Homes Under $500K in Middletown, CT

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3 beds New construction With a pool

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24 of 42 Listings

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Homes Under $500K in Middletown, CT

24 of 42 Listings

New40

42 listings

Homes Under $500K in Middletown, CT

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24 of 42 Listings

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Homes Under $500K in Middletown, CT

24 of 42 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

New40

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

Active

$389,000

2 bd · 3 ba · 123 sqft

46 Clarence Court, Middletown, CT

Nancy Currlin · William Raveis Real Estate

New36Active

$280,000

3 bd · 2 ba · 1,299 sqft

6 Hillside Court, Middletown, CT

Heather Crabtree · RE/MAX RISE

New12Active

$379,900

3 bd · 2 ba · 1,313 sqft

672 East Main Street, Middletown, CT

Marco Rondinone · Berkshire Hathaway NE Prop.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

New22Active

$224,500

3 bd · 1 ba · 1,109 sqft

1231 Washington Street 2, Middletown, CT

Chris Hogan · Century 21 Classic Homes

New28Active

$199,900

2 bd · 2 ba · 866 sqft

316 Carriage Crossing Lane 316, Middletown, CT

Jeff Petersen · Century 21 AllPoints Realty

27Active

$189,900

3 bd · 2 ba · 1,200 sqft

6 McKenna Drive, Middletown, CT

Marco Rondinone · Berkshire Hathaway NE Prop.

19Active

$289,900

2 bd · 2 ba · 1,196 sqft

1 Canterbury Court 2, Middletown, CT

Mark Massaro · Coldwell Banker Realty

40Active

$199,900

2 bd · 2 ba · 1,206 sqft

95 Trolley Crossing Lane 95, Middletown, CT

Roger Lavoie · LAER Realty Partners

23Active

$245,000

3 bd · 2 ba · 1,136 sqft

52 Trolley Crossing Lane 52, Middletown, CT

Jithu Sajeevan · Serhant Connecticut, LLC

2Active

$119,000

1 bd · 1 ba · 533 sqft

500 Washington Street #9, Middletown, CT

Susan Cafourek · Berkshire Hathaway NE Prop.

39Active

$329,900

3 bd · 2 ba · 1,346 sqft

122 Newfield Street 3a, Middletown, CT

Michelle Mazzotta · eXp Realty

2Active

$135,000

2 bd · 2 ba · 880 sqft

500 Washington Street #6, Middletown, CT

Susan Cafourek · Berkshire Hathaway NE Prop.

15Active

$349,000

3 bd · 2 ba · 1,164 sqft

17 East Lake Place, Middletown, CT

Richard Tirado · New England Realty Assoc LLC

40Active

$369,999

3 bd · 2 ba · 1,537 sqft

123 Fisher Road, Middletown, CT

Courtney LeBlanc · Dave Jones Realty, LLC

27Active

$189,900

3 bd · 2 ba · 1,120 sqft

170 Rising Trail Drive 170, Middletown, CT

Marc Seigel · RE/MAX RISE

40Active

$454,900

3 bd · 2 ba · 1,774 sqft

147 Old Mill Road, Middletown, CT

Michelle Mandel · Carl Guild & Associates

34Active

$499,999

3 bd · 3 ba · 2,628 sqft

141 Cimarron Road, Middletown, CT

Nancy Stetson · Coldwell Banker Realty

38Active

$299,900

3 bd · 2 ba · 1,360 sqft

774 Long Hill Road 774, Middletown, CT

Dawn Gagliardi · Serhant Connecticut, LLC

Price Reduced13Active

$104,900

2 bd · 1 ba · 840 sqft

500 Washington Street #4, Middletown, CT

Susan Cafourek · Berkshire Hathaway NE Prop.

28Active

$249,900

2 bd · 2 ba · 960 sqft

210 Carriage Crossing Lane 210, Middletown, CT

Timothy Morse · Alliance Realty LLC

24Active

$220,000

1 bd · 1 ba · 760 sqft

277 Carriage Crossing Lane 277, Middletown, CT

Santo Buccheri · Carl Guild & Associates

37Active

$349,000

5 bd · 2 ba · 1,440 sqft

130 Spencer Drive, Middletown, CT

Julia King · William Raveis Real Estate

39Active

$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

24Active

$379,900

3 bd · 2 ba · 1,536 sqft

492 Long Hill Road, Middletown, CT

Atif Seyal · RE/MAX Heritage

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 housing market

August 2026 · This period is still settling

Selling at 103.2% of asking price

Buyers here are paying above asking. MLS · 48 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 13, 2026

Median sale price: $396,750$330,000–$458,750 typical range
Price per sq. ft.: $242
Sales: 24
Paid in cash: 29.2%

Homes on the market · MLS, as of Aug 30, 2026–Aug 31, 2026

Median list price: $391,450

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

Explore Middletown homes

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas

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 103.2% of asking price

Buyers here are paying above asking. MLS · 48 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 13, 2026

Median sale price: $396,750$330,000–$458,750 typical range
Price per sq. ft.: $242
Sales: 24
Paid in cash: 29.2%

Homes on the market · MLS, as of Aug 30, 2026–Aug 31, 2026

Median list price: $391,450

Homes for sale

42

Median days on market

7 days

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

Year-over-year: 14.5%

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.

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Middletown housing market

Homes that sold · County records, as of Aug 13, 2026

Homes on the market · MLS, as of Aug 30, 2026–Aug 31, 2026

Middletown, CT community profile

Explore Middletown homes

Your local brokerage

Listing data & MLS disclosures

Middletown, CT community profile

Middletown housing market

Homes that sold · County records, as of Aug 13, 2026

Homes on the market · MLS, as of Aug 30, 2026–Aug 31, 2026

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

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