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Browse All Monroe CT Historical Properties for Sale

19 Crestwood Rd, Monroe image
19 Crestwood Rd, Monroe $589,900

Welcome to this wonderful 4 bedroom, 2.5 bath split level home nestled in one of Monroe's most desirable neighborhoods. Offering the perfect blend of comfort and function...

  • 4 Beds
  • 3 Baths
  • 24194477 MLS
87 Jockey Hollow Rd, Monroe image
87 Jockey Hollow Rd, Monroe $559,000

Welcome to 87 Jockey Hollow Road, a wonderful opportunity to own a charming home in one of Monroe's most desirable neighborhoods. Lovingly cared for over the years, this ...

  • 4 Beds
  • 3 Baths
  • 24195196 MLS
94 Swendsen Dr, Monroe image
94 Swendsen Dr, Monroe $799,900

Welcome to this beautifully maintained and thoughtfully designed 4 bedroom home, offering exceptional flexibility, abundant living space, and an ideal location on a quiet...

  • 4 Beds
  • 4 Baths
  • 24192943 MLS
38 Pastors Walk, Monroe image
38 Pastors Walk, Monroe $624,900

Welcome to this charming and surprisingly spacious split-level home, ideally located in one of Monroe's most desirable neighborhoods. This well-maintained home features a...

  • 3 Beds
  • 1 Baths
  • 24191984 MLS
56 Oak Wood Dr, Monroe image
56 Oak Wood Dr, Monroe $449,999

**HIGHEST / BEST DUE MONDAY 7/20 @ 12PM** Nestled on a quiet cul-de-sac in one of Monroe's most desirable neighborhoods, this charming 3 bedroom, 1 bathroom split-level o...

  • 3 Beds
  • 1 Baths
  • 24191495 MLS
602 Fan Hill Rd, Monroe image
602 Fan Hill Rd, Monroe $599,900

Beautifully renovated from top to bottom, this inviting Cape offers the perfect combination of modern finishes and peaceful surroundings. Featuring four generously sized ...

  • 4 Beds
  • 2 Baths
  • 24189609 MLS
216 Cross Hill Rd, Monroe image
216 Cross Hill Rd, Monroe $336,000

Builder & Investor Special! Exceptional opportunity at 216 Cross Hill Road, Monroe, CT, located in a B2 Zone offering flexibility for future development. Whether you're p...

  • 2 Beds
  • 1 Baths
  • 24190492 MLS
47 Hiram Hill Rd, Monroe image
47 Hiram Hill Rd, Monroe $599,000 ▼

Nestled on 3.79 acres in Monroe's desirable Stepney neighborhood, this unique property features two separate residential buildings. The main home (Building 1) is a 2,124...

  • 5 Beds
  • 4 Baths
  • 24188259 MLS
339 Spring Hill Rd, Monroe image
339 Spring Hill Rd, Monroe $429,900

Beautiful ranch home offering the ease and comfort of one-level living at its best. Designed for effortless everyday living, this inviting home features a functional layo...

  • 2 Beds
  • 2 Baths
  • 24188112 MLS
59 Countryside Dr, Monroe image
59 Countryside Dr, Monroe $639,900

Discover the home you've been searching for in a peaceful cul-de-sac within a highly desired community. Offering easy access to all major commutes, this private, well-car...

  • 3 Beds
  • 3 Baths
  • 24187003 MLS
17 Gray St, Monroe image
17 Gray St, Monroe $569,000

HIGHEST AND BEST BY THURSDAY, 7/2, BY 12:00! Experience single-level comfort in this tastefully updated, meticulously cared-for 3BD/2BTH Ranch on a tranquil, level 2-acre...

  • 3 Beds
  • 2 Baths
  • 24187093 MLS
104 Bart Rd, Monroe image
104 Bart Rd, Monroe $549,000

A move-in ready ranch offering comfortable living in a convenient Monroe location. This 3-bedroom, 1-bath home features a bright living room with a fireplace, an updated ...

  • 3 Beds
  • 1 Baths
  • 24187034 MLS
113 Pepper St, Monroe image
113 Pepper St, Monroe $610,000 ▼

1.5 story house. 1939 Cape with 1,649 s.f. of living area. 2.14 AC lot. Wooded. Large level backyard. County: Fairfield Neighborhood: Stepney Wood frame construction Foun...

  • 3 Beds
  • 2 Baths
  • 24186406 MLS
98 Osborn Ln, Monroe image
98 Osborn Ln, Monroe $599,900 ▼

Tucked into one of Monroe's established, tree-lined neighborhoods, 3-bedroom, 1.5 bathrooms approximately 1,696 square feet of comfortable living space on a spacious lot....

  • 3 Beds
  • 2 Baths
  • 24186176 MLS
293 Guinea Rd, Monroe image
293 Guinea Rd, Monroe $474,900 ▼

A rare opportunity to own a ranch-style home that combines comfortable one-level living with versatile finished lower-level space. This 3-bedroom, 1.5-bath home features ...

  • 3 Beds
  • 2 Baths
  • 24185884 MLS
17 Woodlawn Rd, Monroe image
17 Woodlawn Rd, Monroe $559,000 ▼

Curb appeal greets you with a beautifully landscaped circular driveway, creating a welcoming first impression the moment you pull in. Inside, this freshly painted home op...

  • 3 Beds
  • 3 Baths
  • 24184704 MLS
39 Cottage St, Monroe image
39 Cottage St, Monroe $565,000

This Lovely 3-bedroom, 2 Full Bath comes with 2,164 sq.ft. of Living Space. Gently nestled on a Beautifully Landscaped lot, this Ranch Style Home is perfect for your whol...

  • 3 Beds
  • 2 Baths
  • 24181333 MLS
802 Main St, Monroe image
802 Main St, Monroe $999,900

Exceptional mixed-use investment opportunity with tremendous upside potential on Route 25/Main Street. Positioned along a highly traveled corridor with approximately 18,0...

  • 1 Baths
  • 24182113 MLS
48 Crestwood Rd, Monroe image
48 Crestwood Rd, Monroe $749,000 ▼

Step into this beautiful newly remodeled 5 bedroom 2.5 bath split level home with open floor plan. This home boasts a new gourmet kitchen with center island and SS applia...

  • 4 Beds
  • 3 Baths
  • 24182242 MLS
277 Spring Hill Rd, Monroe image
277 Spring Hill Rd, Monroe $349,000 ▼

Set on 1.58 acres in a desirable Monroe location, this charming two-bedroom, one-bath home offers a unique opportunity to enjoy today while planning for tomorrow. Surroun...

  • 2 Beds
  • 1 Baths
  • 24182222 MLS
279 Pastors Walk, Monroe image
279 Pastors Walk, Monroe $449,000 ▼

HIGHEST AND BEST DUE MONDAY, JUNE 22 BY 5PM Set on a beautiful property in Monroe, this inviting raised ranch offers the space, flexibility, and outdoor lifestyle you've ...

  • 2 Beds
  • 1 Baths
  • 24179440 MLS
109 Gay Bower Rd, Monroe image
109 Gay Bower Rd, Monroe $699,000

Your Dream Multigenerational Home Awaits in a quiet, family friendly neighborhood! This beautifully updated home in Monroe's desirable East Village offers the perfect ble...

  • 4 Beds
  • 2 Baths
  • 24180165 MLS
57 Lovers Ln, Monroe image
57 Lovers Ln, Monroe $574,900 ▼

Step into the beauty of an open concept living. Gorgeous new kitchen with quartz counters and an island effortlessly flows into the dining and living area. Two bedrooms w...

  • 3 Beds
  • 3 Baths
  • 24178863 MLS
223 Wheeler Rd, Monroe image
223 Wheeler Rd, Monroe $519,500

Monroe Center! A beautiful one level floor plan sited on flat 1.6 acreage with expansive lawn & garden areas, tall trees & matured landscaped borders which you will enjoy...

  • 4 Beds
  • 2 Baths
  • 24178305 MLS
148 Cross Hill Rd, Monroe image
148 Cross Hill Rd, Monroe $665,000 ▼

Charming Colonial set on a private 1.2acre lot in the heart of Monroe. Step inside and immediately appreciate the spacious living room featuring vaulted ceilings, exposed...

  • 3 Beds
  • 2 Baths
  • 24171474 MLS
368 Webb Cir, Monroe image
368 Webb Cir, Monroe $450,000

Set along a quiet, winding residential street in one of Monroe's most desirable pockets, this property presents a strong opportunity to renovate, invest, or create long-t...

  • 3 Beds
  • 1 Baths
  • 24169975 MLS
395 Cross Hill Rd, Monroe image
395 Cross Hill Rd, Monroe $650,000 ▼

A completely reimagined New England traditional, this fully renovated 4-bedroom, 2.5-bath residence offers the perfect blend of classic charm and suburban tranquility. Se...

  • 4 Beds
  • 3 Baths
  • 24164925 MLS
444 Main St, Monroe image
444 Main St, Monroe $100,000 ▼

Corner of Rte 25 (Main St) and Rte 59 prime Upper Stepney location. Classic ice cream shop business for sale. 20000 cars/ day. High traffic, great visibility, plenty of p...

  • 24137670 MLS
360 Garder Rd, Monroe image
360 Garder Rd, Monroe $575,000 ▼

Bring your vision to this unique property nestled on almost 4 picturesque acres in desirable Monroe, CT. Set back from the road and surrounded by nature, this home offers...

  • 3 Beds
  • 1 Baths
  • 24151805 MLS
176 Main St, Monroe image
176 Main St, Monroe $399,500 ▼

Prime commercial site located on Route 25 (Main Street) in Monroe's B-2 Business District-an area designated for retail, office, restaurant, and general business uses. Th...

  • 1 Baths
  • 24149432 MLS
715 Main St, Monroe image
715 Main St, Monroe $499,000

This is a rare 1.68 acre mix use parcel. Retail, commercial, residential develop site. Old house and small building on property have little value. House is livable and wi...

  • 1 Baths
  • 24139473 MLS
40 Walnut St, Monroe image
40 Walnut St, Monroe $899,000 ▼

Welcome to this magnificent custom-built raised ranch known as 40 Walnut Street located in Fairfield County in the Town of Monroe. Monroe is a beautiful community that of...

  • 5 Beds
  • 6 Baths
  • 24110750 MLS
1480 Monroe Tpke, Monroe image
1480 Monroe Tpke, Monroe $1,500,000

A TOTAL OF 4 ACRES COMMERCIAL/INDUSTRIAL PROPERTY WITH RF-2 ZONING ALLOWING FOR RESIDENTIAL USE 1480 MONROE TPK HAS A 12,500 SQUARE FOOT BRICK BUILDING ON 2 ACRES WITH OF...

  • 3 Baths
  • 24113590 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.

Monroe Historical Real Estate

Our website features the best real estate search for historical properties available in Monroe 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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Trusted Realty Partners, LLC

324 Elm Street, Suite 105B

Monroe, CT 06468

Broker: John Fontana REB.0794755

(203) 880-9675
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