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3 beds New construction With a pool

36 listings

Homes Under $500K in Middletown, CT

Homes Under $500K in Middletown, CT

24 of 36 Listings

Homes Under $500K in Middletown, CT

24 of 36 Listings

New28

Active

$219,900

3 bd · 2 ba · 1,360 sqft

868 Long Hill Road 868, Middletown, CT

Carol Wanat · Rockoff Realty

$369,999

3 bd · 2 ba · 1,537 sqft

123 Fisher Road, Middletown, CT

Courtney LeBlanc · Dave Jones Realty, LLC

$454,900

3 bd · 2 ba · 1,774 sqft

147 Old Mill Road, Middletown, CT

Michelle Mandel · Carl Guild & Associates

$189,900

3 bd · 2 ba · 1,120 sqft

170 Rising Trail Drive 170, Middletown, CT

Marc Seigel · RE/MAX RISE

$399,900

3 bd · 2 ba · 1,239 sqft

65 Murray Street, Middletown, CT

Jeff Coleman · Hagel & Assoc. Real Estate

$299,900

3 bd · 2 ba · 1,360 sqft

774 Long Hill Road 774, Middletown, CT

Dawn Gagliardi · Serhant Connecticut, LLC

$110,000

3 bd · 1 ba · 1,302 sqft

17 Miller Street, Middletown, CT

David Smolowitz · Dave Jones Realty, LLC

$114,900

2 bd · 1 ba · 840 sqft

500 Washington Street #4, Middletown, CT

Susan Cafourek · Berkshire Hathaway NE Prop.

$249,900

2 bd · 2 ba · 960 sqft

210 Carriage Crossing Lane 210, Middletown, CT

Timothy Morse · Alliance Realty LLC

$220,000

1 bd · 1 ba · 760 sqft

277 Carriage Crossing Lane 277, Middletown, CT

Santo Buccheri · Carl Guild & Associates

$349,900

3 bd · 2 ba · 1,275 sqft

34 Overlook Avenue, Middletown, CT

Jeff Petersen · Century 21 AllPoints Realty

$349,000

5 bd · 2 ba · 1,440 sqft

130 Spencer Drive, Middletown, CT

Julia King · William Raveis Real Estate

$330,000

3 bd · 2 ba · 1,440 sqft

19 Kent Court, Middletown, CT

Anower Hossain · Better Homes and Gardens Real Estate Executive Real Estate

$379,900

3 bd · 2 ba · 1,536 sqft

492 Long Hill Road, Middletown, CT

Atif Seyal · RE/MAX Heritage

$389,900

3 bd · 2 ba · 1,236 sqft

46 Middlefield Street, Middletown, CT

Michael Monteiro · Ascend Realty LLC

$339,900

3 bd · 1 ba · 1,071 sqft

100 Jacobs Terrace, Middletown, CT

Stacey McPherson · KW Legacy Partners

$349,800

3 bd · 2 ba · 1,934 sqft

5 Lorraine Terrace, Middletown, CT

Sherry Price · Realhome Services & Solutions

$449,900

3 bd · 2 ba · 1,772 sqft

147 Ridge Road, Middletown, CT

Santo Gulino · William Raveis Real Estate

Price Reduced34Active

$299,900

2 bd · 2 ba · 1,432 sqft

606 Congdon Street West 6, Middletown, CT

James Didato · Berkshire Hathaway NE Prop.

$393,000

3 bd · 2 ba · 1,963 sqft

63 Millbrook Road, Middletown, CT

Robert Link · Sterling REALTORS

$255,000

3 bd · 2 ba · 1,267 sqft

46 Meech Road, Middletown, CT

Lisa Sader · Aspen Realty Group

$429,000

3 bd · 2 ba · 1,581 sqft

76 George Street, Middletown, CT

Santo Gulino · William Raveis Real Estate

$229,000

2 bd · 2 ba · 1,500 sqft

201 College Street 12, Middletown, CT

Sue Hitchcock · Coldwell Banker Realty

$269,900

2 bd · 2 ba · 1,222 sqft

234 South Main Street 203, Middletown, CT

Barbara Puorro · Puorro Realty Group

1 2

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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By feature

New construction
With a pool

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Thomas O'Leary

Realty.com

Lic. #REB.0790925

Listing data & MLS disclosures

SmartMLS: IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

Middletown, CT community profile

Population: 44,815
Median income: $74,448
Housing units: 22,887
People per sq. mi.: 1,020.8
Area: 43.9 sq. mi.

Source: HJN community data

Middletown housing market

August 2026 · This period is still settling

Selling at 103.1% of asking price

Buyers here are paying above asking. MLS · 44 sales · as of Aug 29, 2026

Homes that sold · County records, as of Aug 7, 2026

Median sale price: $425,000$380,000–$485,000 typical range
Price per sq. ft.: $244
Sales: 13
Paid in cash: 15.4%

Homes on the market · MLS, as of Aug 29, 2026–Aug 30, 2026

Median list price: $391,450

Homes for sale

42

Median days on market

6 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 23.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

Median home size: 1,570 sq. ft.

Homes Under $500K in Middletown, CT