Chesterfield Condos for Sale

Chesterfield turns over with some regularity for a gated community of its size, but individual units do not sit long once priced correctly. Across 220 recorded MLS transactions, the complex has demonstrated consistent buyer demand at multiple price points, from compact one-bedroom flats to larger townhouse-style units exceeding 2,600 square feet. That range means Chesterfield draws a genuinely varied pool of buyers, and when a well-priced unit comes to market, competition follows quickly. If you are looking for available Stamford CT condos, Chesterfield is one of the more active complexes to monitor. Active listings change quickly. Contact The Engel Team directly for current availability and any off-market opportunities at this address.

Recently Sold at Chesterfield

The MLS record for Chesterfield covers 220 sales. Closed prices have ranged from $32,700 to $740,000, with a median of $410,000 across the full sales history. The median price per square foot is approximately $307. Unit sizes have ranged from 260 square feet to just over 4,000 square feet, which reflects the genuine diversity of layouts within the complex.

Recent 2025 and 2026 sales tell a more current story. One-bedroom units in the 885-square-foot range have been closing between $379,000 and $440,000. One-bedroom units with two baths and approximately 1,066 to 1,069 square feet have sold from $395,000 to $520,000 depending on condition and building section. Two-bedroom, two-bath units at 1,199 square feet have been closing between $562,000 and $599,000 in early 2026. Larger two-bedroom units in the 2,636-square-foot range, which carry higher HOA fees and taxes, have closed between $650,000 and $740,000. The spread is wide because Chesterfield genuinely contains different product types under one address. A 885-square-foot one-bedroom and a 4,006-square-foot multi-level townhouse are both called Chesterfield, but they are not comparable units and should not be priced as though they are.

Unit	Date	Price	Bed/Bath	SqFt	HOA/mo	Tax/yr
G17	04/02/2026	$599,000	2/2	1,199	$345	$6,843
A8	03/27/2026	$395,000	1/2	1,066	$347	$6,344
H13	03/13/2026	$570,500	2/2	1,199	$332	$6,843
C11	03/13/2026	$400,000	1/1	885	$288	$5,223
H4	02/26/2026	$520,000	1/2	1,066	$348	$6,350
G7	02/12/2026	$400,000	1/1	885	$249	$5,237
G11	01/23/2026	$401,000	1/1	885	$371	$5,237
G7	01/16/2026	$379,000	1/1	885	$245	$5,285
F20	12/22/2025	$435,000	1/2	1,066	$296	$6,344
C13	12/15/2025	$440,000	1/1	885	$269	$5,285
G18	11/24/2025	$568,750	2/2	1,199	$364	$6,843
E6	11/05/2025	$448,300	1/2	1,178	$340	$6,170
APT 33F	10/28/2025	$695,000	2/3	2,148	$364	$6,889
36D	10/23/2025	$740,000	2/3	2,636	$731	$8,764
A12	10/01/2025	$500,000	1/2	1,178	$327	$6,170
D1	09/30/2025	$468,000	1/2	1,178	$297	$6,170
F2	09/26/2025	$575,000	1/2	1,378	$383	$7,591
8C	09/19/2025	$705,000	2/3	2,211	$670	$9,250
36B	08/29/2025	$685,000	2/4	2,636	$732	$8,764
H1	08/28/2025	$445,000	1/2	1,632	$296	$6,344
C19	07/24/2025	$410,000	1/2	1,069	$326	$6,796
A6	07/03/2025	$510,000	1/2	1,069	$326	$6,637
21BB	06/04/2025	$580,000	2/2	1,419	$360	$7,825
APT 33B	05/27/2025	$562,000	2/2	1,199	$332	$6,683
C8	05/14/2025	$670,000	2/3	1,420	$596	$7,829
Apt 38A	04/25/2025	$693,500	2/3	2,636	$803	$8,896
B6	04/17/2025	$583,000	2/2	1,199	$503	$6,683
APT 37D	02/13/2025	$650,000	2/3	2,636	$732	$8,559
A7	02/07/2025	$494,760	1/2	1,069	$273	$6,637

About Chesterfield

Chesterfield is a gated condominium community at 2289 Bedford Street in Stamford, CT. The complex was developed between 1984 and 2000 and contains 274 units total across what functions as a townhouse-style community. Within the gated perimeter, a section of approximately 115 townhouse units gives the complex an open, residential feel that reads more like a neighborhood than a conventional condominium complex. Vaulted ceilings and skylights appear in certain second-floor units, expanding the sense of space well beyond what the square footage alone suggests. The community includes a pool and clubhouse, and garage parking is available. At 274 units, Chesterfield is one of the larger gated condominium communities in Stamford, which supports more active resale comparables than most smaller complexes in the area. That depth of transaction history is useful for both buyers and sellers trying to establish value precisely.

Homes and Layouts at Chesterfield

The unit mix at Chesterfield runs from studios to three-bedroom configurations. Recorded sales reflect square footage ranging from 260 square feet at the compact end to over 4,000 square feet in the largest multi-level townhouse units. The most common transaction footprint falls between 885 and 1,199 square feet for one- and two-bedroom units. Larger townhouse-style units in the 2,200 to 3,700 square-foot range also transact regularly, with those units typically carrying higher HOA fees reflecting their size and configuration. Some units are flats; others are vertically oriented townhouses. The townhouse layouts within the gated community are designed to feel open rather than compressed, and second-floor units with vaulted ceilings and skylights reinforce that. Garage parking is part of the complex. Buyers comparing units within Chesterfield should pay close attention to floor level, layout type, and HOA fee tier, because the variation between a compact flat and a full townhouse here is significant in both price and monthly carrying cost.

What Buyers Need to Know

HOA fees at Chesterfield vary by unit size and section. Recent sales show monthly fees ranging from under $250 for smaller one-bedroom units to over $800 for the largest townhouse configurations. The baseline fee of approximately $355 per month applies to a range of mid-size units, but buyers should confirm the exact fee for any specific unit before drawing budget conclusions from that number. Property taxes also vary substantially: compact one-bedroom units have carried annual tax bills near $3,600, while larger two- and three-bedroom townhouses have carried bills in the $8,700 to $9,800 range.

Because Chesterfield was developed across a 16-year window from 1984 to 2000, building systems and interior finishes vary considerably between units. Some units have been updated multiple times; others retain original construction. A building inspection and a careful review of what has and has not been renovated is essential. Buyers should also request the association’s reserve fund study, the most recent budget, and any history of special assessments before committing. A community of 274 units that spans nearly two decades of construction can carry uneven maintenance histories across its sections.

Rental rules, pet policies, and owner-occupancy ratios affect both financing options and long-term resale potential. Buyers using conventional financing should confirm the owner-occupancy ratio meets lender requirements before proceeding. The resale package, which typically includes meeting minutes, financials, and reserve disclosures, is required reading. Renovation variation between units is real here, and buyers should factor condition into every price comparison rather than treating same-square-footage units as interchangeable. Understanding the resale package is not optional at a complex this size and age.

Buying or Selling at Chesterfield

Pricing a unit correctly at Chesterfield is more complicated than it looks. The 220-sale MLS record is useful, but the spread from $379,000 to $740,000 among what appear to be similar unit types reflects real differences in layout, floor level, condition, HOA tier, and building section. Getting to the right number requires knowing which sales are actually comparable to the unit in question, not just which units share a bedroom count.

The Engel Team works with buyers and sellers across Stamford CT real estate, including active monitoring of Chesterfield and other gated communities along Bedford Street. For sellers, that means a valuation built on the specific characteristics of your unit, not a range pulled from the full complex average. For buyers, it means knowing when a unit is priced accurately and when the asking price does not account for deferred maintenance or an unfavorable HOA fee tier. If you are considering a purchase or sale at Chesterfield, or exploring other Stamford homes for sale as part of a broader search, contact The Engel Team for a direct conversation about current value and strategy.