Woodbury, CT Homes

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  /39

  $874,900

  • 4 Beds
  • 2.5 Baths
  • 3,700 Sq Ft

  339 Main St S, Woodbury, CT 06798

  One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm

  

  Marian Van Egas

  Berkshire Hathaway NE Prop.

  (475) 405-2250

  339 Main St S, Woodbury, CT 06798
• Explore Woodbury

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  /31

  $3,750 Per Month

  • 2 Beds
  • 2 Baths
  • 1,968 Sq Ft
  • House for Rent

  33 Washington Ave, Woodbury, CT 06798

  AVAILABLE FOR $3,950/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes a bright

  

  Rebecca Doh

  W. Raveis Lifestyles Realty

  (203) 872-6274

  33 Washington Ave, Woodbury, CT 06798
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  $1,700,000 Sold Jan 20, 2026

  225 Old Sherman Hill Rd, Woodbury, CT 06798

  • 4 Beds
  • 4.5 Baths
  • 4,517 Sq Ft
  • Built 1969

  Last Sold Summary

  • 19% Below List Price
  • $376/SF
  • 345 Days On Market

  Current Estimated Value $1,625,322

  Last Listing Agent Maria Taylor Klemm Real Estate Inc

  225 Old Sherman Hill Rd, Woodbury, CT 06798
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  Est $348,122 Not Listed For Sale

  51 Joshua Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,508 Sq Ft
  • Built 1960

  51 Joshua Hill Rd, Woodbury, CT 06798

  Last Sold Summary

  • 17% Above List Price
  • $197/SF
  • 10 Days On Market

  • Last Sold Price $297,500
  • Apr 30, 2025

  Last Listing Agent Sarah Perrotti Regency Real Estate, LLC
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  /38

  $299,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,467 Sq Ft

  4 Deer Hill Ct Unit 4, Woodbury, CT 06798

  Welcome to this spacious 3 bedroom, 2.5 bath townhouse in the highly sought-after Woodlake community in Woodbury. Upon entering the unit, you will find a spacious foyer complete with a coat closet and a half bath. The rest of the main level features a large eat-in kitchen, open living room with allocated dining area and a set of sliding doors that lead to a private deck overlooking the tranquil

  

  Allysa DeRosa

  Mapleridge Realty

  (475) 303-6826

  4 Deer Hill Ct Unit 4, Woodbury, CT 06798
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  /35

  Starting at $1,599 Plus Fees

  • Studio - 2 Beds

  302 Tuttle Rd, Woodbury, CT 06798

  Welcome to Woodbury Knoll Apartments, where modern comfort meets tranquil, lakeside living. Life unfolds at a different pace here mornings are inspired by natures quiet beauty, and evenings unwind in serene surroundings. In our apartments in Woodbury, CT, you'll discover a lifestyle thats vibrant yet peaceful, perfectly balanced, and endlessly welcoming.

  Woodbury Knoll

  (860) 590-8441

  302 Tuttle Rd, Woodbury, CT 06798
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  $480,000 Sold Nov 04, 2025

  145 Cat Swamp Rd, Woodbury, CT 06798

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft
  • Built 1961

  Last Sold Summary

  • 4% Above List Price
  • $268/SF
  • 51 Days On Market

  Current Estimated Value $495,938

  Last Listing Agent Nancy Langrock William Raveis Real Estate

  145 Cat Swamp Rd, Woodbury, CT 06798
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  Est $801,067 Not Listed For Sale

  258 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 3 Baths
  • 1,628 Sq Ft
  • Built 1850

  258 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 6% Below List Price
  • $522/SF
  • 260 Days On Market

  • Last Sold Price $850,000
  • May 01, 2025

  Last Listing Agent Pat Lahoud Lahoud William Pitt
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  /40

  $799,900

  • 5 Beds
  • 3.5 Baths
  • 3,607 Sq Ft

  17 Carriage Ln, Woodbury, CT 06798

  Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in

  

  Shane Kropo

  RE/MAX RISE

  (203) 717-5671

  17 Carriage Ln, Woodbury, CT 06798
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  /10

  $1,750 Plus Fees

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  259 Main St S Unit 2, Woodbury, CT 06798

  Property Id: 2072920Light and bright 2 Story 1 Bedroom Condo available for immediate occupancy. This unit comes with a spacious and open first floor lay out, kitchen with extra cabinet space and more. The second floor has a full bathroom and spacious Bedroom with ample closet space. This condo is located on Woodbury most desirable areas and will not last long so dont wait schedule a tour

  (475) 476-1443

  259 Main St S Unit 2, Woodbury, CT 06798
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  $424,950 Sold Oct 23, 2025

  158 Hazel Plain Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • $204/SF
  • 32 Days On Market

  Current Estimated Value $469,754

  Last Listing Agent Michael Ferris eXp Realty

  158 Hazel Plain Rd, Woodbury, CT 06798
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  Est $179,036 Not Listed For Sale

  229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft
  • Built 1971

  229 Bacon Pond Rd Unit 214, Woodbury, CT 06798

  Last Sold Summary

  • 2% Above List Price
  • $192/SF
  • 43 Days On Market

  • Last Sold Price $175,000
  • May 02, 2025

  Last Listing Agent Cindy Sevell Coldwell Banker Realty
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  $1,800,000

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft

  76 Cowles Rd, Woodbury, CT 06798

  Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create an exclusive private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete

  

  Pam Famiglietti

  William Raveis Real Estate

  (475) 252-8273

  76 Cowles Rd, Woodbury, CT 06798
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  $30,000 Per Month

  • 3 Beds
  • 2.5 Baths
  • 3,282 Sq Ft
  • House for Rent

  28 Leavenworth Rd, Woodbury, CT 06798

  STUNNING MEMORIAL DAY - LABOR DAY RENTAL with POOL and TENNIS COURT (with lights). Enjoy a month or all summer at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a

  Diana Bisselle William Pitt Sotheby's Int'l

  28 Leavenworth Rd, Woodbury, CT 06798
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  $390,000 Sold Mar 31, 2026

  142 Washington Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,340 Sq Ft
  • Built 1955

  Last Sold Summary

  • 3% Above List Price
  • $291/SF
  • 44 Days On Market

  Current Estimated Value $376,890

  Last Listing Agent Mary Ann Bennett Drakeley Real Estate, Inc.

  142 Washington Rd, Woodbury, CT 06798
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  Not Listed For Sale

  49 Jacks Bridge Rd, Woodbury, CT 06798

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • Built 1987

  49 Jacks Bridge Rd, Woodbury, CT 06798

  Last Sold Summary

  • $624/SF
  • 228 Days On Market

  • Last Sold Price $628,500
  • Apr 28, 2025

  Last Listing Agent Christine Green Ardor Real Estate
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  /24

  $299,000

  • 2 Beds
  • 2.5 Baths
  • 1,916 Sq Ft

  54 Clubhouse Dr Unit 54, Woodbury, CT 06798

  Welcome to this light-filled and beautifully maintained townhome in the highly sought-after Woodlake community in Woodbury. Spanning three levels, this inviting home offers a rare blend of space, comfort, and seasonal views of Wood Lake. The main level features a spacious living and dining area anchored by a striking floor-to-ceiling fireplace, enhanced with a wood-burning insert (2021). Sliding

  Henrik K Kjaer Keller Williams Realty

  54 Clubhouse Dr Unit 54, Woodbury, CT 06798
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  /13

  $1,650

  Total Monthly Price

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

  495 Main St S Unit C, Woodbury, CT 06798

  Conveniently located in the center of Woodbury’s historic district, this charming set back apartment is close to shops, restaurants, and parks, while located in a quiet wooded setting. The property includes a unique bed/dressing room with a stacking washer/dryer, small entry foyer, one bath, an open living dining area, kitchen with dishwasher, and a private fenced back patio. Forced air heat and

  495 Main St S Unit C, Woodbury, CT 06798
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  $660,000 Sold Feb 05, 2026

  38 Barnhill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2.5 Baths
  • 2,835 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $233/SF
  • 134 Days On Market

  Current Estimated Value $673,616

  Last Listing Agent Donna Bannon BHGRE Gaetano Marra Homes

  38 Barnhill Rd, Woodbury, CT 06798
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  Not Listed For Sale

  44 Woods Way Unit 44, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1979

  44 Woods Way Unit 44, Woodbury, CT 06798

  Last Sold Summary

  • $199/SF
  • 4 Days On Market

  • Last Sold Price $290,000
  • May 09, 2025

  Last Listing Agent Kristie Perry William Pitt
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  /39

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,545 Sq Ft

  45 N Gate Rd, Woodbury, CT 06798

  Welcome to Woodbury, a quintessential New England town. This house is located in a very desirable neighborhood, just north of the town center. An inviting covered front porch will greet you. This leads to a 2 story foyer and an open floor plan opens up in front of you! To the left is a formal LR/Den. (cozy up with a good book) To the right is formal Dining Room with a trey ceiling, seats 8-10

  Jeff Colt Showcase Realty, Inc.

  45 N Gate Rd, Woodbury, CT 06798
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  /13

  $1,600 Per Month

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • House for Rent

  34 Arrowhead Way Unit A1, Woodbury, CT 06798

  Well-maintained first-floor end unit featuring a bright living room with beautiful built-in bookshelves, a cozy galley kitchen, and a spacious bedroom. Rent includes heat, hot water, and electricity for added convenience. Located in the Quassuk Heights community, this home offers easy living with plenty of parking, on-site laundry, lower-level storage, and easy walkways from parking to unit.

  Tim Drakeley Drakeley Real Estate, Inc.

  34 Arrowhead Way Unit A1, Woodbury, CT 06798
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  $350,000 Sold Aug 08, 2025

  306 Upper Grassy Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 1,936 Sq Ft
  • Built 1964

  Last Sold Summary

  • $181/SF
  • 6 Days On Market

  Current Estimated Value $389,288

  Last Listing Agent Shawna Mucherino Coldwell Banker Realty

  306 Upper Grassy Hill Rd, Woodbury, CT 06798
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  Est $864,860 Not Listed For Sale

  11 Saxony Ln, Woodbury, CT 06798

  • 3 Beds
  • 4 Baths
  • 3,124 Sq Ft
  • Built 2019

  11 Saxony Ln, Woodbury, CT 06798

  Last Sold Summary

  • 3% Above List Price
  • $269/SF
  • 84 Days On Market

  • Last Sold Price $840,000
  • May 02, 2025

  Last Listing Agent Chris Carey Carey & Guarrera Real Estate
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  /40

  $649,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,264 Sq Ft

  13 Park Ln, Woodbury, CT 06798

  Set on a picturesque lot with mature landscaping and gorgeous outdoor spaces, this beautifully maintained home offers a flexible layout designed for both entertaining and everyday living. The front entry opens to a bright and inviting living room with built-ins and gas fireplace. The kitchen blends style and function with granite countertops, stainless appliances, and a natural flow into the

  Michael Wright RE/MAX Right Choice

  13 Park Ln, Woodbury, CT 06798
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  /43

  $1,600

  Total Monthly Price

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

  31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798

  Impeccable large 2nd floor end unit, bright, cheerful and safe location with beautiful views. Freshly painted and professionally cleaned with new carpeting throughout. Rent includes heat, hot water and appliances. Tenant pays electric, cable/internet, renters insurance. Trash and recycling services and all grounds maintenance also included. New mini blinds throughout. Neighborhood is quiet and

  31 Pilgrim Trail Unit 31-5 PILGRIM TRAIL, Woodbury, CT 06798
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  $765,000 Sold Jul 29, 2025

  3 Inwood Ln, Woodbury, CT 06798

  • 4 Beds
  • 4 Baths
  • 3,330 Sq Ft
  • Built 1986

  Last Sold Summary

  • 13% Below List Price
  • $230/SF
  • 58 Days On Market

  Current Estimated Value $814,056

  Last Listing Agent Elizabeth Newnham William Pitt Sotheby's Int'l

  3 Inwood Ln, Woodbury, CT 06798
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  Est $929,629 Not Listed For Sale

  35 Fawn Meadow Ln, Woodbury, CT 06798

  • 4 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • Built 2021

  35 Fawn Meadow Ln, Woodbury, CT 06798

  Last Sold Summary

  • 4% Above List Price
  • $344/SF
  • 31 Days On Market

  • Last Sold Price $895,000
  • Apr 29, 2025

  Last Listing Agent Gregory Cohen William Pitt
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  /40

  $699,000 Under Contract

  • 4 Beds
  • 2.5 Baths
  • 2,849 Sq Ft

  54 Bear Run, Woodbury, CT 06798

  HIGHEST & BEST OFFERS DUE BY NOON ON MONDAY, 4/13/26 - Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath Colonial on lovely cul-de-sac neighborhood, privately set back on a wooded lot which backs up to Land Trust in sought-after Bear Run Estates. Proudly offered by its original owners, this home features numerous updates including a high-efficiency propane furnace

  Becky Hood William Pitt Sotheby's Int'l

  54 Bear Run, Woodbury, CT 06798
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  /9

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft
  • House for Rent

  17 Pleasant St, Woodbury, CT 06798

  This darling little cottage style cape is in the center of Woodbury's Historic District. Recently painted inside and out, new roof, No smokers, no pets. Good credit a must!(700 FICO) Year lease. Landlord maintains lawn care and snow removal. Tenant pays all utilities!

  Sindy Butkus Klemm Real Estate Inc

  17 Pleasant St, Woodbury, CT 06798
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  $530,000 Sold May 01, 2026

  31 McVeigh Rd, Woodbury, CT 06798

  • 4 Beds
  • 2.5 Baths
  • 2,256 Sq Ft
  • Built 1987

  Last Sold Summary

  • 12% Below List Price
  • $235/SF
  • 211 Days On Market

  Current Estimated Value $560,691

  Last Listing Agent Jennifer Bundock Coldwell Banker Realty

  31 McVeigh Rd, Woodbury, CT 06798
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  Not Listed For Sale

  31 Woods Way Unit 31, Woodbury, CT 06798

  • 2 Beds
  • 2 Baths
  • 1,582 Sq Ft
  • Built 1980

  31 Woods Way Unit 31, Woodbury, CT 06798

  Last Sold Summary

  • $164/SF
  • 213 Days On Market

  • Last Sold Price $260,000
  • Apr 01, 2025

  Last Listing Agent Eli Carneiro William Raveis Real Estate
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  /40

  $799,000

  • 4 Beds
  • 3 Baths
  • 2,448 Sq Ft

  92 Minortown Rd, Woodbury, CT 06798

  Charming Gentleman's Farm on 5.76 Acres. Welcome to this beautifully maintained gentleman's farm, perfectly set on 5.76 level acres of open pasture and riding space. Ideal for horse enthusiasts, the property features four barns with a total of 10 stalls, two wash stalls, and a 20x60 meter riding arena with quality stone dust and sand footing. The grounds offer a wonderful mix of functionality and

  Heather Crabtree RE/MAX RISE

  92 Minortown Rd, Woodbury, CT 06798
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  /22

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • Apartment for Rent

  4 Main St S Unit 2, Woodbury, CT 06798

  Enjoy an exceptionally renovated historic apartment in the heart of charming downtown Woodbury! Located on the second floor of an historic building, with a private staircase and deck, this apartment has it all. Private parking behind the building, close proximity to shops and restaurants, large bedrooms with well-apportioned closets, and a thoughtful layout are among the many characteristics that

  Matthew Amatruda Drakeley Real Estate, Inc.

  4 Main St S Unit 2, Woodbury, CT 06798
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  $595,000 Sold Nov 03, 2025

  90 Railtree Hill Rd, Woodbury, CT 06798

  • 3 Beds
  • 2 Baths
  • 2,772 Sq Ft
  • Built 1983

  Last Sold Summary

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

  Current Estimated Value $608,686

  Last Listing Agent Matthew Amatruda Drakeley Real Estate, Inc.

  90 Railtree Hill Rd, Woodbury, CT 06798
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  Est $690,060 Not Listed For Sale

  785 Washington Rd, Woodbury, CT 06798

  • 3 Beds
  • 6 Baths
  • 8,747 Sq Ft
  • Built 1982

  785 Washington Rd, Woodbury, CT 06798

  Last Sold Summary

  • 2% Above List Price
  • $77/SF
  • 371 Days On Market

  • Last Sold Price $675,000
  • Aug 30, 2024

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.
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  /24

  $289,000

  • 2 Beds
  • 3 Baths
  • 1,059 Sq Ft

  3 Tamarack Ln Unit 3, Woodbury, CT 06798

  Welcome to this well-maintained condo offering comfortable living in a desirable Woodbury location. This inviting unit features a bright and open layout with spacious living areas, an updated kitchen, and generously sized bedrooms. Enjoy the ample storage and a private outdoor space perfect for relaxing or entertaining. Nestled in a quiet, well-kept complex close to local shops, dining, and major

  Stephen Mele Houlihan Lawrence

  3 Tamarack Ln Unit 3, Woodbury, CT 06798
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  /15

  $2,600 Per Month

  • 3 Beds
  • 2 Baths
  • 2,630 Sq Ft
  • House for Rent

  25 Elephant Rock Rd, Woodbury, CT 06798

  Welcome to this 3BR/2BA rental located on a quiet cul-de-sac, conveniently close to shopping, dining, and major routes. The living space is anchored by a charming fireplace, perfect for cozy winter evenings, while the warmer months invite you outdoors to a private patio and serene backyard framed by mature trees and lush landscaping-an ideal setting for relaxing or entertaining. Enjoy the ease of

  Ashley Russell Kiwi Homes

  25 Elephant Rock Rd, Woodbury, CT 06798
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  $125,000 Sold Sep 16, 2025

  14 Arrowhead Way Unit 6, Woodbury, CT 06798

  • 1 Bed
  • 1 Bath
  • 546 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 91 Days On Market

  Current Estimated Value $128,893

  Last Listing Agent Jeff Boucher Drakeley Real Estate, Inc.

  14 Arrowhead Way Unit 6, Woodbury, CT 06798
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  Not Listed For Sale

  0 Mill Rd, Woodbury, CT 06798

  0 Mill Rd, Woodbury, CT 06798

  Last Sold Summary

  • $0/SF
  • 54 Days On Market

  • Last Sold Price $55,000
  • Mar 21, 2024

  Last Listing Agent Jason Arcuri eXp Realty

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