The Oaks Fairfield CT
- Address: 108 Stillson Road, Fairfield, CT
- Total Units: 32
- Year Built: 1988–1989
- Style: Townhouse
- Bedrooms: 3
- HOA Fee: $695/month (current baseline; some units show higher)
- Property Tax: $15,082/year (approximate)
- MLS Median Sale Price: $880,750 (14 recorded sales)
- Price Range (MLS history): $705,000 to $1,250,000
- Amenities: Pond, golf access, health club
The Oaks Condos for Sale
The Oaks is a 32-unit townhouse condominium community at 108 Stillson Road in Fairfield. With only 32 homes in the complex and strong buyer demand across Fairfield CT condos, availability here moves quickly. This is not a complex where listings sit. The most recent sale closed in March 2025 at $1,250,000, and the prior recorded sale was in June 2023 at $1,100,000 — a two-year gap that reflects how rarely units come to market. If you are waiting for the right unit to appear publicly, you may wait a long time. The Engel Team monitors off-market activity at The Oaks and can alert buyers when a unit is approaching the market before it is listed.
Recently Sold at The Oaks
MLS records show 14 sales at The Oaks since 2015. Closed prices ranged from $705,000 to $1,250,000, with a median sale price of $880,750. Unit sizes ran from 2,700 to 4,937 square feet, and the median price per square foot across recorded sales was approximately $270/SF. The most recent sale, Unit 108, closed on March 14, 2025 at $1,250,000 for a 3-bed, 3-bath unit with 4,262 square feet — $293/SF. That is the highest recorded price in the complex’s MLS history and a meaningful step above the prior sale. Unit 104 sold in June 2023 at $1,100,000 for 2,700 square feet, and Unit 144 sold in December 2022 at $1,165,000 for 4,414 square feet. Buyers should note that pricing at The Oaks reflects both unit size and interior condition — two units with identical bedroom counts can differ by $200,000 or more depending on renovations.
| Unit | Date | Price | Bed/Bath | SqFt | HOA/mo | Tax/yr |
|---|---|---|---|---|---|---|
| 108 | 03/14/2025 | $1,250,000 | 3/3 | 4,262 | $850 | $12,101 |
| 104 | 06/12/2023 | $1,100,000 | 3/3 | 2,700 | $695 | $11,404 |
| 144 | 12/28/2022 | $1,165,000 | 3/4 | 4,414 | $795 | $13,809 |
| 05/26/2022 | $901,000 | 3/3 | 2,914 | $795 | $12,854 | |
| 06/01/2021 | $705,000 | 3/4 | 4,000 | $695 | $15,312 | |
| 202 | 02/09/2021 | $715,000 | 3/3 | 2,995 | $683 | $16,518 |
| 190 | 11/13/2020 | $899,000 | 3/4 | 3,745 | $683 | $16,992 |
| 200 | 10/23/2020 | $720,000 | 3/4 | 3,779 | $683 | $16,713 |
| 134 | 06/06/2019 | $840,000 | 3/3 | 2,914 | $683 | $15,738 |
| 162 | 11/30/2017 | $862,500 | 3/3 | 3,460 | $15,780 | |
| 164 | 09/14/2017 | $845,000 | 3/3 | 2,700 | $14,329 | |
| 152 | 11/29/2016 | $812,000 | 3/3 | 2,946 | $14,851 | |
| 172 | 11/13/2015 | $945,000 | 3/3 | 4,937 | $15,812 | |
| 170 | 07/24/2015 | $924,000 | 4/3 | 3,186 | $14,651 |
About The Oaks
The Oaks is a townhouse condominium community built between 1988 and 1989 at 108 Stillson Road in Fairfield, CT. The complex comprises 32 units across a wooded residential setting with a pond on the grounds. The association provides access to a health club and golf, which is unusual for a complex of this size. At 32 total units, The Oaks is small enough that the community has a defined character — residents tend to know their neighbors. Built in the late 1980s, the structures carry the architectural profile of that era: attached multi-story townhouses with generous square footage relative to what newer construction delivers at comparable price points in Fairfield. The setting on Stillson Road places the complex in a quieter section of town, away from the denser residential blocks closer to downtown and the Post Road corridor. For buyers looking at Fairfield CT real estate, The Oaks represents a distinct ownership category: large-format townhouse living with a small-community feel and meaningful common amenities.
Homes and Layouts at The Oaks
Every recorded sale at The Oaks has been a 3-bedroom unit, with one exception — a 4-bedroom unit that sold in July 2015. Bath counts across sales range from 3 to 4. Unit sizes vary considerably: the smallest recorded sale was 2,700 square feet and the largest was 4,937 square feet. That range within a 32-unit complex indicates real variation in floor plan and unit configuration, not just cosmetic differences. Buyers should not assume any two units are equivalent based on bedroom count alone. The townhouse format means each unit is entered from grade level and spread across multiple floors, which is a different living experience than a flat-style condominium. Parking is typically integrated into the townhouse structure in complexes built during this era, though buyers should confirm garage configuration and guest parking directly with the association. Outdoor space at the unit level should also be verified — some townhouse units in 1980s complexes include private patios or decks; others do not.
What Buyers Need to Know
The baseline HOA fee at The Oaks is $695/month, but recent sales show fees as high as $850/month for some units. That variation suggests either tiered fee structures by unit size or special assessments that have been rolled into monthly charges. Buyers must request a current fee schedule, the most recent reserve study, and a full accounting of any pending or recent special assessments before making an offer. For a building constructed in 1988–1989, reserve funding is a material issue — mechanical systems, roofs, and exterior components at that age typically require capital investment, and a thin reserve fund shifts that cost to owners individually. The complex is not waterfront, which removes the flood insurance complexity present at Fairfield’s coastal properties. Property taxes across recorded sales have ranged from $11,404 to $16,992 per year, with recent sales on the lower end of that range, likely reflecting updated assessments. The resale package, which should include financial statements, meeting minutes, and the current master deed and bylaws, is required reading before any binding commitment. Resale value at The Oaks has held and grown, with the 2025 sale representing the highest recorded price in the complex’s history, but pricing remains sensitive to interior condition and unit size. Buyers should confirm rental restrictions, pet policy, and owner-occupancy ratio with the association directly, as these rules affect both day-to-day living and future resale flexibility.
Buying or Selling at The Oaks
With only 14 recorded sales over roughly a decade at a 32-unit complex, The Oaks does not generate the volume of comparable sales that most buyers and sellers rely on for pricing confidence. That thin comp base cuts both ways: sellers can point to the March 2025 sale at $1,250,000 as a benchmark, but buyers will scrutinize interior condition and size closely because a 2,700-square-foot unit and a 4,937-square-foot unit at The Oaks are not the same product. Getting the pricing right here requires someone who knows this specific complex, not just Fairfield condos in general. Browse available Fairfield homes for sale to understand where The Oaks sits relative to the broader market. The Engel Team has tracked sales at The Oaks and can provide a current valuation for sellers or a detailed comp analysis for buyers considering a unit here. Contact us directly for off-market monitoring, listing strategy, or a no-obligation valuation.
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