless you want your kids mental state decreasing.Student Review11mo ago 
Check out schools near 33 Oak Drive.
What Locals Say about Gray
At least 9 Trulia users voted on each feature.
100 % Say parking is easy
100 % Say yards are well-kept
93 % Say car is needed
88 % Say people would walk alone at night
78 % Say it's dog friendly
77 % Say there's wildlife
71 % Say it's quiet
63 % Say there's holiday spirit
61 % Say neighbors are friendly
60 % Say they plan to stay for at least 5 years
50 % Say kids play outside
43 % Say there are community events
38 % Say there are sidewalks
38 % Say streets are well-lit
36 % Say it's walkable to grocery stores
27 % Say it's walkable to restaurants
Sourced by Trulia users. Learn more about our methodology.
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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.
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Homes for rent near 33 Oak Drive
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Off Market Homes Near 33 Oak Drive
SOLDMAR 9, 2026
SOLDFEB 2, 2026RE/MAX By The Bay, Closed
SOLDDEC 23, 2025Five Star Realty, Closed
SOLDOCT 14, 2025Dream Home Realty LLC, Closed
SOLDSEP 5, 2025
SOLDSEP 5, 2025Cottage & Co Real Estate, Closed
SOLDAUG 20, 2025Cottage & Co Real Estate, Closed- SOLDJUL 30, 2025Spectrum Real Estate, Closed
OFF MARKETLegacy Properties Sotheby's International Realty, Closed- See more homes for sale inGray
33 Oak Drive, Gray, ME 04039 is a 5 bedroom, 5 bathroom, 3,580 sqft single-family home built in 2008. This property is not currently available for sale. 33 Oak Drive was last sold on Sep 27, 2023 for $2,205,000 (0% higher than the asking price of $2,195,000). The current Trulia Estimate for 33 Oak Drive is $2,491,800.