Waterfront cottage in the heart of town. Year-round house on Castine Harbor with a beach and separate guest cottage. Tucked in off Pleasant Street, steps away from shops, restaurants, and the town dock, this light-filled home sits on a hill providing water views from most rooms. Living space on three floors, three full baths, deck and patio. Main floor has a well-appointed kitchen, living room with a gas fireplace, dining room, den/office, full bath, sun room and deck. On the second floor is the primary bedroom with a step-out balcony, walk-in closet, and en suite bath with shower, jacuzzi tub, and a washer and dryer. Also on the second floor is a second bedroom with en suite bath. The walkout basement level has a extra refrigerator, additional extra-large capacity washer and dryer, workshop, storage, and a carpeted bonus room with windows, water views, and door to the garden. 18KW Whole house generator. Across the patio from the front door is a charming seasonal guest cottage with its own full bath and a deck with stunning water views (sleeps 4). An established three-season flower garden wraps around house and lawns. This location offers so many ways to experience all Castine has to offer: enjoy spectacular views of islands to the south and a dynamic working waterfront to the east; launch a kayak, paddle board or dinghy from the beach; walk to town and the Castine Golf, Tennis and Yacht Club.
Single-familyProperty Type
1890Year Built
0.35 acresLot Size
$711Est. Price/Sq.Ft.
1 spaceParking
Listed by Medan {Hank} de Raat• De Raat Realty
Bought with Dennis Cloutier• Sail Away Maine Realty
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Market trends in 04420, ME
Last updated July 2026
Buyer's Market
Seller's Market
Buyer's market
Sale-to-List Price
88.3%
0.0% MoM
Median sale price
$750K
$0 MoM
Avg. days on market
69d
0 days MoM
Recently sold homes
1
0 MoM
Provided by Redfin
Sale history for 2 Pleasant St
Date
Event
Price
MREIS #1563748
Aug 23, 2023
Sold
$1,098,000
$578/sq ft
Jun 29, 2023
Listed
$1,100,000
$579/sq ft
MREIS #1319534
Oct 5, 2017
Sold
$590,000
$311/sq ft
Aug 23, 2017
Price Changed
$599,000
$315/sq ft
Jul 28, 2017
Listed
$650,000
$342/sq ft
+30
CASTINE: Seaside charming cottage style year round home w/ amazing views over Castine Harbor & Penobscot Bay. Tucked into a private setting w/ gardens, lawn, stairs to beach. Chef's kitchen, formal living room w/ propane fireplace, dining room, spacious den/office, hallway full bath, top floor w/ master bedroom w/ balcony, full bath/laundry, second bedroom w/ bath. Glassed in porch, waterside deck. Guest house w/ 2bedrooms, kitchenette, full bath & deck overlooking water. PRICED WELL TO SELL NOW! $650,000
MREIS #1312215
Jun 13, 2017
Listed
$750,000
$395/sq ft
MREIS #1112613
Oct 4, 2013
Listed
$925,000
$487/sq ft
MREIS #1078359
Jan 14, 2013
Listed
$950,000
$500/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$10,236 (+14.3%)
$734,000 + $213,800
$947,800
2024
$8,956 (+6.2%)
$734,000 + $208,700
$942,700
2023
$8,431 (+5.7%)
$556,100 + $158,400
$714,500
2022
$7,978 (+14.0%)
$477,700 + $136,000
$613,700
2021
$6,996
$477,700 + $136,000
$613,700
2020
$6,996
$477,700 + $136,000
$613,700
2019
$6,996 (−3.0%)
$477,700 + $136,000
$613,700
2018
$7,211 (+0.2%)
$477,700 + $136,000
$613,700
2017
$7,199 (+4.6%)
$477,700 + $135,000
$612,700
2016
$6,885
$562,000 + $158,900
$720,900
2015
$6,885
$562,000 + $158,900
$720,900
2014
$6,885 (+2.7%)
$562,000 + $158,900
$720,900
2013
$6,704
$562,000 + $158,900
$720,900
Tax history for 2 Pleasant St
Year
Property tax
Land + Additions
Assessment*
2025
$10,236 (+14.3%)
$734,000 + $213,800
$947,800
2024
$8,956 (+6.2%)
$734,000 + $208,700
$942,700
2023
$8,431 (+5.7%)
$556,100 + $158,400
$714,500
2022
$7,978 (+14.0%)
$477,700 + $136,000
$613,700
2021
$6,996
$477,700 + $136,000
$613,700
2020
$6,996
$477,700 + $136,000
$613,700
2019
$6,996 (−3.0%)
$477,700 + $136,000
$613,700
2018
$7,211 (+0.2%)
$477,700 + $136,000
$613,700
2017
$7,199 (+4.6%)
$477,700 + $135,000
$612,700
2016
$6,885
$562,000 + $158,900
$720,900
2015
$6,885
$562,000 + $158,900
$720,900
2014
$6,885 (+2.7%)
$562,000 + $158,900
$720,900
2013
$6,704
$562,000 + $158,900
$720,900
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.