29 Fairview Rd
Monterey, MA 01245
8 Beds
6.5 Baths
9,300 sqft (on 51.55 acres)
8 Beds
6.5 Baths
9,300 sqft
(on 51.55 acres)
Local Information
- Map ViewExplore the area around 29 Fairview Rd.
- Schools2 Preschool Schools2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2006
Lot Size
51.55 acres
Living Area
9,300 sqft
Price/Sqft
$599
Parking
4 Car Garage
About this House
CROW HOUSE - An Enchanting Private Stone-and-Timber Compound in Monterey.
One of Berkshire County's most atmospheric and luxurious properties, this stone-and-timber 52-acre compound, which abuts thirteen thousand acres of protected State Forest, is a magical world unto itself. A winding driveway through horse pastures leads under a Porte cochere to a European-style courtyard, where a pergola draped in wisteria links the entrances to the five-bedroom, five-bath main house, the three-bedroom, two-bath guest house and a terrace with an outdoor dining pavilion. The compound's origins are a 1929 storybook stone house that was designed to stay cool in summer and be cozy in winter. It is now one wing of the 9,300 square foot residence. It has a screened porch overlooking a cascading stream; a stone-walled master suite with a fireplace, and a sumptuous bathroom with a soaking tub that offers a view toward the woodlands. There's an additional ground floor bedroom suite and a winding stone staircase leading to two more guest rooms on the second floor.
Over twenty years, the current owners have built several coherent and contextual additions that offer grand living-and-entertaining spaces while maintaining the spirit of the original house. The dining room and double-height living room with a massive fireplace have views through glass-and-steel French doors to courtyards, perennial gardens, and extensive lawns. The airy cook's kitchen has state-of-the art appliances, a marble island and a built-in dining banquette that seats ten. The generous mud room entrance has a powder room and a handsome staircase leading to a large vaulted second-story library-media room and gym.
The guest house has a full-kitchen and two porches that look out toward the swimming pool that is discreetly sited on a broad lawn bordered by fruit trees and sensitively-planted perennial beds. In the distance, there are two freestanding heated stone studios, a second two-car garage with pool equipment, paddocks, and a full-size outdoor riding arena that would easily make a terrific tennis court.
Intelligently updated and immaculately maintained, the house has beautiful stone and wide board floors, stone and slate roofs and handsome casement windows. Featured in Elle Décor magazine, this breathtaking, highly livable, one-of-a-kind compound offers bucolic privacy with the convenience of being five minutes to the Monterey General Store and Lake Garfield and just ten minutes to Ski Butternut and Great Barrington.
One of Berkshire County's most atmospheric and luxurious properties, this stone-and-timber 52-acre compound, which abuts thirteen thousand acres of protected State Forest, is a magical world unto itself. A winding driveway through horse pastures leads under a Porte cochere to a European-style courtyard, where a pergola draped in wisteria links the entrances to the five-bedroom, five-bath main house, the three-bedroom, two-bath guest house and a terrace with an outdoor dining pavilion. The compound's origins are a 1929 storybook stone house that was designed to stay cool in summer and be cozy in winter. It is now one wing of the 9,300 square foot residence. It has a screened porch overlooking a cascading stream; a stone-walled master suite with a fireplace, and a sumptuous bathroom with a soaking tub that offers a view toward the woodlands. There's an additional ground floor bedroom suite and a winding stone staircase leading to two more guest rooms on the second floor.
Over twenty years, the current owners have built several coherent and contextual additions that offer grand living-and-entertaining spaces while maintaining the spirit of the original house. The dining room and double-height living room with a massive fireplace have views through glass-and-steel French doors to courtyards, perennial gardens, and extensive lawns. The airy cook's kitchen has state-of-the art appliances, a marble island and a built-in dining banquette that seats ten. The generous mud room entrance has a powder room and a handsome staircase leading to a large vaulted second-story library-media room and gym.
The guest house has a full-kitchen and two porches that look out toward the swimming pool that is discreetly sited on a broad lawn bordered by fruit trees and sensitively-planted perennial beds. In the distance, there are two freestanding heated stone studios, a second two-car garage with pool equipment, paddocks, and a full-size outdoor riding arena that would easily make a terrific tennis court.
Intelligently updated and immaculately maintained, the house has beautiful stone and wide board floors, stone and slate roofs and handsome casement windows. Featured in Elle Décor magazine, this breathtaking, highly livable, one-of-a-kind compound offers bucolic privacy with the convenience of being five minutes to the Monterey General Store and Lake Garfield and just ten minutes to Ski Butternut and Great Barrington.
29 Fairview Rd, Monterey, MA 01245 is a 8 bedroom, 7 bathroom, 9,300 sqft single-family home built in 2006. It last sold for $5,600,000 on Nov 12, 2024 (2% above the $5,500,000 asking price). It is currently off market. The Trulia Estimate is $5,570,100, with a rent estimate of $28,132/month.
Home Details for 29 Fairview Rd
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Interior Details Basement: Walk-Out Access,Partial,Interior Entry,Partially Finished,ConcreteNumber of Rooms: 18Types of Rooms: Master Bedroom, Bedroom, Dining Room, Exercise Room, Kitchen, Library, Living Room, Mud Room, Seasonal Room |
Beds & Baths Number of Bedrooms: 8Number of Bathrooms: 7Number of Bathrooms (full): 6Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 9300 Square Feet |
Appliances & Utilities Utilities: Fiber Optic Availabl, Trash PrivateAppliances: Dishwasher, Dryer, Microwave, Range, Range Hood, Refrigerator, WasherDishwasherDryerMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Propane,Oil,Boiler,Hot Water,Fireplace(s),RadiantNo CoolingHas HeatingHeating Fuel: Propane |
Fireplace & Spa Has a Fireplace |
Gas & Electric Electric: Other, 200 Amp, 200+ Amp Service |
Windows, Doors, Floors & Walls Flooring: Wood |
Levels, Entrance, & Accessibility Accessibility: Accessible Bedroom, Accessible Full Bath, 1st Flr Bdrm w/Bath, 1st Flr Half BathFloors: Wood |
View Has a ViewView: Scenic, Pasture |
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Exterior Home Features Roof: Slate Wood ShakePatio / Porch: Porch, PatioFencing: PartialOther Structures: Barn/Stable, Paddock, OutbuildingExterior: Lighting, Privacy, Deciduous Shade Trees, Mature Landscaping, LandscapedFoundation: SlabHas a Private Pool |
Parking & Garage Number of Garage Spaces: 4Number of Covered Spaces: 4Other Parking: GaragedHas a CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Garage |
Pool Pool: In GroundPool |
Frontage Waterfront: BrookNot on Waterfront |
Water & Sewer Sewer: Private Sewer |
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Year Built Year Built: 2006 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other |
Property Information Condition: Updated/RemodeledParcel Number: M:0226 B:0033 L:0 |
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Price List Price: $5,500,000 |
Status Change & Dates Off Market Date: Tue Nov 12 2024Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: Monterey |
School Information Elementary School: OtherJr High / Middle School: Mount EverettHigh School: Mount Everett |
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Building Area Building Area: 9300 Square Feet |
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Lot Area: 51.55 Acres |
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BasementMls Number: 243798 |
Last check for updates: about 14 hours ago
Listed by Timothy Lovett
BERKSHIRE PROPERTY AGENTS, LLC
Fintan Hanley, (914) 471-3750
BERKSHIRE PROPERTY AGENTS, LLC
Bought with: Elyse Harney Morris, (860) 318-5126, ELYSE HARNEY REAL ESTATE
Co-Buyer's Agent: William Melnick, (917) 330-5241, ELYSE HARNEY REAL ESTATE
Source: BCMLS, MLS#243798
Price History for 29 Fairview Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 11/12/2024 | $5,600,000 | Sold | BCMLS #243798 |
| 07/13/2024 | $5,500,000 | Pending | BCMLS #243798 |
| 07/03/2024 | $5,500,000 | Listed For Sale | BCMLS #243798 |
| 12/31/2016 | $5,750,000 | ListingRemoved | Agent Provided |
| 05/16/2016 | $5,750,000 | Listed For Sale | Agent Provided |
| 01/16/2016 | $6,250,000 | ListingRemoved | Agent Provided |
| 08/11/2015 | $6,250,000 | Listed For Sale | Agent Provided |
Market trends in Monterey
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
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Available listings
11
1MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $29,843 |
| Assessment | $4,634,000 |
Home facts updated by county records
Comparable Sales for 29 Fairview Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
1.22 | Single-Family Home | $820,000 | 11/05/25 | 4 | 2.5 | 2,480 | |
1.45 | Single-Family Home | $655,000 | 08/08/25 | 4 | 3.5 | 4,188 | |
1.49 | Single-Family Home | $1,585,000 | 07/10/26 | 4 | 4 | 2,417 | |
1.46 | Single-Family Home | $1,150,000 | 09/04/25 | 3 | 3 | 2,266 | |
1.84 | Single-Family Home | $760,000 | 03/10/26 | 4 | 3 | 2,362 | |
2.17 | Single-Family Home | $1,800,000 | 02/25/26 | 6 | 3 | 3,000 | |
1.87 | Single-Family Home | $730,000 | 01/02/26 | 4 | 3 | 1,956 | |
1.68 | Single-Family Home | $455,000 | 02/06/26 | 3 | 1.5 | 2,599 | |
1.85 | Single-Family Home | $864,163 | 05/28/26 | 3 | 2 | 1,297 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETRobin Ban, BERKSHIRE PROPERTY AGENTS, LLC
OFF MARKETChristian G Deckert, WILLIAM PITT SOTHEBY'S - GT BARRINGTON
OFF MARKETMatt Amstead, FAIRGROUND REAL ESTATE, INC
OFF MARKETMaureen White-Kirkby, BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
OFF MARKETTimothy Lovett, BERKSHIRE PROPERTY AGENTS, LLC
OFF MARKETAntonio M Segalla, LANCE VERMEULEN RE, INC
OFF MARKETSteven J. Weisz, WILLIAM PITT SOTHEBY'S - GT BARRINGTON
SOLDMAY 11, 2026Antonio M Segalla, WILLIAM RAVEIS - BERKSHIRE
OFF MARKETMary R White, BERKSHIRE HATHAWAY HOMESERVICES BARNBROOK REALTY
Assigned Schools
These are the assigned schools for 29 Fairview Rd.
- Undermountain Elementary School
- PK-5
- Public
- 262 Students
4/10GreatSchools RatingParent Rating AverageWhen my daughter was a student there, the school staff was so supportive & caring. I feel like it is a true example of 'no child left behind'. As well as exemplifying 'it takes a village to raise a child'. I don't believe that this kind of personal care & concern would have been possible in a larger school. Today she is a successful college sophmore studying forensic science thanks to the strong educational foundation that she received at Undermountain Elementary.Parent Review16y ago - Mount Everett Regional School
- 6-12
- Public
- 274 Students
6/10GreatSchools RatingParent Rating AverageMy son attends this school. It is a good school with caring professionals. It can be hard to keep good teachers because we are so rural and housing is so unaffordable here. Last year my son had some struggles and his teachers all met to formulate a plan. They were really invested in his success and with their support he turned the year around.Parent Review2y ago - New Marlborough Central School
- PK-3
- Public
- 47 Students
7/10GreatSchools RatingParent Rating AverageThis is an extraordinary school. it's small enough (85) so that virtually every student is known by all the teachers. The school climate supports learning in creative ways so that kids may be outside in the garden or working on projects or making discoveries through one of the science-through art special units/productions put on in cooperation with Flying cloud Institute. The building is old and lacks a gym, but the really important features for positive learning are present; more than anything else this means a talented and dedicated group of teachers.Other Review12y ago 
Check out schools near 29 Fairview Rd.
What Locals Say about Monterey
At least 1 Trulia users voted on each feature.
100 % Say people would walk alone at night
100 % Say it's dog friendly
100 % Say yards are well-kept
100 % Say they plan to stay for at least 5 years
100 % Say parking is easy
Sourced by Trulia users. Learn more about our methodology.
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The data relating to real estate for sale on this website comes from Berkshire County Board of Realtors and the Broker Reciprocity Program. Copyright 2026 Berkshire County Board of Realtors. All rights reserved.
The data relating to real estate for sale on this website comes from Berkshire County Board of Realtors and the Broker Reciprocity Program. Copyright 2026 Berkshire County Board of Realtors. All rights reserved.