Middletown, CT Homes

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  $549,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,761 Sq Ft

  1 Nathan Hale Rd, Middletown, CT 06457

  To be Built - The Nathan Hale Estates offer an exceptionally private and secluded setting, making it the perfect place for you and your family. Experience modern luxury in this stunning new construction colonial offering 3 bedrooms, 2.5 baths boasting 1,761 sq. ft. of beautifully designed living space. Ushering you from the covered front porch, the first floor features a gourmet chef's kitchen

  Jenna Talbot Coldwell Banker Realty

  1 Nathan Hale Rd, Middletown, CT 06457
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  $2,100 total monthly price

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft
  • Apartment for Rent

  424 Main St Unit J, Middletown, CT 06457

  Welcome to Middletown's newest luxury apartments!! The NEW 424 Main Street apartments are located in the heart of town within walking distance of vibrant restaurants, cafes, shopping and Wesleyan University. 424 Main Street apartments offers luxuriously finished and unique 1 bedroom, and 2 bedroom units that provide an upscale design while capturing the buildings rich history. Each unit at 424

  Marianna Terenzio William Raveis Real Estate

  424 Main St Unit J, Middletown, CT 06457
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  $315,000 Sold Jan 08, 2026

  31 Broadview Pkwy, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,382 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Above List Price
  • $228/SF
  • 6 Days On Market

  Current Estimated Value $306,584

  Last Listing Agent James Harrington Carl Guild & Associates

  31 Broadview Pkwy, Middletown, CT 06457
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  Est $386,079 Not Listed For Sale

  4 Blue Spruce St, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,718 Sq Ft
  • Built 1972

  4 Blue Spruce St, Middletown, CT 06457

  Last Sold Summary

  • 4% Above List Price
  • $215/SF
  • 6 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Jim Treanor Jr ERA Treanor Real Estate
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  $219,900 Pending

  • Land
  • 16.84 Acres
  • $13,058 per Acre

  0 Round Hill Lot 17 Rd, Middletown, CT 06457

  Great opportunity to own this 16.84 acre parcel of vacant land in an R60 zone. Well and septic required. There are no deed resrictions or HOA fees. Possible owner financing available. Please do not walk the property without permission.

  Peter Carbutti Carbutti & Co., Realtors

  0 Round Hill Lot 17 Rd, Middletown, CT 06457
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  $1,400 total monthly price

  • 1 Bed
  • 1 Bath
  • 425 Sq Ft
  • Condo for Rent

  176 Pearl St Unit 1F, Middletown, CT 06457

  Please Read Below Before Clicking the Like Button. If you are a minimalist person with a small scale high style curating a cozy haven, spatial optimization and maximizing the minimal, then this unit is for you. This beautiful 1 bedroom and 1 bath is located in the heart of all of your destinations. It is located within walking distance to Wesleyan University, downtown where

  176 Pearl St Unit 1F, Middletown, CT 06457
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  $385,000 Sold Mar 20, 2026

  7 Blue Bell Ln, Middletown, CT 06457

  • 4 Beds
  • 1.5 Baths
  • 1,568 Sq Ft
  • Built 1973

  Last Sold Summary

  • 5% Above List Price
  • $246/SF
  • 37 Days On Market

  Current Estimated Value $365,821

  Last Listing Agent Steve Wollman Wollman Realty

  7 Blue Bell Ln, Middletown, CT 06457
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  Est $246,499 Not Listed For Sale

  15 Forest Glen Cir Unit 10, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft
  • Built 1989

  15 Forest Glen Cir Unit 10, Middletown, CT 06457

  Last Sold Summary

  • 26% Above List Price
  • $183/SF
  • 5 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Stephen Mele Houlihan Lawrence
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  $279,000 Under Contract

  • 2 Beds
  • 2.5 Baths
  • 1,544 Sq Ft

  565 Newfield St Unit 34, Middletown, CT 06457

  There's something immediately comforting about a home that gives you room to breathe-and this spacious condo does exactly that. With a thoughtfully designed floor plan and generous living spaces, it feels welcoming from the moment you step inside. The living room is warm and inviting, centered around a gas fireplace that sets the tone for quiet evenings, movie nights, or gathering with friends.

  Debbie Huscher Real Broker CT, LLC

  565 Newfield St Unit 34, Middletown, CT 06457
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  $1,400 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  22 Green St, Middletown, CT 06457

  Spacious 2-bedroom, 1-bath apartment available for immediate occupancy. Unit offers a comfortable layout with ample natural light and generous room sizes. Conveniently located near shopping, dining, public transportation, and major highways. Tenant is responsible for utilities. No smoking. Credit/background check required. One-month security deposit. $1,400 monthly rent. Schedule your showing

  Santo Gulino William Raveis Real Estate

  22 Green St, Middletown, CT 06457
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  $465,000 Sold Sep 03, 2025

  266 Ballfall Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 3,568 Sq Ft
  • Built 1956

  Last Sold Summary

  • $130/SF
  • 41 Days On Market

  Current Estimated Value $470,138

  Last Listing Agent Pam Giordano Pam-Gio Real Estate

  266 Ballfall Rd, Middletown, CT 06457
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  Est $344,787 Not Listed For Sale

  275 Middle St, Middletown, CT 06457

  • 3 Beds
  • 2.5 Baths
  • 1,992 Sq Ft
  • Built 1810

  275 Middle St, Middletown, CT 06457

  Last Sold Summary

  • 9% Above List Price
  • $158/SF
  • 83 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Brenden Hultgren Robert C White & Company LLC
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  $549,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft

  70 Jack English Dr, Middletown, CT 06457

  Welcome home to 70 Jack English Drive! This lovely 3-bedroom 2.5 bath Colonial checks off all the boxes today's sophisticated homeowner is looking for. Situated on a cul-de-sac, this beautiful home sits on a private lot and sets the tone for all the wonderful surprises' this home has in store for you! An open floor plan that filters in tons of natural light, this home is always bright and cheery.

  Mary Gurrieri RE/MAX Right Choice

  70 Jack English Dr, Middletown, CT 06457
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  $2,850 total monthly price

  • 4 Beds
  • 1.5 Baths
  • 1,200 Sq Ft
  • House for Rent

  17 Roberta Dr, Middletown, CT 06457

  This property at 17 Roberta Dr features 4 bedrooms and 1.5 bathrooms within a total of 1,200 square feet. The living room offers ample space for relaxation and entertainment. The bathroom includes a tub/shower combination, providing functional amenities for daily use. Each bedroom is designed to accommodate various furniture arrangements. The property is cable ready and includes heating for

  17 Roberta Dr, Middletown, CT 06457
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  $219,000 Sold Jun 20, 2025

  234 S Main St Unit 303, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • Built 1987

  Last Sold Summary

  • $191/SF
  • 49 Days On Market

  Current Estimated Value $226,712

  Last Listing Agent Devon Taylor Assael Dave Jones Realty, LLC

  234 S Main St Unit 303, Middletown, CT 06457
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  Est $412,642 Not Listed For Sale

  271 Ridge Rd, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1990

  271 Ridge Rd, Middletown, CT 06457

  Last Sold Summary

  • 12% Above List Price
  • $264/SF
  • 19 Days On Market

  Last Sold Price $369,000

  Last Listing Agent Edward Lawton iHeart Homes Real Estate LLC
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  $179,000 Pending

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft

  201 College St Unit 26, Middletown, CT 06457

  Welcome to Hamlin Court Condominiums, where historic charm meets comfortable, modern living. This well-maintained 1-bedroom, 1-bath ranch-style condo (Unit 26) offers a move-in-ready opportunity in one of Middletown's most desirable locations. The unit features fresh paint and new flooring throughout, creating a clean, bright, and inviting atmosphere. The kitchen is in good condition, offering

  Jacob Mochkin Roundtree Realty LLC

  201 College St Unit 26, Middletown, CT 06457
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  $2,100 total monthly price

  • 3 Beds
  • 1 Bath
  • 14,820 Sq Ft
  • House for Rent

  360 Main St Unit 3-B, Middletown, CT 06457

  Central downtown district. Welcome to the Historic Pythian Building with an interesting ownership history as hotel and former meeting place of the Pythian Knights. Large 3-bedroom unit on top floor, offers an open floor plan with kitchen, living room and full bath. Great tenant value with all utilities included. There isn't any onsite parking for tenants. There are municipal parking lots nearby

  Patricia Flynn Sterling REALTORS

  360 Main St Unit 3-B, Middletown, CT 06457
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  $430,000 Sold Nov 06, 2025

  85 Spencer Dr, Middletown, CT 06457

  • 5 Beds
  • 2 Baths
  • 1,965 Sq Ft
  • Built 1952

  Last Sold Summary

  • 2% Below List Price
  • $219/SF
  • 18 Days On Market

  Current Estimated Value $421,884

  Last Listing Agent Andrea Thomas SB Realty Group, LLC

  85 Spencer Dr, Middletown, CT 06457
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  Est $349,815 Not Listed For Sale

  455 West St, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 1,604 Sq Ft
  • Built 1948

  455 West St, Middletown, CT 06457

  Last Sold Summary

  • 9% Above List Price
  • $200/SF
  • 21 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Ana Russo William Pitt
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  $350,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,639 Sq Ft

  3 Blue Bird Rd, Middletown, CT 06457

  Charming 3-Bedroom Home in Sought-After Wesleyan Hills Community! Come see this well maintained 3-bedroom, 2-full-bath home located in the desirable Wesleyan Hills neighborhood. The kitchen features stainless steel appliances and tile flooring, opening to a dining room with a sliding door that leads to a spacious 15'x14' deck-perfect for entertaining or relaxing outdoors. The finished lower level

  Jody Bonaiuto William Raveis Real Estate

  3 Blue Bird Rd, Middletown, CT 06457
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  $1,700 total monthly price

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  63 Maynard St Unit 4, Middletown, CT 06457

  LOCATION! LOCATION! LOCATION!! Don't miss this charming opportunity in a 4 unit apartment building located on a lovely rolling hill convenient to route 9, shopping and recreational areas. A few minutes away from Middlesex hospital, Xavier High school, Weslyan College, downtown historic Middletown with incredible dining, nightlife and community events. Off the beaten path, but close to all the

  63 Maynard St Unit 4, Middletown, CT 06457
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  $217,000 Sold Oct 29, 2025

  94 Cynthia Ln Unit C6, Middletown, CT 06457

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Above List Price
  • $235/SF
  • 4 Days On Market

  Current Estimated Value $217,704

  Last Listing Agent David Borges The Borges Group LLC

  94 Cynthia Ln Unit C6, Middletown, CT 06457
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  Est $337,274 Not Listed For Sale

  37 Roberts St, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1919

  37 Roberts St, Middletown, CT 06457

  Last Sold Summary

  • 10% Above List Price
  • $246/SF
  • 26 Days On Market

  Last Sold Price $306,500

  Last Listing Agent Taylor Spadacenta Real Broker CT, LLC
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  $599,900 Under Contract

  • 6 Beds
  • 3.5 Baths
  • 3,148 Sq Ft

  11 Mansfield Terrace, Middletown, CT 06457

  Classic architecture meets modern updates in this beautiful three-story Tudor-style stucco home ideally located just steps from Wesleyan University and within walking distance to vibrant downtown Middletown, where restaurants, shopping, and entertainment are right at your doorstep. Built in 1926, this distinctive residence showcases timeless character while benefiting from numerous thoughtful

  Dawn Satagaj William Raveis Real Estate

  11 Mansfield Terrace, Middletown, CT 06457
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  $1,850 total monthly price

  • 1 Bed
  • 1 Bath
  • 621 Sq Ft
  • Apartment for Rent

  141 Bridge St Unit D, Middletown, CT 06457

  Welcome to 141 Bridge Street, a beautifully reimagined four-unit residence where modern design, everyday comfort, and effortless convenience come together seamlessly. The property includes two spacious one-bedroom units, one two-bedroom unit, and one three-bedroom unit, each thoughtfully designed with high-end finishes and private entrances for added privacy. Inside every unit, you'll find sleek

  Marianna Terenzio William Raveis Real Estate

  141 Bridge St Unit D, Middletown, CT 06457
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  $306,000 Sold Dec 12, 2025

  753 Long Hill Rd Unit A, Middletown, CT 06457

  • 2 Beds
  • 2.5 Baths
  • 1,449 Sq Ft
  • Built 1986

  Last Sold Summary

  • 9% Above List Price
  • $211/SF
  • 30 Days On Market

  Last Listing Agent Tracy Cooley Berkshire Hathaway NE Prop.

  753 Long Hill Rd Unit A, Middletown, CT 06457
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  Est $194,276 Not Listed For Sale

  19 Trolley Crossing Ln, Middletown, CT 06457

  • 2 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Built 1987

  19 Trolley Crossing Ln, Middletown, CT 06457

  Last Sold Summary

  • 15% Above List Price
  • $197/SF
  • 32 Days On Market

  Last Sold Price $169,500

  Last Listing Agent Geoff Luxenberg Century 21 Classic Homes
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  $1,450,000

  • 8 Beds
  • 10 Baths
  • 13,837 Sq Ft

  480 Main St, Middletown, CT 06457

  Welcome to Main St in Middletown! This 10 Unit mixed use brick beauty is anchored by 2 established commercial tenants on the ground level and 8 massive (900+Sq Ft) one-bedroom residential units above- an incredible opportunity for a stabilized asset with additional room for growth in a highly competitive location and market! The long-term ground-floor commercial tenants provide reliable income

  Lindy Hoyt Century 21 AllPoints Realty

  480 Main St, Middletown, CT 06457
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  $2,200 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft
  • Townhouse for Rent

  7 Countryside Ln Unit 1, Middletown, CT 06457

  Spacious Townhouse (end unit) in the southern part of Middletown, Connecticut. Located in a quiet suburban neighborhood and 10 minutes from the downtown shops and restaurants (2 minutes off of Route 9 as well). Two sunny bedrooms and a full bathroom upstairs and a half bath on first floor. Finished deck on the first floor. Laundry appliances and ample storage located in basement. Perfect for

  7 Countryside Ln Unit 1, Middletown, CT 06457
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  $275,000 Sold Jan 23, 2026

  80 Birchwood Dr, Middletown, CT 06457

  • 3 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1961

  Last Sold Summary

  • 1% Below List Price
  • $289/SF
  • 11 Days On Market

  Current Estimated Value $273,044

  Last Listing Agent Thomas Mele Dorrance Realty

  80 Birchwood Dr, Middletown, CT 06457
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  Est $309,640 Not Listed For Sale

  1195 S Main St, Middletown, CT 06457

  • 2 Beds
  • 2 Baths
  • 1,272 Sq Ft
  • Built 1900

  1195 S Main St, Middletown, CT 06457

  Last Sold Summary

  • 9% Above List Price
  • $224/SF
  • 12 Days On Market

  Last Sold Price $285,000

  Last Listing Agent Joe Fazzino eXp Realty
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  $589,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,844 Sq Ft

  270 Higby Rd, Middletown, CT 06457

  **HIGHEST AND BEST DUE BY MONDAY MARCH 23 AT 3 PM** Is there a 4-bedroom Colonial in Middletown with an inground pool and a full acre of land? 270 Higby Rd delivers. With over 2,800+ square feet of living space, this classic 4-bedroom, 3-bath Colonial is set on a private one-acre lot, creating a peaceful setting that's hard to find while still being close to everything Middletown has to offer.

  Devon Taylor Assael Dave Jones Realty, LLC

  270 Higby Rd, Middletown, CT 06457
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  $2,500 total monthly price

  • 3 Beds
  • 1 Bath
  • 2,081 Sq Ft
  • House for Rent

  32 Wall St Unit 2, Middletown, CT 06457

  HEAT INCLUDED IN RENT! Spacious and fully renovated, this 3-bedroom, 1-bathroom apartment offers comfortable living with thoughtful upgrades throughout. The kitchen and bathroom have been completely remodeled with brand-new appliances and fixtures, and the entire unit has been freshly painted. You'll find hardwood floors throughout, new LED lighting, and updated door hardware throughout the

  Kris Robinson Eagle Eye Realty PLLC

  32 Wall St Unit 2, Middletown, CT 06457
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  $350,000 Sold Apr 09, 2025

  56 Navadon Pkwy, Middletown, CT 06457

  • 3 Beds
  • 2 Baths
  • 1,606 Sq Ft
  • Built 1959

  Last Sold Summary

  • 6% Above List Price
  • $218/SF
  • 36 Days On Market

  Current Estimated Value $368,195

  Last Listing Agent Kristen Mok Berkshire Hathaway NE Prop.

  56 Navadon Pkwy, Middletown, CT 06457
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  Est $333,023 Not Listed For Sale

  791 Long Hill Rd Unit F, Middletown, CT 06457

  • 2 Beds
  • 2.5 Baths
  • 1,449 Sq Ft
  • Built 1986

  791 Long Hill Rd Unit F, Middletown, CT 06457

  Last Sold Summary

  • 3% Above List Price
  • $222/SF
  • 14 Days On Market

  Last Sold Price $322,000

  Last Listing Agent Stefania Bramato Berkshire Hathaway Home Services
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  $499,900

  • 3 Beds
  • 1.5 Baths
  • 2,464 Sq Ft

  153 Country Club Rd, Middletown, CT 06457

  Well maintained colonial home with charm & curb appeal! Great commuter location close to highways, shopping & Middletown's vibrant restaurant scene. The backyard at this property is a relaxing sanctuary with a $25,000 swim spa/hot tub, a koi pond, bluestone patio, stone fireplace, large deck, outdoor lighting & mature trees & plantings! The front entryway welcomes you with a covered wraparound

  Laura Bitondo Berkshire Hathaway NE Prop.

  153 Country Club Rd, Middletown, CT 06457
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  $2,100 total monthly price

  • 1 Bed
  • 1 Bath
  • 830 Sq Ft
  • Condo for Rent

  113 Birdsey Ave Unit Floor 1, Middletown, CT 06457

  Beautifully Updated 1–2 Bedroom First-Floor Apartment – Middletown, CTThis recently renovated first-floor apartment offers 830 sq. ft. of flexible living space in a quiet, walkable neighborhood. Officially a 1-bedroom, the layout allows the living room to convert into an additional bedroom, while the dining room can easily serve as the main living area or a bright home office—ideal for

  113 Birdsey Ave Unit Floor 1, Middletown, CT 06457
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  $320,000 Sold Sep 08, 2025

  83 Julia Terrace, Middletown, CT 06457

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1975

  Last Sold Summary

  • $280/SF
  • 27 Days On Market

  Current Estimated Value $322,833

  Last Listing Agent Rick Selph Selph Realty, LLC

  83 Julia Terrace, Middletown, CT 06457
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  Est $141,598 Not Listed For Sale

  1251 Washington St Unit 5, Middletown, CT 06457

  • 1 Bed
  • 1 Bath
  • 704 Sq Ft
  • Built 1985

  1251 Washington St Unit 5, Middletown, CT 06457

  Last Sold Summary

  • 35% Above List Price
  • $149/SF
  • 15 Days On Market

  Last Sold Price $105,000

  Last Listing Agent Clare Guest William Raveis Real Estate

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