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Browse All Westport CT Historical Properties for Sale

19 Vineyard Ln, Westport image
19 Vineyard Ln, Westport $1,425,000

Get ready to make 19 Vineyard Lane home! This wonderful family home is ideally situated in the heart of Westport, offering 5 bedrooms and 2.5 baths designed for comfortab...

  • 5 Beds
  • 3 Baths
  • 24188426 MLS
11 Hitchcock Rd, Westport image
11 Hitchcock Rd, Westport $1,495,000

An exceptional offering on 1.38 private acres in the heart of Westport. Ideally situated just moments from vibrant Main Street, this centrally located property offers con...

  • 1 Beds
  • 1 Baths
  • 24191062 MLS
6 Clapboard Hill Rd, Westport image
6 Clapboard Hill Rd, Westport $4,599,000

At the top of Clapboard Hill, through the gate and over the brick drive, an iconic Westport Colonial welcomes with an immediate feeling of privacy and classic beauty. The...

  • 6 Beds
  • 6 Baths
  • 24193530 MLS
4 Bradley St, Westport image
4 Bradley St, Westport $2,997,000

Just 383 steps from the sands of Compo Beach, this storied 1920s residence claims one of Westport's most sought-after addresses. Approximately 3,255 square feet hold five...

  • 5 Beds
  • 4 Baths
  • 24193283 MLS
4 Crawford Rd, Westport image
4 Crawford Rd, Westport $2,799,000

Privately nestled in Westport's coveted Old Hill neighborhood, this extraordinary five-bedroom New England residence offers a rare opportunity to own a home where timeles...

  • 5 Beds
  • 4 Baths
  • 24189715 MLS
3 Madeline Ave, Westport image
3 Madeline Ave, Westport $899,000

The beach lifestyle, water views, natural light, and endless possibilities await at 3 Madeline Avenue. Freshly painted and furnished, this charming 2-3 bedroom cottage of...

  • 2 Beds
  • 2 Baths
  • 24192304 MLS
107 Roseville Rd, Westport image
107 Roseville Rd, Westport $1,199,000

Sweet Cottage with In-Ground Pool on a lovely 1-acre property in Westport. Fabulous location, close to everything! This peaceful 3 Bedroom, 2 1/2 Bath home feels worlds a...

  • 3 Beds
  • 3 Baths
  • 24190631 MLS
110 Cross Hwy, Westport image
110 Cross Hwy, Westport $1,999,000

Experience modern luxury in this beautifully reimagined home, set on 1.57 scenic, park-like acres. Thoughtfully renovated, this 2,864 sq ft residence offers open-concept ...

  • 5 Beds
  • 4 Baths
  • 24191704 MLS
18 Silver Brook Rd, Westport image
18 Silver Brook Rd, Westport $2,350,000

Welcome to 18 Silver Brook Road, a beautifully updated and meticulously maintained home set on a level, private acre in one of Westport's most beloved neighborhoods. Loca...

  • 4 Beds
  • 5 Baths
  • 24191350 MLS
5 Lehn Farm Rd, Westport image
5 Lehn Farm Rd, Westport $1,299,000

In the owners' words... We moved to this home looking for an escape from city life and a place to grow our family. It has offered us all of that and more. Every inch o...

  • 3 Beds
  • 2 Baths
  • 24189044 MLS
34 Woodside Ave, Westport image
34 Woodside Ave, Westport $2,699,000

Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, excep...

  • 4 Beds
  • 5 Baths
  • 24185246 MLS
119 Kings Hwy N, Westport image
119 Kings Hwy N, Westport $1,150,000

Build your dream house on this beautiful property close to town in the Old Hill section of Westport. This .87 acre lot in a AA zone has views of town and river through th...

  • 2 Beds
  • 2 Baths
  • 24187676 MLS
3 Keller Ln, Westport image
3 Keller Ln, Westport $798,000

Weekender, year-round retreat, or investment opportunity; this condo alternative charmer checks every box. Sun-filled and single-story, this happy home was cherished by i...

  • 2 Beds
  • 1 Baths
  • 24166309 MLS
157 Newtown Tpke, Westport image
157 Newtown Tpke, Westport $1,580,000

Just beautiful! Welcome to 157 Newtown Turnpike, set on a meticulously landscaped acre-plus of property, this is the combination of easy single level living paired with a...

  • 3 Beds
  • 3 Baths
  • 24183959 MLS
240 North Ave, Westport image
240 North Ave, Westport $3,499,000

"MEADOW WOOD" - Nearly two acres of Westport's most spectacular land is the setting for this storied estate, which has been completely remodeled, expanded and transformed...

  • 5 Beds
  • 5 Baths
  • 24181944 MLS
32 Morningside Dr N, Westport image
32 Morningside Dr N, Westport $1,275,000

4 Bedroom 3 Bath Farmhouse in the heart of Westport set on a picturesque level .5 acre. Full of potential, this home awaits your creative vision. Flat, pretty property wi...

  • 4 Beds
  • 3 Baths
  • 24181290 MLS
6 Gray Ln, Westport image
6 Gray Ln, Westport $4,950,000

**Sellers request all offers to be submitted by Sunday 6/28 at noon.** A WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate ...

  • 5 Beds
  • 5 Baths
  • 24184591 MLS
7 High Gate Rd, Westport image
7 High Gate Rd, Westport $1,625,000 ▼

Hamptons sophistication meets timeless Westport charm in this exquisitely renovated 4-bedroom, 3-bath Colonial nestled at the end of a peaceful cul-de-sac on a double lot...

  • 4 Beds
  • 3 Baths
  • 24184506 MLS
16 Harbor Rd, Westport image
16 Harbor Rd, Westport $2,995,000

This beautiful coastal residence, set on a half-acre, offers stunning views of the Saugatuck Yacht Club and the harbor, stretching to the Long Island Sound. Relax and unw...

  • 4 Beds
  • 4 Baths
  • 24183853 MLS
30 Saint Johns Pl, Westport image
30 Saint Johns Pl, Westport $2,895,000

Saint John Place is the street people who know Westport quietly hope opens up. It almost never does. Reimagined in 2007 by Renato Gasparian Associates and refreshed in 20...

  • 5 Beds
  • 4 Baths
  • 24182424 MLS
18 River Ln, Westport image
18 River Ln, Westport $2,100,000

Update: Offers are due at 6pm on Monday June 15th. Set along one of Westport's most coveted stretches of the Saugatuck River, 18 River Lane is a timeless 1939 English Ma...

  • 5 Beds
  • 6 Baths
  • 24120643 MLS
Westport image
Westport $1,499,000

This historic Greens Farms acreage was once part of the famed Winfromere Stables where Edward T. Bedford's world class trotters were kept in grand style. Offering over 22...

  • 3 Beds
  • 2 Baths
  • 24182240 MLS
422 Riverside Ave, Westport image
422 Riverside Ave, Westport $1,800,000

A rare opportunity in the heart of Westport's coveted Saugatuck section. Set on 1.10 dry acres w/ beautiful views overlooking the Saugatuck River, this property known his...

  • 5 Beds
  • 4 Baths
  • 24176205 MLS
31 Stonybrook Rd, Westport image
31 Stonybrook Rd, Westport $5,750,000

Tucked behind a gated entry in Old Hill, this stunning 5 bedroom, 6.2 bath home offers a rare blend of elegance, privacy and natural beauty. The property has multiple ser...

  • 5 Beds
  • 8 Baths
  • 24178699 MLS
34 Pequot Trl, Westport image
34 Pequot Trl, Westport $2,100,000

Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with th...

  • 5 Beds
  • 4 Baths
  • 24178738 MLS
2 Grassy Plains Rd, Westport image
2 Grassy Plains Rd, Westport $1,699,000

*SELLERS ARE AKSING FOR HIGHEST AND BEST OFFERS BY 4PM MONDAY JUNE 1ST*Set on a beautifully landscaped, bucolic acre at the top of a quiet cul-de-sac in Westport's covete...

  • 4 Beds
  • 4 Baths
  • 24176436 MLS
22 Evergreen Ave, Westport image
22 Evergreen Ave, Westport $4,850,000

Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time i...

  • 5 Beds
  • 5 Baths
  • 24172211 MLS
47 Charcoal Hill Rd, Westport image
47 Charcoal Hill Rd, Westport $10,500,000

Designed by renowned architect and builder Frazier Forman Peters, this stone estate is set on nearly 3.5 private, meticulously landscaped acres in Westport. Crafted over ...

  • 4 Beds
  • 6 Baths
  • 24177056 MLS
23 W Parish Rd, Westport image
23 W Parish Rd, Westport $999,000

Unlock the potential of this exceptional corner lot property located in one of Westport's most desirable areas. Set on a prime piece of land, this property presents a rar...

  • 3 Beds
  • 2 Baths
  • 24176734 MLS
10 Grist Mill Ln, Westport image
10 Grist Mill Ln, Westport $1,689,000

Welcome to 10 Grist Mill Lane, a move-in ready home set on a beautiful, level acre at the end of a quiet Long Lots cul-de-sac. Thoughtfully updated throughout, this 3-4 b...

  • 3 Beds
  • 3 Baths
  • 24172940 MLS
5 Farnham Ct, Westport image
5 Farnham Ct, Westport $2,099,000

Timeless elegance meets modern comfort in this stunning 1936 brick Colonial, beautifully updated while preserving the warmth, character, and craftsmanship of its vintage ...

  • 5 Beds
  • 5 Baths
  • 24171058 MLS
Westport image
Westport $2,750,000

31 Franklin & 19 Ketchum combined for redevelopment or reno existing. Multiple redevelopment projects coming to Saugtatuck including townhomes and flats across street as ...

  • 8 Beds
  • 2 Baths
  • 24174545 MLS
19 Ketchum St, Westport image
19 Ketchum St, Westport $900,000

19 Ketchum is for sale as part of 31 Franklin parcel with 2 building next door combined price $2,750,000. Ketchum and Franklin Street are about to be transformed as part ...

  • 4 Beds
  • 24174519 MLS
221 Greens Farms Rd, Westport image
221 Greens Farms Rd, Westport $2,995,000 ▼

The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true ...

  • 5 Beds
  • 6 Baths
  • 24171950 MLS
4 Cardinal Ln, Westport image
4 Cardinal Ln, Westport $2,199,000 ▼

Welcome to 4 Cardinal Lane ~ a beautifully expanded and thoughtfully updated home set on two private, level acres in one of Westport's most desirable cul-de-sac neighborh...

  • 4 Beds
  • 4 Baths
  • 24172650 MLS
28 Bulkley Ave N, Westport image
28 Bulkley Ave N, Westport $2,400,000 ▼

Beautifully renovated 1799 antique Colonial offering timeless charm, modern luxury, flat pool-worthy property, and exceptional convenience, just one light to the Greens F...

  • 5 Beds
  • 5 Baths
  • 24168651 MLS
61 Clapboard Hill Rd, Westport image
61 Clapboard Hill Rd, Westport $3,795,000 ▼

Located in prestigious Greens Farms, this European-inspired Colonial offers a rare opportunity to enjoy immediate charm while planning for the future. Set behind private ...

  • 4 Beds
  • 4 Baths
  • 24171986 MLS
30 Pequot Trl, Westport image
30 Pequot Trl, Westport $1,599,876 ▼

Coveted Old Hill neighborhood! This stone and shingle 10 room colonial is detailed with custom millwork, recessed lighting and beautiful hardwood floors throughout. The f...

  • 5 Beds
  • 4 Baths
  • 24170706 MLS
7 Lincoln St, Westport image
7 Lincoln St, Westport $949,000

Nestled in one of Westport's most sought-after in-town neighborhoods, 7 Lincoln Street offers a rare opportunity to own a home that has been lovingly maintained and quiet...

  • 4 Beds
  • 3 Baths
  • 24170020 MLS
4 Charcoal Ln, Westport image
4 Charcoal Ln, Westport $3,450,000 ▼

A rare offering indeed! Welcome to 4 Charcoal Lane, an unrivaled multi-generational estate mere minutes from top-rated schools, shopping, restaurants and all that Westpor...

  • 5 Beds
  • 5 Baths
  • 24169922 MLS
11 Clapboard Hill Rd, Westport image
11 Clapboard Hill Rd, Westport $3,995,000 ▼

An antique jewel set on 3.5 extraordinary acres in the heart of Greens Farms, ready to be transformed into your forever home. Brimming with timeless charm and endless pot...

  • 6 Beds
  • 8 Baths
  • 24168553 MLS
56 Charcoal Hill Rd, Westport image
56 Charcoal Hill Rd, Westport $2,790,000

A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and re...

  • 5 Beds
  • 3 Baths
  • 24161256 MLS
114 Cross Hwy, Westport image
114 Cross Hwy, Westport $2,700,000

Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophist...

  • 5 Beds
  • 5 Baths
  • 24165047 MLS
3 Stony Point W, Westport image
3 Stony Point W, Westport $5,925,000

Located within the highly desirable Stony Point association, this exceptional home offers a rare combination of privacy, water views, and convenience just moments from th...

  • 6 Beds
  • 9 Baths
  • 24163899 MLS
310 Main St, Westport image
310 Main St, Westport $1,329,000

Spacious sophistication in the heart of Downtown Westport. Perfectly positioned just moments from shopping, dining & recreation, this lovely in-town home offers a rare bl...

  • 3 Beds
  • 3 Baths
  • 24158630 MLS
4 Sherwood Island Ln, Westport image
4 Sherwood Island Ln, Westport $15,000,000

Hidden along a private lane in Westport's Greens Farms neighborhood, this extraordinary 20-acre waterfront estate unfolds as one of the most remarkable shoreline settings...

  • 7 Beds
  • 7 Baths
  • 24160355 MLS
20 Woods Grove Rd, Westport image
20 Woods Grove Rd, Westport $999,000

Set on a picturesque 0.30-acre lot, this ranch-style home is full of potential and waiting for your creative vision. While the home is being sold as-is the possibilities ...

  • 4 Beds
  • 2 Baths
  • 24158900 MLS
4 Woods Grove Rd, Westport image
4 Woods Grove Rd, Westport $999,000

HUGE OPPORTUNITY. PROPERTY TO BE SOLD AS-IS, WHERE IS WITH NO REPRESENTATIONS AS TO CONDITION. PERFECT FOR BUILDER/DEVELOPER TO BUILD ON .41 PARKLIKE ACRES AT IN-TOWN LOC...

  • 4 Beds
  • 3 Baths
  • 24142924 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.

Westport Historical Real Estate

Our website features the best real estate search for historical properties available in Westport 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
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324 Elm Street, Suite 105B

Monroe, CT 06468

Broker: John Fontana REB.0794755

(203) 880-9675
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