Real Estate Investment Properties for Sale in Greenwich, CT

Looking for investment property in Greenwich, CT with high ROI ?

Explore a variety of short-term homes & houses in Greenwich, CT. Invest wisely with VRBO & Greenwich, CT Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Greenwich, CT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
147 Holly Hill Lane Greenwich, CT Prime opportunity to acquire a turn-key investment property featuring 9 duplex-style townh...	2 beds \| 2 baths \| 1,611 sq.ft.	$9,999,999	Airbnb cash on cash: -3.02% Traditional cash on cash: -2.78% Airbnb Rental Income: $1642 Traditional Rental Income: $3419 Airbnb ROI: -3.02% Traditional ROI: -2.78%
36 Putnam Park Greenwich, CT Stunning sun-filled 2-bedroom, 1-bath end unit fully renovated in 2021 with designer finis...	2 beds \| 1 baths \| 986 sq.ft.	$695,000	Airbnb cash on cash: -2.98% Traditional cash on cash: -0.69% Airbnb Rental Income: $1642 Traditional Rental Income: $2669 Airbnb ROI: -2.98% Traditional ROI: -0.69%
34 Edgewood Drive Greenwich, CT Tucked discreetly at the end of a long, private drive in coveted mid-country Greenwich, th...	4 beds \| 6 baths \| 5,244 sq.ft.	$4,995,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.75% Airbnb Rental Income: $4957 Traditional Rental Income: $10225 Airbnb ROI: -0.61% Traditional ROI: 0.75%
201 Shore Road Greenwich, CT On sought-after Belle Haven peninsula near town, this 2008 expanded 5 bed, 3.2 bath home b...	5 beds \| 5 baths \| 3,598 sq.ft.	$2,350,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 1.54% Airbnb Rental Income: $3041 Traditional Rental Income: $6895 Airbnb ROI: -0.54% Traditional ROI: 1.54%
147 Holly Hill Lane #2 Greenwich, CT This sun-filled condo features an open-plan first level with a spacious living room with f...	2 beds \| 3 baths \| 1,611 sq.ft.	$1,250,000	Airbnb cash on cash: -2.19% Traditional cash on cash: -0.04% Airbnb Rental Income: $1642 Traditional Rental Income: $3686 Airbnb ROI: -2.19% Traditional ROI: -0.04%
12 Stallion Trail Greenwich, CT Welcome to 12 Stallion Trails, a unique modern masterpiece located within a private gated ...	4 beds \| 8 baths \| 8,681 sq.ft.	$3,795,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -0.23% Airbnb Rental Income: $4957 Traditional Rental Income: $10315 Airbnb ROI: -2.04% Traditional ROI: -0.23%
148 E Elm Street #2 Greenwich, CT Introducing 148 E Elm Street, Unit 2- Another amazing property by R&R Homes where luxury b...	4 beds \| 5 baths \| 4,095 sq.ft.	$3,600,000	Airbnb cash on cash: -1.98% Traditional cash on cash: -0.77% Airbnb Rental Income: $4957 Traditional Rental Income: $7987 Airbnb ROI: -1.98% Traditional ROI: -0.77%
148 E Elm Street #1 Greenwich, CT Welcome to 148 E Elm Street, Unit 1- Another amazing property by R&R Homes where high-end ...	4 beds \| 6 baths \| 4,472 sq.ft.	$3,600,000	Airbnb cash on cash: -1.98% Traditional cash on cash: -0.25% Airbnb Rental Income: $4957 Traditional Rental Income: $9720 Airbnb ROI: -1.98% Traditional ROI: -0.25%
331 Round Hill Road Greenwich, CT Built in 1758 and masterfully updated, 331 Round Hill Road offers a rare opportunity where...	5 beds \| 7 baths \| 5,257 sq.ft.	$4,350,000	Airbnb cash on cash: -2.58% Traditional cash on cash: -0.51% Airbnb Rental Income: $3041 Traditional Rental Income: $10689 Airbnb ROI: -2.58% Traditional ROI: -0.51%
116 Birch Lane Greenwich, CT A meticulous renovation and expansion has transformed this quintessential New England Colo...	5 beds \| 8 baths \| 6,044 sq.ft.	$6,495,000	Airbnb cash on cash: -2.76% Traditional cash on cash: -1.35% Airbnb Rental Income: $3041 Traditional Rental Income: $10824 Airbnb ROI: -2.76% Traditional ROI: -1.35%
267 Riversville Rd Greenwich, CT Nestled at the end of a quiet dead -end street, this 3- bedroom, 3- bath, home offers a ra...	3 beds \| 3 baths \| 2,882 sq.ft.	$2,995,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.55% Airbnb Rental Income: $3693 Traditional Rental Income: $5420 Airbnb ROI: -0.36% Traditional ROI: 0.55%
1000 North Street Greenwich, CT An exceptional opportunity on a rare, expansive property in coveted Greenwich, presenting ...	4 beds \| 3 baths \| 1,840 sq.ft.	$999,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.98% Airbnb Rental Income: $4957 Traditional Rental Income: $4839 Airbnb ROI: 1.01% Traditional ROI: 1.98%
351 Pemberwick Road #APT 111 Greenwich, CT Located in the desirable Hawthorne Condominium complex, this 1-bedroom, 1-bath unit offers...	1 beds \| 1 baths \| 673 sq.ft.	$445,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.96% Airbnb Rental Income: $1762 Traditional Rental Income: $2126 Airbnb ROI: -1.07% Traditional ROI: 0.96%
10 Carissa Lane Greenwich, CT Welcome to 10 Carissa Lane, a privately situated home on a cul-de-sac street not far from ...	4 beds \| 5 baths \| 3,948 sq.ft.	$2,650,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.43% Airbnb Rental Income: $4957 Traditional Rental Income: $8851 Airbnb ROI: -1.57% Traditional ROI: 0.43%
106 Patterson Avenue Greenwich, CT Beautifully renovated and modernized in 2022, this classic Tudor on one of Greenwich's pre...	5 beds \| 5 baths \| 3,448 sq.ft.	$4,500,000	Airbnb cash on cash: -2.59% Traditional cash on cash: -1.03% Airbnb Rental Income: $3041 Traditional Rental Income: $8887 Airbnb ROI: -2.59% Traditional ROI: -1.03%
70 Byram Terrace Drive Greenwich, CT Set on a flat, open .24-acre lot with vibrant landscaping, this home has been thoughtfully...	2 beds \| 2 baths \| 1,711 sq.ft.	$999,000	Airbnb cash on cash: -1.96% Traditional cash on cash: 0.37% Airbnb Rental Income: $1642 Traditional Rental Income: $3345 Airbnb ROI: -1.96% Traditional ROI: 0.37%
10 Carleton Street Greenwich, CT Address: 10 Carleton Street, Greenwich, CT 06830 * Price: $1,800,000 (best deal in centra...	3 beds \| 3 baths \| 1,257 sq.ft.	$1,850,000	Airbnb cash on cash: -1.5% Traditional cash on cash: -1.03% Airbnb Rental Income: $3693 Traditional Rental Income: $3701 Airbnb ROI: -1.5% Traditional ROI: -1.03%
1018 North Street Greenwich, CT Charming vintage colonial in Banksville area. Close to Bedford shopping and restaurants an...	3 beds \| 2 baths \| 1,546 sq.ft.	$999,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 0.67% Airbnb Rental Income: $3693 Traditional Rental Income: $3626 Airbnb ROI: -0.12% Traditional ROI: 0.67%
39 Homestead Road Greenwich, CT Set on nearly an acre in the heart of Glenville and on a fabulous cul-de-sac, this 3/4 bed...	3 beds \| 2 baths \| 1,905 sq.ft.	$1,375,000	Airbnb cash on cash: -0.94% Traditional cash on cash: -0.3% Airbnb Rental Income: $3693 Traditional Rental Income: $3710 Airbnb ROI: -0.94% Traditional ROI: -0.3%
175 Lake Avenue Greenwich, CT This meticulously renovated and expertly designed 1915 Victorian home seamlessly blends cl...	5 beds \| 5 baths \| 3,056 sq.ft.	$3,295,000	Airbnb cash on cash: -2.4% Traditional cash on cash: -0.38% Airbnb Rental Income: $3041 Traditional Rental Income: $8508 Airbnb ROI: -2.4% Traditional ROI: -0.38%
50 Sound View Drive #4N Greenwich, CT Welcome to Unit 4N, a luxury townhouse in the Beacon Hill Association. Located in the hear...	4 beds \| 6 baths \| 4,033 sq.ft.	$3,795,000	Airbnb cash on cash: -2.04% Traditional cash on cash: -0.32% Airbnb Rental Income: $4957 Traditional Rental Income: $10001 Airbnb ROI: -2.04% Traditional ROI: -0.32%
15 Walker Court Greenwich, CT Welcome to this move-in ready split-level home ideally located in the Glenville neighborho...	3 beds \| 3 baths \| 1,842 sq.ft.	$1,275,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.53% Airbnb Rental Income: $3693 Traditional Rental Income: $4426 Airbnb ROI: -0.77% Traditional ROI: 0.53%
131 Henry Street Greenwich, CT Welcome to this completely renovated 3-bedroom, 3.5-bath luxury home in Greenwich. This st...	3 beds \| 4 baths \| 1,455 sq.ft.	$1,200,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 1% Airbnb Rental Income: $3693 Traditional Rental Income: $4701 Airbnb ROI: -0.62% Traditional ROI: 1%
145 Porchuck Road Greenwich, CT Tucked away on two park-like acres, this expanded 1930s Cape blends timeless charm with mo...	5 beds \| 5 baths \| 4,209 sq.ft.	$3,195,000	Airbnb cash on cash: -2.37% Traditional cash on cash: -0.1% Airbnb Rental Income: $3041 Traditional Rental Income: $9067 Airbnb ROI: -2.37% Traditional ROI: -0.1%
12 Wooddale Road Greenwich, CT Tucked away on a quiet cul-de-sac just off Lake Av., this beautifully renovated & expanded...	5 beds \| 6 baths \| 4,852 sq.ft.	$4,500,000	Airbnb cash on cash: -2.59% Traditional cash on cash: -0.66% Airbnb Rental Income: $3041 Traditional Rental Income: $10392 Airbnb ROI: -2.59% Traditional ROI: -0.66%
47 Lafayette Place #6J Greenwich, CT Perched on the top floor of historic Greenwich Lodge, this spacious one-bedroom blends cla...	1 beds \| 1 baths \| 769 sq.ft.	$759,000	Airbnb cash on cash: -1.45% Traditional cash on cash: -0.19% Airbnb Rental Income: $1762 Traditional Rental Income: $2172 Airbnb ROI: -1.45% Traditional ROI: -0.19%
188 Hamilton Avenue Greenwich, CT Exceptional investment opportunity or perfect for a buyer looking to offset mortgage costs...	6 beds \| 4 baths \| 2,989 sq.ft.	$1,349,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 2.1% Airbnb Rental Income: $3041 Traditional Rental Income: $6651 Airbnb ROI: -1.33% Traditional ROI: 2.1%
15 Dearfield Lane Greenwich, CT Set on a serene private lane, moments from the bustle of Greenwich Avenue, this sophistica...	5 beds \| 6 baths \| 5,080 sq.ft.	$4,250,000	Airbnb cash on cash: -2.56% Traditional cash on cash: -0.62% Airbnb Rental Income: $3041 Traditional Rental Income: $10014 Airbnb ROI: -2.56% Traditional ROI: -0.62%

Real Estate investment in Greenwich, CT

There are 32 properties for sale in the city of Greenwich . The median list price in Greenwich is $2,425,000 and the average price per square foot is $799. In December 2025, the average monthly cash on cash return in Greenwich is N/A%. The average monthly rental income in Greenwich is $4,701.

Greenwich, CT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 32 investment properties available for sale in Greenwich.

In 2025, the best neighborhood to buy investment property is Greenwich.

The ROI for Long-Term is higher than the Short-Term in Greenwich with average rental income of $4,701.

Your search for investment property begins and ends here

Investment Property for Sale in Greenwich, CT

147 Holly Hill Lane

Greenwich, CT

2 beds | 2 baths | 1,611 sq.ft.

$9,999,999

Airbnb cash on cash: -3.02%

Traditional cash on cash: -2.78%

Airbnb Rental Income: $1642

Traditional Rental Income: $3419

Airbnb ROI: -3.02%

Traditional ROI: -2.78%

36 Putnam Park

Greenwich, CT

2 beds | 1 baths | 986 sq.ft.

$695,000

Airbnb cash on cash: -2.98%

Traditional cash on cash: -0.69%

Airbnb Rental Income: $1642

Traditional Rental Income: $2669

Airbnb ROI: -2.98%

Traditional ROI: -0.69%

34 Edgewood Drive

Greenwich, CT

4 beds | 6 baths | 5,244 sq.ft.

$4,995,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 0.75%

Airbnb Rental Income: $4957

Traditional Rental Income: $10225

Airbnb ROI: -0.61%

Traditional ROI: 0.75%

201 Shore Road

Greenwich, CT

5 beds | 5 baths | 3,598 sq.ft.

$2,350,000

Airbnb cash on cash: -0.54%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $3041

Traditional Rental Income: $6895

Airbnb ROI: -0.54%

Traditional ROI: 1.54%

147 Holly Hill Lane #2

Greenwich, CT

2 beds | 3 baths | 1,611 sq.ft.

$1,250,000

Airbnb cash on cash: -2.19%

Traditional cash on cash: -0.04%

Airbnb Rental Income: $1642

Traditional Rental Income: $3686

Airbnb ROI: -2.19%

Traditional ROI: -0.04%

12 Stallion Trail

Greenwich, CT

4 beds | 8 baths | 8,681 sq.ft.

$3,795,000

Airbnb cash on cash: -2.04%

Traditional cash on cash: -0.23%

Airbnb Rental Income: $4957

Traditional Rental Income: $10315

Airbnb ROI: -2.04%

Traditional ROI: -0.23%

148 E Elm Street #2

Greenwich, CT

4 beds | 5 baths | 4,095 sq.ft.

$3,600,000

Airbnb cash on cash: -1.98%

Traditional cash on cash: -0.77%

Airbnb Rental Income: $4957

Traditional Rental Income: $7987

Airbnb ROI: -1.98%

Traditional ROI: -0.77%

148 E Elm Street #1

Greenwich, CT

4 beds | 6 baths | 4,472 sq.ft.

$3,600,000

Airbnb cash on cash: -1.98%

Traditional cash on cash: -0.25%

Airbnb Rental Income: $4957

Traditional Rental Income: $9720

Airbnb ROI: -1.98%