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Middletown, CT Homes for Sale | Realty.com
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3 beds

Homes for Sale in Middletown, CT

Homes for Sale in Middletown, CT

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24 of 76 Listings
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Homes for Sale in Middletown, CT

24 of 76 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #REB.0790925

Call Thomas
  1. 489 Chamberlain Road — photoNew40Active

    $925,000

    3 bd · 3 ba · — sqft

    489 Chamberlain Road, Middletown, CT

    Kerry Hart · William Raveis Real Estate

  2. 162 Trolley Crossing Lane Unit 162 — photo15Active

    $189,900

    2 bd · 2 ba · — sqft

    162 Trolley Crossing Lane Unit 162, Middletown, CT

    Adam Zak · Century 21 Classic Homes

  3. 75 Sisk Street — photo40Active

    $549,900

    4 bd · 3 ba · — sqft

    75 Sisk Street, Middletown, CT

    Jeff Coleman · Hagel & Assoc. Real Estate

  4. 38 Farm Hill Road — photo21Active

    $284,900

    2 bd · 1 ba · — sqft

    38 Farm Hill Road, Middletown, CT

    Benjamin Zupan · William Raveis Real Estate

  5. 127 Carriage Crossing Lane Unit 127 — photo27Active

    $245,000

    2 bd · 2 ba · — sqft

    127 Carriage Crossing Lane Unit 127, Middletown, CT

    Wendi Zuk · Homes Plus of Connecticut

  6. 92 Cynthia Lane Unit E2 — photo40Active

    $200,000

    2 bd · 1 ba · — sqft

    92 Cynthia Lane Unit E2, Middletown, CT

    Gina Lavery · Coldwell Banker Realty

  7. 201 College Street Unit 20 — photo22Active

    $179,000

    2 bd · 2 ba · — sqft

    201 College Street Unit 20, Middletown, CT

    Wally Namane · Keller Williams Realty Prtnrs.

  8. 223 Carriage Crossing Lane Unit 223 — photo40Active

    $195,000

    1 bd · 1 ba · — sqft

    223 Carriage Crossing Lane Unit 223, Middletown, CT

    Cynthia Muska · Coldwell Banker Realty

  9. 1 Russell Street Unit 5 — photo23Active

    $159,900

    1 bd · 2 ba · — sqft

    1 Russell Street Unit 5, Middletown, CT

    Basil Amso · RE/MAX Right Choice

  10. 6 Countryside Lane Unit 6 — photo33Active

    $249,900

    2 bd · 2 ba · — sqft

    6 Countryside Lane Unit 6, Middletown, CT

    Pat Flynn · Sterling REALTORS

  11. 40 Pinehurst Place — photo40Active

    $1,430,000

    6 bd · 6 ba · — sqft

    40 Pinehurst Place, Middletown, CT

    Jody Bonaiuto · William Raveis Real Estate

  12. 161 Cynthia Lane Unit D5 — photo36Active

    $245,900

    3 bd · 2 ba · — sqft

    161 Cynthia Lane Unit D5, Middletown, CT

    Vito Cortese · Coldwell Banker Realty

  13. 9 Burr Avenue — photo20Active

    $314,900

    3 bd · 1 ba · — sqft

    9 Burr Avenue, Middletown, CT

    Gissett Espinal · The Property Shop CT

  14. 368 Bow Lane — photo32Active

    $399,000

    2 bd · 1 ba · — sqft

    368 Bow Lane, Middletown, CT

    Heather Kilbourn · Cavanaugh & Company LLC

  15. 360 Chauncey Road — photo38Active

    $345,000

    3 bd · 2 ba · — sqft

    360 Chauncey Road, Middletown, CT

    Nicholas Greene · eXp Realty

  16. 1511 Country Club Road — photo40Active

    $410,000

    4 bd · 2 ba · — sqft

    1511 Country Club Road, Middletown, CT

    Michelle Wininger · William Pitt Sotheby's Int'l

  17. 38 Trolley Crossing Lane Unit 38 — photo27Active

    $148,000

    1 bd · 1 ba · — sqft

    38 Trolley Crossing Lane Unit 38, Middletown, CT

    Laura Beth Collinson · Carl Guild & Associates

  18. 270 Burgundy Hill Lane Unit 270 — photo16Active

    $139,900

    1 bd · 1 ba · — sqft

    270 Burgundy Hill Lane Unit 270, Middletown, CT

    Travis Bowden · Brickwell Partners LLC

  19. 732 Long Hill Road Unit 732 — photo18Active

    $275,000

    3 bd · 2 ba · — sqft

    732 Long Hill Road Unit 732, Middletown, CT

    Melanie Scull · William Pitt Sotheby's Int'l

  20. 150 Millbrook Road — photo32Active

    $340,000

    4 bd · 1 ba · — sqft

    150 Millbrook Road, Middletown, CT

    Lisa Antrum · KW Legacy Partners

  21. 404 Newfield Street — photo37Active

    $450,000

    3 bd · 3 ba · — sqft

    404 Newfield Street, Middletown, CT

    Christopher Grant · Christopher F. Grant Broker

  22. 212 Carriage Crossing Lane Unit 212 — photo23Active

    $248,500

    2 bd · 2 ba · — sqft

    212 Carriage Crossing Lane Unit 212, Middletown, CT

    Marjorie Clark · Coldwell Banker Realty

  23. 126 Rolling Green — photo40Active

    $474,900

    3 bd · 3 ba · — sqft

    126 Rolling Green, Middletown, CT

    Joe Snell · Luxe Realty LLC

  24. 5 Castanea Court — photo39Active

    $375,000

    2 bd · 1 ba · — sqft

    5 Castanea Court, Middletown, CT

    Siobhan McLaughlin · William Raveis Real Estate

12…4

Explore Middletown homes

By price

  • Homes Under $400K
  • Homes Under $500K
  • Homes Under $600K

By bedrooms

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  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #REB.0790925

    Call Thomas

    Nearby areas

    ZIP codes

    • 06516 (96)
    • 06010 (93)
    • 06457 (76)
    • 06514 (75)
    • 06405 (73)
    • 06512 (58)
    • 06460 (54)
    • 06437 (53)

    Cities

    • Hamden (169)
    • Waterbury (133)
    • New Haven (99)
    • West Haven (96)
    • Bristol (93)
    • West Hartford (81)
    • Meriden (75)
    • Branford (72)

    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

    October 2026 · This period is still settling

    Middletown 12-month median sale price trend

    Selling at 103.3% of asking price

    Buyers here are paying above asking. MLS · 28 sales · as of Oct 30, 2026

    Homes that sold · County records, as of Oct 16, 2026

    Median sale price
    $345,000$317,000–$455,000 typical range
    Price per sq. ft.
    $235
    Sales
    17
    Paid in cash
    29.4%

    Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

    Median list price
    $419,900
    Homes for sale
    71
    Median days on market
    12 days

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

    Year-over-year
    2.2%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,570 sq. ft.