House Price Watch
100 most expensive houses in Portland
In the charming area of Portland, part of Weymouth and Portland, the real estate market has seen some impressive transactions. The most expensive house sold for a staggering £905,000 in 2024, while the least expensive was priced at £405,000. Notably, 8 of the houses on this list are located on the same street, Pennsylvania Road, Wakeham. Since 1995, there have been an astonishing 8,234 sales in the area, showcasing its vibrant housing market. The latest sale recorded was in 2025, reflecting ongoing interest in this beautiful locale.
Sold in 2024
old hill house old hill, dorset
£905,000
Sold in September 2022
pitthays cottage old hill, dorset
£700,000
Sold in November 2007
154 wakeham, dorset
£690,000
Sold for a lower amount since this price
4.
Sold in November 2019
old hill house old hill, dorset
£690,000
5.
Sold in September 2020
70 high street, dorset
£685,000
6.
Sold in 2024
26 wakeham, dorset
£670,000
7.
Sold in May 2021
60 wakeham, dorset
£660,000
8.
Sold in September 2016
castle keep pennsylvania road, dorset
£634,999
9.
Sold in June 2025
8b sweet hill road, dorset
£625,000
10.
Sold in November 2022
3 the verne, dorset
£600,000
Most expensive houses in areas around Portland
£2,600,000
187.29%
£2,600,000
187.29%
11.
Sold in April 2025
12 castle road, dorset
£580,000
12.
Sold in September 2021
223 church ope road, dorset
£575,000
13.
Sold in 2015
the gatehouse cottage church ope, dorset
£555,000
14.
Sold in October 2023
70 southwell street, dorset
£552,500
15.
Sold in September 2022
13 castle road, dorset
£550,000
16.
Sold in November 2008
moontrail pennsylvania road, dorset
£550,000
17.
Sold in July 2021
8a victoria place, dorset
£550,000
18.
Sold in October 2024
rocca , dorset
£545,000
19.
Sold in June 2022
15 castle road, dorset
£525,000
20.
Sold in February 2022
8 fortuneswell, dorset
£525,000
21.
Sold in November 2022
165 fortuneswell, dorset
£525,000
22.
Sold in April 2025
35 kingbarrow drive, dorset
£525,000
23.
Sold in April 2025
37 kingbarrow drive, dorset
£515,000
24.
Sold in April 2025
31 kingbarrow drive, dorset
£515,000
25.
Sold in July 2021
freestone house portland bill, dorset
£515,000
26.
Sold in October 2023
the old vicarage grove road, dorset
£511,500
27.
Sold in November 2022
50 sweet hill road, dorset
£510,000
28.
Sold in May 2018
26 wakeham, dorset
£500,000
29.
Sold in March 2023
71 new street, dorset
£500,000
30.
Sold in October 2023
69 new street, dorset
£500,000
31.
Sold in October 2025
57a southwell street, dorset
£500,000
32.
Sold in 2020
8b sweet hill road, dorset
£499,000
33.
Sold in November 2013
67 new street, dorset
£496,495
34.
Sold in February 2021
customs house castletown, dorset
£495,000
35.
Sold in March 2007
governors house the verne, dorset
£489,950
36.
Sold in August 2023
140 fortuneswell, dorset
£485,000
37.
Sold in May 2025
1 grove road, dorset
£480,000
38.
Sold in October 2018
3 the verne, dorset
£480,000
39.
Sold in September 2019
9 albert villas, dorset
£475,000
40.
Sold in March 2020
167 weston street, dorset
£475,000
41.
Sold in April 2020
159 weston street, dorset
£475,000
42.
Sold in 2020
165 weston street, dorset
£470,000
43.
Sold in April 2025
42 sweet hill road, dorset
£470,000
44.
Sold in February 2025
28 easton street, dorset
£465,000
45.
Sold in February 2023
163 avalanche road, dorset
£465,000
46.
Sold in May 2025
40 sweet hill road, dorset
£465,000
47.
Sold in February 2025
53 officers field, dorset
£460,000
48.
Sold in August 2009
60 wakeham, dorset
£455,000
49.
Sold in April 2020
belle vue house , dorset
£455,000
50.
Sold in March 2025
old school house grove road, dorset
£452,000
51.
Sold in September 2022
175 brandy row, dorset
£450,000
52.
Sold in October 2021
bay view house , dorset
£450,000
53.
Sold in August 2022
33a park road, dorset
£450,000
54.
Sold in March 2023
2 langley close, dorset
£450,000
55.
Sold in March 2025
29 killicks hill, dorset
£445,000
56.
Sold in September 2023
osborne hall osborne terrace, dorset
£440,000
57.
Sold in June 2022
34 park road, dorset
£440,000
58.
Sold in May 2008
10 southwell, dorset
£440,000
59.
Sold in August 2016
lobster farmhouse portland bill, dorset
£440,000
60.
Sold in July 2024
25 sandholes close, dorset
£440,000
61.
Sold in July 2023
50 reap lane, dorset
£439,000
62.
Sold in June 2022
38 queens road, dorset
£437,000
63.
Sold in 2006
50 wakeham, dorset
£436,000
64.
Sold in March 2021
1 grove road, dorset
£435,000
65.
Sold in August 2022
1 moorfield road, dorset
£435,000
66.
Sold in May 2021
7 castle road, dorset
£430,000
67.
Sold in September 2022
58 new street, dorset
£430,000
68.
Sold in February 2023
25 clarence road, dorset
£430,000
69.
Sold in September 2018
36 sweet hill road, dorset
£430,000
70.
Sold in November 2024
39 kingbarrow drive, dorset
£430,000
71.
Sold in December 2021
179 brandy row, dorset
£425,000
Sold for a lower amount since this price
72.
Sold in November 2020
chesil edge clovens road, dorset
£425,000
Sold for a lower amount since this price
73.
Sold in November 2023
5 new church close, dorset
£425,000
74.
Sold in August 2023
122 wakeham, dorset
£425,000
75.
Sold in December 2011
woodbine cottage pennsylvania road, dorset
£425,000
76.
Sold in 2012
woodbine cottage pennsylvania road, dorset
£425,000
77.
Sold in 2024
2 spring gardens, dorset
£425,000
78.
Sold in July 2025
10 sidon mews, dorset
£423,000
79.
Sold in July 2008
32 queens road, dorset
£422,500
80.
Sold in 2025
15 ventnor road, dorset
£420,000
81.
Sold in July 2024
16 park road, dorset
£420,000
82.
Sold in 2016
rocca , weymouth and portland
£420,000
83.
Sold in August 2018
18 castle road, dorset
£415,000
84.
Sold in March 2025
the old police station castle road, dorset
£415,000
85.
Sold in April 2018
24 moorfield road, dorset
£412,500
86.
Sold in November 2025
3 high street, dorset
£412,500
87.
Sold in February 2025
12a ventnor road, dorset
£412,000
88.
Sold in February 2023
24 officers field, dorset
£410,000
89.
Sold in November 2024
42 bumpers lane, dorset
£410,000
90.
Sold in May 2019
parkway house park road, dorset
£410,000
91.
Sold in May 2022
22 clarence road, dorset
£410,000
92.
Sold in October 2019
161 weston street, dorset
£410,000
93.
Sold in August 2023
16 sweet hill road, dorset
£410,000
94.
Sold in March 2024
28 sweet hill road, dorset
£410,000
95.
Sold in November 2024
33 kingbarrow drive, dorset
£410,000
96.
Sold in April 2013
23a sweet hill road, dorset
£408,000
97.
Sold in November 2022
15 high street, dorset
£406,390
98.
Sold in August 2020
chesil edge clovens road, dorset
£406,000
Sold for a lower amount since this price
99.
Sold in April 2010
parkway house park road, dorset
£405,000
100.
Sold in February 2024
51 weston street, dorset
£405,000
Data Source & Update Note:
This list of the 100 most expensive homes sold in Portland is compiled from all-time residential sales recorded by the HM Land Registry. Each entry includes the sale price and transaction date. The dataset was last updated 29 March 2026 at 18:18 with the latest HM Land Registry data (February 2026). The Portland dataset covers 412 postcodes. Prices reflect actual recorded transactions, not current market valuations. Read our full data methodology.