45 Highland Road

Architectural Description: 

The look is a nod to Second Empire/Queen Anne but this house may have been a Four Square when first built.
Steep "mansard" roof seems to have been re-shingled. The roof of this home visually suggests a structural change from a hip to mansard roof to accommodate a full third story.

Historical Narrative: 

Original and Present Owner: Phillips Academy Trustees
Themes: architectural; community development, education

The section of Highland Rd. that once extended from South Main St. to Salem St. has had several names in deeds and on maps through the years. Early deeds state “on the road from Capt. Blunt’s house to Mark Newman’s store”, later “from Salem St. to the store of Albert Abbott.” Blunt’s to Timothy Flagg’s and Blunt’s to Abraham J. Gould’s residence”. The 1872 map labels it Back St. and some deeds and directories reference it as Porter Rd. from Salem to Main St. Locals and students are said to have used the moniker “Bull Dog Alley”
The numbering has also changed through the years. 1885 Back St. #11 , #23 – 1916 -1945, #49 -1947

The property south of this section of Highland Road, along Salem St. to Holt Rd. and out nearly to South Main Street was once owned by brothers Asa and Sylvester Abbott. All the land now occupied by Brother’s Field and the athletic complex of about 26 acres was sold by the Abbott heirs to Ira A. Eastman in June 1889.

Ira Arza Eastman was born on June 16, 1851 in Littleton, NH, son of Arza and Maria (Winch) Eastman. His father was a farmer. Ira married in Andover on April 9, 1873 to Orissa Ellen “Nellie” Clough b. Feb. 7, 1848 in Lisbon, NH dua. of Oramill J. & Olive J. (Chase) Clough. Ira and Ellen had two sons; George Ellsworth b. June 20, 1874 and Lewis Arza b. April 29, 1876.

Erza is listed as a “Coachman” in the 1880 census and was the Mansion House Hack driver. He lived on Salem St. or Highland Rd. at that time. The 1885 and 1891 Directories lists him as a Janitor for the Andover Theological Seminary. On March 7, 1890 the Town of Andover voted to sell the former Phillips District Schoolhouse which closed in June 1889 and stood on leased land on Highland Rd. behing the Borden Gymnasium. Ira Eastman purchased the school at auction and had it moved across the street near the site of the Case Memorial Gage. Ira converted the building into a residence. May 23, 1890 AT p. 4 C. B. Mason is finishing a tenement for Ira Eastman out of the Phillips School building which was moved across the street. (The old school later became the 1924 House and moved twice more.)

About 1892 Ira then built the Eastman house and opened a Boarding house for students at Phillips Academy. Ira and his wife Nellie ran the boarding house. Ira sold off 3.98 acres in Dec. 1900 to the trustees of Phillips Academy and then the 26 acres parcel on July 15, 1901 which allowed the construction of Brother Field. The parcels included the Eastman Boarding house which Ira and his wife Nellie continued to run until 1913 but closed when new dormitories were built for the Academy. The Eastmans moved to Cambridge, MA. Sadly their son George died on May 27, 1914 in Westborough, MA and Nellie in Cambridge on June 21, 1914. Her obituary states; “..born in Littleton, NH, early years of her life were passed as a successful teacher. Mrs. Eastman was a member of the Rebecca Lodge, was P.N.G. of the Merrimack Valley Post Nobel Grand Association and a member of the Odd Ladies of Haverhill, MA. Her helpful nature and kindly face brought cheer wherever she went.”

Son Lewis A. Eastman was a wool sorter and died in 1917. Ira Eastman then moved to Kingston, NH and lived with his sister-in-law Mary Eastman, widow of Ira’s brother Lewis. Ira died on Nov. 4, 1925 and is interred in the family lot at Spring Grove Cemetery.

After Eastman, Mrs. Mary J. Allicon, widow of Phillip, resided here with M. Matilda, William, a chef, and Lillian E. Allican a waitress in 1916. Mary J. Allicon is still renting in 1939. In 1941 Walter E. Winn Jr. b. 1913 and wife Margaret b. 1918 reside here. Walter is the Landscaper and Grounds Superintendent for Phillips Academy and continued to live here through to the 1970s. In the 1960’s the house was converted to multiple apartments for faculty and Academy personnel. Eastman House was razed in the Autumn of 2006. Two of the last tenants listed were Nick Ogles and Weiguo Mei in June 2006.


45 Highland Rd. Formerly 23 Highland, 23 Porter and 11 Back St
Essex County Registry Deeds, Salem, MA
Essex Northern Registry Deeds, Lawrence, MA
Ancestry.com – Eastman Family
Andover Townsman: March 7, 1890, June 26, 1914, Nov. 6, 1925
Andover Maps 1852, 1872, 1884, 1888, 1906
Andover Directories; 1885 - 1953
Phillips Academy Map 1934

Asa Abbott and Sylvester Abbott – land
Asa Abbott Estate Rhoda Abbott Extrx. – Mar. 8, 1886 – Probate
Asa Abbott and Sylvester Abbot Heirs
Ira Chapman – June 17, 1889 – b. 101 p. 117, 119, 120, 136. – 26 acres $1000.
Trustees of Phillips Academy – Dec. 12, 1900 – b. 182 p. 361 – 3.98 acres
Trustees of Phillips Academy – July 15, 1901 – b. 186 p. 538 – 26 acres

Inventory Data:

StreetHighland Rd
PlacePhillips District
Historic DistrictAcademy Hill NRH District
Historic NameEastman House - Phillips Academy
Present Useresidence/dormitory
Original Useresidence/boarding house
Construction Date1892 - 1893
Source ECRDS, NERDL, Styles
Architectural StyleSecond Empire
Wall/Trimclapboards & shingles
Roofsteep mansard
Major AlterationsThird story addition circa 1900, and conversion into apartments in 1960s.
Demolition DetailsAutumn 2006
Acreage5 acres; approx. frontage 133'
Map and parcel58-16
MHC NumberANV.263
Recorded byStack/Mofford, James S. Batchelder
OrganizationAndover Preservation Commission
Date entered1975-77, 2/22/2022