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View PropertiesAs of Apr, 27 2026
Rabbu ROI Score
Greenwich presents a competitive opportunity: investor interest and demand are strong, but higher prices or tighter competition may require more selective deal sourcing.
Greenwich, CT stands out as a premium short-term rental market where high average daily rates of $438 — well above the $373 Connecticut state average — pair with a compact supply of just 40 active Airbnb listings. However, with average home values near $4.7 million and an ROI score of 38 out of 100, the revenue-to-price ratio presents a real challenge for investors seeking strong cash-on-cash returns. The market rewards selective deal sourcing, particularly for hosts who can capture the affluent summer travel crowd that drives July revenues above $8,000 per listing.
According to Rabbu market data, the Greenwich short-term rental market shows:
| Metric | Context | Value |
|---|---|---|
| Active Airbnb Listings | As of Apr, 27 2026 | 40 |
| Average Daily Rate (ADR) | vs. $373 state avg. | $438 |
| Average Occupancy Rate | vs. 37% state avg. | 32% |
| RevPAN | ADR * Occupancy Rate | $141 |
| Average Monthly Revenue | Historical 12-month average | $4,783 |
| Average Annual Revenue | Historical 12-month average | $57,406 |
Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026.
Greenwich attracts investor attention for its affluent Fairfield County location, premium nightly rates, and proximity to New York City, though high property costs demand careful underwriting.
Key investment factors
"Greenwich represents a competitive opportunity where high nightly rates and low listing density create attractive top-line numbers, but the $4.7 million average home value makes the revenue-to-price ratio one of the toughest hurdles for investors. Seasonality is sharp — July peaks at $8,013 in average monthly revenue while January and February dip below $2,400, creating a roughly 3.4x spread between the strongest and weakest months. For investors who can acquire below the market median or convert existing properties, the above-average occupancy stability and premium ADR offer a defensible income floor. Deal selection matters more here than in almost any other Connecticut market."
— Rabbu Market Analysis Team
Greenwich shows strong seasonality, with July ($8,013) and August ($7,744) delivering roughly 3.4 times the revenue of the slowest months like January ($2,387) and February ($2,397). Shoulder months from May through October form a solid mid-tier band around $5,000–$5,200, suggesting meaningful earning potential beyond just the summer peak.
| Month | Trend | Revenue |
|---|---|---|
| January |
|
$2,387 |
| February |
|
$2,397 |
| March |
|
$2,815 |
| April |
|
$3,323 |
| May |
|
$4,998 |
| June |
|
$6,498 |
| July |
|
$8,013 |
| August |
|
$7,744 |
| September |
|
$5,224 |
| October |
|
$5,227 |
| November |
|
$4,407 |
| December |
|
$4,368 |
One-bedroom listings dominate supply with 17 of the 40 active properties, followed by 10 three-bedrooms and 9 two-bedrooms. Given that three-bedrooms generate far higher revenue, the relatively limited supply of larger units may signal an opportunity for investors willing to list properties with more space.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
17 |
| 2 bedrooms |
|
9 |
| 3 bedrooms |
|
10 |
ADR jumps dramatically from $164 for one-bedroom listings to $437 for two-bedrooms and $463 for three-bedrooms, indicating that the premium for adding a second bedroom is far steeper than moving from two to three. Investors targeting two- or three-bedroom units can command rates that are nearly triple what studios and one-bedrooms achieve.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$164 |
| 2 bedrooms |
|
$437 |
| 3 bedrooms |
|
$463 |
Two-bedroom listings lead RevPAN at $181 per available night, edging out three-bedrooms at $156 and far outpacing one-bedrooms at just $45. This suggests two-bedrooms strike the best balance of rate and occupancy, though three-bedrooms still generate the highest total revenue due to their elevated ADR.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$45 |
| 2 bedrooms |
|
$181 |
| 3 bedrooms |
|
$156 |
Two-bedroom units achieve the highest occupancy at 41%, followed by three-bedrooms at 34% and one-bedrooms at 28%. The notably lower fill rate for one-bedrooms — despite making up the largest share of supply — implies that demand in Greenwich skews toward guests needing more space, likely families or groups visiting from New York City.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
28% |
| 2 bedrooms |
|
41% |
| 3 bedrooms |
|
34% |
Three-bedroom listings are the clear top earners at $6,509 per month, nearly triple the $2,145 that one-bedrooms bring in and well ahead of two-bedrooms at $2,465. The gap between two- and three-bedroom monthly revenue is substantial, driven by both higher rates and decent occupancy for larger properties.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$2,145 |
| 2 bedrooms |
|
$2,465 |
| 3 bedrooms |
|
$6,509 |
Three-bedroom properties generate $78,119 in annual revenue — more than three times the $25,741 earned by one-bedroom listings and over 2.6 times the $29,587 from two-bedrooms. For investors evaluating return potential, larger units clearly deliver the strongest gross income, though acquisition and operating costs must be weighed accordingly.
| Size | Trend | Value |
|---|---|---|
| 1 bedroom |
|
$25,741 |
| 2 bedrooms |
|
$29,587 |
| 3 bedrooms |
|
$78,119 |
Parking leads amenity prevalence at 95%, reflecting Greenwich's car-dependent suburban character, followed by kitchen (85%) and workspace (75%) — suggesting guests expect a home-like experience suited to both leisure and remote work. Outdoor features like patios (58%), backyards (58%), and BBQ grills (35%) are common, while niche amenities like beach access (15%) and EV chargers (13%) could serve as meaningful differentiators for new listings.
| Amenity | Trend | Value |
|---|---|---|
| Parking |
|
95% |
| Kitchen |
|
85% |
| Workspace |
|
75% |
| Washer |
|
70% |
| Dryer |
|
70% |
| Self Check-in |
|
63% |
| Patio or Balcony |
|
58% |
| Backyard |
|
58% |
| Pets |
|
48% |
| Outdoor Furniture |
|
45% |
| BBQ Grill |
|
35% |
| Beach Access |
|
15% |
| Lake Access |
|
13% |
| EV Charger |
|
13% |
Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.
| Factor | Greenwich Performance | Weight |
|---|---|---|
| Revenue-to-Price Ratio | Below average | 40% |
| Occupancy Stability | Above average | 30% |
| Market Growth Trend | Below average | 15% |
| Supply/Demand Balance | Average | 15% |
Greenwich's ROI Score of 38 out of 100 falls into the 'Competitive Opportunity' band, signaling that while demand and rates are healthy, the market's high entry costs create a below-average revenue-to-price ratio — the most heavily weighted factor in the score. On the positive side, occupancy stability rates above average, meaning cash flow tends to be more predictable than in many comparable luxury markets. Investors should pair this data with thorough local regulatory research and focus on properties priced well below the $4.7 million market average to improve their return profile.
Understanding local STR regulations is essential before investing in Greenwich. Here's the current regulatory landscape:
Greenwich, Connecticut may require short-term rental hosts to register or obtain a permit before listing a property; investors should verify current requirements directly with the Town of Greenwich and the State of Connecticut, as local rules can change.
Common restrictions in markets like Greenwich can include occupancy limits, minimum stay requirements, noise and parking regulations, and HOA-level prohibitions that may apply in certain neighborhoods or condo associations. Investors should also check whether any cap on the number of STR permits has been enacted locally.
Short-term rental operators in Connecticut are generally subject to state lodging and sales taxes, and hosts should confirm whether any additional municipal occupancy taxes apply in Greenwich. Many booking platforms collect and remit state-level taxes automatically, but it's wise to verify compliance with all obligations.
Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Greenwich can provide current regulatory guidance.
Financing an Airbnb investment in Greenwich requires lenders who understand STR income. Rabbu partner lenders offer:
"Over the next 12–18 months, Greenwich's STR market is likely to maintain its pronounced summer seasonality, with peak monthly revenues estimated in the $7,000–$8,000 range during July and August. Occupancy stability scores above average, which suggests consistent baseline demand even as listing supply grew significantly year-over-year (192%). Investors should anticipate ADR holding steady or rising modestly by 1–3% given the affluent guest profile, though the below-average market growth trend and expanding supply could temper occupancy gains. Operators who optimize pricing during shoulder months like May, September, and October — where revenues already approach $5,000–$5,200 — will be best positioned to maximize annual yield."
— Rabbu Market Analysis Team
Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.
Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Apr, 27 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month averages as of April 2026 and may not capture very recent market shifts. Local regulations, HOA rules, and tax obligations can change; investors should verify current requirements before purchasing or listing a property.
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