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Browse All Greenwich CT Historical Properties for Sale

Greenwich image
Greenwich $1,495,000

Outstanding opportunity to build your dream home on an oversized lot in the coveted Glenville School district. Large lot provides ample room for a home of @4,500 sq. ft. ...

  • 3 Beds
  • 2 Baths
  • 24206719 MLS
105 Glenville St, Greenwich image
105 Glenville St, Greenwich $1,449,000

Completely renovated and move-in ready, this beautifully updated split-level sits on a generous 0.33-acre level lot in Greenwich's desirable Glenville neighborhood. With ...

  • 3 Beds
  • 3 Baths
  • 24206577 MLS
17 Thornhill Rd, Greenwich image
17 Thornhill Rd, Greenwich $1,749,000

Welcome to 17 Thornhill, a beautifully appointed home offering exceptional space, versatility and effortless indoor-outdoor living. Sun-filled interiors feature hardwood ...

  • 4 Beds
  • 3 Baths
  • 24205832 MLS
21 Calhoun Dr, Greenwich image
21 Calhoun Dr, Greenwich $6,150,000

A rare opportunity in one of Greenwich's most coveted in-town settings, 21 Calhoun Drive combines the timeless presence and character of a classic Greenwich estate with e...

  • 5 Beds
  • 8 Baths
  • 24205524 MLS
18 Shady Brook Ln, Greenwich image
18 Shady Brook Ln, Greenwich $3,450,000

Beautifully renovated by the current owners, this 5 bedroom, 5 bath home features refinished hardwood floors throughout, a modern open floor plan with eat-in kitchen/dini...

  • 5 Beds
  • 5 Baths
  • 24202309 MLS
61 Center Dr, Greenwich image
61 Center Dr, Greenwich $1,549,000

Welcome to 61 Center Drive, a move-in-ready Old Greenwich home at the end of a cul de sac. Thoughtfully updated across two levels, this 5-bedroom, 3-full bath home offers...

  • 5 Beds
  • 3 Baths
  • 24200241 MLS
9 Old Forge Rd, Greenwich image
9 Old Forge Rd, Greenwich $3,250,000

Privately set on two magnificent acres at the end of a quiet Mid-Country cul-de-sac, this beautifully updated four-bedroom residence offers an exceptional blend of unders...

  • 4 Beds
  • 3 Baths
  • 24198837 MLS
14 Shoreham Club Rd, Greenwich image
14 Shoreham Club Rd, Greenwich $4,000,000

A rare Shorehame Association lot with unobstructed Long Island Sound sight lines offered as an amazing opportunity to build new or reimagine the existing residence in one...

  • 4 Beds
  • 3 Baths
  • 24205297 MLS
7 Bailiwick Rd, Greenwich image
7 Bailiwick Rd, Greenwich $4,250,000

Exceptional custom-built residence in Greenwich's coveted Bailiwick Association, thoughtfully designed with the finest materials, craftsmanship and an effortless connecti...

  • 5 Beds
  • 6 Baths
  • 24205146 MLS
32 Josephine Evaristo Ave, Greenwich image
32 Josephine Evaristo Ave, Greenwich $995,000

Unique two-family opportunity offering immediate income and future redevelopment potential. The existing up/down two-family features 4 bedrooms, 2 baths and approximately...

  • 4 Beds
  • 2 Baths
  • 24204567 MLS
37 Mary Ln, Greenwich image
37 Mary Ln, Greenwich $2,999,000

Completely reimagined and expanded to nearly twice its original footprint, this exceptional Riverside residence is the result of a meticulous gut renovation by Abode Inte...

  • 5 Beds
  • 4 Baths
  • 24201047 MLS
52 Lafayette Pl Unit 3G, Greenwich image
52 Lafayette Pl Unit 3G, Greenwich — Fairfield House $625,000

Welcome to this beautiful 2-bedroom, 2-bath corner unit offering approximately 990 square feet of comfortable living space. Located on the third floor, this bright and in...

  • 2 Beds
  • 2 Baths
  • 24203644 MLS
  • Fairfield House Bldg.
14 Highview Ave, Greenwich image
14 Highview Ave, Greenwich $3,495,000

Rich with classic character this 1918 Colonial sits on one of the most coveted streets in Old Greenwich. With an expansive 3,670 square feet, this charm filled home pairs...

  • 4 Beds
  • 3 Baths
  • 24203497 MLS
74 Glenville Rd, Greenwich image
74 Glenville Rd, Greenwich $4,500,000

A Greenwich classic, this distinguished five-bedroom residence combines timeless architecture, exceptional craftsmanship, and grand-scale rooms designed for both entertai...

  • 5 Beds
  • 6 Baths
  • 24202628 MLS
55 Cos Cob Ave, Greenwich image
55 Cos Cob Ave, Greenwich $1,800,000

Beautifully renovated and move-in ready. This turnkey 3-bedroom, 2.5-bath home is set in a desirable Cos Cob neighborhood and offers four finished levels of comfortable, ...

  • 3 Beds
  • 3 Baths
  • 24201010 MLS
22 Lyon Ave, Greenwich image
22 Lyon Ave, Greenwich $1,249,000

Welcome to 22 Lyon Avenue, where location, lifestyle, and income potential come together in the heart of Greenwich. Tucked away on a quiet cul-de-sac, this beautifully ma...

  • 4 Beds
  • 2 Baths
  • 24200299 MLS
47 Lafayette Pl Unit 5H, Greenwich image
47 Lafayette Pl Unit 5H, Greenwich — Greenwich Lodge $1,300,000

Set within one of Greenwich's storied residential buildings, this exceptional two-bedroom, two-bath residence has been completely reimagined following an extensive eight-...

  • 2 Beds
  • 2 Baths
  • 24198957 MLS
  • Greenwich Lodge Bldg.
241 Pemberwick Rd, Greenwich image
241 Pemberwick Rd, Greenwich $2,100,000 ▼

Completely reimagined and move-in ready, this spacious 6-bedroom, 4 full and 1 half bath home offers nearly 3,000 square feet of versatile living on a peaceful, private 0...

  • 6 Beds
  • 5 Baths
  • 24197775 MLS
42 Gerry St, Greenwich image
42 Gerry St, Greenwich $1,189,000

Welcome to 42 Gerry Street, a thoughtfully updated two-family property where the big-ticket improvements are already checked off the list, so you can spend more time enjo...

  • 5 Beds
  • 2 Baths
  • 24198916 MLS
316 Valley Rd, Greenwich image
316 Valley Rd, Greenwich $2,750,000

Escape the ordinary. 316 Valley Road offers an increasingly rare combination of sweeping water views, absolute privacy, and uncompromised convenience. Sculpted by the for...

  • 4 Beds
  • 5 Baths
  • 24197532 MLS
16 Dale Dr, Greenwich image
16 Dale Dr, Greenwich $1,695,000

Stylish four-bedroom Colonial with private Trex deck, quiet backyard and seasonal second floor River views is ideally located on a cul-de-sac convenient to schools, park,...

  • 4 Beds
  • 3 Baths
  • 24197486 MLS
5 Bayside Ter, Greenwich image
5 Bayside Ter, Greenwich $1,999,000

Rare Riverside Opportunity with Endless Possibilities! Nestled on a quiet cul-de-sac in sought-after Riverside, this 4-bedroom, 3.5-bath home offers an exceptional opport...

  • 4 Beds
  • 4 Baths
  • 24192398 MLS
1 Hendrie Dr Extension, Greenwich image
1 Hendrie Dr Extension, Greenwich $3,300,000

A once-in-a-generation waterfront opportunity in Old Greenwich, perched above Greenwich Cove with breathtaking sunsets, expansive water views, and direct access to "The C...

  • 5 Beds
  • 3 Baths
  • 24194050 MLS
4 Hassake Rd, Greenwich image
4 Hassake Rd, Greenwich $1,495,000

Move right in and enjoy this charming 3-bedroom home, immediate occupancy and a quick closing. Whether you're looking to settle in before the school year begins or create...

  • 3 Beds
  • 2 Baths
  • 24195428 MLS
25 W Elm St Unit 37, Greenwich image
25 W Elm St Unit 37, Greenwich — Winthrop House $1,350,000 ▼

Ideally located just off Greenwich Avenue, this spacious two-bedroom, two-bath residence is set in a classic 1930s luxury doorman building with an elevator. This condo fe...

  • 2 Beds
  • 2 Baths
  • 24186688 MLS
  • Winthrop House Bldg.
Greenwich image
Greenwich $3,495,000

Welcome to this quintessential Greenwich home, fabulously refurbished and sited on a generous and private .91 acre in central Greenwich. Within an easy reach to schools, ...

  • 4 Beds
  • 4 Baths
  • 24195216 MLS
5 Griffith Rd, Greenwich image
5 Griffith Rd, Greenwich $1,469,000 ▼

This beautiful move-in ready Colonial is tucked away on a peaceful cul-de-sac in the desirable Riverside neighbourhood. It offers the perfect blend of modern style and...

  • 4 Beds
  • 3 Baths
  • 24194042 MLS
17 Rex St, Greenwich image
17 Rex St, Greenwich $899,000

Asking for best offers by Tuesday 7/21 at 9am. Welcome to 17 Rex Street, where charm & comfort come together in one of Greenwich's most convenient neighborhoods. Set with...

  • 3 Beds
  • 2 Baths
  • 24192251 MLS
28 Gregory Rd, Greenwich image
28 Gregory Rd, Greenwich $1,850,000 ▼

Opportunity awaits in one of Greenwich's most desirable communities. Located on a quiet residential street in Cos Cob, this spacious home offers 3,597 square feet of livi...

  • 4 Beds
  • 3 Baths
  • 24191798 MLS
15 Henry St, Greenwich image
15 Henry St, Greenwich $799,000

Multifamily development opportunity. Currently a single family home. Ideal for investors, builders, or end-users looking to customize. Convenient access to Metro-North in...

  • 2 Beds
  • 2 Baths
  • 24191313 MLS
52 Francis Ln, Greenwich image
52 Francis Ln, Greenwich $1,895,000

Located in one of Greenwich's most desirable neighborhoods, this meticulously maintained home offers the perfect blend of timeless elegance and modern comfort. Thoughtful...

  • 3 Beds
  • 4 Baths
  • 24182873 MLS
67 Benjamin St, Greenwich image
67 Benjamin St, Greenwich $2,995,000

Exceptional opportunity in the heart of Old Greenwich! A rare opportunity to own a flat, build-ready lot in the heart of Old Greenwich, offering the perfect setting to ex...

  • 4 Beds
  • 3 Baths
  • 24189215 MLS
10 Steep Hollow Ln, Greenwich image
10 Steep Hollow Ln, Greenwich $2,499,000

Private Cos Cob oasis designed for effortless single-level living, with the added flexibility of a spacious second-floor great room ideal as second home office, fitness s...

  • 4 Beds
  • 3 Baths
  • 24188875 MLS
52 Center Dr, Greenwich image
52 Center Dr, Greenwich $1,495,000

Enjoy the summer in this 4 bedroom Old Greenwich home, where character, comfort, and outdoor enjoyment come together. The inviting living room with fireplace creates a wa...

  • 4 Beds
  • 3 Baths
  • 24188202 MLS
16 Ridgebrook Rd, Greenwich image
16 Ridgebrook Rd, Greenwich $4,495,000 ▼

Just minutes from downtown Greenwich, this beautifully renovated Colonial offers the ideal blend of luxury, comfort, and convenience. The bright, open interior features s...

  • 5 Beds
  • 6 Baths
  • 24188162 MLS
11 Butternut Hollow Rd, Greenwich image
11 Butternut Hollow Rd, Greenwich $3,495,000

Sun-filled Colonial set on 2 private acres with desirable east/west exposures, offering exceptional privacy and natural beauty. Thoughtfully updated throughout, the home ...

  • 5 Beds
  • 6 Baths
  • 24185738 MLS
8 Ernel Dr, Greenwich image
8 Ernel Dr, Greenwich $1,950,000

Tucked away at the end of a peaceful cul-de-sac characterized by minimal traffic and a genuine sense of community, this classic Cape-style residence offers a rare and sou...

  • 4 Beds
  • 3 Baths
  • 24183181 MLS
33 Sachem Rd, Greenwich image
33 Sachem Rd, Greenwich $1,750,000 ▼

Tucked into a parklike half-acre south of the Post Road, 33 Sachem Road is a commuter's dream a block from the train, parks, and shops. This beautifully maintained 3+ bed...

  • 3 Beds
  • 3 Baths
  • 24184423 MLS
991 Lake Ave, Greenwich image
991 Lake Ave, Greenwich $6,750,000

Some properties simply need to be experienced in person, and 991 Lake Avenue is one of them. Set on four beautifully landscaped and exceptionally private acres, this dist...

  • 5 Beds
  • 7 Baths
  • 24182061 MLS
22 Nedley Ln, Greenwich image
22 Nedley Ln, Greenwich $990,000 ▼

Lovingly maintained by the same family for 54 years, this charming 3-bedroom, 2.5-bath home offers the perfect blend of seclusion and convenience. Set back at the end of ...

  • 3 Beds
  • 3 Baths
  • 24176923 MLS
37 Arch St, Greenwich image
37 Arch St, Greenwich $3,600,000

Potential for residential conversion in the heart of downtown Greenwich. Located just two doors from Greenwich Avenue and moments from the Metro-North train station, 37 A...

  • 8 Beds
  • 3 Baths
  • 24174202 MLS
6 Meadowbank Rd, Greenwich image
6 Meadowbank Rd, Greenwich $2,995,000

Updated with a Modern flair this four-bedroom home is near the water, Tod's Point & located on a quiet cul-de-sac in Old Greenwich. Spacious & bright, there is an open de...

  • 4 Beds
  • 4 Baths
  • 24177489 MLS
55 Calhoun Dr, Greenwich image
55 Calhoun Dr, Greenwich $8,795,000

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association....

  • 6 Beds
  • 10 Baths
  • 24177074 MLS
1018 North St, Greenwich image
1018 North St, Greenwich $999,000

Vintage craftsman colonial home on North Street with lots of potential to accentuate its cosy charm or bring your vision to update to suit your personal style. Close to B...

  • 3 Beds
  • 2 Baths
  • 24176002 MLS
276 Bruce Park Ave, Greenwich image
276 Bruce Park Ave, Greenwich $1,525,000

Great opportunity for a buyer or investor to own this Bruce Park walk to train and town center two-family home. There are 2 side-by-side units. The 700 SF unit (A) is a l...

  • 4 Beds
  • 3 Baths
  • 24174043 MLS
38 Francis Ln, Greenwich image
38 Francis Ln, Greenwich $1,395,000

Filled with natural light and impeccably maintained, this beautifully updated 4-bedroom, 2-bath Cape is located in the highly desirable Glenville School District and comb...

  • 4 Beds
  • 2 Baths
  • 24170992 MLS
Greenwich image
Greenwich $1,995,000

Spectacular setting! A true nature lover's paradise-where privacy and natural beauty meet.At the end of a private lane,this home offers a serene escape in the heart of ba...

  • 3 Beds
  • 3 Baths
  • 24168732 MLS
37 Arch St, Greenwich image
37 Arch St, Greenwich $3,600,000

37 Arch Street presents a rare opportunity to own a boutique commercial building in the heart of downtown Greenwich, just two doors from Greenwich Avenue and moments from...

  • 3 Baths
  • 24174195 MLS
47 Ridge St, Greenwich image
47 Ridge St, Greenwich $2,895,000 ▲

Tucked at the end of a private road in Cos Cob, this newly built (2025) Louis Contadino-designed home offers a layout rarely available in central Greenwich at this price ...

  • 4 Beds
  • 5 Baths
  • 24168793 MLS

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Greenwich Historical Real Estate

Our website features the best real estate search for historical properties available in Greenwich and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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Michael Parsell
Trusted Realty Partners
(203) 880-9675
Contact Me

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Trusted Realty Partners, LLC

324 Elm Street, Suite 105B

Monroe, CT 06468

Broker: John Fontana REB.0794755

(203) 880-9675
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