33 Oak Drive, Gray, ME 04039
Property image
Property image
OFF MARKET

33 Oak Drive
Gray, ME 04039

  • 5 Beds
  • 4.5 Baths
  • 3,580 sqft (on 1.80 acres)

$2,529,700

Trulia Estimate
as of Jul 5, 2026

$2,529,700

Trulia Estimate
as of Jul 5, 2026
5 Beds
4.5 Baths
3,580 sqft
(on 1.80 acres)

Local Information

  • Map ViewExplore the area around 33 Oak Drive.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination
Last check for updates: about 9 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!
33 Oak Drive, Gray, ME 04039 is a 5 bedroom, 5 bathroom, 3,580 sqft single-family home built in 2008. It last sold for the $2,195,000 asking price on Sep 27, 2023. It is currently off market. The Trulia Estimate is $2,529,700, with a rent estimate of $4,251/month.

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

Active Status

MLS Status: Closed

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $2,195,000
Status Change & Dates
Off Market Date: Tue Aug 22 2023

Location

Direction & Address
City: Gray

Building

Building Area
Building Area: 3580 Square Feet

HOA

Has an HOAHOA Fee: $125/Annually

Lot Information

Lot Area: 1.8 Acres

Miscellaneous

BasementMls Number: 1568982Above Grade Unfinished Area: 3580

Price History for 33 Oak Drive

DatePriceEventSource
09/27/2023$2,205,000Sold
Maine Listings #1568982
08/23/2023$2,195,000PendingMaine Listings #1568982
08/16/2023$2,195,000Listed For SaleMaine Listings #1568982
11/08/2016$850,000Sold
Maine Listings #1288446
10/02/2012$825,000ListingRemovedAgent Provided
09/01/2012$825,000Listed For SaleAgent Provided

Market trends in Gray

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
22
5MoM
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Property Tax and Assessment

Year2024
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
28 Oak Drive, Gray, ME
0.12
Single-Family Home
$683,000
12/05/25
3
2.5
2,284
35 Westwood Road, Gray, ME
0.88
Single-Family Home
$1,700,000
02/02/26
3
2.5
2,750
21 Westwood Road, Gray, ME
0.92
Single-Family Home
$700,000
12/30/25
4
2.5
2,376
68 May Meadow Drive, Gray, ME
1.17
Single-Family Home
$650,000
07/31/25
4
2.5
2,856
37 Ambrose Circle, Gray, ME
1.21
Single-Family Home
$595,000
07/28/25
4
3
2,372
16 Krams Point Road, Raymond, ME
0.92
Single-Family Home
$1,250,000
09/05/25
3
3
2,207
28 Deer Acres Road, Raymond, ME
1.30
Single-Family Home
$1,300,000
08/20/25
4
2
2,626
157 Egypt Road, Gray, ME
1.20
Single-Family Home
$519,000
12/31/25
3
2
1,568

Nearby homes

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Assigned Schools

These are the assigned schools for 33 Oak Drive.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • Sierra
    "Small town could use people who aren’t afraid of upgrading buildings. I have lived in this town for three years and never questioned my safety "
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  • jpaladino
    "I live and work here. I think this is the perfect area to live in as you get the best of both worlds...a small town feeling with hiking trials, lakes and Gray animal farm but a quick drive to Portland provides you with all the best the city has to offer with LOTS of restaurants and shopping. "
    0
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  • Beth
    "Lived in Gray since 1994. Great area. Good schools. Easy commuteto Portland."
    0
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Apartments for Rent

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6 rentals with a washer/dryer in Gray, ME

Homes for sale near 33 Oak Drive

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Off Market Homes Near 33 Oak Drive

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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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