Mr Edward Rose was an occupier of The Uplands. He was a wine and brandy merchant and died in 1891. He also at one point ran the Talbot Hotel. His widow, Mary, planned to move away and sold many of the contents of her house in 1900. One of the occupants of The Uplands was Lieut. Col. Thomson who was awarded the Croix-des-Guerre, with Gold Star, by the French, for gallantry and devotion to duty in action. He was badly wounded and captured by the Germans in May 1917 
The property was for sale by auction on Tuesday, 18th October 1904. See advertisement below.
-  The Yorkshire Post and Leeds Intelligencer - 14 September 1918
SALE OF VALUABLE FREEHOLD RESIDENCE
FREEHOLD MODERN RESIDENCE, known as 'THE UPLANDS,' Malton, with gardens, pleasure grounds, stabling, coach-house, and other suitable outbuildings and domestic offices, together with Three COTTAGES, with their gardens and out-offices, and a small grass paddock, together embracing an area of about 4 acres. The House has a full south aspect, is in perfect order throughout, and comprises on the ground floor, a large entrance-hall, front and back staircases, dining room (17 1/2ft. by 28 1/2 ft.), drawing-room (21ft by 21ft.), breakfast-room (16ft. by 15ft.), kitchen, scullery, pantries, store closets, and complete domestic offices, on the first floor, 7 bedrooms and dissing-rooms, bathroom (with hot and cold water), w.c., etc.: and on the second floor 4 bedrooms and 2 box-rooms. The sanitary arrangements are modern and in good order, and the house is supplied with hot and cold water and gas throughout. The House is surrounded by pleasant and productive grounds and gardens, comprising altogether an area of our acres or thereabouts, with conservatory, vinery, fernery, and suitable garden offices. The outbuildings comprise modern stabling for four horses (could be increased for six horses), coach house, and harness-room, with hay and corn chambers, as well as cow-house, piggery, and dog kennels. There are Three useful Cottages, with good gardens, forming part of the property, suitable and most convenient for occupation by the gardener, coachman, or other servants employed in the house.
The Yorkshire Post and Leeds Intelligencer, 15 October 1904
This is an imposing property, likely built in the early 1840s. James Dunlop, once a prominent draper in the Market Place was likely the first occupier. He is named as a shareholder in the Malton and Driffield Railway and attributed to Middlecave House  He was appointed Borough Bailiff by Earl Fitzwilliam in March 1854 
The property is advertised for sale by auction in 1891, then in the occupation of a Miss Tinsley (see advertisement below) 
-  Leeds Intelligencer, 1 November 1845
-  York Herald, 1 April 1854
-  Yorkshire Post and Leeds Intelligencer, 11 June 1891
VALUABLE LEASEHOLD PROPERTY FOR SALE
Messrs. BOULTON & COOPER will Sell by Auction at the Sun Hotel, in Malton, on Wednesday, 17th June, 1891, at 3.30 p.m. (subject to the conditions of Sale)
A LEASEHOLD RESIDENCE called MIDDLECAVE HOUSE situate within a mile of Malton, containing 3 reception rooms (with conservatory), 7 bedrooms, bath-room, w.c., kitchen, and out-offices, with the spacious grounds, large garden, and the conservatory therein, gardener's cottage, stables for 7 horses, coah-house, fold-yard, and other buildings, all adjoining being 1a, 1r. 39p, and 3 closes of LAND containing 11a 3r 38p (9 acres in grass) all occupied by Miss Tinsley.
The premises are held for the residue of a term of 50 years, granted by Earl Fitzwilliam, commencing on 5th April 1848, of which about 7 years are yet unexpired at the annual rent of £20044.
For particulars apply to the auctioneers or to
FRANK LANGBORNE Solicitor, Malton
Malton 1st June 1891
Mr. Samuel Ridge (died early 1955), a prominent Malton solicitor lived here. Note the house had gas and electric light. It was probably built in 1879. It came up for sale in 1919 as advertised in the Yorkshire Gazette, 31 May 1919