Maplewood is a three-unit New Canaan condominium complex at 29 Maple Street where verified MLS sales have ranged from $355,000 to $707,500. That spread matters. A one-bedroom unit at 875 square feet and a three-bedroom townhouse at over 3,100 square feet are structurally different products sitting inside the same small association, and each carries a meaningfully different price point and ownership experience. With only three total units, Maplewood is one of the smallest condominium buildings in New Canaan CT real estate, and that scale has real implications for buyers: association dynamics, reserve funding, and resale liquidity all behave differently at this size than in a 30- or 50-unit complex.
No active listings at Maplewood are verified at the time of this writing. That is not unusual. A three-unit building turns over slowly by definition. When a unit does come available here, it rarely stays on the market long. Buyers who are specifically targeting Maple Street or the immediate downtown-adjacent corridor in New Canaan should not wait for a unit to appear on the public MLS before engaging. Off-market awareness is the only reliable strategy in a building this small. Contact The Engel Team directly to monitor availability and get early notice when a unit enters the market.
Three sales are on record through MLS for Maplewood, spanning 2015 to 2018. Closed prices ranged from $355,000 to $707,500, with a median of $436,000. Median price per square foot came in at approximately $329/SF. Unit sizes ranged from 875 to 3,189 square feet across the three recorded transactions.
| Unit | Date | Price | Bed/Bath | SqFt | HOA/mo | Tax/yr |
|---|---|---|---|---|---|---|
| 1 | 08/02/2018 | $707,500 | 3/3 | 3,189 | n/a | $10,506 |
| 3 | 06/08/2017 | $436,000 | 3/2 | 1,325 | n/a | $6,566 |
| 2 | 08/07/2015 | $355,000 | 1/2 | 875 | n/a | $4,527 |
The most important thing to understand about these comps is their age. The most recent sale closed in August 2018. New Canaan’s broader residential market has moved significantly since then, with the town median now sitting at $2,080,000 across all property types. How much of that appreciation applies to a specific unit at Maplewood depends on the unit’s size, condition, and layout. Buyers and sellers alike need a current, unit-specific valuation, not a straight-line projection from a 2018 closing.
Maplewood is a small residential condominium development at 29 Maple Street in New Canaan, CT. With three total units, it sits at the very bottom of the size range for organized condominium associations in town. The address places it close to New Canaan’s compact downtown core, which means walkability to the commercial district is a genuine feature of living here, not a marketing claim. The building offers both townhouse-style and apartment-style configurations, which is unusual for a three-unit property and suggests the building was either converted from an existing structure or designed with deliberate unit variety. Year of construction is not verified in available data. Buyers should confirm this through the town assessor or the resale package. Property taxes vary by unit, ranging from $4,527 to $10,506 per year based on the three recorded MLS sales, which reflects the significant size difference between the smallest and largest units.
Verified MLS data shows three distinct unit configurations at Maplewood. Unit 2 is the smallest at 875 square feet with one bedroom and two baths. Unit 3 is a mid-size three-bedroom, two-bath unit at 1,325 square feet. Unit 1 is the largest by a wide margin at 3,189 square feet with three bedrooms and three baths, which suggests a substantial townhouse-style layout across multiple levels. The gap between 875 and 3,189 square feet in a three-unit building is notable. These are not variations on the same floor plan. They are functionally different residences that happen to share an association. Buyers should confirm whether parking is deeded or assigned, whether outdoor space is exclusive-use or common, and whether the larger townhouse unit has a private entrance or direct garage access.
A three-unit association carries structural risks that buyers in larger buildings do not face in the same way. Reserve funding is split across three owners. If one unit falls behind on dues or a major capital expense hits, the cost falls on a very small group. Before making an offer at Maplewood, buyers should request the full resale package including reserve study, meeting minutes from the last two to three years, current budget, any open special assessments, and the association’s governing documents. If no reserve study exists, that is a red flag worth pricing into any offer.
HOA monthly fees are not verified in available data. That figure must be obtained directly from the association or the listing agent, and buyers should confirm what the fee covers, specifically whether it includes exterior maintenance, landscaping, common area utilities, or building insurance. The property tax spread from $4,527 to $10,506 per year across the three units reflects very different square footages. Buyers of the larger unit should factor the higher tax line into carrying cost calculations.
Rental rules, pet policies, and owner-occupancy requirements are not confirmed from available data. These matter in a three-unit building because association rules can be informal or outdated, and a small association may not have consistently enforced its own bylaws. Confirm the current status of each policy in writing before proceeding. Renovation variation between units is also worth examining at Maplewood. With only three units and sales spanning 2015 to 2018, condition and finish level may differ significantly from one unit to the next. Any valuation should account for what has and has not been updated in the specific unit under consideration.
New Canaan is not a flood-risk market in the way coastal Fairfield County towns are, so flood zone status is unlikely to be a primary due diligence concern here. The more relevant condition issues for a building of this age and size are mechanical systems, roof condition, and exterior upkeep. Confirm maintenance history and responsibility allocation before closing.
Pricing a unit at Maplewood is genuinely difficult. Three recorded sales over a decade, with significant size variation between units and no sales since 2018, means there is no clean comparable set to work from. The building’s downtown-adjacent location and the town’s overall price appreciation since 2018 both support a higher current value than historical comps suggest, but how much higher depends on the specific unit’s condition and configuration. Getting this right requires local knowledge of what comparable condominium square footage is actually trading for in New Canaan today, not a formula applied to stale data.
The Engel Team works the New Canaan market specifically and can provide a current, unit-level valuation for any unit at Maplewood. For sellers, that means understanding what the market will actually support before setting a price. For buyers, it means knowing whether an asking price reflects genuine current value or an optimistic extrapolation from the 2018 peak sale. Reach out directly to discuss availability, off-market monitoring, or a valuation consultation.
© 2025 DOUGLAS ELLIMAN REAL ESTATE. ALL MATERIAL PRESENTED HEREIN IS INTENDED FOR INFORMATION PURPOSES ONLY. WHILE THIS INFORMATION IS BELIEVED TO BE CORRECT, IT IS REPRESENTED SUBJECT TO ERRORS, OMISSIONS, CHANGES OR WITHDRAWAL WITHOUT NOTICE. ALL PROPERTY INFORMATION, INCLUDING, BUT NOT LIMITED TO SQUARE FOOTAGE, ROOM COUNT, NUMBER OF BEDROOMS AND THE SCHOOL DISTRICT IN PROPERTY LISTINGS SHOULD BE VERIFIED BY YOUR OWN ATTORNEY, ARCHITECT OR ZONING EXPERT. EQUAL HOUSING OPPORTUNITY. 
Made By The Speculo Group
